370:
347:
31:
40:
777:
990:
1573:
1566:
749:, determined sulfanilamide as the active form, are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.
1559:
998:
768:
was passed. It was only the solvent and not the sulfanilamide that was the problem, as sulfanilamide was widely and safely used at the time in both tablet and powder form.
1312:"The Antimicrobial Drugs, Second Edition by Eric Scholar and William Pratt New York: Oxford University Press, 2000. 607 pp., illustrated. $ 98.50 (cloth); $ 69.50 (paper)"
2290:
2285:
1510:
Bovet D (1988). "Les étapes de la découverte de la sulfamidochrysoïdine dans les laboratoires de recherche de la firme Bayer à Wuppertal-Elberfeld (1927–1932)".
2086:
708:
Sulfanilamide was first prepared in 1908 by the
Austrian chemist Paul Josef Jakob Gelmo (1879–1961) as part of his dissertation for a doctoral degree from the
71:
568:
to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars. Sulfanilamide is rarely if ever used
1932:
956:
2235:
52:
476:
1442:
On May 18, 1909, Deutsches Reich
Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
1145:
862:
Since sulfanilamide is used almost exclusively in topical vaginal preparations these days, adverse effects are typically limited to
912:
2828:
1925:
1286:
1219:
1095:
2039:
521:
442:
973:
1984:
1252:
496:
2872:
2845:
2128:
1918:
1551:
1526:
1012:
124:
2717:
1117:
681:
do not synthesize their own folic acid so are unaffected by PABA inhibitors, which selectively kill bacteria.
2534:
2420:
2275:
1171:"Sulfa drug screening in yeast: fifteen sulfa drugs compete with p-aminobenzoate in Saccharomyces cerevisiae"
580:
have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of
2486:
2363:
2049:
2764:
2156:
365:
226:
2606:
684:
However, this effect can be reversed by adding the end products of one-carbon transfer reactions, such as
1075:
765:
326:
1910:
1239:. Approaches to Design and Synthesis of Antiparasitic Drugs. Vol. 25. Elsevier. pp. 439–454.
734:
867:
295:
878:
A small amount of sulfanilamide is absorbed following topical application or when administered as a
601:
The term "sulfanilamides" is also sometimes used to describe a family of molecules containing these
2280:
1352:
933:
658:
342:
315:
2833:
2341:
585:
557:
1041:
2189:
2034:
1945:
1758:
1491:-aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin".
907:
654:
647:
643:
539:
275:
2112:
2108:
1992:
1278:
730:
561:
1452:
Domagk G (February 15, 1935). "Ein
Beitrag zur Chemotherapie der bakteriellen Infektionen".
2411:
2335:
1684:
917:
753:
235:
1409:
1048:. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine.
929:
215:
104:
8:
2461:
1766:
141:
369:
346:
150:
2712:
2184:
1469:
1187:
1170:
581:
1390:
1244:
1968:
1626:
1586:
1372:
1333:
1292:
1282:
1248:
1215:
1192:
1091:
1087:
969:
757:
746:
1473:
2457:
2164:
2136:
1885:
1461:
1425:
1364:
1323:
1240:
1182:
1083:
961:
863:
843:
839:
797:
627:
602:
594:
546:
382:
94:
84:
1581:
1235:
Sharma S (January 1997). "Chapter 18 - Antifolates". In Sharma S, Anand N (eds.).
2353:
2179:
1839:
1656:
1631:
742:
175:
1953:
1949:
2839:
2726:
2596:
2396:
2391:
2381:
2245:
2240:
2204:
2062:
1801:
1781:
1663:
1621:
1590:
761:
719:
576:
and because more effective sulfonamides are available for this purpose. Modern
63:
646:(that is, by acting as a substrate analogue of) enzymatic reactions involving
22:
2866:
2694:
2644:
2634:
2592:
2582:
2572:
2504:
2428:
2386:
2306:
2230:
2199:
2118:
2104:
2082:
2076:
2072:
2067:
2057:
2012:
1890:
1791:
1771:
1699:
1695:
1429:
1376:
1368:
1337:
1296:
965:
847:
789:
784:
Sulfanilamide is a yellowish-white or white crystal or fine powder. It has a
613:
569:
542:
463:
358:
2649:
2639:
2624:
2614:
2587:
2567:
2562:
2557:
2552:
2547:
2542:
2524:
2519:
2514:
2509:
2499:
2494:
2453:
2448:
2250:
2141:
2022:
1895:
1849:
1749:
1720:
1688:
1636:
1612:
1594:
1487:
Tréfouël J, Tréfouël T, Nitti F, Bovet D (November 23, 1935). "Activité du
1465:
1196:
738:
618:
565:
306:
99:
89:
79:
1272:
2810:
2802:
2782:
2735:
2669:
2629:
2577:
2466:
2316:
2255:
2209:
2169:
2146:
2017:
1997:
1941:
1940:
1864:
1819:
1814:
1730:
895:
891:
883:
577:
553:
30:
760:, poisoned and killed more than one hundred people as a result of acute
195:
2772:
2698:
2685:
2674:
2619:
2476:
2471:
2443:
2376:
2346:
2194:
2007:
1962:
1834:
1725:
1672:
1652:
1603:
1582:
887:
819:
807:
693:
674:
662:
631:
622:
609:
418:
206:
2792:
2787:
2777:
2759:
2433:
2401:
2371:
2321:
2174:
2097:
1844:
1829:
1824:
1809:
1735:
1710:
1706:
1512:
Une chimie qui guérit : Histoire de la découverte des sulfamides
870:, systemic side effects commonly seen with sulfanilamides may occur.
