Knowledge (XXG)

Pyridostigmine

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461: 45: 36: 3134: 1438: 1431: 1872: 838:. It carbamylates about 30% of peripheral cholinesterase enzyme, and the carbamylated enzyme eventually regenerates by natural hydrolysis and excess acetylcholine (ACh) levels revert to normal. 1918: 1424: 1317:
Kanjwal K, Karabin B, Sheikh M, Elmer L, Kanjwal Y, Saeed B, Grubb BP (June 2011). "Pyridostigmine in the treatment of postural orthostatic tachycardia: a single-center experience".
3179: 845:(Na,) resulting in depolarization. If large enough, this depolarization results in an action potential. To prevent constant stimulation once the ACh is released, an enzyme called 3106: 159: 3111: 741:
Pyridostigmine bromide is contraindicated in cases of mechanical intestinal or urinary obstruction and should be used with caution in patients with bronchial asthma.
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drug toxicity. Pyridostigmine bromide has been FDA approved for military use during combat situations as an agent to be given prior to exposure to the nerve agent
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Common side effects include nausea, diarrhea, frequent urination, and abdominal pain. More severe side effects include
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is present in the endplate membrane close to the receptors on the post synaptic membrane, and quickly hydrolyses ACh.
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The ACh diffuses across the synaptic cleft and binds to receptors on the post synaptic membrane, causing an influx of
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but can also be used by injection. The effects generally begin within 45 minutes and last up to 4 hours.
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Gales BJ, Gales MA (February 2007). "Pyridostigmine in the treatment of orthostatic intolerance".
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Gales BJ, Gales MA (February 2007). "Pyridostigmine in the treatment of orthostatic intolerance".
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Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM (November 2021).
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Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM (November 2021).
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Pyridostigmine was patented in 1945 and came into medical use in 1955. It is on the
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Proceedings of the National Academy of Sciences of the United States of America
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World Health Organization model list of essential medicines: 21st list 2019
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Pyridostigmine bromide is available under the trade name Mestinon (
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in order to increase survival. Used in particular during the first
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InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
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Pyridostigmine is used to treat muscle weakness in people with
