528:
allergic response to sulfonamide antibiotics is the arylamine group at N4, found in sulfamethoxazole, sulfasalazine, sulfadiazine, and the anti-retrovirals amprenavir and fosamprenavir. Other sulfonamide drugs do not contain this arylamine group; available evidence suggests that patients who are allergic to arylamine sulfonamides do not cross-react to sulfonamides that lack the arylamine group, and may therefore safely take non-arylamine sulfonamides. It has therefore been argued that the terms "sulfonamide allergy" or "sulfa allergy" are misleading and should be replaced by a reference to a specific drug (e.g., "
50:
76:
461:
191:
476:
65:
40:
349:. The discovery helped establish the concept of "bioactivation" and dashed the German corporation's dreams of enormous profit; the active molecule sulfanilamide (or sulfa) had first been synthesized in 1906 and was widely used in the dye-making industry; its patent had since expired and the drug was available to anyone.
527:
Hypersensitivity reactions are less common in nonantibiotic sulfonamides, and, though controversial, the available evidence suggests those with hypersensitivity to sulfonamide antibiotics do not have an increased risk of hypersensitivity reaction to the nonantibiotic agents. A key component to the
407:
Many thousands of molecules containing the sulfanilamide structure have been created since its discovery (by one account, over 5,400 permutations by 1945), yielding improved formulations with greater effectiveness and less toxicity. Sulfa drugs are still widely used for conditions such as acne and
308:
that had remarkable effects on stopping some bacterial infections in mice. The first official communication about the breakthrough discovery was not published until 1935, more than two years after the drug was patented by Klarer and his research partner Fritz
Mietzsch.
2986:
295:
which are able to bind preferentially to bacteria and parasites might be used to attack harmful organisms in the body. After years of fruitless trial-and-error work on hundreds of dyes, a team led by physician/researcher
312:
Prontosil, as Bayer named the new drug, was the first medicine ever discovered that could effectively treat a range of bacterial infections inside the body. It had a strong protective action against infections caused by
2979:
523:
Approximately 3% of the general population have adverse reactions when treated with sulfonamide antimicrobials. Of note is the observation that patients with HIV have a much higher prevalence, at about 60%.
2972:
399:
of around 10. This is a very painful experience, so patients are told to take the medication with copious amounts of water. Newer analogous compounds prevent this complication because they have a lower
202:
Sulfonamides are used to treat allergies and coughs, as well as having antifungal and antimalarial functions. The moiety is also present in other medications that are not antimicrobials, including
325:, and a lesser effect on infections caused by other cocci. However, it had no effect at all in the test tube, exerting its antibacterial action only in live animals. Later, it was discovered by
275:
Sulfonamide drugs were the first broadly effective antibacterials to be used systemically, and paved the way for the antibiotic revolution in medicine. The first sulfonamide, trade-named
1221:
Brackett CC, Singh H, Block JH (July 2004). "Likelihood and mechanisms of cross-allergenicity between sulfonamide antibiotics and other drugs containing a sulfonamide functional group".
865:
Tréfouël, J.; Tréfouël, Th.; Nitti, F.; Bovet, D. (23 November 1935). "Activité du p. aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin".
352:
The result was a sulfa craze. For several years in the late 1930s, hundreds of manufacturers produced myriad forms of sulfa. This and the lack of testing requirements led to the
1306:
935:
1343:
546:
The second is the N4 amino nitrogen that, in a stereospecific process, forms reactive metabolites that cause either direct cytotoxicity or immunologic response.
993:"Adaptation and extension of sulfonamide and other antibiotics determination by solid-phase extraction followed by liquid chromatography and mass spectrometry"
179:. Sulfonamides are therefore bacteriostatic and inhibit growth and multiplication of bacteria, but do not kill them. Humans, in contrast to bacteria, acquire
517:
153:
Sulfonamide drugs were the first broadly effective antibacterials to be used systemically, and paved the way for the antibiotic revolution in medicine.
2295:
345:, that the drug was metabolized into two parts inside the body, releasing from the inactive dye portion a smaller, colorless, active compound called
500:
and hypersensitivity reactions. When used in large doses, they may cause a strong allergic reaction. The most serious of these are classified as
408:
urinary tract infections, and are receiving renewed interest for the treatment of infections caused by bacteria resistant to other antibiotics.
1295:
3939:
3413:
2930:
2239:
1336:
828:
1189:
1450:
361:
535:
Two regions of the sulfonamide antibiotic chemical structure are implicated in the hypersensitivity reactions associated with the class.