851:
726:
685:
589:
161:
56:
1020:
2438:
2225:
2002:
1859:
1776:
1677:
1667:
1328:
1311:
1013:"Class 9 Items: Drugs, Chemicals and Biological Stains Sulfa Drugs"
666:
573:
504:
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
255:
186:
39:
441:
2311:
1854:
827:
815:
811:
785:
723:
709:
550:
453:
1274:
Goodman & Gilman's the pharmacological basis of therapeutics
1869:
879:
776:
713:
697:
689:
678:
670:
286:
954:
Actor P, Chow AW, Dutko FJ, McKinlay MA. "Chemotherapeutics".
810:: One gram of sulphanilamide dissolves in approximately 37 ml
764:, prompting new US regulations for drug testing. In 1938, the
1514:. Médecine et Société (in French). Paris: Payot. p. 307.
823:
432:
266:
1270:
331:
246:
1486:
2749:
2725:
642:
As a sulfonamide antibiotic, sulfanilamide functions by
1168:
854:
near term, and in infants less than two months of age.
793:
756:, a medicine consisting of sulfanilamide dissolved in
1118:"US FDA Label: AVC (sulfanilamide) Vaginal Cream 15%"
700:. PABA can also reverse the effects of sulfonamides.
661:. PABA is needed in enzymatic reactions that produce
913:
Nazi human experimentation — Sulfonamide experiments
771:
953:
1271:Brunton LL, Hilal-Dandan R, Knollmann BC (2018).
1169:Castelli LA, Nguyen NP, Macreadie IG (May 2001).
2864:
1080:xPharm: The Comprehensive Pharmacology Reference
174:
1309:
560:group. Powdered sulfanilamide was used by the
149:
957:Ullmann's Encyclopedia of Industrial Chemistry
1926:
1567:
1353:"Über Sulfamide der p-Amidobenzolsulfonsäure"
1125:United States Food & Drug Administration
314:
103:
1933:
1919:
1574:
1560:
991:"The Use of Sulfanilamide in World War II"
800:of Sulfanilamide is 5.8 to 6.1. It has a λ
368:
345:
214:
38:
29:
1327:
1186:
932:at the U.S. National Library of Medicine
584:preparations, primarily for treatment of
234:
988:
775:
1214:. Oxford University Press. p. 46.
1073:
341:
194:
2865:
1524:
1451:
1310:Wormser GP, Chambers HF (2001-02-01).
1234:
637:
359:
1914:
1555:
1509:
1407:
1350:
1266:
1264:
294:
274:
62:
1209:
1082:. New York: Elsevier. pp. 1–5.
1069:
1067:
1065:
1063:
1061:
1059:
1057:
1055:
886:(through the vaginal mucosa). It is
833:
780:Laboratory synthesized sulfanilamide
737:, who along with Federico Nitti and
93:
83:
1454:Deutsche Medizinische Wochenschrift
873:
254:
165:
13:
1261:
1188:10.1111/j.1574-6968.2001.tb10671.x
857:
722:, who directed the testing of the
14:
2884:
1052:
923:
818:. It is practically insoluble in
1088:10.1016/b978-008055232-3.62694-7
1078:. In Enna SJ, Bylund DB (eds.).
1017:Library of Congress Web Archives
898:and excreted through the urine.
