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Chondroitin sulfate

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enrolling 662 people with knee osteoarthritis who satisfied radiographic criteria (Kellgren/Lawrence grade 2 or 3 changes and baseline joint space width of at least 2 mm). This subset continued to receive their randomized treatment (glucosamine 500 mg three times daily, chondroitin sulfate 400 mg three times daily, the combination of glucosamine and chondroitin sulfate, celecoxib 200 mg daily, or placebo) over 24 months. The primary outcome was a 20% reduction in pain over 24 months as measured by the Western Ontario and McMaster University Osteoarthritis Index (WOMAC). Secondary outcomes included an Outcome Measures in Rheumatology/Osteoarthritis Research Society International response and change from baseline in WOMAC pain and function. Over 2 years, none of the treatments (not even the positive control celecoxib) achieved a clinically important difference in WOMAC pain or function as compared with placebo. Adverse reactions were similar among treatment groups and serious adverse events were rare for all treatments.
523:" For conventional foods, this evaluation involves considering whether the ingredient that is the source of the substance is generally recognized as safe (GRAS), approved as a food additive, or authorized by a prior sanction issued by FDA (see 21 CFR 101.70(f)). Dietary ingredients in dietary supplements, however, are not subject to the food additive provisions of the act (see section 201(s)(6) of the Act (21 U.S.C. § 321(s)(6)). Rather, they are subject to the adulteration provisions in section 402 of the Act (21 U.S.C. 342) and, if applicable, the new dietary ingredient provisions in section 413 of the Act (21 U.S.C. 350b), which pertain to dietary ingredients that were not marketed in the United States before October 15, 1994." 20: 261:
One way to look at this difference is in terms of the proportion of disaccharide units: chondroitin sulfate from terrestrial animals is almost exclusively composed of non-sulfated (O) and monosulfated (A and C) units, while in marine species the proportion of disulfated (D, E and B) units is higher. Furthermore, marine chondroitin sulfate chains tend to be longer, with molecular weight of up to 70 kDa in chondroitin sulfate from shark, while in terrestrial animals molecular weight is typically below 45 kDa.
3926: 3946: 3936: 153:. In a 6-year double-blind placebo-controlled study involving 60 test subjects published in 1973, the chondroitin sulfate group showed a 350% reduction in fatal heart attacks compared to the control group. When analyzing the data for non-fatal cardiovascular events, the control group experienced non-fatal heart attacks at a rate of 16%, while those in the chondroitin sulfate-treated group came in at 0%. 442:
New England Journal of Medicine in 2006. Subjects were randomly assigned to one of five orally administered treatments: two 250 mg capsules of glucosamine hydrochloride three times daily, two 200 mg capsules of chondroitin sulfate three times daily, two capsules of 250 mg of glucosamine hydrochloride plus 200 mg of chondroitin sulfate three times daily, 200 mg of
503:. In Europe, chondroitin sulfate formulations are approved as drugs with evidenced efficacy and safety demonstrated by clinical trials in people with osteoarthritis. Adebowale et al. reported in 2000 that of 32 chondroitin supplements they analysed, only 5 were labeled correctly, and more than half contained less than 40% of the labeled amount. With the introduction of 1792:
Letter Regarding the Relationship Between the Consumption of Glucosamine and/or Chondroitin Sulfate and a Reduced Risk of: Osteoarthritis; Osteoarthritis-related Joint Pain, Joint Tenderness, and Joint Swelling; Joint Degeneration; and Cartilage Deterioration(Docket No. 2004P-0059). Addressed to John
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As of 2015 the largest trial conducted with the product was the Glucosamine and Chondroitin Arthritis Intervention Trial (GAIT), a double-blind, randomized, multicenter clinical trial sponsored by the US National Institutes of Health in 1583 people with knee osteoarthritis, which was published in the
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In 2004, a petition was submitted to the FDA that a dietary supplement of chondroitin sulfate be labeled as reducing the risk of osteoarthritis, cartilage deterioration, and osteoarthritis-related joint pain, tenderness, and swelling. The FDA denied the request, stating that experiments conducted by
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Clegg, Daniel O.; Reda, Domenic J.; Harris, Crystal L.; Klein, Marguerite A.; O'Dell, James R.; Hooper, Michele M.; Bradley, John D.; Bingham, Clifton O.; Weisman, Michael H.; Jackson, Christopher G.; Lane, Nancy E.; Cush, John J.; Moreland, Larry W.; Schumacher, H. Ralph; Oddis, Chester V.; Wolfe,
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In the same letter, the FDA found that studies performed on the dietary supplement form of chondroitin sulfate were insufficient to substantiate claims that it is efficacious in the prevention of joint deterioration, and denied the request to be allowed to label the supplement as such. They further
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Chondroitin sulfate is sourced from natural products, with high variability in terms of chain length and sulfation pattern. The variability in chondroitin sulfate composition extends to its origin, making it possible to differentiate between chondroitin sulfate from terrestrial and marine sources.
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Sawitzke A, et al. 2010 evaluated the efficacy and safety of glucosamine and chondroitin sulfate, alone or in combination, as well as celecoxib and placebo on painful knee osteoarthritis over 2 years as a continuation of the GAIT trial. This was a 24-month, double-blind, placebo-controlled study,
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In 2007, Reichenbach et al. used explicit methods to conduct and report a systematic review of 20 trials and concluded "large-scale, methodologically sound trials indicate that the symptomatic benefit of chondroitin is minimal or nonexistent. Use of chondroitin in routine clinical practice should
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Sawitzke, Allen D.; Shi, Helen; Finco, Martha F.; Dunlop, Dorothy D.; Harris, Crystal L.; Singer, Nora G.; Bradley, John D.; Silver, David; Jackson, Christopher G.; Lane, Nancy E.; Oddis, Chester V.; Wolfe, Fred; Lisse, Jeffrey; Furst, Daniel E.; Bingham, Clifton O.; Reda, Domenic J.; Moskowitz,
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Kishimoto, TK; Viswanathan, K; Ganguly, T; Elankumaran, S; Smith, S; Pelzer, K; Lansing, JC; Sriranganathan, N; Zhao, G; Galcheva-Gargova, Z; Al-Hakim, A; Bailey, GS; Fraser, B; Roy, S; Rogers-Cotrone, T; Buhse, L; Whary, M; Fox, J; Nasr, M; Dal Pan, GJ; Shriver, Z; Langer, RS; Venkataraman, G;
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Jevsevar, DS; Brown, GA; Jones, DL; Matzkin, EG; Manner, PA; Mooar, P; Schousboe, JT; Stovitz, S; Sanders, JO; Bozic, KJ; Goldberg, MJ; Martin WR, 3rd; Cummins, DS; Donnelly, P; Woznica, A; Gross, L; American Academy of Orthopaedic Surgeons (Oct 16, 2013). "The American Academy of Orthopaedic
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There are no FDA regulations on chondroitin sulfate as a food additive, as it is recognized by the FDA as a component of food and is "generally recognized as safe". However, a proposed application of chondroitin sulfate dietary supplement as a means of preventing joint degeneration was highly
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Clinical studies have not identified any significant side effects or overdoses of chondroitin sulfate, which suggest its long-term safety. In 2003 the Task Force of the European League Against Rheumatism (EULAR) committee ranked the level of toxicity of chondroitin sulfate 6 in a 0–100 scale.
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of chondroitin sulfate ranges from 15% to 24% of the orally administered dose. More particularly, on the articular tissue, Ronca et al. reported that chondroitin sulfate is not rapidly absorbed in the gastro-intestinal tract and a high content of labeled chondroitin sulfate is found in the
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Guerrini, M; Beccati, D; Shriver, Z; Naggi, A; Viswanathan, K; Bisio, A; Capila, I; Lansing, JC; Guglieri, S; Fraser, B; Al-Hakim, A; Gunay, NS; Zhang, Z; Robinson, L; Buhse, L; Nasr, M; Woodcock, J; Langer, R; Venkataraman, G; Linhardt, RJ; Casu, B; Torri, G; Sasisekharan, R (June 2008).
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Pharmacokinetic studies performed on humans and experimental animals after oral administration of chondroitin sulfate revealed that it can be absorbed orally. Chondroitin sulfate shows first-order kinetics up to single doses of 3,000 mg. Multiple doses of 800 mg in people with
194:, nitric oxide, and other substances that contribute to damage the cartilage matrix and cause death of articular chondrocytes. A recent review summarizes data from relevant reports describing the biochemical basis of the effect of chondroitin sulfate on osteoarthritis articular tissues. 403:
is present in salts of chondroitin sulfate. Commercial preparations of chondroitin sulfate typically are the sodium salt. Barnhill et al. have suggested that all such preparations of chondroitin sulfate be referred to as "sodium chondroitin" regardless of their sulfation status.
