516:. It has been shown that tetracyclines are not only active against broad spectrum of bacteria, but also against viruses, protozoa that lack mitochondria and some noninfectious conditions. The binding of tetracyclines to cellular dsRNA (double stranded RNA) may be an explanation for their wide range of effect. It can also be attributed to the nature of ribosomal protein synthesis pathways among bacteria. Incyclinide was announced to be ineffective for rosacea in September 2007. Several trials have examined modified and unmodified tetracyclines for the treatment of human cancers; of those, very promising results were achieved with CMT-3 for patients with
38:
742:
tetracycline platform towards derivatives with increased potency as well as efficacy against tetracycline-resistant bacteria, with improved pharmacokinetic and chemical properties. Shortly after the introduction of tetracycline therapy, the first tetracycline-resistant bacterial pathogen was identified. Since then, tetracycline-resistant bacterial pathogens have continued to be identified, limiting tetracycline's effectiveness in treatment of bacterial disease.
703:
semisynthetic tetracyclines had entered the market, and now most antibiotic discoveries are of novel active derivatives of older compounds. Other tetracyclines were identified later, either as naturally occurring molecules, e.g., tetracycline from S. aureofaciens, S. rimosus, and S. viridofaciens and dimethyl-chlortetracycline from S. aureofaciens, or as products of semisynthetic approaches, e.g., methacycline, doxycycline, and minocycline.
1674:
3559:
1678:
390:. It increases the risk of sunburn under exposure to light from the sun or other sources. This may be of particular importance for those intending to take on vacations long-term doxycycline as a malaria prophylaxis. They may cause stomach or bowel upsets, and, on rare occasions, allergic reactions. Very rarely, severe headache and vision problems may be signs of dangerous
682:(terramycin) was isolated in 1949 by Alexander Finlay from a soil sample collected on the grounds of a factory in Terre Haute, Indiana. It came from a similar soil bacterium named Streptomyces rimosus. From the beginning, terramycin was a molecule enveloped in controversy. It was the subject of the first mass-marketing campaign by a modern pharmaceutical company.
560:, a class of antibiotic destructase, modifies the tetracycline antibiotic at their oxidative soft spot leading to an inactivation of the tetracycline antibiotic. For example, the oxireductase makes a modification on the C11a site of oxytetracycline. Both Mgchelation and ribosome binding are required for the
529:
group and a C1-C3 diketo substructure. Removal of the dimethylamine group at C4 reduces antibacterial activity. Replacement of the carboxylamine group at C2 results in reduced antibacterial activity but it is possible to add substituents to the amide nitrogen to get more soluble analogs like the prodrug
463:
Tetracycline use should be avoided in pregnant or lactating women, and in children with developing teeth because they may result in permanent staining (dark yellow-gray teeth with a darker horizontal band that goes across the top and bottom rows of teeth), and possibly affect the growth of teeth and
151:
but is still considered as the parent compound for nomenclature purposes. Tetracyclines are among the cheapest classes of antibiotics available and have been used extensively in prophylaxis and in treatment of human and animal infections, as well as at subtherapeutic levels in animal feed as growth
745:
Glycylcyclines and fluorocyclines are new classes of antibiotics derived from tetracycline. These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely resistance mediated by acquired efflux pumps and/or ribosomal protection. In 2005,
702:
itself as a synthetic product. In 1955, Conover discovered that hydrogenolysis of aureomycin gives a deschloro product that is just as active as the original product. This proved for the first time that chemically modified antibiotics could have biological activity. Within a few years, a number of
657:
The history of the tetracyclines involves the collective contributions of thousands of dedicated researchers, scientists, clinicians, and business executives. Tetracyclines were discovered in the 1940s, first reported in scientific literature in 1948, and exhibited activity against a wide range of
218:
can become resistant to tetracyclines, resulting in overgrowth of resistant organisms. The widespread use of tetracyclines is thought to have contributed to an increase in the number of tetracycline-resistant organisms, in turn rendering certain infections more resilient to treatment. Tetracycline
528:
Tetracyclines are composed of a rigid skeleton of 4 fused rings. The rings structure of tetracyclines is divided into an upper modifiable region and a lower non modifiable region. An active tetracycline requires a C10 phenol as well as a C11-C12 keto-enol substructure in conjugation with a 12a-OH
3072:
Solomkin J, Evans D, Slepavicius A, Lee P, Marsh A, Tsai L, et al. (March 2017). "Assessing the
Efficacy and Safety of Eravacycline vs Ertapenem in Complicated Intra-abdominal Infections in the Investigating Gram-Negative Infections Treated With Eravacycline (IGNITE 1) Trial: A Randomized
194:
Tetracyclines all have the same antibacterial spectrum, although there are differences in species' sensitivity to types of tetracyclines. Tetracyclines inhibit protein synthesis in both bacterial and human cells. Bacteria have a system that allows tetracyclines to be transported into the cell,
451:, a potentially fatal disease affecting proximal tubular function in the nephrons of the kidney. Prescriptions of these drugs should be discarded once expired because they can cause hepatotoxicity. It was once believed that tetracycline antibiotics impair the effectiveness of many types of
533:. The simplest tetracycline with measurable antibacterial activity is 6-deoxy-6-demethyltetracycline and its structure is often considered to be the minimum pharmacophore for the tetracycle class of antibiotics. C5-C9 can be modified to make derivatives with varying antibacterial activity.
741:
Tetracyclines were noted for their broad spectrum antibacterial activity and were commercialized with clinical success beginning in the late 1940s to the early 1950s. The second-generation semisynthetic analogs and more recent third-generation compounds show the continued evolution of the
762:
binds to the bacterial 30S ribosome, blocking the entry of transfer RNA. This ultimately prevents protein synthesis and thus inhibiting bacterial growth. However, the addition of an N,N,-dimethylglycylamido group at the 9 position of the minocycline molecule increases the affinity of
567:
In the most common mechanism of reaction, efflux, various resistance genes encode a membrane protein that actively pumps tetracycline out of the cell by exchanging a proton for a tetracycline cation complex. This exchange leads to a reduced cytoplasmic concentration of tetracycline.
455:. Recent research has shown no significant loss of effectiveness in oral contraceptives while using most tetracyclines. Despite these studies, many physicians still recommend the use of barrier contraception for people taking any tetracyclines to prevent unwanted pregnancy.
3417:
Zhu, Z., Zheng, T., Lee, C. G., Homer, R. J., & Elias, J. A. (2002). Tetracycline-controlled transcriptional regulation systems: advances and application in transgenic animal modeling. Seminars in Cell & Developmental
Biology, 13(2), 121β128.
410:
under 8 years of age. Some adults also experience teeth discoloration (mild grey hue) after use. They are, however, safe to use in the first 18 weeks of pregnancy. Some patients taking tetracyclines require medical supervision because they can cause
1034:. The mechanism of action for the antibacterial effect of tetracyclines relies on disrupting protein translation in bacteria, thereby damaging the ability of microbes to grow and repair; however protein translation is also disrupted in eukaryotic
468:, but the number of reports is too small to be sure if there actually is any risk. In tetracycline preparation, stability must be considered in order to avoid formation of toxic epi-anhydrotetracyclines.
754:, alterations to the molecule resulted in its expanded spectrum of activity and decreased susceptibility to the development of resistance when compared with other tetracycline antibiotics. Like
750:, the first member of a new subgroup of tetracyclines named glycylcyclines, was introduced to treat infections that are resistant to other antimicrobials. Although it is structurally related to
227:
of tetracyclines or for a protein that protects bacterial ribosomes from the action of tetracyclines. Furthermore, a limited number of bacteria acquire resistance to tetracyclines by mutations.
2070:
Ryan ME, Usman A, Ramamurthy NS, Golub LM, Greenwald RA (February 2001). "Excessive matrix metalloproteinase activity in diabetes: inhibition by tetracycline analogues with zinc reactivity".