772:Chemical and physical properties
399:
393:
1518:
1503:
1480:
1445:
1436:
1401:
1383:
1344:
1303:
1228:
1146:"Drugs@FDA: FDA-Approved Drugs"
509:Key:FDDDEECHVMSUSB-UHFFFAOYSA-N
1203:
1162:
1138:
1110:
1034:
1005:
982:
947:
411:
405:
387:
1:
2276:Trimethoprim/sulfamethoxazole
1418:Journal fĂĽr Praktische Chemie
1357:Journal fĂĽr Praktische Chemie
1245:10.1016/s0165-7208(97)80040-2
940:
1316:Clinical Infectious Diseases
995:The History of WWII Medicine
866:or local skin reactions. If
792:of 164.5-166.5 °C. The
716:. It was patented in 1909.
7:
2281:Ormetoprim/sulfadimethoxine
1277:(13th ed.). New York:
901:
766:Food, Drug and Cosmetic Act
545:drug. Chemically, it is an
10:
2889:
703:
377:Chemical and physical data
2823:
2801:
2758:
2748:
2711:
2683:
2662:
2605:
2533:
2485:
2419:
2410:
2362:
2334:
2299:
2291:Pyrimethamine/sulfadoxine
2268:
2218:
2155:
2127:
2048:
2033:
1983:
1961:
1878:
1800:
1757:
1748:
1645:
1611:
1602:
1237:Pharmacochemistry Library
1175:FEMS Microbiology Letters
653:(PABA). Specifically, it
517:
492:
472:
468:165 °C (329 °F)
462:
452:
430:
417:
381:
376:
357:
325:
305:
285:
265:
245:
225:
205:
185:
160:
140:
132:4-aminobenzenesulfonamide
120:
115:
70:
64:Consumer Drug Information
51:
46:
37:
28:
1527:"Sulfanilamide Disaster"
1430:10.1002/prac.19080770129
1414:-Amidobenzolsulfonsäure"
1369:10.1002/prac.19080770129
1074:Scholar E (2007-01-01).
966:10.1002/14356007.a06_173
934:Medical Subject Headings
804:of 255 and 312 nm.
659:dihydropteroate synthase
644:competitively inhibiting
586:vaginal yeast infections
2873:Sulfonamide antibiotics
1408:Gelmo P (14 May 1908).
960:. Weinheim: Wiley-VCH.
2190:Sulfamethoxypyridazine
1466:10.1055/s-0028-1129486
1150:www.accessdata.fda.gov
908:Sulfonamide (medicine)
781:
655:competitively inhibits
2663:Newer non-fluorinated
2300:Other DHPS inhibitors
2286:Pyrimethamine/dapsone
2113:Succinylsulfathiazole
2109:Phthalylsulfathiazole
1993:2,4-Diaminopyrimidine
1279:McGraw Hill Education
842:in those known to be
779:
741:in the laboratory of
710:Technische Hochschule
605:. Examples include:
484:O=S(=O)(c1ccc(N)cc1)N
2087:Acetyl sulfisoxazole
1946:inhibit nucleic acid
1410:"Ăśber Sulfamide der
918:Elixir sulfanilamide
846:to sulfonamides, in
754:Elixir sulfanilamide
669:in the synthesis of
2462:Alalevonadifloxacin
2129:Intermediate-acting
1767:Silver sulfadiazine
989:Steinert D (2000).
788:of 1.08 g/cm and a
638:Mechanism of action
25:
2850:Never to phase III
2351:thereby inhibiting
2339:(inhibit bacterial
2185:Sulfametoxydiazine
1973:thereby inhibiting
1966:(inhibit bacterial
782:
665:, which acts as a
651:-aminobenzoic acid
21:
2860:
2859:
2819:
2818:
2744:
2743:
2707:
2706:
2658:
2657:
2330:
2329:
2264:
2263:
1969:purine metabolism
1908:
1907:
1904:
1903:
1750:Chemotherapeutics
1744:
1743:
1627:Chlortetracycline
1587:chemotherapeutics
1288:978-1-259-58473-2
1221:978-0-19-914195-1
1097:978-0-08-055232-3
838:Sulfanilamide is
834:Contraindications
758:diethylene glycol
747:Pasteur Institute
603:functional groups
549:consisting of an
529:
528:
443:Interactive image
327:CompTox Dashboard
16:Chemical compound
2880:
2756:
2755:
2723:
2722:
2458:Levonadifloxacin
2417:
2416:
2412:Fluoroquinolones
2360:
2359:
2165:Sulfadimethoxine
2137:Sulfamethoxazole
2058:Sulfaisodimidine
2046:
2045:
1981:
1980:
1935:
1928:
1921:
1912:
1911:
1886:Ingenol mebutate
1755:
1754:
1609:
1608:
1576:
1569:
1562:
1553:
1552:
1546:
1545:
1543:
1541:
1531:
1522:
1516:
1515:
1507:
1501:
1500:
1484:
1478:
1477:
1449:
1443:
1440:
1434:
1433:
1405:
1399:
1398:
1395:Encyclopedia.com
1387:
1381:
1380:
1351:Gelmo P (1908).