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Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
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2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
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family of medications. It works by blocking the action of
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Mestinon Official FDA information, side effects and uses
1095:"Acetylcholinesterase inhibitors and Gulf War illnesses" 1052:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 662:
World Health Organization's List of Essential Medicines
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and underactive bladder. It is also used together with
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inhibitor of cholinesterase that does not cross the
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Pyridostigmine is an 26: 3112:Nicotinic acetylcholine receptor modulators 2991:Tooltip Vesicle-associated membrane protein 2904:Tooltip Vesicular acetylcholine transporter 2858: 2960:Tooltip Synaptosomal-associated protein 25 2941: 2853: 1478: 1439: 1425: 1417: 973: 971: 969: 967: 965: 963: 961: 959: 957: 885:. World Health Organization. p. 429. 710:Pyridostigmine sometimes is used to treat 459: 368: 43: 34: 16:Medication used to treat myasthenia gravis 1136: 1118: 1047: 727:postural orthostatic tachycardia syndrome 388: 3129: 2064:Dimethyl 4-(methylthio)phenyl phosphate 1064:"Competitive Generic Therapy Approvals" 870: 573: 553: 455: 348: 283: 90: 1010:. John Wiley & Sons. p. 540. 861:), Regonol and Gravitor (SUN Pharma). 653:and therefore increases the levels of 25: 2254:Methylfluorophosphonylcholine (MFPCh) 1504:2-(α-Naphthoyl)ethyltrimethylammonium 1319:Pacing and Clinical Electrophysiology 1160:Steenhuysen, Julie (March 10, 2008). 1042:. Geneva: World Health Organization. 985:from the original on 21 December 2016 428: 76: 7: 1412:. U.S. National Library of Medicine. 171: 3051: 1554:N,N-Dimethylaminoethylchloroacetate 780:Facial flushing due to vasodilation 664:. Pyridostigmine is available as a 408: 319: 14: 1488:Tooltip Choline acetyltransferase 787:Additional side effects include: 616:neuromuscular blocking medication 3132: 2548:Fasciculins (green mamba toxins) 2039:Dicyclohexyl phosphorofluoridate 1331:10.1111/j.1540-8159.2011.03047.x 1024:from the original on 2016-12-20. 494: 488: 3155:Acetylcholinesterase inhibitors 2479:Tetraethyl pyrophosphate (TEPP) 2204:Hexaethyl tetraphosphate (HETP) 1004:Fischer J, Ganellin CR (2006). 581:Key:RVOLLAQWKVFTGE-UHFFFAOYSA-N 1549:N,N-Dimethylaminoethylacrylate 805:acetylcholinesterase inhibitor 774:Increased bronchial secretions 682:congenital myasthenic syndrome 643:acetylcholinesterase inhibitor 606:is a medication used to treat 500: 482: 149:Acetylcholinesterase inhibitor 1: 3102:Receptor/signaling modulators 2874:Hemicholinium-3 (hemicholine) 2773:Tooltip Butyrylcholinesterase 1276:The Annals of Pharmacotherapy 1230:The Annals of Pharmacotherapy 1007:Analogue-based Drug Discovery 749:Common side effects include: 684:and to combat the effects of 3170:Peripherally