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residues of certain proteins. Exactly how proteins are selected for attachment of glycosaminoglycans is not understood. Glycosylated serines are often followed by a glycine and have neighboring acidic residues, but this motif does not always predict glycosylation.
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Richmond, J; Hunter, D; Irrgang, J; Jones, MH; Levy, B; Marx, R; Snyder-Mackler, L; Watters WC, 3rd; Haralson RH, 3rd; Turkelson, CM; Wies, JL; Boyer, KM; Anderson, S; St Andre, J; Sluka, P; McGowan, R; American Academy of Orthopaedic Surgeons (Sep 2009).
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Aravamudhan, Aja; Ramos, Daisy M.; Nada, Ahmed A.; Kumbar, Sangamesh G. (2014-01-01), Kumbar, Sangamesh G.; Laurencin, Cato T.; Deng, Meng (eds.), "Chapter 4 – Natural Polymers: Polysaccharides and Their Derivatives for Biomedical Applications",
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Letter Regarding the Relationship Between the Consumption of Glucosamine and/or Chondroitin Sulfate and a Reduced Risk of: Osteoarthritis; Osteoarthritis-related Joint Pain, Joint Tenderness, and Joint Swelling; Joint Degeneration; and Cartilage
483:, fish, and bird cartilage are also used. Since chondroitin is not a uniform substance, and is naturally present in a wide variety of forms, the precise composition of each supplement will vary. In fact, although many 145:
Chondroitin, along with commonly used glucosamine, should not be used to treat people who have symptomatic osteoarthritis of the knee as evidence shows that these treatments fail to provide relief for that condition.
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Chondroitin sulfate was originally isolated well before the structure was characterised, leading to changes in terminology with time. Early researchers identified different fractions of the substance with letters.
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therefore be discouraged." In contrast, and also in 2007, Bruyere et al. concluded that "there is compelling evidence that glucosamine sulfate and chondroitin sulfate may interfere with progression of OA."
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The effect of chondroitin sulfate in people with osteoarthritis is likely the result of a number of reactions including its anti-inflammatory activity, the stimulation of the synthesis of proteoglycans and
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McAtee, Caitlin O.; Barycki, Joseph J.; Simpson, Melanie A. (2014-01-01), Simpson, Melanie A.; Heldin, Paraskevi (eds.), "Chapter One – Emerging Roles for Hyaluronidase in Cancer Metastasis and Therapy",
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Frederick; Molitor, Jerry A.; Yocum, David E.; Schnitzer, Thomas J.; Furst, Daniel E.; Sawitzke, Allen D.; Shi, Helen; Brandt, Kenneth D.; Moskowitz, Roland W.; Williams, H. James (23 February 2006).
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Mazzucchelli, Ramón; Rodríguez-Martín, Sara; García-Vadillo, Alberto; Gil, Miguel; Rodríguez-Miguel, Antonio; Barreira-Hernández, Diana; García-Lledó, Alberto; de Abajo, Francisco J. (2021-07-12).
1136:"an evidence based approach to the management of knee osteoarthritis: Report of a Task Force of the Standing Committee for International Clinical Studies Including Therapeutic Trials (ESCISIT)" 1182:
Andermann G, Dietz M. The influence of the route of administration on the bioavailability of an endogenous macromolecule: chondroitin sulfate (CSA). Eur J Drug Metab Pharmacokinet 1982;7:11–6
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Vergés J, Castañeda-Hernández, G. On the bioavailability of oral chondroitin sulfate formulations: proposed criteria for bioequivalence studies. Proc. West. Pharmacol. Soc., 2004; 47: 50–53
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Chondroitin sulfate is used as a dietary supplement for diabetes management. It exhibits anti-inflammatory properties, making it a potential alternative to cortisol for treating enteritis.
78:. A chondroitin chain can have over 100 individual sugars, each of which can be sulfated in variable positions and quantities. Chondroitin sulfate is an important structural component of 2245:
by Winston Wicomb, Ph.D., September 24, 2002. Information on methods for extraction of chondroitin sulfate from cow trachea, at the Stone Clinic of San Francisco, at stoneclinic.com
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Valcarcel, Jesus; Novoa-Carballal, Ramon; Pérez-Martín, Ricardo; Reis, Rui L; Vázquez, José Antonio (2017). "Glycosaminoglycans from marine sources as therapeutic agents Authors".
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in 2008, chondroitin sulfate preparations are subject in the US to mandatory labeling standards as well as testing requirements for identity, purity, strength, and composition.
1862:"Clinical efficacy and safety of glucosamine, chondroitin sulphate, their combination, celecoxib or placebo taken to treat osteoarthritis of the knee: 2-year results from GAIT" 535:
denied the request to market it as safe, given that no human clinical trials were done, citing that animal studies are not sufficient for the approval of a dietary supplement.
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review of clinical trials found that most were of low quality, but that there was some evidence of short-term improvement in pain and few side effects; it does not appear to
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Monfort, J; Pelletier, JP; Garcia-Giralt, N; Martel-Pelletier, J (June 2008). "Biochemical basis of the effect of chondroitin sulphate on osteoarthritis articular tissues".
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Barnhill, JG; Fye, CL; Williams, DW; Reda, DJ; Harris, CL; Clegg, DO (2006). "Chondroitin product selection for the glucosamine/chondroitin arthritis intervention trial".
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Baeurle SA, Kiselev MG, Makarova ES, Nogovitsin EA (2009). "Effect of the counterion behavior on the frictional–compressive properties of chondroitin sulfate solutions".
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Valcarcel, Jesus; García, Míriam R.; Sampayo, Lucia F.; Vázquez, José A. (2020). "Marine chondroitin sulfate of defined molecular weight by enzymatic depolymerization".
491:, most of them do not produce their products in compliance with the GMP regulations for pharmaceuticals, resulting in products not meeting pharmaceutical requirements. 2019: 280:– Gal – GlcA. Each sugar is attached by a specific enzyme, allowing for multiple levels of control over GAG synthesis. Xylose begins to be attached to proteins in the 1625:
Barnhill JG, Fye CL, Williams DW, Reda DJ, Harris CL, Clegg DO (2006). "Chondroitin product selection for the glucosamine/chondroitin arthritis intervention trial".
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Klecker, Christina; Nair, Lakshmi S. (2017-01-01), Vishwakarma, Ajaykumar; Karp, Jeffrey M. (eds.), "Chapter 13 – Matrix Chemistry Controlling Stem Cell Behavior",
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Manohar, Krishna; Mesfin, Fikir (2024). "Effect of Oral Chondroitin Sulfate Supplementation on Acute Brain Injury in a Murine Necrotizing Enterocolitis Model".
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the company did not sufficiently demonstrate the effectiveness of the claim. Among other comments, the FDA noted the poor experimental design of some trials.
3929: 1012:"Chondroitin Sulfate Alleviates Diabetic Osteoporosis and Repairs Bone Microstructure via Anti-Oxidation, Anti-Inflammation, and Regulating Bone Metabolism" 2998: 2252: 399:, this is not the case, as sulfate is covalently bonded to the sugar. Rather, since the molecule has multiple negative charges at physiological pH, a 1289:
Conte, A; Volpi, N; Palmieri, L; Bahous, I; Ronca, G (1995). "Biochemical and pharmacokinetic aspects of oral treatment with chondroitin sulfate".
3346: 965: 863: 2050:"Analysis of glucosamine and chondroitin sulfate content in marketed products and the Caco-2 permeability of chondroitin sulfate raw materials" 428: 2218: 1235:
Conte, A; Palmieri, L; Segnini, D; Ronca, G (1991). "Metabolic fate of partially depolymerized chondroitin sulfate administered to the rat".
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Schieber, A.; Lopes-Lutz, D. (2011-01-01), Moo-Young, Murray (ed.), "4.40 – Analytical Methods – Functional Foods and Dietary Supplements",
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Conte, A; de Bernardi, M; Palmieri, L; Lualdi, P; Mautone, G; Ronca, G (1991). "Metabolic fate of exogenous chondroitin sulfate in man".