3345:
820:
The Demon Under the
Microscope: From Battlefield Hospitals to Nazi Labs, One Doctor's Heroic Search for the World's First Miracle Drug
760:
501:
162:
3665:
1395:
852:
739:
992:
1286:
3998:
3763:
1329:
330:
939:
3925:
3842:
3811:
3792:
884:
3988:
1145:
Knowles S, Shapiro L, Shear NH (2001). "Should
Celecoxib Be Contraindicated in Patients Who Are Allergic to Sulfonamides?".
2288:
1686:
373:
562:
505:
467:
3382:
2817:
2175:
334:
3956:
2947:
2478:
2256:
364:
in 1938 in the United States. As the first and only effective broad-spectrum antibiotic available in the years before
1301:
3651:
566:
509:
264:
818:
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2964:
1281:
377:
1316:
3797:
3578:
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1701:
594:
172:
909:
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2935:
2697:
2655:
2534:
2244:
1752:
615:
429:
118:
43:
1696:
1067:
Tilles SA (August 2001). "Practical issues in the management of hypersensitivity reactions: sulfonamides".
561:. However, there are several life-threatening manifestations of hypersensitivity to sulfa drugs, including
3655:
3574:
2564:
2128:
1600:
1497:
1356:
384:. Sulfa had a central role in preventing wound infections during the war. American soldiers were issued a
198:(center) is the basis for the inhibitory activity of sulfa drugs on tetrahydrofolate (right) biosynthesis.
143:
4003:
3993:
3693:
3409:
2524:
1523:
1519:
1403:
1321:
395:
form. The drug has very low solubility and sometimes can crystallize in the kidneys, due to its first pK
168:
2603:
684:
962:
436:
is the largest exporter worldwide of sulfonamides, accounting for approximately 32% of total exports.
3983:
3723:
3097:
2706:
2333:
2017:
1945:
1897:
1831:
1822:
1774:
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599:
445:
353:
1032:
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3179:
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1872:
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604:
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195:
53:
49:
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305:
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3564:
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3331:
2123:
1595:
1246:
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1170:
1092:
582:
133:
709:
3879:
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3039:
2999:
2638:
2553:
2502:
2448:
1379:
1238:
1162:
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1007:
848:
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357:
342:
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3524:
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656:
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540:
421:
176:
90:
79:
75:
3801:
3759:
3386:
3252:
3069:
3044:
1764:
1590:
968:
570:
460:
338:
250:
3950:
3848:
3708:
3519:
3437:
3372:
3214:
3194:
3076:
3034:
3003:
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2716:
2452:
2392:
2326:
2304:
2250:
2137:
2007:
1807:
1802:
1792:
1656:
1651:
1615:
1473:
513:
493:
489:
318:
297:
122:
661:
636:
372:. They are credited with saving the lives of tens of thousands of patients, including
3977:
3890:
3587:
3529:
3467:
3405:
3395:
3303:
3204:
3199:
3184:
3112:
3108:
2907:
2836:
2831:
2746:
2721:
2660:
2650:
2367:
2362:
2105:
2055:
2045:
2003:
1993:
1983:
1915:
1839:
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1641:
1610:
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1493:
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529:
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114:
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2897:
2877:
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2583:
2347:
2308:
2060:
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2035:
2025:
1998:
1978:
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1968:
1963:
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1953:
1935:
1930:
1925:
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1905:
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1661:
1552:
1433:
1364:
1360:
1096:
425:
369:
326:
139:
129:
652:
388:
containing sulfa pills and powder and were told to sprinkle it on any open wound.