464:
bones. Usage during the first 12 weeks of pregnancy does not appear to increase the risk of any major birth defects. There may be a small increased risk for minor birth defects such as an
68:
or produced semi-synthetically from those isolated compounds. Tetracycline molecules comprise a linear fused tetracyclic nucleus (rings designated A, B, C and D) to which a variety of
3591:
613:) be taken with a full glass of water, either two hours after eating or two hours before eating. This is partly because most tetracyclines bind with food and also easily with
2920:
3348:
1396:
Critically important antimicrobials for human medicine : ranking of antimicrobial agents for risk management of antimicrobial resistance due to non-human use
235:
Tetracyclines are generally used in the treatment of infections of the urinary tract, respiratory tract, and the intestines and are also used in the treatment of
3029:
Zhanel GG, Cheung D, Adam H, Zelenitsky S, Golden A, Schweizer F, et al. (April 2016). "Review of
Eravacycline, a Novel Fluorocycline Antibacterial Agent".
1713:
Deboyser D, Goethals F, Krack G, Roberfroid M (March 1989). "Investigation into the mechanism of tetracycline-induced steatosis: study in isolated hepatocytes".
686:
advertised the drug heavily in medical journals, eventually spending twice as much on marketing as it did to discover and develop terramycin. Still, it turned
3584:
1030:
biomedical research experiments involving bacteria as well in experiments in eukaryotic cells and organisms with inducible protein expression systems using
649:
can be taken with dairy products because it does not chelate calcium as readily, although dairy products do decrease absorption of minocycline slightly.
1089:
1031:
72:
are attached. Tetracyclines are named after their four ("tetra-") hydrocarbon rings ("-cycl-") derivation ("-ine"). They are defined as a subclass of
3577:
2175:"Tetracycline: Classification, Structure Activity Relationship and Mechanism of Action as a Theranostic Agent for Infectious Lesions-A Mini Review"
1783:
Ekwall B, Acosta D (1982). "In vitro comparative toxicity of selected drugs and chemicals in HeLa cells, Chang liver cells, and rat hepatocytes".
496:. This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs (like
443:. Antacids containing aluminium and calcium reduce the absorption of all tetracyclines, and dairy products reduce absorption greatly for all but
1853:
DrΓ©no B, Bettoli V, Ochsendorf F, Layton A, Mobacken H, Degreef H (2004). "European recommendations on the use of oral antibiotics for acne".
1519:
Taylor, MJ; Makunde, WH; McGarry, HF; Turner, JD; Mand, S; Hoerauf, A (June 2005). "Macrofilaricidal activity after doxycycline treatment of
3165:
1066:
in the USA. However, this is an invasive procedure for the animal and labour-intensive for the researcher. Therefore, other dyes such as
427:
Tetracyclines should be used with caution by those with liver impairment. Also, because the molecules are soluble in water it can worsen
206:. Tetracyclines remain the treatment of choice for some specific indications. Because not all of the tetracycline administered orally is
678:
was scouring the globe for new antibiotics. Soil samples were collected from jungles, deserts, mountaintops, and oceans. But ultimately
1699:
80:
of polycyclic naphthacene carboxamide. While all tetracyclines have a common structure, they differ from each other by the presence of
492:
complex. Some studies have shown that tetracyclines may bind to both 16S and 23S rRNAs. Tetracyclines also have been found to inhibit
3563:
779:
was the first tetracycline approved in over 20 years, other, newer versions of tetracyclines are currently in human clinical trials.
2131:
Richards C, Pantanowitz L, Dezube BJ (February 2011). "Antimicrobial and non-antimicrobial tetracyclines in human cancer trials".
30:
This article is about the group of antibiotics known as the tetracyclines. For the specific antibiotic called "tetracycline", see
3569:
1928:
1427:
Simonart T, Dramaix M, De
Maertelaer V (February 2008). "Efficacy of tetracyclines in the treatment of acne vulgaris: a review".
637:
and preparations containing iron should be avoided near the time of taking the drug. Partial exceptions to these rules occur for
17:
2959:
1351:
Sloan B, Scheinfeld N (September 2008). "The use and safety of doxycycline hyclate and other second-generation tetracyclines".
729:
light β the deposits are fluorescent, just as are modern ones. Armelagos suggested that this was due to ingestion of the local
961:(formerly known as TP-434) received FDA approval on August 27, 2018, for treatment of complicated intra-abdominal infections.
4387:
2661:
1242:
1058:, a UV lamp can be used to check if it is in a tooth pulled from an animal. For example, it was used to check uptake of oral
666:, a 73-year-old emeritus professor of botany employed by American Cyanamid β Lederle Laboratories, under the leadership of
395:
391:
2741:
2343:"Tetracycline resistance determinants: mechanisms of action, regulation of expression, genetic mobility, and distribution"
725:
period (around AD 350) had deposits of tetracycline in their bones, detectable through analyses of cross-sections through
564:
of oxytetracycline and the modification attenuate the binding, leading to inactivation of the oxytetracycline antibiotic.
1644:
2859:
775:. This allows for an expanded spectrum of activity and decreased susceptibility to the development of resistance. While
658:
microorganisms. The first members of the tetracycline group to be described were chlortetracycline and oxytetracycline.
3352:
694:
group, led by
Francis A. Hochstein, in loose collaboration with and Robert Burns Woodward, determined the structure of
670:. Duggar derived the substance from a Missouri soil sample, golden-colored, fungus-like, soil-dwelling bacterium named
4431:
1403:
1279:
1178:"Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance"
1094:
1004:
791:
4404:
3301:"Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris"
3430:"Tetracyclines Disturb Mitochondrial Function across Eukaryotic Models: A Call for Caution in Biomedical Research"
3527:
163:) and are only effective against multiplying microorganisms. They are short-acting and passively diffuse through
1952:
1748:
Amacher DE, Martin BA (December 1997). "Tetracycline-induced steatosis in primary canine hepatocyte cultures".
195:
whereas human cells do not. Human cells therefore are spared the effects of tetracycline on protein synthesis.
571:
In ribosomal protection, a resistance gene encodes a protein that can have several effects, depending on what
2105:
1818:
Archer JS, Archer DF (June 2002). "Oral contraceptive efficacy and antibiotic interaction: a myth debunked".
585:
binding to the ribosome and distorting the structure to still allow t-RNA binding while tetracycline is bound
247:; however, their use for these indications is less popular than it once was due to widespread development of
406:
in the fetus as they develop in infancy. For this same reason, tetracyclines are contraindicated for use in
1000:
440:
347:
974:(formerly known as WC 3035) received FDA approval on October 1, 2018, for treatment of moderate to severe
3604:
1393:
477:
4092:
3996:
3647:
2783:
979:
59:
compounds that have a common basic structure and are either isolated directly from several species of
4336:
671:
630:
493:
207:
3479:"Tetracycline antibiotics impair mitochondrial function and its experimental use confounds research"
1894:
542:
332:
220:
203:
3599:
4392:
1472:"Comparative susceptibility of anaerobic bacteria to minocycline, doxycycline, and tetracycline"
1258:
Blackwood RK, English AR (1970). "StructureβActivity
Relationships in the Tetracycline Series".
662:(Aureomycin) was first discovered as an ordinary item in 1945 and initially endorsed in 1948 by
251:
in the causative organisms. Tetracyclines are widely used in the treatment of moderately severe
3738:
1889:
452:
211:
124:
77:
2540:
DΓΆnhΓΆfer A, Franckenberg S, Wickles S, Berninghausen O, Beckmann R, Wilson DN (October 2012).
4436:
3396:
3374:
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3230:
730:
667:
663:
550:
481:
312:
248:
224:
180:
172:
93:
2650:
378:, although drug-resistance is mounting and their effect on overall mortality is questioned.
4045:
2935:
2825:
2695:
2553:
2496:
403:
184:
115:
Tetracyclines were discovered in the 1940s and exhibited activity against a wide range of
8:
3674:
3428:
Moullan N, Mouchiroud L, Wang X, Ryu D, Williams EG, Mottis A, et al. (March 2015).
3118:"Functional, biophysical, and structural bases for antibacterial activity of tigecycline"
710:
561:
371:
236:
2939:
2829:
2699:
2557:
2500:
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from binding to the A site of the ribosome. They also bind to some extent the bacterial
3503:
3478:
3454:
3429:
3325:
3300:
3142:
3117:
3098:
3054:
2719:
2576:
2541:
2517:
2484:
2483:
Li W, Atkinson GC, Thakor NS, Allas U, Lu CC, Chan KY, et al. (12 February 2013).