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While it is a prescription or over-the-counter drug in 22 countries, chondroitin is regulated in the U.S. as a dietary supplement by the
388:, without the "sulfate", has been used to describe a fraction with little or no sulfation. However, this distinction is not used by all. 3361: 3321: 2976: 2049: 3939: 2991: 797: 1315:
Palmieri L, Conte A, Giovannini L, Lualdi P, Ronca G. Metabolic fate of exogenous chondroitin sulfate in the experimental animal"
2251:, A thorough review of available information on the use of chondroitin sulfate in humans from the National Toxicology Program at 1121: 801: 3904: 3007: 2619: 2227: 139: 3585: 2984: 1794: 1497: 724: 665: 1606: 1539: 2856: 2300: 1661: 2965: 2754: 2257: 2280: 2262: 3975: 2614: 500: 2759: 3970: 2849: 2293: 2273:," ClinicalTrials.gov information on the purpose, design, and analysis of the study at clinicaltrials.gov 1911:"Risk of acute myocardial infarction among new users of chondroitin sulfate: A nested case-control study" 512: 504: 488: 3006: 2181:
Goodrich, LR; Nixon, AJ (January 2006). "Medical treatment of osteoarthritis in the horse – a review".
515:(USP) testing standards for the identification and quantification of chondroitin are well-established. 2277:"NIH News: Efficacy of Glucosamine and Chondroitin Sulfate May Depend on Level of Osteoarthritis Pain" 1691:"Oversulfated chondroitin sulfate is a contaminant in heparin associated with adverse clinical events" 3883: 2729: 1741:"Contaminated heparin associated with adverse clinical events and activation of the contact system" 1558: 980:
Morrison LM, Enrick N. "Coronary heart disease: reduction of death rate by chondroitin sulfate A".
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Singh, JA; Noorbaloochi, S; MacDonald, R; Maxwell, LJ (28 January 2015). Singh, Jasvinder A (ed.).
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Summary of a Consumer Labs test of the actual composition of these supplements at consumerlabs.com
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daily, or placebo. Treatment was administered for 24 weeks. It showed no difference from placebo.
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Ronca F, Palmieri L, Panicucci P, Ronca G. "Anti-inflammatory activity of chondroitin sulfate"
1809:"Glucosamine, chondroitin sulfate, and the two in combination for painful knee osteoarthritis" 874:"Glucosamine, Chondroitin Sulfate, and the Two in Combination for Painful Knee Osteoarthritis" 3888: 3878: 3873: 3863: 2360: 959: 857: 828:
Surgeons evidence-based guideline on: treatment of osteoarthritis of the knee, 2nd edition".
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Most chondroitin appears to be made from extracts of cartilaginous cow and pig tissues (cow
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Chemical structure of one unit in a chondroitin sulfate chain. Chondroitin-4-sulfate: R
2841: 2260:, summary of information on the use of chondroitin sulfate from the publishers of the 1589: 1572: 1530: 1513: 190:, and the decrease in catabolic activity of chondrocytes, inhibiting the synthesis of 3945: 3805: 3655: 3218: 3193: 2876: 2704: 2438: 2233: 2198: 2167: 2155: 2106: 1993: 1958: 1940: 1891: 1830: 1795:
https://www.fda.gov/food/ingredientspackaginglabeling/labelingnutrition/ucm073400.htm
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Chondroitin and glucosamine are also used in veterinary medicine for osteoarthritis.
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risk in current chondroitin sulfate users in the high risk cardiovascular subgroups.
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13. Hathcock JN, Shao a. Risk assessment for glucosamine and chondroitin sulfate.
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Attachment of the GAG chain begins with four monosaccharides in a fixed pattern:
225: 204: 187: 169: 71: 3015: 3011: 3661: 3436: 3301: 3213: 3138: 3123: 3118: 3112: 3041: 2872: 2784: 2739: 2483: 2236:, News report of the analysis of commercial supplements by Adebowale et al. at 2194: 1989: 1808: 1638: 989: 873: 221: 209: 119: 99: 95: 1028: 3964: 3795: 3672: 3485: 3470: 3351: 3286: 2820: 2649: 2634: 2369: 2141: 1944: 1908: 1191: 253:(IdoA) at which point the resulting glycosaminoglycan is then referred to as 247: 1877: 1205: 1151: 3667: 3630: 3615: 3559: 3544: 3539: 3490: 3465: 3455: 3450: 3208: 3086: 3066: 3061: 3051: 3033: 2825: 2335: 2202: 2159: 2110: 1997: 1962: 1895: 1834: 1774: 1724: 1646: 1603: 1598: 1457: 1448: 1431: 1408: 1363: 1213: 1169: 1107: 1047: 951: 899: 849: 783: 635: 575: 552: 75: 1756: 1302: 1275: 1248: 997: 487:
companies produce their products in compliance with human food processing
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indicates initially developed first-in-class compound of specific group;
3800: 3780: 3749: 3734: 3625: 3590: 3579: 3389: 3311: 3239: 3228: 3178: 3173: 2911: 2744: 2724: 2719: 2679: 2249:"Testing Status of Glucosamine Hydrochloride + Chondroitin Sulfate 09029" 2077:"Glucosamine and chondroitin use in canines for osteoarthritis: A review" 1825: 1536: 890: 564:– a glycosaminoglycan of major pharmaceutical importance for many decades 131: 87: 2248: 1399: 1341: 1133: 796: 411:(FDA) identified "oversulfated chondroitin sulfate" as a contaminant in 3830: 3820: 3815: 3810: 3759: 3724: 3574: 3522: 3517: 3512: 3507: 3480: 3404: 3341: 3280: 3274: 3249: 3244: 3183: 3168: 3158: 3128: 3096: 3081: 3028: 2890: 2815: 2769: 2571: 2566: 2456: 2429: 2415: 2340: 2228:"Product Review: Joint Supplements (Glucosamine, Chondroitin, and MSM)" 2092: 292: 123: 2285: 1737: 3825: 3790: 3754: 3744: 3739: 3729: 3719: 3714: 3703: 3697: 3650: 3564: 3549: 3534: 3502: 3496: 3460: 3426: 3415: 3409: 3371: 3336: 3331: 3326: 3306: 3269: 3264: 3198: 3153: 3106: 3071: 3056: 2830: 2779: 2709: 2684: 2624: 2576: 2561: 2556: 2509: 2504: 2499: 2494: 2410: 2365: 2126:"Osteoarthritis in the cat: 2. how should it be managed and treated?" 826: 443: 277: 203:
osteoarthritis do not alter the kinetics of chondroitin sulfate. The
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A 2021 study showed a remarkable (about 40%) reduction of the acute
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Roland W.; Williams, H. James; Clegg, Daniel O. (4 June 2010).
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of variable length containing two alternating monosaccharides:
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failed to demonstrate any symptomatic benefit of chondroitin.
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Bennett, D; Zainal Ariffin, SM; Johnston, P (January 2012).
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Chondroitin sulfate chains are linked to hydroxyl groups on
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and some other countries. It is commonly sold together with
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Glucosamine/Chondroitin Arthritis Intervention Trial (GAIT)
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The Journal of the American Academy of Orthopaedic Surgeons
918:"Treatment of osteoarthritis of the knee (nonarthroplasty)" 2020:
National Center for Complementary and Integrative Medicine
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Chondroitin has shown to be promising in the treatment of
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carbon 2 of the glucuronic acid and 6 of the GalNAc sugar
74:). It is usually found attached to proteins as part of a 2075:
Bhathal, A; Spryszak, M; Louizos, C; Frankel, G (2017).
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Austen, KF; Woodcock, J; Sasisekharan, R (5 June 2008).
