1096:
nerve endings or secreted by the adrenal glands, they bind to β-1 adrenergic receptors found primarily in cardiac tissues such as the heart. This binding activates these receptors, leading to various physiological responses, including an increase in heart rate, force of contraction (inotropic effect), conduction speed through electrical pathways in the heart, and release of renin from the kidneys. Metoprolol competes with adrenaline and noradrenaline for binding sites on these β-1 receptors. By occupying these receptor sites without activating them, metoprolol blocks or inhibits their activation by endogenous catecholamines like adrenaline or noradrenaline.
1284:
1273:
703:
680:
40:
1213:
31:
3611:
3621:
3647:
1051:, seizures, and cardiorespiratory arrest. Blood or plasma concentrations may be measured to confirm a diagnosis of overdose or poisoning in hospitalized patients or to assist in a medicolegal death investigation. Plasma levels are usually less than 200 μg/L during therapeutic administration, but can range from 1–20 mg/L in overdose victims.
1095:
Metoprolol exerts its effects by blocking the action of certain neurotransmitters, specifically adrenaline and noradrenaline. It does this by selectively binding to and antagonizing β-1 adrenergic receptors in the body. When adrenaline (epinephrine) or noradrenaline (norepinephrine) are released from
1011:
Metoprolol reduces long-term mortality and hospitalisation due to worsening heart failure. A meta-analysis further supports reduced incidence of heart failure worsening in patients treated with beta-blockers compared to placebo. However, in some circumstances, particularly when initiating metoprolol
1314:
In the 2000s, a lawsuit was brought against the manufacturers of Toprol XL (a time-release formula version of metoprolol) and its generic equivalent (metoprolol succinate) claiming that to increase profits, lower cost generic versions of Toprol XL were intentionally kept off the market. It alleged
2190:
Hjalmarson A, Goldstein S, Fagerberg B, Wedel H, Waagstein F, Kjekshus J, et al. (March 2000). "Effects of controlled-release metoprolol on total mortality, hospitalizations, and well-being in patients with heart failure: the
Metoprolol CR/XL Randomized Intervention Trial in congestive heart
1144:
Metoprolol is mostly absorbed from the intestine with an absorption fraction of 0.95. The systemic bioavailability after oral administration is approximately 50%. Less than 5% of an orally administered dose of metoprolol is excreted unchanged in urine; most of it is eliminated in metabolized form
983:
Adverse effects, especially with higher doses, include dizziness, drowsiness, fatigue, diarrhea, unusual dreams, trouble sleeping, depression, and vision problems such as blurred vision or dry eyes. β-blockers, including metoprolol, reduce salivary flow via inhibition of the direct sympathetic
1128:
Decrease in cardiac output, i.e., decrease in both heart rate and contractility within myocardium cells, where beta-(β)-1 is predominantly located, overall blood output per minute lowers called cardiac output/dysfunction, allowing decreased demands placed onto impaired hearts, reducing oxygen
2289:
Gottlieb SS, Fisher ML, Kjekshus J, Deedwania P, Gullestad L, Vitovec J, et al. (John
Wikstrand; MERIT-HF Investigators) (March 2002). "Tolerability of beta-blocker initiation and titration in the Metoprolol CR/XL Randomized Intervention Trial in Congestive Heart Failure (MERIT-HF)".
996:
and metoprolol are more likely than other less lipophilic beta blockers to cause sleep disturbances such as insomnia, vivid dreams and nightmares. Patients should be cautious while driving or operating machinery due to its potential to cause decreased alertness.
909:, and abdominal discomfort. Large doses may cause serious toxicity. Risk in pregnancy has not been ruled out. It appears to be safe in breastfeeding. The metabolism of metoprolol can vary widely among patients, often as a result of hepatic impairment or
1026:
This medicine may cause changes in blood sugar levels or cover up signs of low blood sugar, such as a rapid pulse rate. It also may cause some people to become less alert than they are normally, making it dangerous for them to drive or use machines.
1012:
in patients with more symptomatic disease, an increased prevalence of hospitalisation and mortality has been reported within the first two months of starting. Patients should monitor for swelling of extremities, fatigue, and shortness of breath.
964:. Both oral and intravenous forms of metoprolol are available for administration. The different salt versions of metoprolol – metoprolol tartrate and metoprolol succinate – are approved for different conditions and are not interchangeable.
2805:
1194:
Metoprolol was synthesized and its activity discovered in 1969. The specific agent in on-market formulations of metoprolol is either metoprolol tartrate or metoprolol succinate, where tartrate is an immediate-release
1186:. Metoprolol binds mainly to human serum albumin with an unbound fraction of 0.88. It has a large volume of distribution at steady state (3.2 L/kg), indicating extensive distribution throughout the body.
1331:
Because beta blockers can be used to reduce heart rate and minimize tremors, which can enhance performance in sports such as archery, metoprolol is banned by the world anti-doping agency in some sports.
2700:
Swaisland HC, Ranson M, Smith RP, Leadbetter J, Laight A, McKillop D, et al. (2005). "Pharmacokinetic drug interactions of gefitinib with rifampicin, itraconazole and metoprolol".
1107:, thereby decreasing the slope of phase 4 in the nodal action potential (reducing Na uptake) and prolonging repolarization of phase 3 (slowing down K release). It also suppresses the
320:
2442:
Albers S, Elshoff JP, Völker C, Richter A, Läer S (April 2005). "HPLC quantification of metoprolol with solid-phase extraction for the drug monitoring of pediatric patients".
2629:"Norepinephrine-Induced Adrenergic Activation Strikingly Increased the Atrial Fibrillation Duration through β1- and α1-Adrenergic Receptor-Mediated Signaling in Mice"
1122:
Heart rate reduction, i.e., decrease of the resting heart rate (negative chronotropic effect) and reduction of excessive elevations resulting from exercise or stress.
2346:
3702:
1039:
C in
Australia, meaning that it may be suspected of causing harmful effects on the human fetus (but no malformations). It appears to be safe in breastfeeding.
275:
2242:"Systematic review of genuine versus spurious side-effects of beta-blockers in heart failure using placebo control: recommendations for patient information"
2360:
Lafuente-Lafuente C, Valembois L, Bergmann J, Belmin J (2015). "Antiarrhythmics for maintaining sinus rhythm after cardioversion of atrial fibrillation".
3677:
2567:
Zamir A, Hussain I, Ur Rehman A, Ashraf W, Imran I, Saeed H, et al. (August 2022). "Clinical
Pharmacokinetics of Metoprolol: A Systematic Review".
1392:
1125:
Reduction of the force of contraction, i.e., decrease in contractility (negative inotropic effect), which lessens how hard each heartbeat contracts.