356:
disaster in the fall of 1937, during which at least 100 people were poisoned with
553:
The most common manifestations of a hypersensitivity reaction to sulfa drugs are
3909:
3904:
3898:
3875:
3683:
3602:
3592:
3447:
3277:
3232:
3227:
3143:
2887:
2882:
2768:
2726:
2672:
2643:
2618:
2613:
2588:
2468:
2463:
2427:
2407:
2352:
2342:
2221:
2213:
2193:
2146:
2080:
2040:
1988:
1877:
1727:
1666:
1620:
1580:
1557:
1428:
1408:
1352:
1234:
31:
3827:
3822:
3817:
3739:
3718:
3627:
3612:
3607:
3549:
3472:
3462:
3452:
3432:
3422:
3247:
3138:
3085:
3065:
3016:
2995:
2912:
2902:
2892:
2851:
2846:
2796:
2778:
2773:
2756:
2751:
2736:
2687:
2682:
2677:
2667:
2633:
2623:
2507:
2497:
2487:
2432:
2402:
2382:
2183:
2109:
2096:
2085:
2030:
1887:
1882:
1854:
1787:
1757:
1605:
1418:
1373:
1123:
1019:
392:
365:
322:
226:
222:
218:
214:
147:
121:
group. Some sulfonamides are also devoid of antibacterial activity, e.g., the
98:
68:
1011:
3832:
3713:
3673:
3622:
3617:
3597:
3534:
3457:
3427:
3257:
3242:
3237:
3222:
3148:
3123:
3119:
2872:
2763:
2711:
2628:
2593:
2573:
2539:
2529:
2492:
2458:
2437:
2422:
2417:
2387:
2377:
2372:
2317:
2203:
2198:
2188:
2170:
1844:
1812:
1782:
1732:
1585:
1508:
497:
288:
276:
263:, in addition to its use as an antibiotic, is also used in the treatment of
254:
246:
242:
230:
1242:
1166:
1131:
1088:
794:
777:
670:
17:
803:
190:
3894:
3777:
3772:
3678:
3637:
3514:
3504:
3495:
3482:
3442:
3354:
3272:
3189:
3090:
3080:
2867:
2841:
2598:
2578:
2412:
2397:
1849:
1636:
1413:
206:
203:
125:
113:. The original antibacterial sulfonamides are synthetic (nonantibiotic)
94:
57:
2273:
475:
304:) finally found one that worked: a red dye synthesized by Bayer chemist
39:
3871:
3267:
2444:
1722:
1045:
292:
280:
64:
150:; hence medications containing sulfonamides are prescribed carefully.
3282:
845:
Une chimie qui guérit : Histoire de la découverte des sulfamides
180:
1287:
A History of the Fight
Against Tuberculosis in Canada (Chemotherapy)
520:. Any one of these SCARs may be triggered by certain sulfonamides.
404:, around 5–6, making them more likely to remain in a soluble form.
3323:
558:
284:
283:. Experiments with Prontosil began in 1932 in the laboratories of
189:
74:
63:
48:
38:
136:
are newer drug groups based upon the antibacterial sulfonamides.
3782:
847:, Paris, Payot, coll. « Médecine et sociétés », 1988 (
554:
420:
with ammonia or an amine. Certain sulfonamides (sulfadiazine or
3327:
2968:
2277:
1325:
1195:. Western Australian Therapeutic Advisory Group. Archived from
287:
AG, at that time a component of the huge German chemical trust
2160:
1110:
Slatore CG, Tilles SA (2004). "Sulfonamide hypersensitivity".
550:
The nonantibiotic sulfonamides lack both of these structures.
1190:"ALLERGIES TO SULFONAMIDE ANTIBIOTICS AND CROSS-REACTIVITIES"
539:
The first is the N1 heterocyclic ring, which causes a type I
368:, heavy use of sulfa drugs continued into the early years of
300:(working under the general direction of IG Farben executive
481:
Allergic urticaria on the skin induced by an antibiotic
194:
Structural similarity between sulfanilamide (left) and
488:
Sulfonamides have the potential to cause a variety of
991:
Kadenczki, Lajos; Szopkó, Henrietta Stefánné (2012).
710:"Sulfa Drugs Allergy -- Sulfa Bactrim Drug Allergies"
704:
702:
142:
to sulfonamides are common. The overall incidence of
3918:
3864:
3791:
3754:
3692:
3664:
3650:
3573:
3481:
3404:
3381:
3366:
3291:
3213:
3170:
3161:
3058:
3024:
3015:
2860:
2816:
2809:
2787:
2696:
2563:
2552:
2516:
2477:
2325:
2316:
2212:
2169:
2159:
2136:
2122:
2094:
2073:
2016:
1944:
1896:
1830:
1821:
1773:
1745:
1710:
1679:
1629:
1566:
1538:
1459:
1444:
1394:
1372:
1265:
Harrison's
Principles of Internal Medicine, 13th Ed
146:to sulfa antibiotics is approximately 3%, close to
961:
778:"Domagk and the development of the sulphonamides"
391:The sulfanilamide compound is more active in the
1035:The National WWII Museum. Accessed 29 July 2021.