1348:
1342:
1341:
1331:
1307:
1301:
1300:
1268:
1259:
1258:
1232:
1226:
1225:
1212:Advanced Biology
1207:
1201:
1200:
1190:
1166:
1160:
1159:
1157:
1156:
1142:
1136:
1135:
1133:
1131:
1122:
1114:
1108:
1107:
1105:
1104:
1071:
1050:
1049:
1038:
1032:
1031:
1029:
1028:
1019:. Archived from
1009:
1003:
1002:
997:. Archived from
986:
980:
979:
951:
874:Pharmacokinetics
864:hypersensitivity
798:aqueous solution
735:Thérèse Tréfouël
731:Jacques Tréfouël
628:Sulfamethoxazole
595:Candida albicans
547:organic compound
525:
524:
445:
425:
413:
407:
401:
395:
389:
372:
361:
350:
349:
335:
333:
318:
298:
278:
258:
238:
218:
198:
178:
168:
167:
153:
107:
97:
87:
66:
42:
33:
26:
24:
20:
2888:
2887:
2883:
2882:
2881:
2879:
2878:
2877:
2863:
2862:
2861:
2856:
2855:
2840:Clinical trials
2815:
2797:
2763:
2740:
2716:
2703:
2679:
2654:
2601:
2529:
2481:
2406:
2354:DNA replication
2352:
2350:
2344:
2340:
2338:
2326:
2295:
2260:
2219:Other/ungrouped
2214:
2180:Sulfametomidine
2151:
2123:
2037:
2029:
1976:
1974:
1972:
1967:
1965:
1957:
1939:
1909:
1900:
1874:
1840:Podophyllotoxin
1796:
1740:
1664:Aminoglycosides
1657:Chloramphenicol
1641:
1632:Oxytetracycline
1615:and derivatives
1598:
1580:
1550:
1549:
1539:
1537:
1529:
1523:
1519:
1508:
1504:
1493:C. R. Soc. Biol
1485:
1481:
1450:
1446:
1441:
1437:
1406:
1402:
1389:
1388:
1384:
1349:
1345:
1308:
1304:
1289:
1269:
1262:
1255:
1233:
1229:
1222:
1210:Kent M (2000).
1208:
1204:
1167:
1163:
1154:
1152:
1144:
1143:
1139:
1129:
1127:
1120:
1116:
1115:
1111:
1102:
1100:
1098:
1076:"Sulfanilamide"
1072:
1053:
1042:"Sulfanilamide"
1040:
1039:
1035:
1026:
1024:
1011:
1010:
1006:
987:
983:
976:
952:
948:
943:
926:
904:
876:
860:
858:Adverse effects
848:nursing mothers
840:contraindicated
836:
803:
774:
743:Ernest Fourneau
706:
640:
520:
518:
513:
510:
505:
500:
499:
488:
485:
480:
479:
448:
423:
410:
404:
398:
392:
353:
329:
321:
301:
281:
261:
241:
221:
201:
181:
164:
156:
136:
133:
128:
127:
111:
17:
12:
11:
5:
2886:
2876:
2875:
2858:
2857:
2854:
2853:
2852:
2851:
2848:
2837:
2831:
2825:
2824:
2821:
2820:
2817:
2816:
2814:
2813:
2807:
2805:
2799:
2798:
2796:
2795:
2790:
2785:
2780:
2775:
2769:
2767:
2765:RNA polymerase
2753:
2746:
2745:
2742:
2741:
2739:
2738:
2732:
2730:
2727:Nitroimidazole
2720:
2709:
2708:
2705:
2704:
2702:
2701:
2695:Aminocoumarins
2691:
2689:
2681:
2680:
2678:
2677:
2672:
2666:
2664:
2660:
2659:
2656:
2655:
2653:
2652:
2647:
2642:
2637:
2632:
2627:
2622:
2617:
2611:
2609:
2603:
2602:
2600:
2599:
2597:Alatrofloxacin
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2539:
2537:
2535:4th generation
2531:
2530:
2528:
2527:
2522:
2517:
2512:
2507:
2502:
2497:
2491:
2489:
2487:3rd generation
2483:
2482:
2480:
2479:
2474:
2469:
2464:
2451:
2446:
2441:
2436:
2431:
2425:
2423:
2421:2nd generation
2414:
2408:
2407:
2405:
2404:
2399:
2397:Piromidic acid
2394:
2392:Pipemidic acid
2389:
2384:
2382:Nalidixic acid
2379:
2374:
2368:
2366:
2364:1st generation
2357:
2332:
2331:
2328:
2327:
2325:
2324:
2319:
2314:
2309:
2303:
2301:
2297:
2296:
2294:
2293:
2288:
2283:
2278:
2272:
2270:
2266:
2265:
2262:
2261:
2259:
2258:
2253:
2248:
2246:Sulfaguanidine
2243:
2241:Sulfadicramide
2238:
2233:
2228:
2222:
2220:
2216:
2215:
2213:
2212:
2207:
2205:Sulfaphenazole
2202:
2197:
2192:
2187:
2182:
2177:
2172:
2167:
2161:
2159:
2153:
2152:
2150:
2149:
2144:
2139:
2133:
2131:
2125:
2124:
2122:
2121:
2116:
2102:
2101:
2100:
2090:
2080:
2070:
2065:
2063:Sulfamethizole
2060:
2054:
2052:
2043:
2040:DHPS inhibitor
2031:
2030:
2028:
2027:
2026:
2025:
2020:
2015:
2010:
2005:
2000:
1989:
1987:
1985:DHFR inhibitor
1978:
1959:
1958:
1942:Antibacterials
1938:
1937:
1930:
1923:
1915:
1906:
1905:
1902:
1901:
1899:
1898:
1893:
1888:
1882:
1880:
1876:
1875:
1873:
1872:
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1832:
1827:
1822:
1817:
1812:
1806:
1804:
1798:
1797:
1795:
1794:
1789:
1784:
1782:Sulfamethizole
1779:
1774:
1769:
1763:
1761:
1752:
1746:
1745:
1742:
1741:
1739:
1738:
1733:
1728:
1723:
1714:
1713:
1703:
1702:
1692:
1691:
1681:
1680:
1675:
1670:
1660:
1659:
1649:
1647:
1643:
1642:
1640:
1639:
1634:
1629:
1624:
1622:Demeclocycline
1618:
1616:
1606:
1600:
1599:
1591:dermatological
1579:
1578:
1571:
1564:
1556:
1548:
1547:
1525:Ballentine C.
1517:
1502:
1479:
1444:
1435:
1400:
1382:
1363:(1): 369–382.
1343:
1329:10.1086/318515
1302:
1287:
1260:
1253:
1227:
1220:
1202:
1161:
1137:
1109:
1096:
1051:
1033:
1004:
1001:on 2016-06-07.
981:
975:978-3527306732
974:
945:
944:
942:
939:
938:
937:
930:Sulfanilamides
925:
924:External links
922:
921:
920:
915:
910:
903:
900:
875:
872:
859:
856:
844:hypersensitive
835:
832:
801:
773:
770:
762:kidney failure
720:Gerhard Domagk
705:
702:
639:
636:
635:
634:
625:
616:
590:vulvovaginitis
536:sulphanilamide
534:(also spelled
527:
526:
515:
514:
512:
511:
508:
506:
503:
495:
494:
493:
490:
489:
487:
486:
483:
475:
474:
473:
470:
469:
466:
460:
459:
458:1.08 g/cm
456:
450:
449:
447:
446:
438:
436:
428:
427:
421:
415:
414:
408:
402:
396:
390:
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323:
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76:
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68:
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59:
49:
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44:
43:
35:
34:
15:
9:
6:
4:
3:
2:
2885:
2874:
2871:
2870:
2868:
2849:
2847:
2844:
2843:
2841:
2838:
2835:
2832:
2830:
2827:
2826:
2822:
2812:
2809:
2808:
2806:
2804:
2800:
2794:
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2784:
2781:
2779:
2776:
2774:
2771:
2770:
2768:
2766:
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2751:
2747:
2737:
2734:
2733:
2731:
2728:
2724:
2721:
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2714:
2710:
2700:
2696:
2693:
2692:
2690:
2687:
2682:
2676:
2673:
2671:
2668:
2667:
2665:
2661:
2651:
2648:
2646:
2645:Pradofloxacin
2643:
2641:
2638:
2636:
2635:Marbofloxacin
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2612:
2610:
2608:
2604:
2598:
2594:
2593:Trovafloxacin
2591:
2589:
2586:
2584:
2583:Prulifloxacin
2581:
2579:
2576:
2574:
2573:Clinafloxacin
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2540:
2538:
2536:
2532:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2505:Grepafloxacin
2503:
2501:
2498:
2496:
2493:
2492:
2490:
2488:
2484:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2459:
2455:
2452:
2450:
2447:
2445:
2442:
2440:
2437:
2435:
2432:
2430:
2429:Ciprofloxacin
2427:
2426:
2424:
2422:
2418:
2415:
2413:
2409:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2387:Oxolinic acid
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2369:
2367:
2365:
2361:
2358:
2355:
2348:
2343:
2342:topoisomerase
2337:
2333:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2307:Acediasulfone
2305:
2304:
2302:
2298:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2273:
2271:
2267:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2231:Sulfacetamide
2229:
2227:
2224:
2223:
2221:
2217:
2211:
2208:
2206:
2203:
2201:
2200:Sulfamerazine
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2162:
2160:
2158:
2154:
2148:
2145:
2143:
2140:
2138:
2135:
2134:
2132:
2130:
2126:
2120:
2119:Sulfathiourea
2117:
2114:
2110:
2106:
2105:Sulfathiazole
2103:
2099:
2096:
2095:
2094:
2093:Sulfanilamide
2091:
2088:
2084:
2083:Sulfafurazole
2081:
2078:
2077:Sulfasalazine
2074:
2073:Sulfapyridine
2071:
2069:
2068:Sulfadimidine
2066:
2064:
2061:
2059:
2056:
2055:
2053:
2051:
2047:
2044:
2041:
2036:
2032:
2024:
2021:
2019:
2016:
2014:
2013:Pyrimethamine
2011:
2009:
2006:
2004:
2001:
1999:
1996:
1995:
1994:
1991:
1990:
1988:
1986:
1982:
1979:
1970:
1964:
1960:
1955:
1951:
1947:
1943:
1936:
1931:
1929:
1924:
1922:
1917:
1916:
1913:
1897:
1894:
1892:
1891:Metronidazole
1889:
1887:
1884:
1883:
1881:
1877:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1821:
1818:
1816:
1813:
1811:
1808:
1807:
1805:
1803:
1799:
1793:
1792:Sulfamerazine
1790:
1788:
1787:Sulfanilamide
1785:
1783:
1780:
1778:
1775:
1773:
1772:Sulfathiazole
1770:
1768:
1765:
1764:
1762:
1760:
1756:
1753:
1751:
1747:
1737:
1734:
1732:
1729:
1727:
1724:
1722:
1719:
1716:
1715:
1712:
1708:
1705:
1704:
1701:
1700:Virginiamycin
1697:
1696:Streptogramin
1694:
1693:
1690:
1686:
1683:
1682:
1679:
1676:
1674:
1671:
1669:
1665:
1662:
1661:
1658:
1654:
1651:
1650:
1648:
1644:
1638:
1635:
1633:
1630:
1628:
1625:
1623:
1620:
1619:
1617:
1614:
1610:
1607:
1605:
1601:
1596:
1592:
1588:
1584:
1577:
1572:
1570:
1565:
1563:
1558:
1557:
1554:
1535:
1528:
1521:
1513:
1506:
1498:
1494:
1490:
1483:
1475:
1471:
1467:
1463:
1459:
1455:
1448:
1439:
1431:
1427:
1423:
1419:
1415:
1413:
1404:
1396:
1392:
1386:
1378:
1374:
1370:
1366:
1362:
1358:
1354:
1347:
1339:
1335:
1330:
1325:
1321:
1317:
1313:
1306:
1298:
1294:
1290:
1284:
1280:
1276:
1275:
1267:
1265:
1256:
1254:9780444894762
1250:
1246:
1242:
1238:
1231:
1223:
1217:
1213:
1206:
1198:
1194:
1189:
1184:
1180:
1176:
1172:
1165:
1151:
1147:
1141:
1126:
1119:
1113:
1099:
1093:
1089:
1085:
1081:
1077:
1070:
1068:
1066:
1064:
1062:
1060:
1058:
1056:
1047:
1043:
1037:
1023:on 2013-12-04
1022:
1018:
1014:
1008:
1000:
996:
992:
985:
977:
971:
967:
963:
959:
958:
950:
946:
935:
931:
928:
927:
919:
916:
914:
911:
909:
906:
905:
899:
897:
893:
889:
885:
881:
871:
869:
865:
855:
853:
849:
845:
841:
831:
829:
825:
821:
817:
813:
809:
805:
799:
795:
791:
790:melting point
787:
778:
769:
767:
763:
759:
755:
750:
748:
744:
740:
736:
732:
729:in 1935, and
728:
725:
721:
717:
715:
711:
701:
699:
695:
691:
687:
682:
680:
676:
672:
668:
664:
660:
656:
652:
650:
645:
633:
629:
626:
624:
620:
617:
615:
614:loop diuretic
611:
608:
607:
606:
604:
599:
597:
596:
591:
587:
583:
579:
575:
571:
567:
563:
559:
555:
552:
548:
544:
543:antibacterial
541:
537:
533:
532:Sulfanilamide
523:
516:
507:
502:
501:
498:
491:
482:
481:
478:
471:
467:
465:
464:Melting point
461:
457:
455:
451:
444:
440:
439:
437:
434:
429:
422:
420:
416:
386:
384:
380:
375:
371:
367:
364:
362:
360:ECHA InfoCard
356:
348:
344:
343:DTXSID4023622
340:
339:
337:
328:
324:
317:
313:
312:
310:
308:
304:
297:
293:
292:
290:
288:
284:
277:
273:
272:
270:
268:
264:
257:
253:
252:
250:
248:
244:
237:
233:
232:
230:
228:
224:
217:
213:
212:
210:
208:
204:
197:
193:
192:
190:
188:
184:
177:
173:
172:
170:
163:
159:
152:
148:
147:
145:
143:
139:
130:
129:
126:
119:
114:
106:
101:
96:
91:
86:
81:
78:
77:
75:
73:
69:
65:
60:
58:
54:
50:
47:Clinical data
45:
41:
36:
32:
27:
23:Sulfanilamide
19:
2803:Lipiarmycins
2650:Sarafloxacin
2640:Orbifloxacin
2625:Enrofloxacin
2615:Danofloxacin
2588:Sitafloxacin
2568:Moxifloxacin
2563:Gemifloxacin
2558:Finafloxacin
2553:Gatifloxacin
2548:Delafloxacin
2543:Besifloxacin
2525:Tosufloxacin
2520:Temafloxacin
2515:Sparfloxacin
2510:Pazufloxacin
2500:Balofloxacin
2495:Levofloxacin
2454:Nadifloxacin
2449:Lomefloxacin
2269:Combinations
2251:Sulfametrole
2236:Sulfaclozine
2142:Sulfadiazine
2092:
2050:Short-acting
2035:Sulfonamides
2023:Trimethoprim
1896:Tirbanibulin
1850:Tromantadine
1786:
1759:Sulfonamides
1721:Fusidic acid
1717:
1689:Nadifloxacin
1637:Tetracycline
1613:Tetracycline
1538:. Retrieved
1533:
1520:
1511:
1505:
1496:
1492:
1488:
1482:
1457:
1453:
1447:
1438:
1421:
1417:
1411:
1403:
1394:
1391:"Paul Gelmo"
1385:
1360:
1356:
1346:
1319:
1315:
1305:
1273:
1236:
1230:
1211:
1205:
1181:(2): 181–4.
1178:
1174:
1164:
1153:. Retrieved
1149:
1140:
1128:. Retrieved
1124:
1112:
1101:. Retrieved
1079:
1045:
1036:
1025:. Retrieved
1021:the original
1016:
1007:
999:the original
994:
984:
955:
949:
896:sulfonamides
877:
861:
837:
806:
783:
751:
739:Daniel Bovet
718:
707:
683:
648:
641:
619:Sulfadiazine
600:
593:
570:systemically
566:World War II
535:
531:
530:
519:
307:NIAID ChemDB
18:
2836:from market
2811:Fidaxomicin
2783:Rifapentine
2736:Secnidazole
2729:derivatives
2670:Nemonoxacin
2630:Ibafloxacin
2578:Garenoxacin
2467:Norfloxacin
2317:Solasulfone
2256:Sulfanitran
2210:Sulfamazone
2170:Sulfadoxine
2157:Long-acting
2147:Sulfamoxole
2018:Tetroxoprim
1998:Brodimoprim
1975:DNA and RNA
1963:Antifolates
1865:Ibacitabine
1820:Idoxuridine
1815:Penciclovir
1731:Tyrothricin
1604:Antibiotics
1583:Antibiotics
1424:: 369–382.