2457:
2432:
2408:
2383:
2359:
2342:
2318:
2293:
2244:
2217:
2005:
1980:
1591:
1548:
1452:
1376:
1328:
1301:
575:
is transferred. Twelve classes of ribosomal protection genes/proteins have been found.
285:
275:). Anaerobic bacteria are not as susceptible to tetracyclines as are aerobic bacteria.
2625:
2600:
1935:
1903:
1622:
1536:
1496:
1471:
1271:
4316:
4312:
3881:
3508:
3459:
3330:
3274:
3212:
3191:"Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines"
3147:
3090:
3046:
3011:
2951:
2841:
2711:
2707:
2657:
2630:
2616:
2581:
2522:
2462:
2413:
2364:
2323:
2249:
2218:"Classification Framework and Chemical Biology of Tetracycline-Structure-Based Drugs"
2148:
2087:
2010:
1907:
1862:
1835:
1800:
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1730:
1726:
1693:
1626:
1583:
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1501:
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1440:
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1207:
1202:
1177:
823:
659:
436:
168:
144:
69:
3102:
3058:
2723:
2683:
2294:"The Tetracycline Destructases: A Novel Family of Tetracycline-Inactivating Enzymes"
2056:
1652:
1595:
1552:
1380:
645:, which may be taken with food (though not iron, antacids, or calcium supplements).
4364:
4308:
3936:
3498:
3490:
3449:
3441:
3320:
3312:
3202:
3137:
3129:
3082:
3038:
3001:
2943:
2901:
2833:
2703:
2620:
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2512:
2504:
2452:
2444:
2403:
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2354:
2313:
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2189:
2174:
2140:
2079:
2052:
2000:
1992:
1899:
1827:
1792:
1757:
1722:
1618:
1575:
1532:
1491:
1483:
1456:
1436:
1360:
1323:
1313:
1267:
1230:
1197:
1193:
1189:
911:
714:
489:
448:
3624:
3494:
2886:
2763:
2194:
1394:
WHO Advisory Group on
Integrated Surveillance of Antimicrobial Resistance (2017).
1122:
480:. They inhibit the initiation of translation in variety of ways by binding to the
4355:
4350:
4062:
3931:
3926:
3477:
Chatzispyrou IA, Held NM, Mouchiroud L, Auwerx J, Houtkooper RH (November 2015).
3445:
835:
695:
679:
602:
465:
295:
264:
164:
148:
97:
3620:
3616:
3612:
3608:
2837:
2399:
4398:
4215:
4145:
4130:
3891:
3776:
3764:
3642:
3086:
2919:
Bassett EJ, Keith MS, Armelagos GJ, Martin DL, Villanueva AR (September 1980).
2546:
Proceedings of the
National Academy of Sciences of the United States of America
2234:
2144:
1981:"rRNA Binding Sites and the Molecular Mechanism of Action of the Tetracyclines"
1934:. Organization of Teratology Information Specialists. July 2010. Archived from
1566:
Bhattacharya SK (February 2003). "An evaluation of current cholera treatment".
1059:
847:
606:
557:
517:
485:
428:
416:
300:
176:
156:
132:
116:
53:
3042:
2601:"Ribosomal protection proteins and their mechanism of tetracycline resistance"
1796:
4425:
4360:
4304:
4296:
4258:
4248:
4220:
4200:
4190:
4185:
4150:
4135:
4072:
4067:
3991:
3956:
3744:
3116:
Olson MW, Ruzin A, Feyfant E, Rush TS, O'Connell J, Bradford PA (June 2006).
2863:
2485:"Mechanism of tetracycline resistance by ribosomal protection protein Tet(O)"
2433:"Mosaic tetracycline resistance genes encoding ribosomal protection proteins"
2083:
1579:
1413:
1364:
1318:
1079:
975:
598:
399:
387:
252:
188:
160:
120:
109:
2947:
2566:
1880:
DeRossi SS, Hersh EV (October 2002). "Antibiotics and oral contraceptives".
1831:
1234:
1018:
Members of the tetracycline class of antibiotics are often used as research
484:, which is made up of 16S rRNA and 21 proteins. They inhibit the binding of
4344:
4340:
4268:
4205:
4175:
4140:
4110:
3946:
3921:
3906:
3896:
3886:
3860:
3801:
3749:
3696:
3669:
3659:
3512:
3463:
3334:
3216:
3151:
3094:
3050:
3015:
2845:
2813:
2715:
2634:
2585:
2526:
2466:
2417:
2327:
2253:
2152:
2091:
2014:
1911:
1866:
1839:
1761:
1630:
1587:
1544:
1448:
1372:
1337:
1295:
1293:
1291:
1211:
1084:
1035:
987:
950:
887:
874:
808:
772:
707:
699:
610:
359:
280:
260:
61:
42:
31:
2955:
2905:
2368:
1804:
1769:
1734:
1505:
1046:
in wildlife to check if wild animals are consuming a bait that contains a
733:(very much like the Egyptian beer), made from contaminated stored grains.
386:
Side-effects from tetracyclines are not common, but of particular note is
4330:
4276:
4253:
4180:
4165:
4160:
4077:
3964:
3941:
3916:
3911:
3901:
3876:
3720:
3691:
3316:
3207:
3190:
3133:
2448:
1996:
1067:
1051:
966:
935:
923:
899:
859:
776:
768:
764:
759:
755:
751:
747:
726:
646:
642:
638:
530:
497:
444:
432:
363:
351:
324:
320:
276:
272:
268:
240:
136:
128:
37:
3528:"A Review of Biomarkers Used For Wildlife Damage and Disease Management"
2921:"Tetracycline-labeled human bone from ancient Sudanese Nubia (A.D. 350)"
2539:
1953:"Mechanism of Action of Tetracyclines - Animations - PharmaXChange.info"
1288:
311:. Tetracyclines remain the treatment of choice for infections caused by
4326:
4286:
4281:
4230:
4210:
4195:
4170:
4125:
4120:
4054:
4025:
4005:
3825:
3820:
3811:
3806:
3791:
3786:
3734:
3686:
3600:
3166:"How Paratek hopes to succeed in antibiotics despite Tetraphase's fail"
2508:
1559:
1487:
355:
339:
328:
308:
76:, having an octahydrotetracene-2-carboxamide skeleton and are known as
73:
56:
4155:
4115:
4102:
4035:
4030:
4020:
4015:
4010:
3841:
3796:
3759:
3754:
3725:
3715:
3705:
1043:
618:
614:
601:, short-acting tetracyclines (plain tetracycline, chlortetracycline,
578:
Possible mechanisms of action of these protective proteins include:
556:
Inactivation is the rarest type of resistance, where NADPH-dependent
412:
244:
215:
101:
553:, ribosomal protection, reduced permeability and ribosome mutation.
4240:
3710:
3681:
3006:
2989:
1229:. International Union of Pure and Applied Chemistry (IUPAC). 2009.
1039:
634:
513:
509:
407:
367:
316:
199:
140:
89:
65:
722:
447:. The breakdown products of tetracyclines are toxic and can cause
4225:
1063:
1055:
1047:
1019:
626:
501:
375:
304:
290:
256:
105:
3476:
374:. They may have a role in reducing the duration and severity of
96:
do not change their broad antibacterial activity, but do affect
4322:
3558:
1712:
691:
687:
683:
675:
546:
343:
202:, although their usefulness has been reduced with the onset of
85:
81:
2599:
Connell SR, Tracz DM, Nierhaus KH, Taylor DE (December 2003).
1602:
431:(this is not true of the lipid-soluble agents doxycycline and
3535:
Proceedings of the 12th
Wildlife Damage Management Conference
718:
2542:"Structural basis for TetM-mediated tetracycline resistance"
2291:
2028:
Spreitzer H (July 2, 2007). "Neue
Wirkstoffe β Incyclinid".