selective drugs 1569:Tooltip Acetylcholinesterase 1187:Neurourology and Urodynamics 1070:Food and Drug Administration 920:Neurourology and Urodynamics 721:It is also being prescribed 622:type. It is typically given 2863:Tooltip Choline transporter 2809:Profenamine (ethopropazine) 2049:Diisopropyl fluorophosphate 1514:4-(1-Naphthylvinyl)pyridine 1499:1-(-Benzoylethyl)pyridinium 3196: 2712:Dimethylcarbamoyl fluoride 1519:Acetylseco hemicholinium-3 794:Muscle cramps and weakness 637:. It is unclear if use in 472:Chemical and physical data 18: 3094: 1036:World Health Organization 879:World Health Organization 589: 564: 544: 274: 42: 33: 2582:Methanesulfonyl fluoride 1093:Golomb BA (March 2008). 883:WHO Model Formulary 2008 818:, thus slowing down the 19:Not to be confused with 3165:Dimethylamino compounds 1759:+glycopyrronium bromide 1410:Drug Information Portal 1120:10.1073/pnas.0711986105 859:Valeant Pharmaceuticals 826:. Like its predecessor 712:orthostatic hypotension 1509:3-Chloro-4-stillbazole 731:Ehlers–Danlos syndrome 614:to end the effects of 979:"Neostigmine Bromide" 830:, it is a quaternary 803:Pyridostigmine is an 556:O=C(Oc1ccc(c1)C)N(C)C 286:3--1-methylpyridinium 3175:Pyridinium compounds 3070:Atracotoxins (e.g., 2697:Tetrahydrocannabinol 2044:Diisopropylphosphate 847:acetylcholinesterase 812:acetylcholinesterase 783:Erectile dysfunction 768:Increased salivation 651:acetylcholinesterase 3160:Aromatic carbamates 3056:Tooltip Latrophilin 2758:Trimedoxime bromide 2687:Stercuronium iodide 2504:Tricresyl phosphate 1979:Chlorpyrifos-methyl 1111:2008PNAS..105.4295G 836:blood–brain barrier 799:Mechanism of action 705:parasympathomimetic 207:(Prescription only) 153:Parasympathomimetic 30: 2575:Onchidella binneyi 1917:Organophosphates: 1388:2008-05-24 at the 1370:2008-05-13 at the 777:Constricted pupils 666:generic medication 635:allergic reactions 631:low blood pressure 3120: 3119: 3090: 3089: 2938: 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765:Abdominal cramps 633:, weakness, and 620:non-depolarizing 597: 596: 537: 517: 502: 496: 490: 484: 464: 463: 449: 447: 432: 412: 392: 372: 352: 332: 322: 321: 307: 249: 213: 210: 200: 197: 175: 112: 109: 94: 80: 62:Mestinon, others 47: 38: 31: 29: 3195: 3194: 3190: 3189: 3188: 3186: 3185: 3184: 3145: 3144: 3143: 3133: 3131: 3123: 3121: 3116: 3086: 3055: 3036: 2996:Botulinum toxin 2990: 2965:Botulinum toxin 2959: 2931: 2919: 2903: 2893: 2879:Triethylcholine 2862: 2843: 2831: 2772: 2762: 2682:Rosmarinic acid 2449:Sulfotep (TEDP) 2119:Ethylsarin (GE) 1999:Cyclosarin (GF) 1969:Chlorfenvinphos 1959:Carbophenothion 1939:Azinphos-methyl 1568: 1558: 1524:Acryloylcholine 1487: 1468: 1460: 1445: 1404: 1401: 1396: 1395: 1390:Wayback Machine 1381: 1377: 1372:Wayback Machine 1365:Mestinon | Home 1363: 1354: 1316: 1315: 1311: 1273: 1272: 1265: 1227: 1226: 1222: 1180: 1179: 1175: 1159: 1158: 1154: 1092: 1091: 1087: 1077: 1075: 1062: 1061: 1057: 1034: 1033: 1029: 1018: 1003: 1002: 998: 988: 986: 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1779:Quilostigmine 1777: 1775: 1772: 1770: 1769:Physostigmine 1767: 1765: 1762: 1760: 1757: 1754: 1752: 1749: 1747: 1744: 