1112:Immunology and Allergy Clinics of North America
416:Sulfonamides are prepared by the reaction of a
167:In bacteria, antibacterial sulfonamides act as
27:Molecular moiety or the drug class that uses it
3339:
2980:
2289:
1337:
730:M. Madigan, J. Martinko, D. Stahl, D. Clark,
516:, and a not quite as serious SCARs reaction,
8:
221:, among others), loop diuretics (including
30:For chemistry of the functional group, see
3661:
3378:
3346:
3332:
3324:
3167:
3021:
2987:
2973:
2965:
2813:
2560:
2322:
2296:
2282:
2274:
2166:
2133:
1827:
1770:
1456:
1391:
1344:
1330:
1322:
1307:"Five Medical Miracles of the Sulfa Drugs"
732:Brock Biology of Microorganisms (13th ed.)
518:acute generalized exanthematous pustulosis
793:
660:
97:) that is the basis of several groups of
1539:
755:. Oxford University Press. p. 543.
1048:. Massachusetts Institute of Technology
627:
1296:Nobel Prize in Physiology and Medicine
1267:. McGraw-Hill Inc. 1994. p. 604.
782:Journal of Antimicrobial Chemotherapy
492:, including urinary tract disorders,
71:is a sulfonamide, but not a thiazide.
7:
637:"The Mode of Action of Sulfonamides"
512:(also known as Lyell syndrome), the
424:) are sometimes mixed with the drug
362:Federal Food, Drug, and Cosmetic Act
2826:
817:Hager, Thomas (1 September 2006).
734:, Pearson Education, 2012, p. 797
581:, fulminant hepatic necrosis, and
502:severe cutaneous adverse reactions
163:Dihydropteroate synthase inhibitor
25:
1460:
910:"Bad Health—Elixir Sulfanilamide"
607:(1920–2001) German medical doctor
360:. This led to the passage of the
1567:
1159:10.2165/00002018-200124040-00001
1081:10.1097/00007611-200108000-00013
1033:Medical Innovations: Antibiotics
474:
459:
337:, a French research team led by
82:is an antibacterial sulfonamide.
3926:Hydrochlorothiazide/triamterene
3793:Vasopressin receptor inhibitors
685:"SULFONAMIDE CLASS ANTIBIOTICS"
291:. The Bayer team believed that
317:, including blood infections,
175:(DHPS), an enzyme involved in
1:
1687:Trimethoprim/sulfamethoxazole
1302:The History of WW II Medicine
653:10.1128/MMBR.7.4.175-262.1943
504:(i.e. SCARs) and include the
374:Franklin Delano Roosevelt Jr.
1313:, June 1942, pp. 73–78.
44:Sulfonamide functional group
1692:Ormetoprim/sulfadimethoxine
1235:10.1592/phco.24.9.856.36106
1000:Geosciences and Engineering
753:A Dictionary of Biomedicine
4020:
936:"History of WWII Medicine"
567:toxic epidermal necrolysis
510:toxic epidermal necrolysis
443:
265:inflammatory bowel disease
249:, among others), and some
160:
29:
3934:
2925:
2234:
1702:Pyrimethamine/sulfadoxine
1124:10.1016/j.iac.2004.03.011
378:Franklin Delano Roosevelt
1317:A history of antibiotics
1069:Southern Medical Journal
595:Dihydropteroate synthase
563:Stevens–Johnson syndrome
506:Stevens–Johnson syndrome
468:Stevens–Johnson syndrome
173:dihydropteroate synthase
117:agents that contain the
3999:Sulfonamide antibiotics
3694:Aldosterone antagonists
2656:Eslicarbazepine acetate
1046:"Trade of Sulfonamides"
889:Encyclopædia Britannica
641:Bacteriological Reviews
616:Timeline of antibiotics
430:dihydrofolate reductase
56:is a sulfonamide and a
1601:Sulfamethoxypyridazine
329:, Federico Nitti, and
199:
169:competitive inhibitors
144:adverse drug reactions
83:
72:
61:
46:
3989:Disulfiram-like drugs
2074:Newer non-fluorinated
1711:Other DHPS inhibitors
1697:Pyrimethamine/dapsone
1524:Succinylsulfathiazole
1520:Phthalylsulfathiazole
1404:2,4-Diaminopyrimidine
963:"Medicine: Prontosil"
885:"History of medicine"
751:Lackie, John (2010).
712:. allergies.about.com
428:, which acts against
376:(son of US President
193:
78:
67:
52:
42:
3919:Combination products
3724:Potassium canrenoate
1498:Acetyl sulfisoxazole
1357:inhibit nucleic acid
1282:List of sulfonamides
795:10.1093/jac/17.6.689
687:. chemicalland21.com
600:Elixir sulfanilamide
446:List of sulfonamides
354:elixir sulfanilamide
187:) through the diet.