1148:
Metoprolol undergoes extensive metabolism in the liver, mainly α-hydroxylation and O-demethylation through various cytochrome P450 enzymes such as
1315:
that the pharmaceutical companies AstraZeneca AB, AstraZeneca LP, AstraZeneca
Pharmaceuticals LP, and Aktiebolaget Hassle violated antitrust and
1199:
and the succinate is an extended-release formulation (with 100 mg metoprolol tartrate corresponding to 95 mg metoprolol succinate).
2916:
1800:
The selection and use of essential medicines 2023: web annex A: World Health
Organization model list of essential medicines: 23rd list (2023)
157:
3337:
805:
1754:
1016:
2806:"$ 11 Million Settlement Reached in Lawsuit Involving the Heart Medication, Toprol XL, and its generic equivalent, metoprolol succinate"
1607:
Regårdh CG, Jordö L, Ervik M, Lundborg P, Olsson R, Rönn O (1981). "Pharmacokinetics of metoprolol in patients with hepatic cirrhosis".
1593:
1502:
3692:
2744:
1461:
984:
innervation of the salivary glands. Metoprolol may also cause the hands and feet to feel cold. Due to the high penetration across the
1705:
1974:
3667:
3522:
2953:
769:
2686:
2610:
2362:
2226:
2001:
1552:
1319:
law. In a settlement by the companies in 2012, without admission to the claims, they agreed to a settlement pay-out of US$ 11
1135:
Antiarrhythmic effects, such as supraventricular tachycardia prevention. Metoprolol also prevents electrical wave propagation.
3259:
3203:
1831:
917:
3697:
2785:
Rote Liste 2017 – Arzneimittelverzeichnis für
Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte)
2792:
2030:
1779:
1748:
1587:
1525:
1496:
1426:
1089:
850:
208:
3687:
3392:
3377:
825:
3220:
2338:
2085:
453:
305:
189:
3492:
1224: with: a statement from secondary sources of the importance/relevance of this information. You can help by
1118:
Through this mechanism of selective blockade at beta-(β)-1 receptors, metoprolol exerts the following effects:
3565:
2126:
1377:
528:
3624:
1711:
1386:
968:
945:
698:
579:
2046:
Turner MD (April 2016). "Hyposalivation and
Xerostomia: Etiology, Complications, and Medical Management".
3167:
2946:
1349:
941:
659:
1000:
There may also be an impact on blood sugar levels and it can potentially mask signs of low blood sugar.
916:
Metoprolol was first made in 1969, patented in 1970, and approved for medical use in 1978. It is on the
3682:
3637:
3145:
3063:
1196:
1081:
924:. In 2022, it was the sixth most commonly prescribed medication in the United States, with more than 65
1878:
Geffner DL, Hershman JM (July 1992). "Beta-adrenergic blockade for the treatment of hyperthyroidism".
1115:(SR) Ca leak and the spontaneous SR Ca release, which are the major triggers for atrial fibrillation.
3252:
1795:
833:
InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3
648:
2975:
953:
675:
1073:
3560:
3208:
1225:
1172:
985:
949:
245:
147:
3672:
3596:
3512:
3507:
3402:
2939:
1176:
1112:
390:
2497:
Cojocariu SA, Maștaleru A, Sascău RA, Stătescu C, Mitu F, Leon-Constantin MM (February 2021).
1769:
1738:
1577:
1484:
3467:
3332:
2680:
2604:
2220:
876:
780:
628:
519:
1457:
167:
3614:
3245:
2759:
2640:
588:
483:
420:
568:
8:
2395:"The use of high-dose insulin-glucose euglycemia in beta-blocker overdose: a case report"
1421:(in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 916–919.
1316:
1077:
1069:
1020:
474:
252:
2644:
1939:
702:
679:
2849:
2824:
2725:
2663:
2628:
2592:
2525:
2498:
2419:
2394:
2315:
2266:
2241:
1966:
1679:
1654:
1632:
1283:
1272:
1048:
1036:
957:
921:
906:
219:
3352:
2920:
2854:
2788:
2717:
2713:
2668:
2596:
2584:
2530:
2459:
2424:
2375:
2307:
2271:
2208:
2172:
2149:
2108:
2063:
2026:
1921:
1895:
1891:
1775:
1744:
1684:
1624:
1620:
1583:
1521:
1492:
1422:
902:
357:
344:
332:
181:
2319:
2844:
2836:
2729:
2709:
2658:
2648:
2627:
Suita K, Fujita T, Hasegawa N, Cai W, Jin H, Hidaka Y, et al. (23 July 2015).
2576:
2520:
2510:
2451:
2414:
2406:
2371:
2367:
2299:
2261:
2253:
2200:
2055:
1887:
1803:
1674:
1666:
1636:
1616:
1544:
1180:
1164:. The primary metabolites formed are α-hydroxymetoprolol and O-demethylmetoprolol.
715:
370:
288:
101:
57:
1853:
1823:
3651:
3482:
3322:
2840:
2653:
2257:
2171:. Bethesda (MD): National Institute of Child Health and Human Development. 1994.
2148:. Bethesda (MD): National Institute of Child Health and Human Development. 2006.
1655:"A meta-analysis of CYP2D6 metabolizer phenotype and metoprolol pharmacokinetics"
961:
872:
785:
508:
400:
378:
2906:
3292:
3214:
2910:
2580:
2059:
1108:
1104:
2875:
3661:
3347:
3302:
3282:
2515:
2481:(8th ed.). Foster City, CA: Biomedical Publications. pp. 1023–1025.
2240:
Barron AJ, Zaman N, Cole GD, Wensel R, Okonko DO, Francis DP (October 2013).
2204:
1354:
1306:
Metoprolol was approved for medical use in the United States in August 1978.
1023:
recurrence, it is unclear whether the long-term benefits outweigh the risks.
972:
792:
691:
39:
3591:
3537:
3527:
3457:
3367:
3317:
3312:
3033:
2966:
2962:
2924:
2858:
2721:
2672:
2588:
2534:
2463:
2428:
2379:
2311:
2275:
2212:
2176:
2153:
2112:
2067:
1925:
1688:
1065:
887:
283:
268:
22:
2303:
1899:
1628:
3532:
3487:
3477:
3472:
3452:
3447:
3432:
3427:
3412:
3382:
3342:
3297:
3287:
3268:
3038:
2006:
1670:
1245:
1183:
993:
256:
175:
2359:
2081:
1808:
1212:
548:
3517:
3502:
3462:
3442:
3422:
3362:
3357:
3327:
3184:
3179:
3157:
3100:
3095:
3090:
3075:
3048:
3024:
3019:
3009:
3004:
2994:
2989:
2984:
2410:
1168:
989:
745:
559:
263:
30:
2931:
3570:
3497:
3397:
3387:
3372:
3189:
3135:
3130:
3125:
3115:
3085:
2999:
494:
433:
161:
2455:
1967:"Metoprolol tartrate vs. succinate: Differences in uses and effects"
1003:
The safety of metoprolol during pregnancy is not fully established.