1742: 1739:; Stigmines: 1738: 1735: 1733: 1730: 1728: 1725: 1723: 1720: 1718: 1715: 1713: 1710: 1708: 1705: 1703: 1700: 1698: 1695: 1693: 1690: 1688: 1685: 1683: 1680: 1678: 1675: 1673: 1670: 1668: 1665: 1663: 1660: 1658: 1655: 1653: 1650: 1648: 1645: 1643: 1640: 1638: 1637:Chloropropham 1635: 1633: 1630: 1628: 1625: 1623: 1620: 1618: 1615: 1613: 1610: 1608: 1605: 1603: 1600: 1598: 1595: 1593: 1590: 1588: 1584: 1581: 1579: 1575: 1574: 1572: 1567: 1561: 1555: 1552: 1550: 1547: 1545: 1542: 1540: 1537: 1535: 1532: 1530: 1527: 1525: 1522: 1520: 1517: 1515: 1512: 1510: 1507: 1505: 1502: 1500: 1497: 1494: 1493: 1491: 1486: 1480: 1477: 1473: 1467: 1463: 1459: 1456: 1452: 1449: 1448:Acetylcholine 1442: 1437: 1435: 1430: 1428: 1423: 1422: 1419: 1411: 1407: 1403: 1402: 1398: 1391: 1387: 1384: 1379: 1376: 1373: 1369: 1366: 1361: 1359: 1357: 1353: 1348: 1344: 1340: 1336: 1332: 1328: 1324: 1320: 1313: 1310: 1305: 1301: 1297: 1293: 1289: 1285: 1281: 1277: 1270: 1268: 1264: 1259: 1255: 1251: 1247: 1243: 1239: 1235: 1231: 1224: 1221: 1216: 1212: 1208: 1204: 1200: 1196: 1192: 1188: 1184: 1177: 1174: 1169: 1168: 1163: 1156: 1153: 1148: 1144: 1139: 1134: 1130: 1126: 1121: 1116: 1112: 1108: 1104: 1100: 1096: 1089: 1086: 1073: 1071: 1065: 1059: 1056: 1050: 1045: 1041: 1037: 1031: 1028: 1023: 1019: 1017:9783527607495 1013: 1009: 1008: 1000: 997: 984: 980: 974: 972: 970: 968: 966: 964: 962: 960: 958: 954: 949: 945: 941: 937: 933: 929: 925: 921: 917: 910: 907: 902: 900:9789241547659 896: 892: 888: 884: 880: 874: 871: 864: 862: 860: 852: 850: 848: 844: 839: 837: 833: 829: 825: 824:acetylcholine 821: 817: 813: 810: 806: 798: 793: 790: 789: 788: 782: 779: 776: 773: 770: 767: 764: 761: 758: 755: 752: 751: 750: 744: 742: 736: 734: 732: 728: 724: 719: 717: 713: 708: 706: 701: 699: 695: 691: 687: 683: 679: 671: 669: 667: 663: 658: 656: 655:acetylcholine 652: 648: 644: 640: 636: 632: 627: 625: 621: 617: 613: 609: 605: 595: 588: 579: 574: 570: 563: 554: 550: 543: 536: 532: 531: 529: 526: 521: 514: 512: 508: 481: 479: 475: 470: 462: 458: 454: 453: 451: 442: 438: 431: 427: 426: 424: 422: 418: 411: 407: 406: 404: 402: 398: 391: 387: 386: 384: 382: 378: 371: 367: 366: 364: 362: 358: 351: 347: 346: 344: 342: 338: 331: 327: 326: 324: 317: 313: 306: 302: 301: 299: 297: 293: 284: 280: 273: 268: 265: 262: 260: 256: 252: 250: 243: 239: 237: 233: 229: 225: 219: 209: 206: 196: 195: 193: 191: 187: 182: 174: 169: 166: 165: 163: 161: 157: 154: 150: 147: 145: 141: 138: 134: 131: 129: 123: 117: 108: 107: 105: 103: 97: 93: 89: 87: 83: 79: 75: 73: 69: 65: 61: 59: 55: 52:Clinical data 50: 46: 41: 37: 32: 22: 21:Physostigmine 3067: 3061:α-Latrotoxin 3049: 3019: 2984: 2953: 2911: 2885: 2870: 2814:Rivastigmine 2780: 2734:Reactivators 2707:Ungiminorine 2662:Kobophenol A 2627:Coronaridine 2617:Bulbocapnine 2612:Arisugacin A 2588: 2573: 2459:Tebupirimfos 2339:Phosphamidon 2244:Methidathion 2149:Fenitrothion 1974:Chlorpyrifos 1914: 1789:Terestigmine 1784:Rivastigmine 1773: 1746:Eptastigmine 1697:Phenmedipham 1667:Formparanate 1652:Ethiofencarb 1585:Carbamates: 1582: 1576: 1495: 1409: 1378: 1322: 1318: 1312: 1279: 1275: 1233: 1229: 1223: 1190: 1186: 1176: 1165: 1155: 