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General Glucosamine and Chondroitin Sulfate information
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W. Emford, Esq. William K. Hubbard. Oct. 7, 2004. <
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The Journal of Bone and Joint Surgery. American Volume
802:"Five Things Physicians and Patients Should Question" 578:
in a wide range of vertebrate & invertebrate life
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carbon 4 of the N-acetylgalactosamine (GalNAc) sugar
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National Institute of Environmental Health Sciences
2234:"Glucosamine/Chondroitin Products Not Measuring Up" 2048:Adebowale AO Cox DS, Liang Z, Eddington ND (2000). 1134:Jordan KM; Recommendations Arden NK. EULAR (2003). 391:Although the name "chondroitin sulfate" suggests a 284:, while the rest of the sugars are attached in the 257:, previously referred to as chondroitin sulfate B. 215: 706: 479:and pig ear and nose), but other sources such as 140:improve or maintain the health of affected joints 66:(GAG) composed of a chain of alternating sugars ( 3962: 1429: 1978:Journal of the American Pharmacists Association 1854: 1852: 1627:Journal of the American Pharmacists Association 711:, Burlington: Academic Press, pp. 487–99, 90:, chondroitin sulfate has become a widely used 2500:Ergocalciferol and Cholecalciferol (Vitamin D) 1432:"Biosynthesis of chondroitin/dermatan sulfate" 743: 741: 739: 737: 735: 429:Clinical trials on glucosamine and chondroitin 2992: 2857: 2301: 2180: 1800: 1570: 1085: 242:(GalNAc). Some of these GlcA residues may be 1849: 1423: 709:Comprehensive Biotechnology (Second Edition) 652:, Boston: Academic Press, pp. 195–213, 1620: 1618: 964:: CS1 maint: numeric names: authors list ( 862:: CS1 maint: numeric names: authors list ( 754:The Cochrane Database of Systematic Reviews 732: 650:Biology and Engineering of Stem Cell Niches 647: 378:"Chondroitin sulfate B" is an old name for 2999: 2985: 2864: 2850: 2308: 2294: 1127: 814:, American Academy of Orthopaedic Surgeons 220:Chondroitin sulfate chains are unbranched 168:Chondroitin sulfate is not metabolized by 2149: 2100: 1952: 1934: 1885: 1824: 1764: 1714: 1588: 1557:at the U.S. National Library of Medicine 1529: 1482:Natural and Synthetic Biomedical Polymers 1447: 1398: 1159: 1037: 1027: 941: 889: 773: 625: 82:, and provides much of its resistance to 16:Sulfated glycosaminoglycan (GAG) compound 1788: 1786: 1784: 1615: 798:American Academy of Orthopaedic Surgeons 18: 2315: 1659: 1573:"Chondroitin, a new mucopolysaccharide" 790: 180: 3963: 2130:Journal of Feline Medicine and Surgery 1122:Regulatory Toxicology and Pharmacology 1009: 465: 3008:Non-steroidal anti-inflammatory drugs 2980: 2845: 2289: 1806: 1781: 1512:P. A. Levene; F. B. La Forge (1913). 608:, Hyaluronan Signaling and Turnover, 3935: 1484:, Oxford: Elsevier, pp. 67–89, 598: 596: 519:scrutinized by the FDA, who stated: 198:Bioavailability and pharmacokinetics 3586:COX-inhibiting nitric oxide donator 2279:, Wednesday, February 22, 2006, at 1745:The New England Journal of Medicine 574:– a glycosaminoglycan component of 369:carbons 4 and 6 of the GalNAc sugar 13: 1490:10.1016/b978-0-12-396983-5.00004-1 717:10.1016/b978-0-08-088504-9.00320-2 658:10.1016/b978-0-12-802734-9.00013-5 618:10.1016/b978-0-12-800092-2.00001-0 423:Clinical trials for osteoarthritis 159: 14: 3987: 2212: 1669:U.S. Food and Drug Administration 593: 538: 489:Good Manufacturing Practice (GMP) 409:U.S. Food and Drug Administration 3944: 3934: 3925: 3924: 1866:Annals of the Rheumatic Diseases 1430:Silbert JE, Sugumaran G (2002). 1356:10.1016/j.biotechadv.2017.07.008 1194:Annals of the Rheumatic Diseases 934:10.5435/00124635-200909000-00006 842:10.2106/00004623-201310160-00010 750:"Chondroitin for osteoarthritis" 216:Physical and chemical properties 3836:Superoxide dismutase / orgotein 2174: 2117: 2068: 2041: 2032: 2004: 1969: 1902: 1807:Clegg, DO; et al. (2006). 1731: 1681: 1662:"FDA Media Briefing on Heparin" 1653: 1564: 1548: 1514:"On Chondroitin Sulphuric Acid" 1505: 1472: 1370: 1335: 1322: 1309: 1282: 1255: 1228: 1185: 1176: 1114: 1079: 878:New England Journal of Medicine 494: 175: 3148:Aspirin (acetylsalicylic acid) 2966:Polysulfated glycosaminoglycan 1054: 1003: 974: 766:10.1002/14651858.CD005614.pub2 700: 673: 641: 470: 291:Chondroitin sulfate is highly 126:for this disease (SYSADOA) in 105: 1: 2281:National Institutes of Health 1660:Zawisza, Julie (2008-03-19). 1590:10.1016/S0021-9258(18)71150-2 1571:Davidson EA, Meyer K (1954). 1531:10.1016/S0021-9258(18)88542-8 1391:10.1016/j.carbpol.2019.115450 1010:Qi, Shan; Shao, Meng (2021). 694:10.1016/j.polymer.2009.01.066 587: 39:= H. Chondroitin-6-sulfate: R 1936:10.1371/journal.pone.0253932 1330:Osteoarthritis and Cartilage 1100:10.1097/XCS.0000000000000896 501:Food and Drug Administration 343:carbon 6 of the GalNAc sugar 7: 3214:Salicylic acid (salicylate) 606:Advances in Cancer Research 546: 513:United States Pharmacopoeia 453: 10: 3992: 2620:β-hydroxy β-methylbutyrate 2510:Naphthoquinone (Vitamin K) 2263:Physicians' Desk Reference 2195:10.1016/j.tvjl.2004.07.008 1990:10.1331/154434506775268616 1639:10.1331/154434506775268616 990:10.1177/000331977302400503 426: 302: 3920: 3897: 3849: 3768: 3686: 3599: 3435: 3380: 3227: 3137: 3027: 2958: 2942: 2904: 2884:Unsulfated, extracellular 2883: 2793: 2605: 2495:Ascorbic acid (Vitamin C) 2394: 2323: 1029:10.3389/fendo.2021.759843 984:. 1973 May;24(5):269–87. 3884:Naproxen/diphenhydramine 2142:10.1177/1098612X11432829 1559:Medical Subject Headings 612:, Academic Press: 1–34, 372:chondroitin-4,6-sulfate 359:chondroitin-2,6-sulfate 3905:WHO-Essential Medicines 2943:Sulfated, intracellular 2905:Sulfated, extracellular 2331:Bodybuilding supplement 2081:Open Veterinary Journal 2060:: 37–44. Archived from 1878:10.1136/ard.2009.120469 1206:10.1136/ard.2006.068882 1152:10.1136/ard.2003.011742 809:: an initiative of the 151:coronary artery disease 110:Chondroitin is used in 3233:and related substances 2505:Tocopherol (Vitamin E) 1449:10.1080/15216540214923 1344:Biotechnology Advances 532: 346:chondroitin-6-sulfate 333:chondroitin-4-sulfate 56: 3889:Naproxen/esomeprazole 3879:Meloxicam/bupivacaine 3874:Ibuprofen/paracetamol 3864:Ibuprofen/hydrocodone 1757:10.1056/NEJMoa0803200 1379:Carbohydrate Polymers 1332:1998;6 Suppl A:14–21. 