1852:
1741:
1426:
307:
treatment and prophylaxis, as well as treating elephantitis
3349:"Antibiotic Firm Paratek Joins IPO Queue; Aiming for $ 92M"
3071:
2918:
1645:"Drugs and their categories in pregnancy and breastfeeding"
1398:(5th revision 2016 ed.). : World Health Organization.
622:
572:
505:
3028:
2598:
2292:
Forsberg KJ, Patel S, Wencewicz TA, Dantas G (July 2015).
1518:
767:
for the ribosomal target up to 5 times when compared with
3982:
3633:
3299:
Zhanel G, Critchley I, Lin LY, Alvandi N (January 2019).
3298:
2182:
Biomedical Journal of Scientific & Technical Research
2130:
1070:
that can be detected in hair and whiskers are preferred.
996:
690:, then a small company, into a pharmaceutical giant. The
3427:
2069:
1523:: a double-blind, randomised placebo-controlled trial".
674:. About the same time as Lederle discovered aureomycin,
597:
When ingested, it is usually recommended that the more
2430:
1706:
1042:
experimental results. It can be used as an artificial
3115:
2482:
2106:"CollaGenex says incyclinide ineffective for rosacea"
1776:
2431:
Warburton PJ, Amodeo N, Roberts AP (December 2016).
2043:
Viera MH, Perez OA, Berman B (2007). "Incyclinide".
698:, enabling Lloyd H. Conover to successfully produce
2894:
Journal of the American Society of Brewing Chemists
782:
588:
binding to the ribosome and dislodging tetracycline
582:
blocking tetracyclines from binding to the ribosome
2649:
1090:Tetracycline controlled transcriptional activation
1032:tetracycline-controlled transcriptional activation
523:
2647:
2268:"Tetracycline β Structure-activity relationships"
4423:
2816:(January 1950). "Terramycin, a new antibiotic".
2042:
1299:
1257:
143:. Tetracycline itself was discovered later than
2334:
2172:
1350:
629:, which reduces their ability to be completely
159:) rather than killers of the infectious agent (
45:with atoms and four rings numbered and labeled.
3519:
1820:Journal of the American Academy of Dermatology
1469:
999:approval on October 2, 2018, for treatment of
3585:
3188:
2983:
2981:
2979:
2124:
1747:
1188:(2): 232β60, second page, table of contents.
1175:
3470:
3421:
3292:
3109:
2742:"Tetracycline: History, Properties and Uses"
1879:
1873:
1846:
1817:
1811:
1782:
1565:
1117:
1115:
1113:
1111:
1109:
2811:
2388:Cold Spring Harbor Perspectives in Medicine
2173:Tariq S, Rizvi SF, Anwar U (25 July 2018).
1974:
1972:
1970:
1470:Chow AW, Patten V, Guze LB (January 1975).
1013:
4053:
3592:
3578:
2976:
2688:Annals of the New York Academy of Sciences
2681:
1182:Microbiology and Molecular Biology Reviews
536:
198:Tetracyclines retain an important role in
3525:
3502:
3453:
3324:
3206:
3195:The Journal of Antimicrobial Chemotherapy
3141:
3005:
2735:
2733:
2677:
2675:
2673:
2624:
2575:
2565:
2516:
2456:
2437:The Journal of Antimicrobial Chemotherapy
2424:
2407:
2384:"Tetracycline Antibiotics and Resistance"
2358:
2317:
2243:
2233:
2193:
2168:
2166:
2164:
2162:
2063:
2027:
2004:
1893:
1495:
1327:
1317:
1201:
1171:
1169:
1167:
1165:
1163:
1106:
191:components to leak from bacterial cells.
2652:Drug Interactions in Infectious Diseases
2533:
2381:
2375:
2285:
2211:
2209:
2207:
2205:
1978:
1967:
1300:Markley JL, Wencewicz TA (30 May 2018).
1227:IUPAC Compendium of Chemical Terminology
1161:
1159:
1157:
1155:
1153:
1151:
1149:
1147:
1145:
1143:
435:). They may increase muscle weakness in
167:in the bacterial membrane. They inhibit
36:
2987:
2592:
2340:
2260:
1923:
1921:
1420:
171:by binding reversibly to the bacterial
14:
4424:
3022:
2884:
2777:
2775:
2773:
2739:
2730:
2670:
2159:
1698:: CS1 maint: archived copy as title (
995:(formerly known as PTK-0796) received
471:
3573:
3305:Antimicrobial Agents and Chemotherapy
3122:Antimicrobial Agents and Chemotherapy
2605:Antimicrobial Agents and Chemotherapy
2478:
2476:
2215:
2202:
1985:Antimicrobial Agents and Chemotherapy
1608:
1476:Antimicrobial Agents and Chemotherapy
1140:
239:, especially in patients allergic to
155:Tetracyclines are growth inhibitors (
3189:Agwuh KN, MacGowan A (August 2006).
3065:
2682:Nelson ML, Levy SB (December 2011).
1918:
1218:
458:
396:idiopathic intracranial hypertension
3281:. U.S. National Library of Medicine
2887:"Archaeology of ancient Egypt beer"
2770:
1715:Toxicology and Applied Pharmacology
1302:"Tetracycline-Inactivating Enzymes"
392:secondary intracranial hypertension
24:
2684:"The history of the tetracyclines"
2473:
2360:10.1111/j.1574-6976.1996.tb00251.x
1750:Fundamental and Applied Toxicology
1429:The British Journal of Dermatology
1251:
1005:skin and skin structure infections
214:, the bacterial population of the
25:
4448:
3551:
3418:doi:10.1016/s1084-9521(02)00018-6
2648:Piscitelli SC, Rodvold K (2005).
1568:Expert Opinion on Pharmacotherapy
1176:Chopra I, Roberts M (June 2001).
1095:Animal Drug Availability Act 1996
592:
402:due to the likelihood of causing
27:Type of broad-spectrum antibiotic
3557:
2708:10.1111/j.1749-6632.2011.06354.x
2617:10.1128/AAC.47.12.3675-3681.2003
2030:Γsterreichische Apothekerzeitung
1609:Parsi VK (May 2001). "Cholera".
1441:10.1111/j.1365-2133.2007.08286.x
1260:Advances in Applied Microbiology
783:List of tetracycline antibiotics
3411:
3389:
3367:
3341:
3267:
3245:
3223:
3182:
3158:
2912:
2878:
2852:
2805:
2781:
2756:
2641:
2098:
2057:10.1358/dof.2007.032.03.1083308
2036:
2021:
1945:
1882:Dental Clinics of North America
1855:European Journal of Dermatology
1667:
1637:
1611:Primary Care Update for Ob/Gyns
1512:
524:Structure-activity relationship
381:
230:
219:resistance is often due to the
4093:transpeptidation/translocation
3253:"Drug Trial Snapshot: Seysara"
2990:"Tetracycline therapy: update"
2744:. Nottingham, UK: UKEssays.com
2310:10.1016/j.chembiol.2015.05.017
1463:
1387:
1344:
1194:10.1128/MMBR.65.2.232-260.2001
736:
549:inactivation of tetracycline,
13:
1:
3495:10.1158/0008-5472.CAN-15-1626
3397:"Drug Trial Snapshot: Nuzyra"
3375:"Drug Trial Snapshot: Nuzyra"
3231:"Drug Trial Snapshot: Xerava"
2195:10.26717/BJSTR.2018.07.001475
1904:10.1016/S0011-8532(02)00017-4
1623:10.1016/S1068-607X(00)00086-X
1537:10.1016/S0140-6736(05)66591-9
1353:Expert Opinion on Drug Safety
1272:10.1016/S0065-2164(08)70405-2
1100:
633:by the body. Dairy products,
476:Tetracycline antibiotics are
223:of new genes, which code for
3446:10.1016/j.celrep.2015.02.034
2994:Clinical Infectious Diseases
2988:Roberts MC (February 2003).
2764:"The Pharmaceutical Century"
2740:Essays, UK (November 2013).
1929:"Tetracycline and Pregnancy"
1785:Drug and Chemical Toxicology
1727:10.1016/0041-008X(89)90252-4
1038:leading to effects that may
1001:community-acquired pneumonia
478:protein synthesis inhibitors
441:systemic lupus erythematosus
348:Rocky Mountain spotted fever
7:
2838:10.1126/science.111.2874.85
2400:10.1101/cshperspect.a025387
2341:Roberts MC (October 1996).