1102: 1098: 1088: 1076:. Retrieved 1067: 1058: 1049:10665/325771 1039: 1030: 1006: 999: 987:. Retrieved 923: 919: 909: 882: 873: 856: 840: 802: 786: 748: 745:Side effects 740: 720: 709: 702: 680:or forms of 675: 672:Medical uses 659: 628: 603: 602: 591:   246:Elimination 190:Legal status 184:Legal status 2912:Inhibitors: 2889:Coluracetam 2871:Inhibitors: 2841:Transporter 2781:Inhibitors: 2753:Pralidoxime 2647:Cyclanoline 2597:α-Viniferin 2494:Trichlorfon 2259:Metrifonate 2174:Fosthiazate 2159:Fluorotabun 2034:Dicrotophos 1989:Crotylsarin 1833:Huperzine A 1828:Galantamine 1823:Edrophonium 1756:Neostigmine 1751:Ganstigmine 1717:Propamocarb 1662:Formetanate 1647:Ethienocarb 1627:Carbosulfan 1617:Carbetamide 1612:Carbendazim 1583:Reversible: 1496:Inhibitors: 891:10665/44053 828:neostigmine 647:cholinergic 518: g·mol 270:Identifiers 137:intravenous 86:MedlinePlus 58:Trade names 3149:Categories 3076:versutoxin 3072:robustoxin 2946:Inhibitors 2935:modulators 2886:Enhancers: 2847:modulators 2804:Ladostigil 2794:Conodurine 2789:Affinisine 2702:Ungeremine 2677:Phosacetim 2637:Corynoline 2632:Corydaline 2622:Conodurine 2607:Affinisine 2543:Demecarium 2541:; Others: 2454:Tabun (GA) 2444:Soman (GD) 2434:Sarin (GB) 2354:Profenofos 2214:Isoxathion 2199:Guanitoxin 2169:Formothion 2144:Fenamiphos 2074:Disulfoton 2069:Dioxathion 2059:Dimethoate 2029:Dichlorvos 1863:Ladostigil 1853:Ipidacrine 1798:Ambenonium 1793:Acotiamide 1791:; Others: 1764:Phenserine 1741:Distigmine 1732:Thiodicarb 1707:Pirimicarb 1672:Methiocarb 1657:Fenobucarb 1632:Chlorbufam 1622:Carbofuran 1597:Bendiocarb 1578:Inhibitors 1472:modulators 1458:modulators 1451:metabolism 989:8 December 865:References 820:hydrolysis 686:curariform 523:3D model ( 511:Molar mass 430:ChEMBL1115 390:19QM69HH21 361:ChemSpider 296:CAS Number 279:IUPAC name 240:7.6 ± 2.4% 144:Drug class 3058:agonists: 3042:Enhancers 2915:Vesamicol 2799:Cymserine 2748:Obidoxime 2743:Methoxime 2657:Harmaline 2652:Cymserine 2642:Crimidine 2589:Unsorted: 2484:Triazofos 2424:Ro 3-0433 2419:Ro 3-0422 2414:Ro 3-0419 2409:Ro 3-0417 2404:Ro 3-0412 2399:Ro 3-0411 2394:Ro 3-0397 2389:Ro 3-0352 2384:Ro 3-0351 2379:Ro 3-0347 2374:Ro 3-0346 2369:Ro 3-0340 2359:Prothoate 2329:Phosfolan 2324:Phosalone 2309:Parathion 2294:Omethoate 2264:Mevinphos 2229:Malathion 2219:Leptophos 2124:Endothion 2004:Demephion 1994:Cyanophos 1984:Coumaphos 1954:Cadusafos 1949:Bensulide 1944:BAY-29952 1908:Zanapezil 1868:Minaprine 1848:Huprine Y 1843:Huprine X 1838:Huprine W 1808:Donepezil 1737:Thiofanox 1712:Promecarb 1702:Pinmicarb 1682:Metolcarb 1642:Dimetilan 1602:Bufencarb 1592:Aminocarb 1544:CM-54,903 1455:transport 1215:244530010 948:244530010 832:carbamate 723:off-label 639:pregnancy 259:Excretion 248:half-life 126:Routes of 100:Pregnancy 78:Monograph 72:Drugs.com 3139:Medicine 3098:See also 3082:Crotoxin 2784:Affinine 2717:BW284C51 2672:Lycorine 2602:Affinine 2592:α-Pinene 2570:Onchidal 2489:Tribufos 2469:Terbufos 2439:Schradan 2304:Paraoxon 2224:Malaoxon 2154:Fenthion 2139:Ethoprop 2024:Diazinon 2019:Dialifor 1924:Acephate 1858:Itopride 1803:Caffeine 1727:Propoxur 1677:Methomyl 1607:Carbaryl 1587:Aldicarb 1386:Archived 1368:Archived 1347:20405336 1339:21410722 1304:22855759 1296:17284509 1258:22855759 1250:17284509 1207:34816481 1147:18332428 1129:25461411 1038:(2019). 