1317:Arzneimittelforschung 1291:Arzneimittelforschung 1264:Arzneimittelforschung 1062:"Chondroitin Sulfate" 582:Methylsulfonylmethane 521: 460:myocardial infarction 365:Chondroitin sulfate E 352:Chondroitin sulfate D 339:Chondroitin sulfate C 326:Chondroitin sulfate A 314:Letter identification 282:endoplasmic reticulum 68:N-acetylgalactosamine 22: 3859:Ibuprofen/famotidine 3317:Indometacin farnesil 3189:Magnesium salicylate 3010:(NSAIDs) (primarily 2705:Japanese honeysuckle 2223:Arthritis Foundation 1826:10.1056/nejmoa052771 1695:Nature Biotechnology 1555:Chondroitin+sulfates 891:10.1056/NEJMoa052771 181:Mechanisms of action 116:alternative medicine 3976:Dietary supplements 3869:Ibuprofen/oxycodone 3786:Chondroitin sulfate 3164:Carbasalate calcium 2917:Chondroitin sulfate 2630:Chondroitin sulfate 2448:Pantothenic acid (B 2411:Retinol (Vitamin A) 2381:Protein supplements 2317:Dietary supplements 2258:Chondroitin Sulfate 1927:2021PLoSO..1653932M 509:dietary supplements 466:Society and culture 192:proteolytic enzymes 112:dietary supplements 60:Chondroitin sulfate 3971:Glycosaminoglycans 3776:Aminopropionitrile 2896:Sodium hyaluronate 2877:glycosaminoglycans 2801:Codex Alimentarius 2690:Grape seed extract 2351:Herbal supplements 2183:Veterinary Journal 2093:10.4314/ovj.v7i1.6 1609:2008-09-22 at the 1542:2008-11-05 at the 1237:Drugs Exp Clin Res 1066:Stanford Chemicals 92:dietary supplement 57: 3958: 3957: 3806:Glycosaminoglycan 3656:Meclofenamic acid 3219:Sodium salicylate 3194:Methyl salicylate 2974: 2973: 2839: 2838: 2484:Cyanocobalamin (B 2401:chemical elements 2064:on April 7, 2006. 1124:, 2007; 47: 78–83 800:(February 2013), 415:originating from 376: 375: 317:Site of sulfation 250: 239: 228: 98:, although large 94:for treatment of 64:glycosaminoglycan 3983: 3948: 3938: 3937: 3928: 3927: 3688:COX-2 inhibitors 3603:-arylanthranilic 3570:Tiaprofenic acid 3001: 2994: 2987: 2978: 2977: 2922:Dermatan sulfate 2866: 2859: 2852: 2843: 2842: 2794:Related articles 2700:Iron supplements 2640:Copper gluconate 2310: 2303: 2296: 2287: 2286: 2207: 2206: 2178: 2172: 2171: 2153: 2121: 2115: 2114: 2104: 2072: 2066: 2065: 2045: 2039: 2036: 2030: 2029: 2028: 2027: 2008: 2002: 2001: 1973: 1967: 1966: 1956: 1938: 1906: 1900: 1899: 1889: 1856: 1847: 1846: 1828: 1804: 1798: 1790: 1779: 1778: 1768: 1735: 1729: 1728: 1718: 1685: 1679: 1678: 1676: 1675: 1666: 1657: 1651: 1650: 1622: 1613: 1602: 1592: 1568: 1562: 1552: 1546: 1535: 1533: 1509: 1503: 1502: 1476: 1470: 1469: 1451: 1427: 1421: 1420: 1402: 1374: 1368: 1367: 1339: 1333: 1326: 1320: 1313: 1307: 1306: 1286: 1280: 1279: 1259: 1253: 1252: 1232: 1226: 1225: 1189: 1183: 1180: 1174: 1173: 1163: 1131: 1125: 1118: 1112: 1111: 1083: 1077: 1076: 1074: 1072: 1058: 1052: 1051: 1041: 1031: 1016:Front Endocrinol 1007: 1001: 978: 972: 969: 963: 955: 945: 911: 893: 867: 861: 853: 822: 821: 819: 794: 788: 787: 777: 745: 730: 729: 704: 698: 697: 677: 671: 670: 645: 639: 638: 629: 600: 530: 507:regulations for 380:dermatan sulfate 320:Systematic name 311: 310: 255:dermatan sulfate 248: 237: 229:-glucuronic acid 226: 3991: 3990: 3986: 3985: 3984: 3982: 3981: 3980: 3961: 3960: 3959: 3954: 3916: 3909:withdrawn drugs 3893: 3851: 3845: 3764: 3690: 3682: 3678:Tolfenamic acid 3636:Flufenamic acid 3604: 3595: 3439: 3431: 3376: 3232: 3223: 3133: 3102:Oxyphenbutazone 3032: 3023: 3005: 2975: 2970: 2954: 2938: 2934:Keratan sulfate 2929:Heparan sulfate 2900: 2879: 2873:Polysaccharides 2870: 2840: 2835: 2789: 2607: 2601: 2487: 2478: 2469: 2460: 2451: 2442: 2433: 2424: 2402: 2399: 2390: 2375:Bifidobacterium 2319: 2314: 2215: 2210: 2179: 2175: 2122: 2118: 2073: 2069: 2054:J Am Nutr Assoc 2046: 2042: 2037: 2033: 2025: 2023: 2010: 2009: 2005: 1974: 1970: 1921:(7): e0253932. 1907: 1903: 1857: 1850: 1805: 1801: 1791: 1782: 1751:(23): 2457–67. 1736: 1732: 1707:10.1038/nbt1407 1686: 1682: 1673: 1671: 1664: 1658: 1654: 1623: 1616: 1611:Wayback Machine 1604:Free PDF online 1569: 1565: 1553: 1549: 1544:Wayback Machine 1537:Free PDF online 1510: 1506: 1500: 1477: 1473: 1428: 1424: 1375: 1371: 1340: 1336: 1327: 1323: 1319:1990;40:319–23. 1314: 1310: 1287: 1283: 1260: 1256: 1233: 1229: 1190: 1186: 1181: 1177: 1146:(12): 1145–55. 1132: 1128: 1119: 1115: 1084: 1080: 1070: 1068: 1060: 1059: 1055: 1008: 1004: 979: 975: 957: 956: 855: 854: 836:(20): 1885–86. 817: 815: 811:ABIM Foundation 807:Choosing Wisely 795: 791: 760:(4): CD005614. 746: 733: 727: 705: 701: 678: 674: 668: 646: 642: 601: 594: 590: 549: 541: 531: 527: 497: 485:food supplement 473: 468: 456: 431: 425: 395:with a sulfate 305: 286:Golgi apparatus 222:polysaccharides 218: 212:and cartilage. 205:bioavailability 200: 188:hyaluronic acid 183: 178: 170:cytochrome P450 162: 160:Adverse effects 108: 100:clinical trials 72:glucuronic acid 54: 50: 46: 42: 38: 34: 30: 26: 17: 12: 11: 5: 3989: 3979: 3978: 3973: 3956: 3955: 3953: 3952: 3942: 3932: 3921: 3918: 3917: 3913:veterinary use 3898: 3895: 3894: 3892: 3891: 3886: 3881: 3876: 3871: 3866: 3861: 3855: 3853: 3847: 3846: 3844: 3843: 3838: 3833: 3828: 3823: 3818: 3813: 3808: 3803: 3798: 3793: 3788: 3783: 3778: 3772: 3770: 3766: 3765: 3763: 3762: 3757: 3752: 3747: 3742: 3737: 3732: 3727: 3722: 3717: 3712: 3700: 3694: 3692: 3684: 3683: 3681: 3680: 3675: 3670: 3665: 3662:Mefenamic acid 3658: 3653: 3648: 3643: 3638: 3633: 3628: 3623: 3618: 3612: 3610: 3597: 3596: 3594: 3593: 3582: 3577: 3572: 3567: 3562: 3557: 3552: 3547: 3542: 3537: 3532: 3525: 3520: 3515: 3510: 3505: 3500: 3493: 3488: 3483: 3478: 3473: 3468: 3463: 3458: 3453: 3447: 3445: 3437:propionic acid 3433: 3432: 3430: 3429: 3424: 3419: 3412: 3407: 3402: 3397: 3392: 3386: 3384: 3378: 3377: 3375: 3374: 3369: 3364: 3359: 3354: 3349: 3344: 3339: 3334: 3329: 3324: 3319: 3314: 3309: 3304: 3302:Fenclozic acid 3299: 3294: 