3555:
3437:
3417:
3307:
3105:
3080:
3029:
1249:
895:
880:
608:
539:
203:
1047:
Excessive doses of metoprolol can cause bradycardia, hypotension,
768:
3110:
3053:
3043:
3014:
2189:
2496:
1700:
1698:
1518:
Rosen's emergency medicine : concepts and clinical practice
3575:
2288:
1161:
1157:
1153:
1149:
937:
910:
868:
639:
438:
413:
409:
3237:
2699:
1854:"Metoprolol Drug Usage Statistics, United States, 2013 - 2022"
1171:
beta blocker. More lipophilic beta blockers tend to cross the
2909:. In Pratt VM, McLeod HL, Rubinstein WS, et al. (eds.).
1695:
759:
619:
405:
131:
87:
1653:
Blake CM, Kharasch ED, Schwab M, Nagele P (September 2013).
664:
2787:. Rote Liste Service GmbH, Frankfurt/Main, 2017, Aufl. 57,
2566:
2499:"Neuropsychiatric Consequences of Lipophilic Beta-Blockers"
1035:
Risk for the fetus has not been ruled out, per being rated
599:
125:
113:
107:
81:
72:
63:
2441:
2099:
Cruickshank JM (2010). "Beta-blockers and heart failure".
875:. It is also used to prevent further heart problems after
1794:
1652:
1606:
936:
Metoprolol is used for a number of conditions, including
1582:. Lippincott Williams & Wilkins. 2004. p. 684.
1175:
more readily, with greater potential for effects in the
1539:
1537:
1244:
Metoprolol contains a stereocenter and consists of two
1019:
concluded that although metoprolol reduces the risk of
918:
2825:"The World Anti-Doping Code in sport: Update for 2015"
2626:
1145:
through feces via bile secretion into the intestines.
3635:
2239:
1520:(8th ed.). Philadelphia, PA: Elsevier/Saunders.
1516:
Marx JA (2014). "Chapter 152: Cardiovascular Drugs".
1460:. The American Society of Health-System Pharmacists.
1572:
1570:
1534:
134:
128:
122:
119:
110:
90:
84:
78:
75:
69:
16:
Medication of the selective β1 receptor blocker type
1485:"Diuretics, Antihypertensives, and Antiarrhythmics"
527:
116:
104:
66:
60:
2392:
1732:
1730:
2393:Page C, Hacket LP, Isbister GK (September 2009).
1567:
3659:
507:
2562:
2560:
2558:
2556:
2554:
2552:
2550:
2548:
2546:
2544:
2492:
2490:
2488:
2479:Disposition of Toxic Drugs and Chemicals in Man
1996:
1994:
1992:
1920:. Treasure Island (FL): StatPearls Publishing.
1911:
1909:
1877:
1767:
1727:
1648:
1646:
482:
1030:
901:Common side effects include trouble sleeping,
3703:World Health Organization essential medicines
3253:
2947:
2917:National Center for Biotechnology Information
2333:
2331:
2329:
2160:
1740:Technological systems and industrial dynamics
1545:"Prescribing medicines in pregnancy database"
3338:Budesonide/glycopyrronium bromide/formoterol
2541:
2485:
2353:
2282:
2233:
2183:
2137:
2092:
1989:
1915:
1906:
1643:
1410:
1378:"Metolar 25/50 (metoprolol tartrate) tablet"
867:among others, is a medication used to treat
207:
2363:The Cochrane Database of Systematic Reviews
2191:failure (MERIT-HF). MERIT-HF Study Group".
2098:
1871:
1743:. Dordrecht: Kluwer Academic. p. 106.
1491:. Jaypee Brothers Publishers. p. 303.
362:In general: ℞ (Prescription only)
3678:Chemical substances for emergency medicine
3260:
3246:
2954:
2940:
2777:
2326:
1600:
1452:
1450:
1448:
1446:
1444:
1442:
1440:
1438:
701:
678:
567:
38:
29:
2848:
2752:Pharmacist's Letter / Prescriber's Letter
2662:
2652:
2524:
2514:
2418:
2265:
1916:Morris J, Dunham A (2023). "Metoprolol".
1807:
1678:
1167:Metoprolol is classified as a moderately
587:
2907:"Metoprolol Therapy and CYP2D6 Genotype"
2020:
1736:
1509:
871:and a number of conditions involving an
152:Lopressor, Metolar XR, Toprol XL, others
2961:
2870:
2868:
2745:"Alternatives for Metoprolol Succinate"
2169:Drugs and Lactation Database (LactMed®)
2146:Drugs and Lactation Database (LactMed®)
1788:
1435:
960:. It is an adjunct in the treatment of
879:and to prevent headaches in those with
674:
547:
180:
3660:
2822:
2476:
2045:
1977:from the original on 25 September 2019
1774:. John Wiley & Sons. p. 461.
1659:Clinical Pharmacology and Therapeutics
1482:
1296:
1059:
692:
338:
3241:
2935:
2622:
2620:
2339:"Metoprolol (Oral Route) Precautions"
2088:from the original on 21 January 2010.
2074:
1802:. Geneva: World Health Organization.
1416:
647:
627:
351:
198:
166:
3620:
2904:
2865:
2742:
1964:
1940:"Metoprolol vs Toprol-XL Comparison"
1515:
1206:
287:
2349:from the original on 16 April 2009.
2246:International Journal of Cardiology
2127:"Common questions about metoprolol"
2025:(3rd ed.). Saunders Elsevier.
1834:from the original on 30 August 2024
1139:
607:
498:
13:
2898:
2685:: CS1 maint: overridden setting (
2617:
2609:: CS1 maint: overridden setting (
2225:: CS1 maint: overridden setting (
1757:from the original on 3 March 2017.
1464:from the original on 12 March 2014
1202:
1090:intrinsic sympathomimetic activity
978:
14:
3714:
3693:N-isopropyl-phenoxypropanolamines
3393:Glycopyrronium bromide/formoterol
2783:Rote Liste Service GmbH (Hrsg.):
1596:from the original on 7 July 2017.
1555:from the original on 8 April 2014
1505:from the original on 7 July 2017.
1398:from the original on 3 March 2016
314:
230:
3645:
3619:
3610:
3609:
2714:10.2165/00003088-200544100-00005
1880:The American Journal of Medicine
1621:10.2165/00003088-198106050-00004
1282:
1271:
1211:
732:
726:
100:
56:
3267:
2816:
2798:
2736:
2693:
2470:
2435:
2386:
2119:
2048:Dental Clinics of North America
2039:
2014:
1958:
1932:
1846:
1816:
1768:Fischer J, Ganellin CR (2006).