1022:Archived 983:Archived 940:34816481 809:inhibits 762:Vomiting 756:Diarrhea 753:Sweating 694:Gulf War 624:by mouth 612:atropine 594:(verify) 341:DrugBank 305:155-97-5 160:ATC code 133:By mouth 102:category 3068:Others: 3020:Others: 2956:SNAP-25 2929:Release 2819:Tacrine 2727:3152 CT 2692:Taspine 2464:Temefos 2364:R-16661 2334:Phosmet 2319:Phorate 2269:Mipafox 2234:Mazidox 2164:Fonofos 2109:EA-4352 2104:EA-3148 2099:EA-2613 2094:EA-2192 2089:EA-2098 2084:EA-2054 2079:EA-2012 2054:Dimefox 2009:Demeton 1903:Tacrine 1898:TL-1238 1818:EA-4056 1813:EA-3990 1722:Propham 1687:Miotine 1167:Reuters 1138:2393741 1107:Bibcode 1078:6 March 814:in the 771:Tearing 645:in the 618:of the 516:181.215 478:Formula 350:DB00545 316:PubChem 176:) 170: ( 168:N07AA02 115: C 92:a682229 3125:Portal 2429:Ronnel 2344:Phoxim 2134:Ethion 1929:Armine 1893:TL-599 1888:T-1194 1883:T-1152 1878:T-1123 1692:Oxamyl 1466:Enzyme 1345:  1337:  1302:  1294:  1256:  1248:  1213:  1205:  1145:  1135:  1127:  1014:  946:  938:  897:  843:sodium 759:Nausea 549:SMILES 421:ChEMBL 410:C07410 264:kidney 218:℞-only 216: 203: 2900:VAChT 2722:TMTFA 2284:Naled 2189:GT-45 2179:GD-42 1529:AF64A 1343:S2CID 1300:S2CID 1254:S2CID 1211:S2CID 1125:JSTOR 1072:(FDA) 1068:U.S. 944:S2CID 853:Names 807:. It 690:Soman 569:InChI 525:JSmol 3052:LPHN 2987:VAMP 2769:BChE 2279:MSPI 1565:AChE 1539:BETA 1534:B115 1484:ChAT 1453:and 1335:PMID 1292:PMID 1246:PMID 1203:PMID 1143:PMID 1080:2023 1012:ISBN 991:2016 936:PMID 895:ISBN 725:for 401:KEGG 381:UNII 370:4817 330:4991 230:data 68:AHFS 2859:CHT 2129:EPN 1327:doi 1284:doi 1238:doi 1195:doi 1133:PMC 1115:doi 1103:105 1044:hdl 928:doi 887:hdl 822:of 446:EPA 320:CID 205:POM 173:WHO 3151:: 3074:, 3029:, 3010:, 3006:, 3002:, 2975:, 2971:, 2736:: 2562:, 2558:, 2554:, 2539:VX 2534:VR 2529:VS 2524:VP 2519:VM 2514:VG 2509:VE 2194:GV 2184:GH 1408:. 1355:^ 1341:. 1333:. 1323:34 1321:. 1298:. 1290:. 1280:41 1278:. 1266:^ 1252:. 1244:. 1234:41 1232:. 1209:. 1201:. 1191:41 1189:. 1185:. 1164:. 1141:. 1131:. 1123:. 1113:. 1101:. 1097:. 1066:. 1020:. 956:^ 942:. 934:. 924:41 922:. 918:. 893:. 733:. 718:. 700:. 668:. 657:. 492:13 212:US 199:UK 151:; 135:, 111:AU 3127:: 3078:) 3033:) 3025:( 3014:) 3012:G 3008:F 3004:D 3000:B 2998:( 2979:) 2977:E 2973:C 2969:A 2967:( 2937:) 2933:( 2849:) 2845:( 2578:) 2572:( 2566:) 2564:4 2560:3 2556:2 2552:1 2550:( 1580:: 1474:) 1470:( 1440:e 1433:t 1426:v 1349:. 1329:: 1306:. 1286:: 1260:. 1240:: 1217:. 1197:: 1170:. 1149:. 1117:: 1109:: 1082:. 1046:: 993:. 950:. 930:: 903:. 889:: 527:) 504:2 501:O 498:2 495:N 489:H 486:9 483:C 448:) 444:( 214:: 201:: 113:: 70:/ 23:.

Index

Physostigmine


Trade names
AHFS
Drugs.com
Monograph
MedlinePlus
a682229
Pregnancy
category

Routes of
administration

By mouth
intravenous
Drug class
Acetylcholinesterase inhibitor
Parasympathomimetic
ATC code
N07AA02
WHO
Legal status
POM
℞-only
Pharmacokinetic
Bioavailability
Elimination half-life
Excretion
kidney
IUPAC name
CAS Number
155-97-5

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