3289: 3284: 3277: 3272: 3267: 3262: 3257: 3252: 3247: 3242: 3236: 3234: 3225: 3224: 3222: 3221: 3216: 3211: 3206: 3201: 3196: 3191: 3186: 3181: 3176: 3171: 3166: 3161: 3156: 3151: 3143: 3141: 3135: 3134: 3132: 3131: 3126: 3124:Sulfinpyrazone 3121: 3119:Propyphenazone 3116: 3113:Phenylbutazone 3109: 3104: 3099: 3094: 3089: 3084: 3079: 3074: 3069: 3064: 3059: 3054: 3049: 3044: 3042:Aminophenazone 3038: 3036: 3025: 3024: 3004: 3003: 2996: 2989: 2981: 2972: 2971: 2969: 2968: 2962: 2960: 2956: 2955: 2953: 2952: 2946: 2944: 2940: 2939: 2937: 2936: 2931: 2926: 2925: 2924: 2919: 2908: 2906: 2902: 2901: 2899: 2898: 2893: 2887: 2885: 2881: 2880: 2869: 2868: 2861: 2854: 2846: 2837: 2836: 2834: 2833: 2828: 2823: 2818: 2813: 2808: 2803: 2797: 2795: 2791: 2790: 2788: 2787: 2785:Zinc gluconate 2782: 2777: 2772: 2767: 2762: 2760:St John's wort 2757: 2752: 2747: 2742: 2740:Red yeast rice 2737: 2732: 2727: 2722: 2717: 2712: 2707: 2702: 2697: 2692: 2687: 2682: 2677: 2672: 2667: 2662: 2657: 2652: 2647: 2642: 2637: 2632: 2627: 2622: 2617: 2611: 2609: 2603: 2602: 2600: 2599: 2594: 2589: 2584: 2579: 2574: 2569: 2564: 2559: 2554: 2549: 2544: 2539: 2534: 2529: 2524: 2519: 2513: 2512: 2507: 2502: 2497: 2492: 2491: 2490: 2485: 2481: 2476: 2472: 2467: 2463: 2458: 2454: 2449: 2445: 2440: 2436: 2431: 2427: 2422: 2413: 2407: 2405: 2392: 2391: 2389: 2388: 2383: 2378: 2372: 2363: 2358: 2353: 2348: 2343: 2338: 2333: 2327: 2325: 2321: 2320: 2313: 2312: 2305: 2298: 2290: 2284: 2283: 2274: 2267: 2255: 2246: 2240: 2231: 2225: 2214: 2213:External links 2211: 2209: 2208: 2173: 2116: 2067: 2040: 2031: 2003: 1968: 1901: 1872:(8): 1459–64. 1848: 1819:(8): 795–808. 1799: 1780: 1730: 1680: 1652: 1614: 1563: 1547: 1504: 1499:978-0123969835 1498: 1471: 1422: 1369: 1334: 1321: 1308: 1281: 1254: 1227: 1184: 1175: 1126: 1113: 1088:J Am Coll Surg 1078: 1053: 1002: 973: 971: 970: 928:(9): 591–600. 912: 884:(8): 795–808. 868: 823:, which cites 789: 731: 726:978-0080885049 725: 699: 688:(7): 1805–13. 672: 667:978-0128027349 666: 640: 591: 589: 586: 585: 584: 579: 565: 555: 548: 545: 540: 539:Veterinary use 537: 525: 496: 493: 472: 469: 467: 464: 455: 452: 427:Main article: 424: 421: 374: 373: 370: 367: 361: 360: 357: 354: 348: 347: 344: 341: 335: 334: 331: 328: 322: 321: 318: 315: 304: 301: 251:-iduronic acid 240:-galactosamine 217: 214: 210:synovial fluid 199: 196: 182: 179: 177: 174: 161: 158: 120:osteoarthritis 107: 104: 96:osteoarthritis 62:is a sulfated 52: 48: 44: 40: 36: 32: 28: 24: 15: 9: 6: 4: 3: 2: 3988: 3977: 3974: 3972: 3969: 3968: 3966: 3951: 3947: 3943: 3941: 3933: 3931: 3923: 3922: 3919: 3914: 3910: 3906: 3902: 3896: 3890: 3887: 3885: 3882: 3880: 3877: 3875: 3872: 3870: 3867: 3865: 3862: 3860: 3857: 3856: 3854: 3848: 3842: 3839: 3837: 3834: 3832: 3829: 3827: 3824: 3822: 3819: 3817: 3814: 3812: 3809: 3807: 3804: 3802: 3799: 3797: 3796:Fluproquazone 3794: 3792: 3789: 3787: 3784: 3782: 3779: 3777: 3774: 3773: 3771: 3767: 3761: 3758: 3756: 3753: 3751: 3748: 3746: 3743: 3741: 3738: 3736: 3733: 3731: 3728: 3726: 3723: 3721: 3718: 3716: 3713: 3710: 3706: 3705: 3701: 3699: 3696: 3695: 3693: 3689: 3685: 3679: 3676: 3674: 3673:Niflumic acid 3671: 3669: 3666: 3664: 3663: 3659: 3657: 3654: 3652: 3649: 3647: 3644: 3642: 3639: 3637: 3634: 3632: 3629: 3627: 3624: 3622: 3619: 3617: 3614: 3613: 3611: 3608: 3602: 3598: 3592: 3588: 3587: 3583: 3581: 3578: 3576: 3573: 3571: 3568: 3566: 3563: 3561: 3558: 3556: 3553: 3551: 3548: 3546: 3543: 3541: 3538: 3536: 3533: 3531: 3530: 3526: 3524: 3521: 3519: 3516: 3514: 3511: 3509: 3506: 3504: 3501: 3499: 3498: 3494: 3492: 3489: 3487: 3486:Flunoxaprofen 3484: 3482: 3479: 3477: 3474: 3472: 3471:Dexketoprofen 3469: 3467: 3464: 3462: 3459: 3457: 3454: 3452: 3449: 3448: 3446: 3443: 3440:derivatives ( 3438: 3434: 3428: 3425: 3423: 3420: 3418: 3417: 3413: 3411: 3408: 3406: 3403: 3401: 3398: 3396: 3393: 3391: 3388: 3387: 3385: 3383: 3379: 3373: 3370: 3368: 3365: 3363: 3360: 3358: 3355: 3353: 3352:Proglumetacin 3350: 3348: 3347:Prodolic acid 3345: 3343: 3340: 3338: 3335: 3333: 3330: 3328: 3325: 3323: 3320: 3318: 3315: 3313: 3310: 3308: 3305: 3303: 3300: 3298: 3295: 3293: 3290: 3288: 3287:Difenpiramide 3285: 3283: 3282: 3278: 3276: 3273: 3271: 3268: 3266: 3263: 3261: 3258: 3256: 3253: 3251: 3248: 3246: 3243: 3241: 3238: 3237: 3235: 3230: 3226: 3220: 3217: 3215: 3212: 3210: 3207: 3205: 3202: 3200: 3197: 3195: 3192: 3190: 3187: 3185: 3182: 3180: 3177: 3175: 3172: 3170: 3167: 3165: 3162: 3160: 3157: 3155: 3152: 3150: 3149: 3145: 3144: 3142: 3140: 3136: 3130: 3127: 3125: 3122: 3120: 3117: 3115: 3114: 3110: 3108: 3105: 3103: 3100: 3098: 3095: 3093: 3090: 3088: 3085: 3083: 3080: 3078: 3075: 3073: 3070: 3068: 3065: 3063: 3060: 3058: 3055: 3053: 3050: 3048: 3045: 3043: 3040: 3039: 3037: 3035: 3034:pyrazolidines 3030: 3026: 3021: 3017: 3013: 3009: 3002: 2997: 2995: 2990: 2988: 2983: 2982: 2979: 2967: 2964: 2963: 2961: 2957: 2951: 2948: 2947: 2945: 2941: 2935: 2932: 2930: 2927: 2923: 2920: 2918: 2915: 2914: 2913: 2910: 2909: 2907: 2903: 2897: 2894: 2892: 2889: 2888: 2886: 2882: 2878: 2874: 2867: 2862: 2860: 2855: 2853: 2848: 2847: 2844: 2832: 2829: 2827: 2824: 2822: 2821:Nutraceutical 2819: 2817: 2814: 2812: 2809: 2807: 2804: 2802: 2799: 2798: 2796: 2792: 2786: 2783: 2781: 2778: 2776: 2773: 2771: 2768: 2766: 2763: 2761: 2758: 2756: 2753: 2751: 2748: 2746: 2743: 2741: 2738: 2736: 2733: 2731: 2728: 2726: 2723: 2721: 2718: 2716: 2713: 2711: 2708: 2706: 2703: 2701: 2698: 2696: 2693: 2691: 2688: 2686: 2683: 2681: 2678: 2676: 2673: 2671: 2668: 2666: 2663: 2661: 2658: 2656: 2653: 2651: 2650:Dietary fiber 2648: 2646: 2643: 2641: 2638: 2636: 2635:Cod liver oil 2633: 2631: 2628: 2626: 2623: 2621: 2618: 2616: 2613: 2612: 2610: 2606:Other common 2604: 2598: 2595: 2593: 2590: 2588: 2585: 2583: 2580: 2578: 2575: 2573: 2570: 2568: 2565: 2563: 2560: 2558: 2555: 2553: 2550: 2548: 2545: 2543: 2540: 2538: 2535: 2533: 2530: 2528: 2525: 2523: 2520: 2518: 2515: 2514: 2511: 2508: 2506: 2503: 2501: 2498: 2496: 2493: 2489: 2482: 2480: 2475:Folic acid (B 2473: 2471: 2464: 2462: 2457:Pyridoxine (B 2455: 2453: 2446: 2444: 2437: 2435: 