3886:mercurial diuretics
3540:Hydrochlorothiazide
3510:Bendroflumethiazide
3180:Silver sulfadiazine
2358:Methylphenobarbital
1873:Alalevonadifloxacin
1540:Intermediate-acting
1292:Presentation speech
1118:(3): 477–490, vii.
605:Hellmuth Kleinsorge
434:Republic of Ireland
211:hydrochlorothiazide
101:, which are called
54:Hydrochlorothiazide
3961:Never to phase III
3565:Trichlormethiazide
3545:Hydroflumethiazide
2952:Never to phase III
2261:Never to phase III
1762:thereby inhibiting
1750:(inhibit bacterial
1596:Sulfametoxydiazine
1384:thereby inhibiting
1377:(inhibit bacterial
972:. 28 December 1936
942:on 14 October 1999
843:Cf. Daniel Bovet,
583:acute pancreatitis
432:. As of 2013, the
200:
134:thiazide diuretics
84:
73:
62:
47:
3971:
3970:
3854:Lithium carbonate
3756:Osmotic diuretics
3750:
3749:
3652:Potassium-sparing
3646:
3645:
3321:
3320:
3317:
3316:
3163:Chemotherapeutics
3157:
3156:
3040:Chlortetracycline
3000:chemotherapeutics
2962:
2961:
2921:
2920:
2805:
2804:
2789:Potassium openers
2707:Oxazolidinediones
2639:Valproate pivoxil
2604:Acetylpheneturide
2548:
2547:
2503:Valproate pivoxil
2479:GABA-T inhibitors
2449:potassium bromide
2271:
2270:
2230:
2229:
2155:
2154:
2118:
2117:
2069:
2068:
1741:
1740:
1675:
1674:
1380:purine metabolism
916:. 9 February 2009
830:978-0-307-35228-6
635:Henry RJ (1943).
418:sulfonyl chloride
382:Winston Churchill
358:diethylene glycol
343:Pasteur Institute
16:(Redirected from
4011:
3662:
3555:Methyclothiazide
3525:Cyclopenthiazide
3379:
3348:
3341:
3334:
3325:
3299:Ingenol mebutate
3168:
3022:
2989:
2982:
2975:
2966:
2814:
2698:Calcium blockers
2609:Chlorphenacemide
2561:
2535:GAT-1 inhibitors
2323:
2298:
2291:
2284:
2275:
2167:
2134:
1869:Levonadifloxacin
1828:
1823:Fluoroquinolones
1771:
1576:Sulfadimethoxine
1548:Sulfamethoxazole
1469:Sulfaisodimidine
1457:
1392:
1346:
1339:
1332:
1323:
1269:
1268:
1261:
1255:
1254:
1218:
1212:
1211:
1209:
1207:
1201:
1194:
1185:
1179:
1178:
1142:
1136:
1135:
1107:
1101:
1100:
1064:
1058:
1057:
1055:
1053:
1042:
1036:
1030:
1024:
1023:
997:
988:
982:
981:
979:
977:
965:
958:
952:
951:
949:
947:
938:. Archived from
932:
926:
925:
923:
921:
906:
900:
899:
897:
895:
881:
875:
874:
862:
856:
841:
835:
834:
814:
808:
807:
797:
776:Otten H (1986).
773:
767:
766:
748:
742:
728:
722:
721:
719:
717:
706:
697:
696:
694:
692:
681:
675:
674:
664:
632:
585:, among others.