1761:
1706:"Lopressor: FDA-Approved Drugs"
1350:"Lopressor Product information"
1301:
1054:
931:
838:Key:IUBSYMUCCVWXPE-UHFFFAOYSA-N
3668:Drugs developed by AstraZeneca
3493:Sodium zirconium cyclosilicate
2372:10.1002/14651858.CD005049.pub4
1476:
1370:
1342:
1006:
735:
720:
327:
1:
3566:Cambridge Antibody Technology
2399:Journal of Medical Toxicology
2131:National Health Service (NHS)
1771:Analogue-based Drug Discovery
1335:
813:O(c1ccc(cc1)CCOC)CC(O)CNC(C)C
385:70% (repeated administration)
2841:10.18773/austprescr.2015.059
2654:10.1371/journal.pone.0133664
2258:10.1016/j.ijcard.2013.05.068
1965:Eske J (25 September 2019).
1892:10.1016/0002-9343(92)90681-Z
1712:Food and Drug Administration
1387:Food and Drug Administration
1309:
1189:
969:supraventricular tachycardia
946:supraventricular tachycardia
863:, sold under the brand name
7:
3698:Drugs developed by Novartis
1132:Lowering of blood pressure.
1042:
1031:Pregnancy and breastfeeding
942:acute myocardial infarction
898:or is given intravenously.
10:
3719:
2927:. Bookshelf ID: NBK425389.
2912:Medical Genetics Summaries
2581:10.1007/s40262-022-01145-y
2060:10.1016/j.cden.2015.11.003
1812:. WHO/MHP/HPS/EML/2023.02.
1266:Enantiomers of metoprolol
873:abnormally fast heart rate
710:Chemical and physical data
3605:
3584:
3546:
3275:
3198:
3166:
3144:
3062:
2974:
2823:Hughes D (October 2015).
2702:Clinical Pharmacokinetics
2569:Clinical Pharmacokinetics
2444:Biomedical Chromatography
2002:"Metoprolol (Oral Route)"
1796:World Health Organization
1609:Clinical Pharmacokinetics
1489:Modern Medical Toxicology
1265:
1252:, i.e. a 1:1 mixture of (
1111:-induced increase in the
1103:-adrenergic receptors in
846:
821:
801:
797:120 °C (248 °F)
791:
779:
757:
744:
714:
709:
690:
658:
638:
618:
598:
578:
558:
538:
518:
493:
473:
449:
444:
432:
419:
399:
389:
377:
369:
304:
299:
274:
262:
244:
218:
188:
174:
156:
146:
51:
46:
37:
28:
3688:Isopropylamino compounds
2880:World Anti Doping Agency
2758:(250302). Archived from
2516:10.3390/medicina57020155
2205:10.1001/jama.283.10.1295
1737:Carlsson B, ed. (1997).
1326:
954:congestive heart failure
894:medication. It is taken
3561:Alexion Pharmaceuticals
1129:demand-supply mismatch.
1076:. It is specifically a
967:Off-label uses include
950:ventricular tachycardia
928:million prescriptions.
920:. It is available as a
3513:Trastuzumab deruxtecan
3508:Tixagevimab/cilgavimab
3403:Isosorbide mononitrate
1289:CAS-Nummer: 81024-42-2
1278:CAS-Nummer: 81024-43-3
1179:as well as associated
1177:central nervous system
1113:sarcoplasmic reticulum
1074:β-adrenergic receptors
992:beta blockers such as
3468:Salbutamol/budesonide
3333:Budesonide/formoterol
2876:"The Prohibited List"
2829:Australian Prescriber
2304:10.1161/hc1002.105180
1824:"The Top 300 of 2022"
1549:Australian Government
1417:Jasek W, ed. (2007).
877:myocardial infarction
2765:on 20 September 2016
2101:Indian Heart Journal
1671:10.1038/clpt.2013.96
1086:-adrenergic receptor
956:, and prevention of
2645:2015PLoSO..1033664S
2021:Costanzo L (2009).
1317:consumer protection
1297:Society and culture
1173:blood–brain barrier
1099:Metoprolol blocks β
1060:Mechanism of action
1021:atrial fibrillation
986:blood–brain barrier
347:(Prescription only)
323:(Prescription only)
25:
3549:acquired companies
3225:Never to phase III
2810:www.prnewswire.com
2411:10.1007/bf03161225
1971:Medical News Today
1579:Medical Toxicology
1483:Pillay VV (2012).
1105:heart muscle cells
1080:antagonist of the
1049:metabolic acidosis
1037:pregnancy category
958:migraine headaches
922:generic medication
465:)-1--3-propan-2-ol
21:
3683:CYP2D6 inhibitors
3633:
3632:
3353:Disufenton sodium
3235:
3234:
2708:(10): 1067–1081.
2477:Baselt R (2008).
2199:(10): 1295–1302.
1358:. 22 October 2009
1294:
1293:
1290:
1279:
1242:
1241:
858:
857:
770:Interactive image
660:CompTox Dashboard
383:50% (single dose)
355:
342:
330:
318:
234:
201:
3710:
3650:
3649:
3648:
3641:
3623:
3622:
3613:
3612:
3597:Louis Schweitzer
3547:Predecessors and
3262:
3255:
3248:
3239:
3238:
2956:
2949:
2942:
2933:
2932:
2928:
2892:
2891:
2889:
2887:
2882:. 3 January 2023
2872:
2863:
2862:
2852:
2820:
2814:
2813:
2812:(Press release).
2802:
2796:
2781:
2775:
2774:
2772:
2770:
2764:
2749:
2740:
2734:
2733:
2697:
2691:
2690:
2684:
2676:
2666:
2656:
2624:
2615:
2614:
2608:
2600:
2575:(8): 1095–1114.
2564:
2539:
2538:
2528:
2518:
2494:
2483:
2482:
2474:
2468:
2467:
2439:
2433:
2432:
2422:
2390:
2384:
2383:
2357:
2351:
2350:
2343:Drug Information
2335:
2324:
2323:
2286:
2280:
2279:
2269:
2237:
2231:
2230:
2224:
2216:
2187:
2181:
2180:
2164:
2158:
2157:
2141:
2135:
2134:
2133:. 15 March 2022.
2123:
2117:
2116:
2096:
2090:
2089:
2078:
2072:
2071:
2043:
2037:
2036:
2018:
2012:
2011:
1998:
1987:
1986:
1984:
1982:
1962:
1956:
1955:
1953:
1951:
1936:
1930:
1929:
1913:
1904:
1903:
1875:
1869:
1868:
1866:
1864:
1850:
1844:
1843:
1841:
1839:
1820:
1814:
1813:
1811:
1792:
1786:
1785:
1765:
1759:
1758:
1734:
1725:
1724:
1722:
1720:
1702:
1693:
1692:
1682:
1650:
1641:
1640:
1604:
1598:
1597:
1574:
1565:
1564:
1562:
1560:
1551:. 3 March 2014.