2072:Current Medicinal Chemistry
2032:(in German) (14/2007): 655.
1979:Chukwudi CU (August 2016).
1073:
1050:or medication. Since it is
422:
293:) and is effective against
283:treatment for infection by
10:
4453:
3526:Fry TL, Dunbar MR (2007).
3087:10.1001/jamasurg.2016.4237
2382:Grossman TH (April 2016).
2235:10.3390/antibiotics1010001
2145:10.1016/j.phrs.2010.10.008
652:
299:, the infectious agent of
29:
4382:
4337:Quinupristin/dalfopristin
4295:
4267:
4239:
4101:
4090:
4044:
3990:
3981:
3955:
3869:
3854:
3834:
3773:
3656:
3641:
3632:
3605:inhibit protein synthesis
3043:10.1007/s40265-016-0545-8
2347:FEMS Microbiology Reviews
1797:10.3109/01480548209041054
1306:Frontiers in Microbiology
954:
863:
812:
672:Streptomyces aureofaciens
494:matrix metalloproteinases
370:). They are also used in
4432:Tetracycline antibiotics
3856:Tetracycline antibiotics
3564:Tetracycline antibiotics
2133:Pharmacological Research
2084:10.2174/0929867013373598
1580:10.1517/14656566.4.2.141
1365:10.1517/14740338.7.5.571
1319:10.3389/fmicb.2018.01058
1014:Use as research reagents
2948:10.1126/science.7001623
2567:10.1073/pnas.1208037109
2298:Chemistry & Biology
1832:10.1067/mjd.2002.120448
1235:10.1351/goldbook.T06287
1127:Encyclopedia Britannica
892:12 hours (intermediate)
852:12 hours (intermediate)
537:Mechanism of resistance
500:) for the treatment of
225:energy-dependent efflux
18:Tetracycline antibiotic
2860:"Lemelson-MIT Program"
1762:10.1006/faat.1997.2389
706:Research conducted by
453:hormonal contraception
356:spirochetal infections
303:. It is also used for
212:gastrointestinal tract
125:gram-negative bacteria
46:
2906:10.1094/ASBCJ-54-0003
2489:Nature Communications
2272:University of Bristol
2216:Fuoco D (June 2012).
882:(no longer marketed)
668:Yellapragada Subbarow
664:Benjamin Minge Duggar
512:and various types of
482:30S ribosomal subunit
204:antibiotic resistance
181:50S ribosomal subunit
173:30S ribosomal subunit
40:
4046:Peptidyl transferase
3566:at Wikimedia Commons
3317:10.1128/AAC.01297-18
3134:10.1128/AAC.01499-05
2784:"The teteracyclines"
1997:10.1128/AAC.00594-16
1655:on 14 September 2009
1521:Wuchereria bancrofti
978:. Sarecycline is a
717:showed that ancient
404:teeth discolouration
398:. Tetracyclines are
185:cytoplasmic membrane
41:Skeletal formula of
3675:Dihydrostreptomycin
2940:1980Sci...209.1532B
2830:1950Sci...111...85F
2700:2011NYASA1241...17N
2558:2012PNAS..10916900D
2501:2013NatCo...4.1477L
2112:. 26 September 2016
2045:Drugs of the Future
813:Naturally occurring
711:George J. Armelagos
562:biological activity
545:to tetracycline by
472:Mechanism of action
372:veterinary medicine
175:and preventing the
100:properties such as
4409:Never to phase III
3355:on 18 October 2017
3208:10.1093/jac/dkl224
2509:10.1038/ncomms2470
2449:10.1093/jac/dkw304
1488:10.1128/aac.7.1.46
286:Bacillus anthracis
279:is also used as a
183:and may alter the
47:
4419:
4418:
4378:
4377:
4374:
4373:
4086:
4085:
3977:
3976:
3973:
3972:
3882:Chlortetracycline
3850:
3849:
3562:Media related to
3440:(10): 1681β1691.
3073:Clinical Trial".
2885:Samuel D (1996).
2663:978-1-58829-455-5
2443:(12): 3333β3339.
1531:(9477): 2116β21.
1244:978-0-9678550-9-7
1225:"Tetracyclines".
1011:
1010:
916:6β8 hours (short)
879:6β8 hours (short)
867:6β8 hours (short)
840:6β8 hours (short)
828:6β8 hours (short)
824:Chlortetracycline
816:6β8 hours (short)
660:Chlortetracycline
541:Cells can become
459:Contraindications
437:myasthenia gravis
169:protein synthesis
145:chlortetracycline
70:functional groups
16:(Redirected from
4444:
4099:
4098:
4051:
4050:
3988:
3987:
3937:Rolitetracycline
3867:
3866:
3654:
3653:
3639:
3638:
3594:
3587:
3580:
3571:
3570:
3561:
3546:
3545:
3543:
3542:
3532:
3523:
3517:
3516:
3506:
3474:
3468:
3467:
3457:
3425:
3419:
3415:
3409:
3408:
3406:
3404:
3393:
3387:
3386:
3384:
3382:
3371:
3365:
3364:
3362:
3360:
3351:. Archived from
3345:
3339:
3338:
3328:
3296:
3290:
3289:
3287:
3286:
3271:
3265:
3264:
3262:
3260:
3249:
3243:
3242:
3240:
3238:
3227:
3221:
3220:
3210:
3186:
3180:
3179:
3177:
3176:
3162:
3156:
3155:
3145:
3113:
3107:
3106:
3069:
3063:
3062:
3026:
3020:
3019:
3009:
2985:
2974:
2973:
2971:
2970:
2964:
2958:. Archived from
2934:(4464): 1532β4.
2925:
2916:
2910:
2909:
2891:
2882:
2876:
2875:
2873:
2871:
2866:on 18 March 2003
2862:. Archived from
2856:
2850:
2849:
2809:
2803:
2802:
2800:
2798:
2788:
2779:
2768:
2767:
2760:
2754:
2753:
2751:
2749:
2737:
2728:
2727:
2679:
2668:
2667:
2656:. Humana Press.
2655:
2645:
2639:
2638:
2628:
2596:
2590:
2589:
2579:
2569:
2537:
2531:
2530:
2520:
2480:
2471:
2470:
2460:
2428:
2422:
2421:
2411:
2379:
2373:
2372:
2362:
2338:
2332:
2331:
2321:
2289:
2283:
2282:
2280:
2278:
2264:
2258:
2257:
2247:
2237:
2213:
2200:
2199:
2197:
2179:
2170:
2157:
2156:
2128:
2122:
2121:
2119:
2117:
2102:
2096:
2095:
2067:
2061:
2060:
2040:
2034:
2033:
2025:
2019:
2018:
2008:
1976:
1965:
1964:
1962:
1960:
1949:
1943:
1942:
1940:
1933:
1925:
1916:
1915:
1897:
1877:
1871:
1870:
1850:
1844:
1843:
1815:
1809:
1808:
1780:
1774:
1773:
1745:
1739:
1738:
1710:
1704:
1703:
1697:
1689:
1687:
1686:
1677:. Archived from
1671:
1665:
1664:
1662:
1660:
1651:. Archived from
1641:
1635:
1634:
1606:
1600:
1599:
1563:
1557:
1556:
1516:
1510:
1509:
1499:
1467:
1461:
1460:
1424:
1418:
1417:
1391:
1385:
1384:
1348:
1342:
1341:
1331:
1321:
1297:
1286:
1285:
1255:
1249:
1248:
1222:
1216:
1215:
1205:
1173:
1138:
1137:
1135:
1133:
1119:
992:16+ hours (long)
971:16+ hours (long)
958:16+ hours (long)
943:16+ hours (long)
928:16+ hours (long)
912:Rolitetracycline
904:16+ hours (long)
787:
786:
715:Emory University
713:and his team at
490:mRNA translation
449:Fanconi syndrome
394:, also known as
139:, and protozoan
21:
4452:
4451:
4447:
4446:
4445:
4443:
4442:
4441:
4422:
4421:
4420:
4415:
4414:
4399:Clinical trials
4370:
4356:Streptogramin B
4351:Streptogramin A
4291:
4263:
4235:
4082:
4063:Chloramphenicol
4040:
3994:
3969:
3951:
3932:Penimepicycline
3927:Oxytetracycline
3858:
3846:
3830:
3769:
3645:
3643:Aminoglycosides
3628:
3598:
3554:
3549:
3540:
3538:
3530:
3524:
3520:
3483:Cancer Research
3475:
3471:
3426:
3422:
3416:
3412:
3402:
3400:
3395:
3394:
3390:
3380:
3378:
3373:
3372:
3368:
3358:
3356:
3347:
3346:
3342:
3297:
3293:
3284:
3282:
3273:
3272:
3268:
3258:
3256:
3251:
3250:
3246:
3236:
3234:
3229:
3228:
3224:
3187:
3183:
3174:
3172:
3170:Bizjournals.com
3164:
3163:
3159:
3114:
3110:
3070:
3066:
3027:
3023:
2986:
2977:
2968:
2966:
2962:
2923:
2917:
2913:
2889:
2883:
2879:
2869:
2867:
2858:
2857:
2853:
2810:
2806:
2796:
2794:
2786:
2780:
2771:
2762:
2761:
2757:
2747:
2745:
2738:
2731:
2680:
2671:
2664:
2646:
2642:
2611:(12): 3675β81.