579:thrombocytopenia
575:hemolytic anemia
541:hypersensitivity
478:
463:
422:sulfamethoxazole
335:Thérèse Tréfouël
302:Heinrich Hörlein
251:COX-2 inhibitors
177:folate synthesis
91:functional group
80:Sulfamethoxazole
21:
4019:
4018:
4014:
4013:
4012:
4010:
4009:
4008:
3974:
3973:
3972:
3967:
3966:
3951:Clinical trials
3930:
3914:
3860:
3795:
3787:
3746:
3688:
3642:
3569:
3496:Calcium-sparing
3494:
3477:
3400:
3370:
3362:
3352:
3322:
3313:
3287:
3253:Podophyllotoxin
3209:
3153:
3077:Aminoglycosides
3070:Chloramphenicol
3054:
3045:Oxytetracycline
3028:and derivatives
3011:
2993:
2963:
2958:
2957:
2942:Clinical trials
2917:
2856:
2801:
2783:
2692:
2565:Sodium blockers
2555:
2544:
2512:
2473:
2393:Benzodiazepines
2330:
2312:
2305:Anticonvulsants
2302:
2272:
2267:
2266:
2251:Clinical trials
2226:
2208:
2174:
2151:
2127:
2114:
2090:
2065:
2012:
1940:
1892:
1817:
1765:DNA replication
1763:
1761:
1755:
1751:
1749:
1737:
1706:
1671:
1630:Other/ungrouped
1625:
1591:Sulfametomidine
1562:
1534:
1448:
1440:
1387:
1385:
1383:
1378:
1376:
1368:
1350:
1311:Popular Science
1278:
1273:
1272:
1263:
1262:
1258:
1223:Pharmacotherapy
1220:
1219:
1215:
1205:
1203:
1202:on 3 March 2011
1199:
1192:
1187:
1186:
1182:
1144:
1143:
1139:
1109:
1108:
1104:
1066:
1065:
1061:
1051:
1049:
1044:
1043:
1039:
1031:
1027:
995:
990:
989:
985:
975:
973:
960:
959:
955:
945:
943:
934:
933:
929:
919:
917:
914:The Blog of Bad
908:
907:
903:
893:
891:
883:
882:
878:
867:C. R. Soc. Biol
864:
863:
859:
842:
838:
831:
816:
815:
811:
775:
774:
770:
763:
750:
749:
745:
729:
725:
715:
713:
708:
707:
700:
690:
688:
683:
682:
678:
634:
633:
629:
624:
591:
571:agranulocytosis
490:adverse effects
486:
485:
484:
483:
482:
479:
471:
470:
464:
453:
448:
442:
414:
403:
398:
339:Ernest Fourneau
273:
186:
165:
159:
35:
28:
23:
22:
15:
12:
11:
5:
4017:
4015:
4007:
4006:
4001:
3996:
3991:
3986:
3976:
3975:
3969:
3968:
3965:
3964:
3963:
3962:
3959:
3948:
3942:
3936:
3935:
3932:
3931:
3929:
3928:
3922:
3920:
3916:
3915:
3913:
3912:
3907:
3902:
3882:
3868:
3866:
3862:
3861:
3859:
3858:
3857:
3856:
3851:
3849:Demeclocycline
3838:
3837:
3836:
3835:
3830:
3825:
3820:
3807:
3805:
3789:
3788:
3786:
3785:
3780:
3775:
3769:
3767:
3752:
3751:
3748:
3747:
3745:
3744:
3743:
3742:
3729:
3728:
3727:
3726:
3721:
3716:
3711:
3709:Spironolactone
3698:
3696:
3690:
3689:
3687:
3686:
3681:
3676:
3670:
3668:
3659:
3648:
3647:
3644:
3643:
3641:
3640:
3635:
3630:
3625:
3620:
3615:
3610:
3605:
3600:
3595:
3590:
3584:
3582:
3575:Thiazide-likes
3571:
3570:
3568:
3567:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3527:
3522:
3520:Chlorothiazide
3517:
3512:
3507:
3501:
3499:
3479:
3478:
3476:
3475:
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3438:Etacrynic acid
3435:
3430:
3425:
3419:
3417:
3402:
3401:
3399:
3398:
3392:
3390:
3376:
3373:etacrynic acid
3364:
3363:
3353:
3351:
3350:
3343:
3336:
3328:
3319:
3318:
3315:
3314:
3312:
3311:
3306:
3301:
3295:
3293:
3289:
3288:
3286:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3250:
3245:
3240:
3235:
3230:
3225:
3219:
3217:
3211:
3210:
3208:
3207:
3202:
3197:
3195:Sulfamethizole
3192:
3187:
3182:
3176:
3174:
3165:
3159:
3158:
3155:
3154:
3152:
3151:
3146:
3141:
3136:
3127:
3126:
3116:
3115:
3105:
3104:
3094:
3093:
3088:
3083:
3073:
3072:
3062:
3060:
3056:
3055:
3053:
3052:
3047:
3042:
3037:
3035:Demeclocycline
3031:
3029:
3019:
3013:
3012:
3004:dermatological
2994:
2992:
2991:
2984:
2977:
2969:
2960:
2959:
2956:
2955:
2954:
2953:
2950:
2939:
2933:
2927:
2926:
2923:
2922:
2919:
2918:
2916:
2915:
2910:
2905:
2900:
2895:
2890:
2885:
2880:
2875:
2870:
2864:
2862:
2858:
2857:
2855:
2854:
2849:
2844:
2839:
2834:
2822:
2820:
2811:
2807:
2806:
2803:
2802:
2800:
2799:
2793:
2791:
2785:
2784:
2782:
2781:
2776:
2771:
2766:
2754:
2747:Gabapentinoids
2739:
2734:
2719:
2717:Paramethadione
2714:
2702:
2700:
2694:
2693:
2691:
2690:
2685:
2680:
2675:
2670:
2658:
2653:
2648:
2636:
2631:
2616:
2611:
2606:
2591:
2586:
2581:
2569:
2567:
2558:
2550:
2549:
2546:
2545:
2543:
2542:
2525:GABAR agonists
2520:
2518:
2514:
2513:
2511:
2510:
2505:
2500:
2495:
2490:(and related):
2483:
2481:
2475:
2474:
2472:
2471:
2466:
2461:
2456:
2453:sodium bromide
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2385:
2370:
2365:
2360:
2355:
2350:
2338:
2336:
2328:
2320:
2314:
2313:
2303:
2301:
2300:
2293:
2286:
2278:
2269:
2268:
2265:
2264:
2263:
2262:
2259:
2248:
2242:
2236:
2235:
2232:
2231:
2228:
2227:
2225:
2224:
2218:
2216:
2210:
2209:
2207:
2206:
2201:
2196:
2191:
2186:
2180:
2178:
2176:RNA polymerase
2164:
2157:
2156:
2153:
2152:
2150:
2149:
2143:
2141:
2138:Nitroimidazole
2131:
2120:
2119:
2116:
2115:
2113:
2112:
2106:Aminocoumarins
2102:
2100:
2092:
2091:
2089:
2088:
2083:
2077:
2075:
2071:
2070:
2067:
2066:
2064:
2063:
2058:
2053:
2048:
2043:
2038:
2033:
2028:
2022:
2020:
2014:
2013:
2011:
2010:
2008:Alatrofloxacin
2001:
1996:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1950:
1948:
1946:4th generation
1942:
1941:
1939:
1938:
1933:
1928:
1923:
1918:
1913:
1908:
1902:
1900:
1898:3rd generation
1894:
1893:
1891:
1890:
1885:
1880:
1875:
1862:
1857:
1852:
1847:
1842:
1836:
1834:
1832:2nd generation
1825:
1819:
1818:
1816:
1815:
1810:
1808:Piromidic acid
1805:
1803:Pipemidic acid
1800:
1795:
1793:Nalidixic acid
1790:
1785:
1779:
1777:
1775:1st generation
1768:
1743:
1742:
1739:
1738:
1736:
1735:
1730:
1725:
1720:
1714:
1712:
1708:
1707:
1705:
1704:
1699:
1694:
1689:
1683:
1681:
1677:
1676:
1673:
1672:
1670:
1669:
1664:
1659:
1657:Sulfaguanidine
1654:
1652:Sulfadicramide
1649:
1644:
1639:
1633:
1631:
1627:
1626:
1624:
1623:
1618:
1616:Sulfaphenazole
1613:
1608:
1603:
1598:
1593:
1588:
1583:
1578:
1572:
1570:
1564:
1563:
1561:
1560:
1555:
1550:
1544:
1542:
1536:
1535:
1533:
1532:
1527:
1513:
1512:
1511:
1501:
1491:
1481:
1476:
1474:Sulfamethizole
1471:
1465:
1463:
1454:
1451:DHPS inhibitor
1442:
1441:
1439:
1438:
1437:
1436:
1431:
1426:
1421:
1416:
1411:
1400:
1398:
1396:DHFR inhibitor
1389:
1370:
1369:
1353:Antibacterials
1351:
1349:
1348:
1341:
1334:
1326:
1320:
1319:
1314:
1304:
1299:
1289:
1284:
1277:
1276:External links
1274:
1271:
1270:
1256:
1213:
1180:
1153:(4): 239–247.
1137:
1102:
1059:
1037:
1025:
983:
953:
927:
901:
876:
857:
836:
829:
809:
788:(6): 689–696.
768:
762:978-0199549351
761:
743:
723:
698:
676:
647:(4): 175–262.