1541:
1532:
1531:
1513:
1507:
1506:
1480:
1474:
1473:
1471:
1469:
1454:
1433:
1432:
1414:
1408:
1407:
1405:
1403:
1397:
1382:
1374:
1368:
1367:
1365:
1363:
1346:
1322:
1288:
1286:
1277:
1275:
1263:
1262:
1237:
1234:
1215:
1207:
1181:neuropsychiatric
1140:Pharmacokinetics
1064:Metoprolol is a
927:
892:receptor blocker
854:
853:
772:
752:
737:
734:
728:
722:
705:
694:
683:
682:
668:
666:
651:
631:
611:
591:
571:
551:
531:
511:
501:
500:
486:
424:
353:
350:
340:
337:
329:
326:
316:
313:
291:
232:
229:
211:
200:
197:
184:
170:
141:
140:
137:
136:
133:
130:
127:
124:
121:
118:
115:
112:
109:
106:
97:
96:
93:
92:
89:
86:
83:
80:
77:
74:
71:
68:
65:
62:
42:
33:
26:
24:
20:
3718:
3717:
3713:
3712:
3711:
3709:
3708:
3707:
3658:
3657:
3656:
3646:
3644:
3636:
3634:
3629:
3601:
3580:
3548:
3542:
3483:Sebelipase alfa
3323:Brompheniramine
3271:
3266:
3236:
3231:
3230:
3215:Clinical trials
3194:
3173:- + β-selective
3171:
3162:
3149:
3140:
3067:
3058:
2978:, non-selective
2970:
2960:
2905:Dean L (2017).
2901:
2899:Further reading
2896:
2895:
2885:
2883:
2874:
2873:
2866:
2821:
2817:
2804:
2803:
2799:
2782:
2778:
2768:
2766:
2762:
2747:
2743:Cupp M (2009).
2741:
2737:
2698:
2694:
2678:
2677:
2639:(7): e0133664.
2625:
2618:
2602:
2601:
2565:
2542:
2495:
2486:
2475:
2471:
2456:10.1002/bmc.436
2440:
2436:
2391:
2387:
2366:(3): CD005049.
2358:
2354:
2345:. Mayo Clinic.
2337:
2336:
2327:
2287:
2283:
2238:
2234:
2218:
2217:
2188:
2184:
2166:
2165:
2161:
2143:
2142:
2138:
2125:
2124:
2120:
2097:
2093:
2080:
2079:
2075:
2044:
2040:
2033:
2019:
2015:
2000:
1999:
1990:
1980:
1978:
1963:
1959:
1949:
1947:
1946:. 1 August 2019
1938:
1937:
1933:
1914:
1907:
1876:
1872:
1862:
1860:
1852:
1851:
1847:
1837:
1835:
1822:
1821:
1817:
1793:
1789:
1782:
1766:
1762:
1751:
1735:
1728:
1718:
1716:
1704:
1703:
1696:
1651:
1644:
1605:
1601:
1590:
1576:
1575:
1568:
1558:
1556:
1543:
1542:
1535:
1528:
1514:
1510:
1499:
1481:
1477:
1467:
1465:
1456:
1455:
1436:
1429:
1415:
1411:
1401:
1399:
1395:
1380:
1376:
1375:
1371:
1361:
1359:
1348:
1347:
1343:
1338:
1329:
1320:
1312:
1304:
1299:
1287:
1276:
1238:
1232:
1229:
1222:needs expansion
1216:
1205:
1203:Stereochemistry
1192:
1142:
1102:
1085:
1062:
1057:
1045:
1033:
1017:Cochrane Review
1009:
981:
979:Adverse effects
962:hyperthyroidism
934:
925:
891:
849:
847:
842:
839:
834:
829:
828:
817:
814:
809:
808:
786:Racemic mixture
775:
750:
740:
731:
725:
686:
662:
654:
634:
614:
594:
574:
554:
534:
514:
497:
489:
469:
466:
457:
456:
422:
391:Protein binding
384:
379:Bioavailability
371:Pharmacokinetic
365:
295:
247:
240:
221:
214:
103:
99:
59:
55:
17:
12:
11:
5:
3716:
3706:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3655:
3654:
3631:
3630:
3628:
3627:
3617:
3606:
3603:
3602:
3600:
3599:
3594:
3588:
3586:
3582:
3581:
3579:
3578:
3573:
3568:
3563:
3558:
3552:
3550:
3544:
3543:
3541:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3293:Andexanet alfa
3290:
3285:
3279:
3277:
3273:
3272:
3265:
3264:
3257:
3250:
3242:
3233:
3232:
3229:
3228:
3227:
3226:
3223:
3212:
3206:
3200:
3199:
3196:
3195:
3193:
3192:
3187:
3182:
3176:
3174:
3169:
3164:
3163:
3161:
3160:
3154:
3152:
3147:
3142:
3141:
3139:
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3093:
3088:
3083:
3078:
3072:
3070:
3065:
3060:
3059:
3057:
3056:
3051:
3046:
3041:
3036:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2981:
2979:
2972:
2971:
2959:
2958:
2951:
2944:
2936:
2930:
2929:
2900:
2897:
2894:
2893:
2864:
2835:(5): 167–170.
2815:
2797:
2793:978-3946057109
2776:
2735:
2692:
2616:
2540:
2484:
2469:
2450:(3): 202–207.
2434:
2405:(3): 139–143.
2385:
2352:
2325:
2298:(10): 1182–8.
2281:
2232:
2182:
2167:"Metoprolol".
2159:
2144:"Metoprolol".
2136:
2118:
2107:(2): 101–110.
2091:
2073:
2054:(2): 435–443.
2038:
2032:978-1416023203
2031:
2013:
1988:
1957:
1931:
1905:
1870:
1845:
1815:
1787:
1781:978-3527607495
1780:
1760:
1750:978-0792399728
1749:
1726:
1694:
1642:
1615:(5): 375–388.
1599:
1589:978-0781728454
1588:
1566:
1533:
1527:978-1455706051
1526:
1508:
1498:978-9350259658
1497:
1475:
1434:
1428:978-3852001814
1427:
1409:
1369:
1340:
1339:
1337:
1334:
1328:
1325:
1311:
1308:
1303:
1300:
1298:
1295:
1292:
1291:
1280:
1268:
1267:
1240:
1239:
1219:
1217:
1210:
1204:
1201:
1191:
1188:
1141:
1138:
1137:
1136:
1133:
1130:
1126:
1123:
1109:norepinephrine
1100:
1083:
1061:
1058:
1056:
1053:
1044:
1041:
1032:
1029:
1008:
1005:
980:
977:
933:
930:
913:polymorphism.