2430:Riboflavin (B 2428: 2426: 2419: 2418: 2417: 2414: 2412: 2409: 2408: 2406: 2404: 2397: 2393: 2387: 2384: 2382: 2379: 2376: 2373: 2371: 2370:Lactobacillus 2367: 2364: 2362: 2359: 2357: 2354: 2352: 2349: 2347: 2344: 2342: 2339: 2337: 2334: 2332: 2329: 2328: 2326: 2322: 2318: 2311: 2306: 2304: 2299: 2297: 2292: 2291: 2288: 2282: 2278: 2275: 2272: 2268: 2265: 2264: 2259: 2256: 2254: 2250: 2247: 2244: 2241: 2239: 2235: 2232: 2229: 2226: 2224: 2220: 2217: 2216: 2204: 2200: 2196: 2192: 2188: 2184: 2177: 2169: 2165: 2161: 2157: 2152: 2147: 2143: 2139: 2135: 2131: 2127: 2120: 2112: 2108: 2103: 2098: 2094: 2090: 2086: 2082: 2078: 2071: 2063: 2059: 2055: 2051: 2044: 2035: 2021: 2017: 2013: 2007: 1999: 1995: 1991: 1987: 1983: 1979: 1972: 1964: 1960: 1955: 1950: 1946: 1942: 1937: 1932: 1928: 1924: 1920: 1916: 1912: 1905: 1897: 1893: 1888: 1883: 1879: 1875: 1871: 1867: 1863: 1855: 1853: 1844: 1840: 1836: 1832: 1827: 1822: 1818: 1814: 1810: 1803: 1796: 1789: 1787: 1785: 1776: 1772: 1767: 1762: 1758: 1754: 1750: 1746: 1742: 1734: 1726: 1722: 1717: 1712: 1708: 1704: 1701:(6): 669–75. 1700: 1696: 1692: 1684: 1670: 1663: 1656: 1648: 1644: 1640: 1636: 1632: 1628: 1621: 1619: 1612: 1608: 1605: 1600: 1596: 1591: 1586: 1583:(2): 605–11. 1582: 1578: 1574: 1567: 1560: 1556: 1551: 1545: 1541: 1538: 1532: 1527: 1523: 1519: 1518:J. Biol. Chem 1515: 1508: 1501: 1495: 1491: 1487: 1483: 1475: 1467: 1463: 1459: 1455: 1450: 1445: 1442:(4): 177–86. 1441: 1437: 1433: 1426: 1418: 1414: 1410: 1406: 1401: 1396: 1392: 1388: 1384: 1380: 1373: 1365: 1361: 1357: 1353: 1350:(6): 711–25. 1349: 1345: 1338: 1331: 1325: 1318: 1312: 1304: 1300: 1297:(8): 918–25. 1296: 1292: 1285: 1277: 1273: 1270:(7): 768–72. 1269: 1265: 1258: 1250: 1246: 1242: 1238: 1231: 1223: 1219: 1215: 1211: 1207: 1203: 1200:(6): 735–40. 1199: 1195: 1188: 1179: 1171: 1167: 1162: 1157: 1153: 1149: 1145: 1141: 1140:Ann Rheum Dis 1137: 1130: 1123: 1117: 1109: 1105: 1101: 1097: 1093: 1089: 1082: 1067: 1063: 1057: 1049: 1045: 1040: 1035: 1030: 1025: 1021: 1017: 1013: 1006: 999: 995: 991: 987: 983: 977: 967: 961: 953: 949: 944: 939: 935: 931: 927: 923: 919: 913: 909: 905: 901: 897: 892: 887: 883: 879: 875: 869: 865: 859: 851: 847: 843: 839: 835: 831: 825: 824: 813: 812: 808: 803: 799: 793: 785: 781: 776: 771: 767: 763: 759: 755: 751: 744: 742: 740: 738: 736: 728: 722: 718: 714: 710: 703: 695: 691: 687: 683: 676: 669: 663: 659: 655: 651: 644: 637: 633: 628: 623: 619: 615: 611: 607: 599: 597: 592: 583: 580: 577: 576:proteoglycans 573: 571: 566: 563: 561: 556: 554: 551: 550: 544: 536: 529:Deterioration 524: 520: 516: 514: 510: 506: 502: 492: 490: 486: 482: 478: 463: 461: 451: 447: 445: 439: 435: 430: 420: 418: 414: 410: 405: 402: 398: 397:counter-anion 394: 389: 387: 383: 381: 371: 368: 366: 363: 362: 358: 355: 353: 350: 349: 345: 342: 340: 337: 336: 332: 329: 327: 324: 323: 319: 316: 313: 312: 309: 300: 298: 294: 289: 287: 283: 279: 275: 270: 267: 262: 258: 256: 252: 245: 241: 235: 230: 223: 213: 211: 206: 195: 193: 189: 173: 171: 166: 157: 154: 152: 147: 143: 141: 137: 133: 129: 125: 121: 117: 113: 103: 101: 97: 93: 89: 86:. Along with 85: 81: 77: 73: 69: 65: 61: 21: 3900: 3852:combinations 3785: 3702: 3668:Morniflumate 3660: 3631:Floctafenine 3616:Azapropazone 3600: 3584: 3560:Tarenflurbil 3545:Piketoprofen 3540:Pelubiprofen 3527: 3495: 3491:Flurbiprofen 3466:Dexibuprofen 3456:Benoxaprofen 3451:Alminoprofen 3414: 3279: 3209:Salicylamide 3146: 3111: 3087:Mofebutazone 3067:Famprofazone 3062:Difenamizole 3052:Azapropazone 2916: 2826:Multivitamin 2750:Saw palmetto 2730:Milk thistle 2629: 2403:("minerals") 2336:Energy drink 2261: 2189:(1): 51–69. 2186: 2182: 2176: 2136:(1): 76–84. 2133: 2129: 2119: 2087:(1): 36–49. 2084: 2080: 2070: 2062:the original 2057: 2053: 2043: 2034: 2024:, retrieved 2022:, 2006-01-02 2016:Backgrounder 2015: 2006: 1984:(1): 14–24. 1981: 1977: 1971: 1918: 1914: 1904: 1869: 1865: 1816: 1813:N Engl J Med 1812: 1802: 1748: 1744: 1733: 1698: 1694: 1683: 1672:. Retrieved 1655: 1633:(1): 14–24. 1630: 1626: 1580: 1576: 1566: 1550: 1521: 1517: 1507: 1481: 1474: 1439: 1435: 1425: 1400:10261/193588 1382: 1378: 1372: 1347: 1343: 1337: 1329: 1324: 1316: 1311: 1294: 1290: 1284: 1267: 1263: 1257: 1243:(1): 27–33. 1240: 1236: 1230: 1197: 1193: 1187: 1178: 1143: 1139: 1129: 1116: 1094:(1): 82–98. 1091: 1087: 1081: 1069:. Retrieved 1065: 1056: 1019: 1015: 1005: 981: 976: 960:cite journal 925: 921: 881: 877: 858:cite journal 833: 829: 816:, retrieved 805: 792: 757: 753: 708: 702: 685: 681: 675: 649: 643: 609: 605: 569: 559: 553:Proteoglycan 542: 533: 522: 517: 498: 495:Legal status 474: 457: 448: 440: 436: 432: 407:In 2008 the 406: 390: 385: 384: 377: 364: 351: 338: 325: 306: 290: 271: 263: 259: 233: 219: 201: 184: 176:Pharmacology 167: 163: 155: 148: 144: 109: 76:proteoglycan 59: 58: 3801:Glucosamine 3781:Benzydamine 3750:Robenacoxib 3735:Lumiracoxib 3626:Etofenamate 3591:Naproxcinod 3580:Zaltoprofen 3390:Ampiroxicam 3312:Indometacin 3240:Aceclofenac 3231:derivatives 3229:acetic acid 3179:Ethenzamide 3174:Dipyrocetyl 3139:salicylates 3029:pyrazolones 2912:Chondroitin 2745:Royal jelly 2725:Lipoic acid 2720:Linseed oil 2680:Glucosamine 2608:ingredients 2421:Thiamine (B 2346:Fatty acids 1577:J Biol Chem 471:Manufacture 386:Chondroitin 231:(GlcA) and 132:glucosamine 106:Medical use 88:glucosamine 84:compression 3965:Categories 3831:Proquazone 3821:Nimesulide 3816:Nabumetone 3811:Hyperforin 3760:Valdecoxib 3725:Etoricoxib 3575:Vedaprofen 3523:Miroprofen 3518:Loxoprofen 3513:Ketoprofen 3508:Indoprofen 3481:Fenoprofen 3405:Lornoxicam 3342:Oxametacin 3281:Diclofenac 3275:Bumadizone 3250:Alclofenac 3245:Acemetacin 3184:Guacetisal 3169:Diflunisal 3159:Benorylate 3129:Suxibuzone 3097:Nifenazone 3082:Metamizole 2891:Hyaluronan 2816:Herbal tea 2770:Wheatgrass 2670:Folic acid 2572:Phosphorus 2567:Molybdenum 2416:B vitamins 2366:Probiotics 2361:Prebiotics 2341:Energy bar 2026:2013-10-17 1674:2008-04-23 1436:IUBMB Life 1385:: 115450. 