2597:
2593:
2552:(42): 16900β5.
2538:
2534:
2481:
2474:
2429:
2425:
2380:
2376:
2339:
2335:
2290:
2286:
2276:
2274:
2266:
2265:
2261:
2214:
2203:
2177:
2171:
2160:
2129:
2125:
2115:
2113:
2104:
2103:
2099:
2068:
2064:
2041:
2037:
2026:
2022:
1977:
1968:
1958:
1956:
1951:
1950:
1946:
1938:
1931:
1927:
1926:
1919:
1895:10.1.1.620.9933
1878:
1874:
1851:
1847:
1816:
1812:
1781:
1777:
1746:
1742:
1711:
1707:
1691:
1690:
1684:
1682:
1675:"Archived copy"
1673:
1672:
1668:
1658:
1656:
1643:
1642:
1638:
1607:
1603:
1564:
1560:
1517:
1513:
1468:
1464:
1425:
1421:
1406:
1392:
1388:
1349:
1345:
1298:
1289:
1282:
1256:
1252:
1245:
1224:
1223:
1219:
1174:
1141:
1131:
1129:
1121:
1120:
1107:
1103:
1076:
1016:
980:narrow-spectrum
836:Oxytetracycline
785:
739:
696:oxytetracycline
680:oxytetracycline
655:
603:oxytetracycline
595:
539:
526:
474:
466:inguinal hernia
461:
439:and exacerbate
425:
384:
296:Yersinia pestis
265:oxytetracycline
233:
149:oxytetracycline
104:and binding to
98:pharmacological
52:are a group of
35:
28:
23:
22:
15:
12:
11:
5:
4450:
4440:
4439:
4434:
4417:
4416:
4413:
4412:
4411:
4410:
4407:
4396:
4390:
4384:
4383:
4380:
4379:
4376:
4375:
4372:
4371:
4369:
4368:
4358:
4353:
4348:
4334:
4320:
4301:
4299:
4297:Streptogramins
4293:
4292:
4290:
4289:
4284:
4279:
4273:
4271:
4265:
4264:
4262:
4261:
4256:
4251:
4245:
4243:
4237:
4236:
4234:
4233:
4228:
4223:
4218:
4216:Troleandomycin
4213:
4208:
4203:
4198:
4193:
4188:
4183:
4178:
4173:
4168:
4163:
4158:
4153:
4148:
4146:Flurithromycin
4143:
4138:
4133:
4131:Clarithromycin
4128:
4123:
4118:
4113:
4107:
4105:
4096:
4088:
4087:
4084:
4083:
4081:
4080:
4075:
4070:
4065:
4059:
4057:
4048:
4042:
4041:
4039:
4038:
4033:
4028:
4023:
4018:
4013:
4008:
4002:
4000:
3985:
3979:
3978:
3975:
3974:
3971:
3970:
3968:
3967:
3961:
3959:
3957:Glycylcyclines
3953:
3952:
3950:
3949:
3944:
3939:
3934:
3929:
3924:
3919:
3914:
3909:
3904:
3899:
3894:
3892:Demeclocycline
3889:
3884:
3879:
3873:
3871:
3864:
3852:
3851:
3848:
3847:
3845:
3844:
3838:
3836:
3832:
3831:
3829:
3828:
3823:
3817:
3816:
3815:
3814:
3809:
3804:
3799:
3794:
3783:
3781:
3777:Micromonospora
3771:
3770:
3768:
3767:
3765:Nourseothricin
3762:
3757:
3752:
3747:
3742:
3731:
3730:
3729:
3728:
3723:
3718:
3713:
3702:
3701:
3700:
3699:
3694:
3689:
3678:
3677:
3672:
3666:
3664:
3651:
3636:
3630:
3629:
3601:Antibacterials
3597:
3596:
3589:
3582:
3574:
3568:
3567:
3553:
3552:External links
3550:
3548:
3547:
3518:
3489:(21): 4446β9.
3469:
3420:
3410:
3388:
3366:
3340:
3291:
3266:
3244:
3222:
3181:
3157:
3128:(6): 2156β66.
3108:
3081:(3): 224β232.
3064:
3021:
3007:10.1086/367622
2975:
2911:
2877:
2851:
2804:
2769:
2755:
2729:
2669:
2662:
2640:
2591:
2532:
2472:
2423:
2394:(4): a025387.
2374:
2333:
2284:
2259:
2201:
2158:
2123:
2097:
2062:
2051:(3): 209β214.
2035:
2020:
1991:(8): 4433β41.
1966:
1944:
1941:on 2011-08-27.
1917:
1872:
1845:
1810:
1775:
1740:
1705:
1666:
1636:
1617:(3): 106β109.