889:
856:
855:
844:
843:
841:
840:
837:
835:
832:
824:
823:
822:
819:
818:
816:
815:
812:
804:
803:
802:
799:
798:
795:
789:
788:
783:
777:
776:
774:
773:
765:
763:
755:
754:
748:
742:
741:
738:
729:
723:
718:
712:
711:
707:
706:
696:
688:
687:
685:
684:
671:
669:
656:
655:
653:
652:
644:
642:
636:
635:
633:
632:
624:
622:
616:
615:
613:
612:
604:
602:
596:
595:
593:
592:
584:
582:
576:
575:
573:
572:
564:
562:
556:
555:
553:
552:
544:
542:
536:
535:
533:
532:
524:
522:
516:
515:
513:
512:
504:
502:
491:
490:
488:
487:
479:
477:
471:
470:
468:
467:
460:
452:
451:
450:
447:
446:
442:
441:
436:
430:
429:
426:
417:
416:
403:
397:
396:
393:
387:
386:
381:
375:
374:
367:
366:
364:
363:
360:
348:
335:
324:
310:
308:
302:
301:
297:
296:
294:
293:
280:
278:
272:
271:
266:
260:
259:
250:
248:administration
242:
241:
239:
238:
236:
226:
224:
216:
215:
213:
212:
194:
192:
186:
185:
178:
172:
171:
164:
154:
153:
150:
144:
143:
53:
49:
48:
44:
43:
35:
34:
15:
9:
6:
4:
3:
2:
3715:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3673:Beta blockers
3671:
3669:
3666:
3665:
3663:
3653:
3643:
3642:
3639:
3626:
3618:
3616:
3608:
3607:
3604:
3598:
3595:
3593:
3590:
3589:
3587:
3583:
3577:
3574:
3572:
3569:
3567:
3564:
3562:
3559:
3557:
3554:
3553:
3551:
3545:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3348:Dapagliflozin
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3303:Asfotase alfa
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3283:Acalabrutinib
3281:
3280:
3278:
3274:
3270:
3263:
3258:
3256:
3251:
3249:
3244:
3243:
3240:
3224:
3222:
3219:
3218:
3216:
3213:
3210:
3207:
3205:
3202:
3201:
3197:
3191:
3188:
3186:
3183:
3181:
3178:
3177:
3175:
3172:
3165:
3159:
3156:
3155:
3153:
3150:
3143:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3092:
3089:
3087:
3084:
3082:
3079:
3077:
3074:
3073:
3071:
3068:
3061:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2982:
2980:
2977:
2973:
2968:
2964:
2963:Beta blockers
2957:
2952:
2950:
2945:
2943:
2938:
2937:
2934:
2926:
2922:
2918:
2914:
2913:
2908:
2903:
2902:
2881:
2877:
2871:
2869:
2860:
2856:
2851:
2846:
2842:
2838:
2834:
2830:
2826:
2819:
2811:
2807:
2801:
2794:
2790:
2786:
2780:
2761:
2757:
2753:
2746:
2739:
2731:
2727:
2723:
2719:
2715:
2711:
2707:
2703:
2696:
2688:
2682:
2674:
2670:
2665:
2660:
2655:
2650:
2646:
2642:
2638:
2634:
2630:
2623:
2621:
2612:
2606:
2598:
2594:
2590:
2586:
2582:
2578:
2574:
2570:
2563:
2561:
2559:
2557:
2555:
2553:
2551:
2549:
2547:
2545:
2536:
2532:
2527:
2522:
2517:
2512:
2508:
2504:
2500:
2493:
2491:
2489:
2480:
2473:
2465:
2461:
2457:
2453:
2449:
2445:
2438:
2430:
2426:
2421:
2416:
2412:
2408:
2404:
2400:
2396:
2389:
2381:
2377:
2373:
2369:
2365:
2364:
2356:
2348:
2344:
2340:
2334:
2332:
2330:
2321:
2317:
2313:
2309:
2305:
2301:
2297:
2293:
2285:
2277:
2273:
2268:
2263:
2259:
2255:
2252:(4): 3572–9.
2251:
2247:
2243:
2236:
2228:
2222:
2214:
2210:
2206:
2202:
2198:
2194:
2186:
2178:
2174:
2170:
2163:
2155:
2151:
2147:
2140:
2132:
2128:
2122:
2114:
2110:
2106:
2102:
2095:
2087:
2084:. Drugs.com.
2083:
2077:
2069:
2065:
2061:
2057:
2053:
2049:
2042:
2034:
2028:
2024:
2017:
2009:
2008:
2003:
1997:
1995:
1993:
1976:
1972:
1968:
1961:
1945:
1941:
1935:
1927:
1923:
1919:
1912:
1910:
1901:
1897:
1893:
1889:
1885:
1881:
1874:
1859:
1855:
1849:
1833:
1829:
1825:
1819:
1810:
1805:
1801:
1797:
1791:
1783:
1777:
1773:
1772:
1764:
1756:
1752:
1746:
1742:
1741:
1733:
1731:
1715:
1713:
1707:
1701:
1699:
1690:
1686:
1681:
1676:
1672:
1668:
1664:
1660:
1656:
1649:
1647:
1638:
1634:
1630:
1626:
1622:
1618:
1614:
1610:
1603:
1595:
1591:
1585:
1581:
1580:
1573:
1571:
1554:
1550:
1546:
1540:
1538:
1529:
1523:
1519:
1512:
1504:
1500:
1494:
1490:
1486:
1479:
1463:
1459:
1453:
1451:
1449:
1447:
1445:
1443:
1441:
1439:
1430:
1424:
1420:
1419:Austria-Codex
1413:
1394:
1390:
1388:
1379:
1373:
1357:
1356:
1355:Health Canada
1351:
1345:
1341:
1333:
1324:
1318:
1307:
1285:
1281:
1274:
1270:
1269:
1264:
1261:
1259:
1255:
1251:
1247:
1236:
1233:November 2022
1227:
1223:
1220:This section
1218:
1214:
1209:
1208:
1200:
1198:
1187:
1185:
1182:
1178:
1174:
1170:
1165:
1163:
1159:
1155:
1151:
1146:
1134:
1131:
1127:
1124:
1121:
1120:
1119:
1116:
1114:
1110:
1106:
1097:
1093:
1091:
1087:
1079:
1075:
1071:
1067:
1052:
1050:
1040:
1038:
1028:
1024:
1022:
1018:
1013:
1004:
1001:
998:
995:
991:
987:
976:
974:
973:thyroid storm
970:
965:
963:
959:
955:
951:
947:
943:
939:
929:
923:
919:
914:
912:
908:
904:
903:feeling tired
899:
897:
893:
886:
882:
878:
874:
870:
866:
862:
852:
845:
836:
831:
830:
827:
820:
811:
810:
807:
800:
796:
794:
793:Melting point
790:
787:
784:
782:
778:
771:
767:
766:
764:
761:
756:
749:
747:
743:
719:
717:
713:
708:
704:
700:
697:
695:
693:ECHA InfoCard
689:
681:
677:
676:DTXSID2023309
673:
672:
670:
661:
657:
650:
646:
645:
643:
641:
637:
630:
626:
625:
623:
621:
617:
610:
606:
605:
603:
601:
597:
590:
586:
585:
583:
581:
577:
570:
566:
565:
563:
561:
557:
550:
546:
545:
543:
541:
537:
530:
526:
525:
523:
521:
517:
510:
506:
505:
503:
496:
492:
485:
481:
480:
478:
476:
472:
464:
459:
458:
455:
448:
443:
440:
437:
435:
431:
427:
425:
418:
415:
411:
407:
404:
402:
398:
394:
392:
388:
382:
380:
376:
372:
368:
361:
359:
349:
346:
336:
334:
325:
322:
312:
311:
309:
307:
303:
298:
290:
285:
282:
281:
279:
277:
273:
270:
267:
265:
261:
258:
254:
251:
249:
243:
237:
228:
227:
225:
223:
217:
210:
205:
196:
195:
193:
191:
187:
183:
179:
177:
173:
169:
165:
163:
159:
155:
151:
149:
145:
139:
95:
54:
52:Pronunciation
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
3592:Tom McKillop
3538:Zolmitriptan
3528:Ximelagatran
3458:Rosuvastatin
3407:
3368:Esomeprazole
3318:Bicalutamide
3313:Benralizumab
3120:
3034:Iodopindolol
2911:
2884:. Retrieved
2879:
2832:
2828:
2818:
2809:
2800:
2784:
2779:
2767:. Retrieved
2760:the original
2755:
2751:
2738:
2705:
2701:
2695:
2681:cite journal
2636:
2632:
2605:cite journal
2572:
2568:
2506:
2502:
2478:
2472:
2447:
2443:
2437:
2402:
2398:
2388:
2361:
2355:
2342:
2295:
2291:
2284:
2249:
2245:
2235:
2221:cite journal
2196:
2192:
2185:
2168:
2162:
2145:
2139:
2130:
2121:
2104:
2100:
2094:
2082:"Metoprolol"
2076:
2051:
2047:
2041:
2022:
2016:
2005:
1981:24 September
1979:. Retrieved
1970:
1960:
1950:24 September
1948:. Retrieved
1943:
1934:
1917:
1886:(1): 61–68.
1883:
1879:
1873:
1861:. Retrieved
1857:
1848:
1836:. Retrieved
1827:
1818:
1809:10665/371090
1799:
1790:
1770:
1763:
1739:
1717:. Retrieved
1709:
1665:(3): 394–9.
1662:
1658:
1612:
1608:
1602:
1578:
1557:. Retrieved
1548:
1517:
1511:
1488:
1478:
1466:. Retrieved
1458:"Metoprolol"
1418:
1412:
1400:. Retrieved
1384:
1372:
1360:. Retrieved
1353:
1344:
1330:
1313:
1305:
1302:Legal status
1257:
1256:)- and the (
1253:
1248:. This is a
1243:
1230:
1226:adding to it
1221:
1193:
1184:side effects
1166:
1147:
1143:
1117:
1098:
1094:
1066:beta blocker
1063:
1055:Pharmacology
1046:
1034:
1025:
1014:
1010:
1002:
999:
982:
966:
935:
932:Medical uses
915:
900:
884:
864:
860:
859:
848:
462:
421:Elimination
306:Legal status
300:Legal status
269:Beta blocker
190:License data
18:
3533:Zafirlukast
3488:Selumetinib
3478:Saxagliptin
3473:Savolitinib
3453:Roflumilast
3448:Ravulizumab
3433:Palivizumab
3428:Osimertinib
3413:Motavizumab
3383:Fulvestrant
3343:Candesartan
3298:Anifrolumab
3288:Anastrozole
3269:AstraZeneca
3211:from market
3039:Propranolol
2292:Circulation
2007:Mayo Clinic
1246:enantiomers
1197:formulation
1152:(primary),
1088:and has no
1007:Precautions
994:propranolol
753: g·mol
699:100.051.952
445:Identifiers
257:intravenous
176:MedlinePlus
148:Trade names
3662:Categories
3518:Vandetanib
3503:Ticagrelor
3463:Roxadustat
3443:Quetiapine
3423:Omeprazole
3408:Metoprolol
3363:Eculizumab
3358:Durvalumab
3328:Budesonide
3185:Carvedilol
3180:Arotinolol
3158:Butaxamine
3151:-selective
3121:Metoprolol
3101:Celiprolol
3096:Bisoprolol
3091:Bevantolol
3076:Acebutolol
3069:-selective
3049:Tertatolol
3025:Penbutolol
3020:Oxprenolol
3010:Mepindolol
3005:Cloranolol
2995:Bupranolol
2990:Bopindolol
2985:Alprenolol
2509:(2): 155.
2023:Physiology
1918:StatPearls
1336:References
1169:lipophilic
1070:antagonist
990:lipophilic
905:, feeling
883:. It is a
861:Metoprolol
758:3D model (
746:Molar mass
629:CHEBI:6904
589:GEB06NHM23
560:ChemSpider
520:IUPHAR/BPS
484:51384-51-1
475:CAS Number
454:IUPAC name
401:Metabolism
264:Drug class
209:Metoprolol
23:Metoprolol
3571:MedImmune
3523:Vaxzevria
3498:Tamoxifen
3398:Goserelin
3388:Gefitinib
3373:Exenatide
3221:Phase III
3209:Withdrawn
3190:Labetalol
3136:Talinolol
3131:Practolol
3126:Nebivolol
3116:Landiolol
3086:Betaxolol
3000:Carteolol
2795:, S. 200.
2597:250094483
1944:Drugs.com
1863:30 August
1838:30 August
1323:million.
1310:Economics
1190:Chemistry
1078:selective
885:selective
881:migraines
865:Lopressor
781:Chirality
434:Excretion
428:3–7 hours
423:half-life
246:Routes of
220:Pregnancy
168:Monograph
162:Drugs.com
3652:Medicine
3615:Category
3556:Astra AB
3438:Propofol
3418:Olaparib
3308:Atenolol
3276:Products
3106:Epanolol
3081:Atenolol
3030:Pindolol
2925:28520381
2919:(NCBI).