588:References 244:epimerized 3901:underline 3826:Oxaceprol 3791:Diacerein 3755:Rofecoxib 3745:Parecoxib 3740:Mavacoxib 3730:Firocoxib 3720:Deracoxib 3715:Cimicoxib 3709:+tramadol 3704:Celecoxib 3698:Apricoxib 3651:Glafenine 3646:Flutiazin 3607:fenamates 3565:Tepoxalin 3550:Pirprofen 3535:Oxaprozin 3503:Ibuproxam 3497:Ibuprofen 3461:Carprofen 3427:Tenoxicam 3422:Pivoxicam 3416:Piroxicam 3410:Meloxicam 3372:Zomepirac 3337:Mofezolac 3332:Lonazolac 3327:Ketorolac 3307:Fentiazac 3270:Bufexamac 3265:Bromfenac 3199:Salsalate 3154:Aloxiprin 3107:Phenazone 3072:Feprazone 3057:Clofezone 2959:Synthetic 2831:Nutrition 2780:Yohimbine 2775:Wolfberry 2755:Spirulina 2735:Melatonin 2710:Krill oil 2685:Glutamine 2655:Echinacea 2625:Carnitine 2577:Potassium 2562:Manganese 2557:Magnesium 2466:Biotin (B 2439:Niacin (B 2168:206691363 1945:1932-6203 1524:: 69–79. 1417:208599006 982:Angiology 444:celecoxib 134:. A 2015 118:to treat 80:cartilage 3930:category 3691:(coxibs) 3641:Flunixin 3621:Clonixin 3555:Suprofen 3529:Naproxen 3476:Fenbufen 3400:Isoxicam 3395:Droxicam 3367:Tolmetin 3362:Tiopinac 3357:Sulindac 3322:Isoxepac 3297:Felbinac 3292:Etodolac 3260:Bendazac 3092:Morazone 3077:Kebuzone 3047:Ampyrone 2665:Fish oil 2645:Creatine 2582:Selenium 2542:Fluorine 2527:Chromium 2396:Vitamins 2386:Vitamins 2356:Minerals 2203:16427582 2160:22247327 2151:11148914 2111:28331832 1998:16529337 1963:34252115 1915:PLOS ONE 1896:20525840 1835:16495392 1775:18434646 1725:18437154 1647:16529337 1607:Archived 1599:13221568 1540:Archived 1466:11564009 1458:12512856 1409:31826487 1364:28739506 1222:41984358 1214:17644553 1170:14644851 1108:37870229 1071:July 26, 1048:34777254 952:19726743 900:16495392 850:24288804 784:25629804 636:25081524 547:See also 526:—  454:Research 236:-acetyl- 136:Cochrane 3940:commons 3841:Tenidap 3605:acids ( 3442:profens 3382:oxicams 3255:Amfenac 3204:Salicin 3018:, also 2950:Heparin 2811:Hadacol 2765:Taurine 2715:Lingzhi 2695:Guarana 2675:Ginseng 2660:Ephedra 2522:Choline 2517:Calcium 2102:5356289 1954:8274913 1923:Bibcode 1887:3086604 1843:1609605 1766:3778681 1716:3491566 1303:7575762 1276:1772467 1249:1914833 1161:1754382 1039:8579055 998:4267673 943:3170838 908:1609605 775:4881293 682:Polymer 627:4445717 572:sulfate 562:sulfate 477:trachea 413:heparin 303:History 293:soluble 3950:portal 2806:Enzyte 2592:Sulfur 2587:Sodium 2547:Iodine 2537:Copper 2532:Cobalt 2201:  2166:  2158:  2148:  2109:  2099:  1996:  1961:  1951:  1943:  1894:  1884:  1841:  1833:  1773:  1763:  1723:  1713:  1645:  1597:  1561:(MeSH) 1496:  1464:  1456:  1415:  1407:  1362:  1301:  1274:  1247:  1220:  1212:  1168:  1158:  1106:  1046:  1036:  1022:: 16. 996:  950:  940:  906:  898:  848:  818:19 May 782:  772:  723:  664:  634:  624:  401:cation 266:serine 128:Europe 114:as an 27:= H; R 3899:Key: 3850:NSAID 3769:other 3020:N02BA 2324:Types 2238:WebMD 2164:S2CID 1839:S2CID 1665:(PDF) 1462:S2CID 1413:S2CID 1218:S2CID 904:S2CID 568:Hepar 558:Hepar 481:shark 417:China 297:water 246:into 3016:M02A 3014:and 3012:M01A 2615:AAKG 2597:Zinc 2552:Iron 2199:PMID 2156:PMID 2107:PMID 1994:PMID 1959:PMID 1941:ISSN 1892:PMID 1831:PMID 1797:> 1771:PMID 1721:PMID 1643:PMID 1595:PMID 1494:ISBN 1454:PMID 1405:PMID 1360:PMID 1299:PMID 1272:PMID 1245:PMID 1210:PMID 1166:PMID 1104:PMID 1073:2024 1044:PMID 994:PMID 966:link 948:PMID 896:PMID 864:link 846:PMID 820:2013 780:PMID 721:ISBN 662:ISBN 632:PMID 393:salt 124:drug 70:and 55:= H. 47:H; R 43:= SO 35:H; R 31:= SO 2398:and 2221:at 2191:doi 2187:171 2146:PMC 2138:doi 2097:PMC 2089:doi 1986:doi 1949:PMC 1931:doi 1882:PMC 1874:doi 1821:doi 1817:354 1761:PMC 1753:doi 1749:358 1711:PMC 1703:doi 1635:doi 1585:doi 1581:211 1526:doi 1486:doi 1444:doi 1395:hdl 1387:doi 1383:229 1352:doi 1202:doi 1156:PMC 1148:doi 1096:doi 1092:238 1034:PMC 1024:doi 986:doi 938:PMC 930:doi 886:doi 882:354 838:doi 770:PMC 762:doi 713:doi 690:doi 654:doi 622:PMC 614:doi 610:123 505:GMP 295:in 278:Gal 274:Xyl 51:, R 3967:: 3911:; 3907:; 3589:: 2875:: 2486:12 2197:. 2185:. 2162:. 2154:. 2144:. 2134:14 2132:. 2128:. 2105:. 2095:. 2083:. 2079:. 2056:. 2052:. 2018:, 2014:, 1992:. 1982:46 1980:. 1957:. 1947:. 1939:. 1929:. 1919:16 1917:. 1913:. 1890:. 1880:. 1870:69 1868:. 1864:. 1851:^ 1837:. 1829:. 1815:. 1811:. 1783:^ 1769:. 1759:. 1747:. 1743:. 1719:. 1709:. 1699:26 1697:. 1693:. 1667:. 1641:. 1631:46 1629:. 1617:^ 1593:. 1579:. 1575:. 1522:15 1520:. 1516:. 1492:, 1460:. 1452:. 1440:54 1438:. 1434:. 1411:. 1403:. 1393:. 1381:. 1358:. 1348:35 1346:. 1295:45 1293:. 1268:41 1266:. 1241:17 1239:. 1216:. 1208:. 1198:67 1196:. 1164:. 1154:. 1144:62 1142:. 1138:. 1102:. 1090:. 1064:. 1042:. 1032:. 1020:12 1018:. 1014:. 992:. 962:}} 958:{{ 946:. 936:. 926:17 924:. 920:. 902:. 894:. 880:. 876:. 860:}} 856:{{ 844:. 834:95 832:. 804:, 778:. 768:. 756:. 752:. 734:^ 719:, 686:50 684:. 660:, 630:, 620:, 595:^ 570:an 560:in 419:. 299:. 288:. 276:– 172:. 142:. 3915:. 3711:) 3707:( 3609:) 3601:n 3444:) 3031:/ 3022:) 3000:e 2993:t 2986:v 2865:e 2858:t 2851:v 2488:) 2479:) 2477:9 2470:) 2468:7 2461:) 2459:6 2452:) 2450:5 2443:) 2441:3 2434:) 2432:2 2425:) 2423:1 2377:) 2368:( 2309:e 2302:t 2295:v 2269:" 2266:. 2205:. 2193:: 2170:. 2140:: 2113:. 2091:: 2085:7 2058:3 2000:. 1988:: 1965:. 1933:: 1925:: 1898:. 1876:: 1845:. 1823:: 1777:. 1755:: 1727:. 1705:: 1677:. 1649:. 1637:: 1601:. 1587:: 1534:. 1528:: 1488:: 1468:. 1446:: 1419:. 1397:: 1389:: 1366:. 1354:: 1305:. 1278:. 1251:. 1224:. 1204:: 1172:. 1150:: 1110:. 1098:: 1075:. 1050:. 1026:: 1000:. 988:: 968:) 954:. 932:: 910:. 888:: 866:) 852:. 840:: 786:. 764:: 758:1 715:: 696:. 692:: 656:: 616:: 249:L 238:D 234:N 227:D 53:3 49:2 45:3 41:1 37:3 33:3 29:2 25:1

Index


glycosaminoglycan
N-acetylgalactosamine
glucuronic acid
proteoglycan
cartilage
compression
glucosamine
dietary supplement
osteoarthritis
clinical trials
dietary supplements
alternative medicine
osteoarthritis
drug
Europe
glucosamine
Cochrane
improve or maintain the health of affected joints
coronary artery disease
cytochrome P450
hyaluronic acid
proteolytic enzymes
bioavailability
synovial fluid
polysaccharides
D-glucuronic acid
N-acetyl-D-galactosamine
epimerized
L-iduronic acid

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