1601:
1558:
1511:
1462:
1419:
1404:
1386:
1343:
1287:
1280:
1250:
1243:
1217:
1139:
1123:"Tetracycline"
1104:
1102:
1099:
1098:
1097:
1092:
1087:
1082:
1075:
1072:
1060:rabies vaccine
1015:
1012:
1009:
1008:
993:
990:
984:
983:
972:
969:
963:
962:
959:
956:
953:
947:
946:
944:
941:
940:Glycylcyclines
938:
932:
931:
929:
926:
920:
919:
917:
914:
908:
907:
905:
902:
896:
895:
893:
890:
884:
883:
880:
877:
871:
870:
868:
865:
864:Semi-synthetic
862:
856:
855:
853:
850:
848:Demeclocycline
844:
843:
841:
838:
832:
831:
829:
826:
820:
819:
817:
814:
811:
805:
804:
801:
798:
795:
784:
781:
738:
735:
721:from the post-
708:anthropologist
654:
651:
607:demeclocycline
594:
593:Administration
591:
590:
589:
586:
583:
558:oxidoreductase
538:
535:
525:
522:
518:Kaposi Sarcoma
486:aminoacyl-tRNA
473:
470:
460:
457:
429:kidney failure
424:
421:
417:liver toxicity
383:
380:
301:bubonic plague
232:
229:
177:aminoacyl tRNA
165:porin channels
157:bacteriostatic
133:mycoplasmatota
117:microorganisms
92:groups. These
54:broad-spectrum
26:
9:
6:
4:
3:
2:
4449:
4438:
4435:
4433:
4430:
4429:
4427:
4408:
4406:
4403:
4402:
4400:
4397:
4394:
4391:
4389:
4386:
4385:
4381:
4366:
4362:
4361:Virginiamycin
4359:
4357:
4354:
4352:
4349:
4346:
4342:
4338:
4335:
4332:
4328:
4324:
4321:
4318:
4314:
4310:
4306:
4305:Pristinamycin
4303:
4302:
4300:
4298:
4294:
4288:
4285:
4283:
4280:
4278:
4275:
4274:
4272:
4270:
4266:
4260:
4259:Solithromycin
4257:
4255:
4252:
4250:
4249:Telithromycin
4247:
4246:
4244:
4242:
4238:
4232:
4229:
4227:
4224:
4222:
4221:Tulathromycin
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4201:Telithromycin
4199:
4197:
4194:
4192:
4191:Solithromycin
4189:
4187:
4186:Roxithromycin
4184:
4182:
4179:
4177:
4174:
4172:
4169:
4167:
4164:
4162:
4159:
4157:
4154:
4152:
4151:Gamithromycin
4149:
4147:
4144:
4142:
4139:
4137:
4136:Dirithromycin
4134:
4132:
4129:
4127:
4124:
4122:
4119:
4117:
4114:
4112:
4109:
4108:
4106:
4104:
4100:
4097:
4094:
4089:
4079:
4076:
4074:
4073:Thiamphenicol
4071:
4069:
4068:Azidamfenicol
4066:
4064:
4061:
4060:
4058:
4056:
4052:
4049:
4047:
4043:
4037:
4034:
4032:
4029:
4027:
4024:
4022:
4019:
4017:
4014:
4012:
4009:
4007:
4004:
4003:
4001:
3998:
3993:
3992:Oxazolidinone
3989:
3986:
3984:
3980:
3966:
3963:
3962:
3960:
3958:
3954:
3948:
3945:
3943:
3940:
3938:
3935:
3933:
3930:
3928:
3925:
3923:
3920:
3918:
3915:
3913:
3910:
3908:
3905:
3903:
3900:
3898:
3895:
3893:
3890:
3888:
3885:
3883:
3880:
3878:
3875:
3874:
3872:
3870:Tetracyclines
3868:
3865:
3862:
3857:
3853:
3843:
3840:
3839:
3837:
3833:
3827:
3824:
3822:
3819:
3818:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3789:
3788:
3785:
3784:
3782:
3779:
3778:
3772:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3745:Spectinomycin
3743:
3740:
3736:
3733:
3732:
3727:
3724:
3722:
3719:
3717:
3714:
3712:
3709:
3708:
3707:
3704:
3703:
3698:
3695:
3693:
3690:
3688:
3685:
3684:
3683:
3680:
3679:
3676:
3673:
3671:
3668:
3667:
3665:
3662:
3661:
3655:
3652:
3649:
3644:
3640:
3637:
3635:
3631:
3626:
3622:
3618:
3614:
3610:
3606:
3602:
3595:
3590:
3588:
3583:
3581:
3576:
3575:
3572:
3565:
3560:
3556:
3555:
3536:
3529:
3522:
3514:
3510:
3505:
3500:
3496:
3492:
3488:
3484:
3480:
3473:
3465:
3461:
3456:
3451:
3447:
3443:
3439:
3435:
3431:
3424:
3414:
3398:
3392:
3376:
3370:
3354:
3350:
3344:
3336:
3332:
3327:
3322:
3318:
3314:
3310:
3306:
3302:
3295:
3280:
3276:
3275:"Sarecycline"
3270:
3254:
3248:
3232:
3226:
3218:
3214:
3209:
3204:
3201:(2): 256β65.
3200:
3196:
3192:
3185:
3171:
3167:
3161:
3153:
3149:
3144:
3139:
3135:
3131:
3127:
3123:
3119:
3112:
3104:
3100:
3096:
3092:
3088:
3084:
3080:
3076:
3068:
3060:
3056:
3052:
3048:
3044:
3040:
3037:(5): 567β88.
3036:
3032:
3025:
3017:
3013:
3008:
3003:
2999:
2995:
2991:
2984:
2982:
2980:
2965:on 2016-03-04
2961:
2957:
2953:
2949:
2945:
2941:
2937:
2933:
2929:
2922:
2915:
2907:
2903:
2899:
2895:
2888:
2881:
2865:
2861:
2855:
2847:
2843:
2839:
2835:
2831:
2827:
2823:
2819:
2815:
2808:
2792:
2785:
2778:
2776:
2774:
2765:
2759:
2743:
2736:
2734:
2725:
2721:
2717:
2713:
2709:
2705:
2701:
2697:
2693:
2689:
2685:
2678:
2676:
2674:
2665:
2659:
2654:
2653:
2644:
2636:
2632:
2627:
2622:
2618:
2614:
2610:
2606:
2602:
2595:
2587:
2583:
2578:
2573:
2568:
2563:
2559:
2555:
2551:
2547:
2543:
2536:
2528:
2524:
2519:
2514:
2510:
2506:
2502:
2498:
2494:
2490:
2486:
2479:
2477:
2468:
2464:
2459:
2454:
2450:
2446:
2442:
2438:
2434:
2427:
2419:
2415:
2410:
2405:
2401:
2397:
2393:
2389:
2385:
2378:
2370:
2366:
2361:
2356:
2352:
2348:
2344:
2337:
2329:
2325:
2320:
2315:
2311:
2307:
2304:(7): 888β97.
2303:
2299:
2295:
2288:
2273:
2269:
2263:
2255:
2251:
2246:
2241:
2236:
2231:
2227:
2223:
2219:
2212:
2210:
2208:
2206:
2196:
2191:
2187:
2183:
2176:
2169:
2167:
2165:
2163:
2154:
2150:
2146:
2142:
2138:
2134:
2127:
2111:
2107:
2101:
2093:
2089:
2085:
2081:
2078:(3): 305β16.
2077:
2073:
2066:
2058:
2054:
2050:
2046:
2039:
2031:
2024:
2016:
2012:
2007:
2002:
1998:
1994:
1990:
1986:
1982:
1975:
1973:
1971:
1955:. 27 May 2011
1954:
1948:
1937:
1930:
1924:
1922:
1913:
1909:
1905:
1901:
1896:
1891:
1888:(4): 653β64.
1887:
1883:
1876:
1868:
1864:
1860:
1856:
1849:
1841:
1837:
1833:
1829:
1826:(6): 917β23.
1825:
1821:
1814:
1806:
1802:
1798:
1794:
1791:(3): 219β31.
1790:
1786:
1779:
1771:
1767:
1763:
1759:
1756:(2): 256β63.
1755:
1751:
1744:
1736:
1732:
1728:
1724:
1720:
1716:
1709:
1701:
1695:
1681:on 2016-04-09
1680:
1676:
1670:
1654:
1650:
1649:www.tg.org.au
1646:
1640:
1632:
1628:
1624:
1620:
1616:
1612:
1605:
1597:
1593:
1589:
1585:
1581:
1577:
1573:
1569:
1562:
1554:
1550:
1546:
1542:
1538:
1534:
1530:
1526:
1522:
1515:
1507:
1503:
1498:
1493:
1489:
1485:
1481:
1477:
1473:
1466:
1458:
1454:
1450:
1446:
1442:
1438:
1435:(2): 208β16.