2859:26648655
2722:16176119
2673:26203906
2633:PLOS ONE
2589:35764772
2535:33572109
2503:Medicina
2464:15484221
2429:19655287
2380:25820938
2347:Archived
2320:24119608
2312:11889011
2276:23796325
2213:10714728
2177:35952115
2154:30000215
2113:21180298
2086:Archived
2068:27040294
1975:Archived
1926:30422518
1858:ClinCalc
1832:Archived
1828:ClinCalc
1798:(2023).
1755:Archived
1689:23665868
1594:Archived
1559:22 April
1553:Archived
1503:Archived
1468:21 April
1462:Archived
1393:Archived
1260:)-form:
1250:racemate
1068:, or an
1043:Overdose
896:by mouth
851:(verify)
649:ChEMBL13
540:DrugBank
276:ATC code
253:By mouth
222:category
204:DailyMed
3625:Commons
3378:FluMist
3111:Esmolol
3054:Timolol
3044:Sotalol
3015:Nadolol
2886:20 June
2850:4657305
2730:1570605
2664:4512675
2641:Bibcode
2526:7914867
2420:3550395
2267:3819624
1900:1352658
1719:20 June
1680:3818912
1637:1042204
1629:7333059
1362:20 June
1072:of the
751:267.369
716:Formula
549:DB00264
495:PubChem
331::
292:)
286: (
284:C07AB02
235: C
206::
182:a682864
3638:Portal
3585:People
3576:Zeneca
3204:WHO-EM
2923:
2857:
2847:
2791:
2769:6 July
2728:
2720:
2671:
2661:
2595:
2587:
2533:
2523:
2462:
2427:
2417:
2378:
2318:
2310:
2274:
2264:
2211:
2175:
2152:
2111:
2066:
2029:
1924:
1898:
1778:
1747:
1687:
1677:
1635:
1627:
1586:
1524:
1495:
1425:
1321:
1162:CYP2C9
1160:, and
1158:CYP2B6
1154:CYP3A4
1150:CYP2D6
938:angina
926:
911:CYP2D6
869:angina
806:SMILES
640:ChEMBL
609:D02358
439:Kidney
414:CYP3A4
410:CYP2D6
358:℞-only
356:
343:
333:℞-only
319:
202:
142:
2763:(PDF)
2748:(PDF)
2726:S2CID
2593:S2CID
2316:S2CID
1714:(FDA)
1710:U.S.
1633:S2CID
1402:5 May
1396:(PDF)
1389:(FDA)
1385:U.S.
1381:(PDF)
1327:Sport
907:faint
826:InChI
760:JSmol
620:ChEBI
406:Liver
2921:PMID
2888:2023
2855:PMID
2789:ISBN
2771:2012
2718:PMID
2687:link
2669:PMID
2611:link
2585:PMID
2531:PMID
2460:PMID
2425:PMID
2376:PMID
2308:PMID
2272:PMID
2227:link
2209:PMID
2193:JAMA
2173:PMID
2150:PMID
2109:PMID
2064:PMID
2027:ISBN
1983:2019
1952:2019
1922:PMID
1896:PMID
1865:2024
1840:2024
1776:ISBN
1745:ISBN
1721:2023
1685:PMID
1625:PMID
1584:ISBN
1561:2014
1522:ISBN
1493:ISBN
1470:2014
1423:ISBN
1404:2015
1364:2023
971:and
600:KEGG
580:UNII
569:4027
509:4171
408:via
373:data
158:AHFS
2967:C07
2845:PMC
2837:doi
2710:doi
2659:PMC
2649:doi
2577:doi
2521:PMC
2511:doi
2452:doi
2415:PMC
2407:doi
2368:doi
2300:doi
2296:105
2262:PMC
2254:doi
2250:168
2201:doi
2197:283
2056:doi
1888:doi
1804:hdl
1675:PMC
1667:doi
1617:doi
1228:.
665:EPA
529:553
499:CID
395:12%
345:POM
289:WHO
3664::
3217::
2915:.
2878:.
2867:^
2853:.
2843:.
2833:38
2831:.
2827:.
2808:.
2756:25
2754:.
2750:.
2724:.
2716:.
2706:44
2704:.
2683:}}
2679:{{
2667:.
2657:.
2647:.
2637:10
2635:.
2631:.
2619:^
2607:}}
2603:{{
2591:.
2583:.
2573:61
2571:.
2543:^
2529:.
2519:.
2507:57
2505:.
2501:.
2487:^
2458:.
2448:19
2446:.
2423:.
2413:.
2401:.
2397:.
2374:.
2341:.
2328:^
2314:.
2306:.
2294:.
2270:.
2260:.
2248:.
2244:.
2223:}}
2219:{{
2207:.
2195:.
2129:.
2105:62
2103:.
2062:.
2052:60
2050:.
2004:.
1991:^
1973:.
1969:.
1942:.
1908:^
1894:.
1884:93
1882:.
1856:.
1830:.
1826:.
1753:.
1729:^
1708:.
1697:^
1683:.
1673:.
1663:94
1661:.
1657:.
1645:^
1631:.
1623:.
1611:.
1592:.
1569:^
1547:.
1536:^
1501:.
1487:.
1437:^
1391:.
1383:.
1352:.
1156:,
1092:.
1015:A
988:,
975:.
952:,
948:,
944:,
940:,
730:25
724:15
463:RS
412:,
352:US
339:UK
328:CA
321:S4
315:AU
255:,
231:AU
199:US
132:ɑː
126:oʊ
114:oʊ
98:,
88:ɑː
82:oʊ
73:oʊ
3640::
3261:e
3254:t
3247:v
3170:1
3168:α
3148:2
3146:β
3066:1
3064:β
3032:/
2976:β
2969:)
2965:(
2955:e
2948:t
2941:v
2890:.
2861:.
2839::
2773:.
2732:.
2712::
2689:)
2675:.
2651::
2643::
2613:)
2599:.
2579::
2537:.
2513::
2466:.
2454::
2431:.
2409::
2403:5
2382:.
2370::
2322:.
2302::
2278:.
2256::
2229:)
2215:.
2203::
2179:.
2156:.
2115:.
2070:.
2058::
2035:.
2010:.
1985:.
1954:.
1928:.
1902:.
1890::
1867:.
1842:.
1806::
1784:.
1723:.
1691:.
1669::
1639:.
1619::
1613:6
1563:.
1530:.
1472:.
1431:.
1406:.
1366:.
1258:S
1254:R
1235:)
1231:(
1101:1
1084:1
1082:β
890:1
888:β
762:)
739:3
736:O
733:N
727:H
721:C
667:)
663:(
461:(
354::
341::
317::
233::
160:/
138:/
135:l
129:l
123:r
120:p
117:ˈ
111:t
108:ɛ
105:m
102:/
94:/
91:l
85:l
79:r
76:p
70:t
67:ˈ
64:ɛ
61:m
58:/
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