894:like other
892:acetylation
888:metabolized
884:suppository
814:or in 5 ml
675:pyrimidines
657:the enzyme
578:antibiotics
558:sulfonamide
554:derivatized
540:sulfonamide
426: g·mol
366:100.000.513
276:CHEBI:45373
116:Identifiers
61:salonemide
2773:Rifampicin
2760:Rifamycins
2718:inhibitors
2699:Novobiocin
2675:Ozenoxacin
2620:Difloxacin
2607:Veterinary
2477:Rufloxacin
2472:Pefloxacin
2444:Fleroxacin
2377:Flumequine
2347:DNA gyrase
2336:Quinolones
2195:Sulfaperin
2008:Ormetoprim
1977:synthesis)
1835:Resiquimod
1802:Antivirals
1726:Bacitracin
1685:Quinolones
1673:Gentamicin
1653:Amphenicol
1460:(7): 250.
1322:(3): 521.
1155:2021-10-02
1103:2021-10-02
1027:2014-06-13
941:References
820:chloroform
808:Solubility
796:of a 0.5%
694:methionine
663:folic acid
632:antibiotic
623:antibiotic
610:Furosemide
592:caused by
431:3D model (
419:Molar mass
236:21240MF57M
207:ChemSpider
142:CAS Number
125:IUPAC name
2846:Phase III
2834:Withdrawn
2793:Rifalazil
2788:Rifaximin
2778:Rifabutin
2752:synthesis
2713:Anaerobic
2684:Related (
2434:Ofloxacin
2402:Rosoxacin
2372:Cinoxacin
2322:Sulfoxone
2175:Sulfalene
2098:Prontosil
1845:Docosanol
1830:Imiquimod
1825:Edoxudine
1810:Aciclovir
1736:Mupirocin
1711:Rifaximin
1707:Rifamycin
1377:1521-3897
1338:1058-4838
1297:993810322
1130:3 October
882:cream or
852:pregnancy
850:, during
752:In 1937,
727:Prontosil
686:thymidine
57:Drugs.com
2867:Category
2439:Enoxacin
2226:Mafenide
2003:Iclaprim
1860:Lysozyme
1777:Mafenide
1678:Amikacin
1668:Neomycin
1474:70515565
1197:11377864
902:See also
868:absorbed
667:coenzyme
588:such as
574:toxicity
522:(verify)
296:ChEMBL21
187:DrugBank
100:QJ01EQ06
72:ATC code
2345:and/or
2312:Dapsone
1855:Inosine
1534:fda.gov
1046:PubChem
880:vaginal
828:benzene
816:acetone
812:alcohol
786:density
745:at the
724:prodrug
704:History
690:purines
679:Mammals
671:purines
582:topical
572:due to
556:with a
551:aniline
538:) is a
454:Density
383:Formula
196:DB00259
162:PubChem
151:63-74-1
102: (
92: (
90:D06BA05
88:)
82: (
80:J01EB06
2829:WHO-EM
1870:Lysine
1718:other:
1646:Others
1499:: 756.
1472:
1375:
1336:
1295:
1285:
1251:
1218:
1195:
1094:
972:
936:(MeSH)
714:Vienna
698:serine
696:, and
562:Allies
477:SMILES
424:172.20
316:019103
287:ChEMBL
256:D08543
1944:that
1879:Other
1593:use (
1540:5 May
1536:. FDA
1530:(PDF)
1470:S2CID
1121:(PDF)
826:, or
824:ether
630:, an
621:, an
497:InChI
433:JSmol
267:ChEBI
1954:J01M
1950:J01E
1589:for
1585:and
1542:2022
1373:ISSN
1334:ISSN
1293:OCLC
1283:ISBN
1249:ISBN
1216:ISBN
1193:PMID
1132:2021
1092:ISBN
970:ISBN
733:and
673:and
649:para
612:, a
247:KEGG
227:UNII
216:5142
176:5333
53:AHFS
2750:RNA
2715:DNA
1595:D06
1497:120
1462:doi
1426:doi
1365:doi
1324:doi
1241:doi
1183:doi
1179:199
1084:doi
962:doi
890:by
802:max
712:of
564:in
332:EPA
166:CID
105:WHO
95:WHO
85:WHO
2869::
2842::
2697::
2686:DG
2111:,
1952:,
1709::
1698::
1687::
1666::
1655::
1532:.
1495:.
1468:.
1458:61
1456:.
1422:77
1420:.
1416:.
1393:.
1371:.
1361:77
1359:.
1355:.
1332:.
1320:32
1318:.
1314:.
1291:.
1281:.
1263:^
1247:.
1191:.
1177:.
1173:.
1148:.
1123:.
1090:.
1054:^
1044:.
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