1434:
1430:
1423:
1415:
1411:
1407:
1405:9789241512220
1401:
1397:
1390:
1382:
1378:
1374:
1370:
1366:
1362:
1358:
1354:
1347:
1339:
1335:
1330:
1325:
1320:
1315:
1311:
1307:
1303:
1296:
1294:
1292:
1283:
1281:9780120026135
1277:
1273:
1269:
1265:
1261:
1254:
1246:
1240:
1236:
1232:
1228:
1221:
1213:
1209:
1204:
1199:
1195:
1191:
1187:
1183:
1179:
1172:
1170:
1168:
1166:
1164:
1162:
1160:
1158:
1156:
1154:
1152:
1150:
1148:
1146:
1144:
1128:
1124:
1118:
1116:
1114:
1112:
1110:
1105:
1096:
1093:
1091:
1088:
1086:
1083:
1081:
1080:Glycylcycline
1078:
1077:
1071:
1069:
1065:
1061:
1057:
1054:and binds to
1053:
1049:
1045:
1041:
1037:
1033:
1029:
1025:
1021:
1006:
1002:
998:
994:
991:
989:
986:
985:
981:
977:
976:acne vulgaris
973:
970:
968:
965:
964:
960:
957:
952:
949:
948:
945:
942:
939:
937:
934:
933:
930:
927:
925:
922:
921:
918:
915:
913:
910:
909:
906:
903:
901:
898:
897:
894:
891:
889:
886:
885:
881:
878:
876:
873:
872:
869:
866:
861:
858:
857:
854:
851:
849:
846:
845:
842:
839:
837:
834:
833:
830:
827:
825:
822:
821:
818:
815:
810:
807:
806:
802:
799:
796:
793:
789:
788:
780:
778:
774:
770:
766:
761:
757:
753:
749:
743:
734:
732:
728:
724:
720:
716:
712:
709:
704:
701:
697:
693:
689:
685:
681:
677:
673:
669:
665:
661:
650:
648:
644:
640:
636:
632:
628:
624:
620:
616:
612:
608:
604:
600:
599:water-soluble
587:
584:
581:
580:
579:
576:
574:
569:
565:
563:
559:
554:
552:
548:
544:
534:
532:
521:
519:
515:
511:
507:
503:
499:
495:
491:
487:
483:
479:
469:
467:
456:
454:
450:
446:
442:
438:
434:
430:
420:
418:
414:
409:
405:
401:
397:
393:
389:
388:phototoxicity
379:
377:
373:
369:
365:
361:
357:
353:
349:
345:
341:
337:
335:
330:
326:
322:
318:
314:
310:
306:
302:
298:
297:
292:
288:
287:
282:
278:
274:
270:
266:
262:
258:
254:
250:
246:
242:
238:
228:
226:
222:
217:
213:
209:
205:
201:
196:
192:
190:
189:intracellular
186:
182:
178:
174:
170:
166:
162:
161:bacteriocidal
158:
153:
150:
146:
142:
138:
134:
130:
126:
122:
121:gram-positive
118:
113:
111:
107:
103:
99:
95:
94:modifications
91:
87:
83:
79:
75:
71:
67:
64:
63:
58:
55:
51:
50:Tetracyclines
44:
39:
33:
19:
4437:Hepatotoxins
4345:Quinupristin
4341:Dalfopristin
4269:Lincosamides
4206:Tildipirosin
4176:Oleandomycin
4141:Erythromycin
4111:Azithromycin
3947:Tetracycline
3922:Omadacycline
3907:Meclocycline
3897:Eravacycline
3887:Clomocycline
3855:
3802:Micronomicin
3775:
3750:Hygromycin B
3739:+loteprednol
3697:Ribostamycin
3670:Streptomycin
3660:Streptomyces
3658:
3539:. Retrieved
3534:
3521:
3486:
3482:
3472:
3437:
3434:Cell Reports
3433:
3423:
3413:
3401:. Retrieved
3391:
3379:. Retrieved
3369:
3357:. Retrieved
3353:the original
3343:
3308:
3304:
3294:
3283:. Retrieved
3278:
3269:
3257:. Retrieved
3247:
3235:. Retrieved
3225:
3198:
3194:
3184:
3173:. Retrieved
3169:
3160:
3125:
3121:
3111:
3078:
3075:JAMA Surgery
3074:
3067:
3034:
3030:
3024:
3000:(4): 462β7.
2997:
2993:
2967:. Retrieved
2960:the original
2931:
2927:
2914:
2897:
2893:
2880:
2868:. Retrieved
2864:the original
2854:
2824:(2874): 85.
2821:
2817:
2807:
2795:. Retrieved
2793:. Baran labs
2790:
2758:
2746:. Retrieved
2694:(1): 17β32.
2691:
2687:
2651:
2643:
2608:
2604:
2594:
2549:
2545:
2535:
2492:
2488:
2440:
2436:
2426:
2391:
2387:
2377:
2350:
2346:
2336:
2301:
2297:
2287:
2275:. Retrieved
2271:
2262:
2225:
2221:
2185:
2181:
2139:(2): 151β6.
2136:
2132:
2126:
2114:. Retrieved
2109:
2100:
2075:
2071:
2065:
2048:
2044:
2038:
2029:
2023:
1988:
1984:
1957:. Retrieved
1947:
1936:the original
1885:
1881:
1875:
1861:(6): 391β9.
1858:
1854:
1848:
1823:
1819:
1813:
1788:
1784:
1778:
1753:
1749:
1743:
1721:(3): 473β9.
1718:
1714:
1708:
1683:. Retrieved
1679:the original
1669:
1657:. Retrieved
1653:the original
1648:
1639:
1614:
1610:
1604:
1574:(2): 141β6.
1571:
1567:
1561:
1528:
1524:
1520:
1514:
1479:
1475:
1465:
1432:
1428:
1422:
1395:
1389:
1359:(5): 571β7.
1356:
1352:
1346:
1309:
1305:
1263:
1259:
1253:
1226:
1220:
1185:
1181:
1130:. Retrieved
1126:
1085:Eravacycline
1036:mitochondria
1027:
1023:
1017:
988:Omadacycline
982:antibiotic.
951:Eravacycline
888:Methacycline
875:Meclocycline
809:Tetracycline
790:Antibiotic (
773:tetracycline
744:
740:
731:ancient beer
705:
700:tetracycline
656:
611:methacycline
596:
577:
570:
566:
555:
540:
527:
475:
462:
426:
385:
382:Side effects
360:Lyme disease
333:
294:
284:
281:prophylactic
261:tetracycline
234:
231:Medical uses
197:
193:
154:
114:
62:Streptomyces
60:
49:
48:
43:tetracycline
32:tetracycline
4395:from market
4331:Linopristin
4277:Clindamycin
4254:Cethromycin
4181:Rokitamycin
4166:Midecamycin
4161:Kitasamycin
4078:Florfenicol
4055:Amphenicols
3999:inhibitors)
3965:Tigecycline
3942:Sarecycline
3917:Minocycline
3912:Metacycline
3902:Lymecycline
3877:Doxycycline
3721:Bekanamycin
3692:Paromomycin
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2900:(1): 3β12.
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2495:(1): 1477.
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2228:(1): 1β13.
2222:Antibiotics
1482:(1): 46β9.
1266:: 237β266.
1068:rhodamine B
1052:fluorescent
967:Sarecycline
936:Tigecycline
924:Doxycycline
900:Minocycline
860:Lymecycline
777:tigecycline
769:minocycline
765:tigecycline
760:tigecycline
756:minocycline
752:minocycline
748:tigecycline
737:Development
727:ultraviolet
647:Minocycline
643:minocycline
639:doxycycline
531:lymecycline
498:incyclinide
445:minocycline
433:minocycline
364:borreliosis
352:brucellosis
334:L. venereum
325:salpingitis
321:psittacosis
277:Doxycycline
273:minocycline
269:doxycycline
221:acquisition
152:promoters.
137:rickettsiae
129:chlamydiota
78:derivatives
74:polyketides
4426:Categories
4327:Flopristin
4287:Pirlimycin
4282:Lincomycin
4231:Tylvalosin
4211:Tilmicosin
4196:Spiramycin
4171:Miocamycin
4126:Carrimycin
4121:Carbomycin
4103:Macrolides
4026:Ranbezolid
4006:Eperezolid
3997:initiation
3826:Astromicin
3821:Verdamicin
3812:Isepamicin
3807:Plazomicin
3792:Netilmicin
3787:Gentamicin
3735:Tobramycin
3687:Framycetin
3648:initiation
3541:2017-05-03
3403:8 February
3381:8 February
3285:2020-06-07
3259:8 February
3175:2017-03-13
2969:2014-06-19
1685:2019-04-16
1659:3 February
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1003:and acute
400:teratogens
340:Rickettsia
329:urethritis
309:filariasis
249:resistance
245:macrolides
119:including
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4405:Phase III
4393:Withdrawn
4241:Ketolides
4156:Josamycin
4116:Boromycin
4036:Tedizolid
4031:Sutezolid
4021:Radezolid
4016:Posizolid
4011:Linezolid
3842:Butirosin
3797:Sisomicin
3760:Apramycin
3755:Totomycin
3726:Dibekacin
3716:Arbekacin
3706:Kanamycin
3537:: 217β222
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2797:3 October
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1132:1 October
1062:baits by
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615:magnesium
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3774:-micin (
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1024:in vitro
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631:absorbed
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423:Cautions
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