626:
625:
623:
620:
619:
618:
613:
608:
602:
597:
590:
587:
548:
547:
544:
514:DRESS syndrome
480:
473:
472:
465:
458:
457:
456:
455:
454:
452:
449:
444:Main article:
441:
438:
413:
410:
401:
396:
319:childbed fever
298:Gerhard Domagk
272:
269:
184:
171:of the enzyme
161:Main article:
158:
155:
123:anticonvulsant
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4016:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3981:
3979:
3960:
3958:
3955:
3954:
3952:
3949:
3946:
3943:
3941:
3938:
3937:
3933:
3927:
3924:
3923:
3921:
3917:
3911:
3908:
3906:
3903:
3900:
3896:
3892:
3891:Chlormerodrin
3888:
3887:
3883:
3881:
3877:
3873:
3870:
3869:
3867:
3863:
3855:
3852:
3850:
3847:
3846:
3845:
3844:
3840:
3839:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3815:
3814:
3813:
3809:
3808:
3806:
3803:
3799:
3794:
3790:
3784:
3781:
3779:
3776:
3774:
3771:
3770:
3768:
3765:
3761:
3757:
3753:
3741:
3738:
3737:
3736:
3735:
3731:
3730:
3725:
3722:
3720:
3717:
3715:
3712:
3710:
3707:
3706:
3705:
3704:
3703:Spirolactones
3700:
3699:
3697:
3695:
3691:
3685:
3682:
3680:
3677:
3675:
3672:
3671:
3669:
3667:
3663:
3660:
3657:
3653:
3649:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3588:Chlortalidone
3586:
3585:
3583:
3580:
3576:
3572:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3530:Cyclothiazide
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3502:
3500:
3497:
3492:
3488:
3484:
3480:
3474:
3471:
3469:
3468:Tienilic acid
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3420:
3418:
3415:
3411:
3407:
3403:
3397:
3396:Acetazolamide
3394:
3393:
3391:
3388:
3384:
3383:CA inhibitors
3380:
3377:
3374:
3369:
3365:
3360:
3356:
3349:
3344:
3342:
3337:
3335:
3330:
3329:
3326:
3310:
3307:
3305:
3304:Metronidazole
3302:
3300:
3297:
3296:
3294:
3290:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3251:
3249:
3246:
3244:
3241:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3220:
3218:
3216:
3212:
3206:
3205:Sulfamerazine
3203:
3201:
3200:Sulfanilamide
3198:
3196:
3193:
3191:
3188:
3186:
3185:Sulfathiazole
3183:
3181:
3178:
3177:
3175:
3173:
3169:
3166:
3164:
3160:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3129:
3128:
3125:
3121:
3118:
3117:
3114:
3113:Virginiamycin
3110:
3109:Streptogramin
3107:
3106:
3103:
3099:
3096:
3095:
3092:
3089:
3087:
3084:
3082:
3078:
3075:
3074:
3071:
3067:
3064:
3063:
3061:
3057:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3032:
3030:
3027:
3023:
3020:
3018:
3014:
3009:
3005:
3001:
2997:
2990:
2985:
2983:
2978:
2976:
2971:
2970:
2967:
2951:
2949:
2946:
2945:
2943:
2940:
2937:
2934:
2932:
2929:
2928:
2924:
2914:
2911:
2909:
2908:Levetiracetam
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2865:
2863:
2859:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2837:Ethoxzolamide
2835:
2833:
2832:Acetazolamide
2830:
2828:
2824:
2823:
2821:
2819:
2818:CA inhibitors
2815:
2812:
2808:
2798:
2795:
2794:
2792:
2790:
2786:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2758:
2755:
2753:
2750:
2748:
2743:
2740:
2738:
2735:
2733:
2729:
2728:
2723:
2722:Trimethadione
2720:
2718:
2715:
2713:
2710:
2708:
2704:
2703:
2701:
2699:
2695:
2689:
2686:
2684:
2681:
2679:
2676:
2674:
2671:
2669:
2666:
2662:
2661:Oxcarbazepine
2659:
2657:
2654:
2652:
2651:Carbamazepine
2649:
2647:
2645:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2620:
2617:
2615:
2612:
2610:
2607:
2605:
2602:
2600:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2571:
2570:
2568:
2566:
2562:
2559:
2557:
2551:
2541:
2538:
2536:
2531:
2527:
2526:
2522:
2521:
2519:
2515:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2485:
2484:
2482:
2480:
2476:
2470:
2467:
2465:
2462:
2460:
2457:
2454:
2450:
2446:
2443:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2395:
2394:
2389:
2386:
2384:
2380:
2379:
2374:
2371:
2369:
2368:Phenobarbital
2366:
2364:
2363:Pentobarbital
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2340:
2339:
2337:
2335:
2332:
2324:
2321:
2319:
2315:
2310:
2306:
2299:
2294:
2292:
2287:
2285:
2280:
2279:
2276:
2260:
2258:
2255:
2254:
2252:
2249:
2246:
2243:
2241:
2238:
2237:
2233:
2223:
2220:
2219:
2217:
2215:
2211:
2205:
2202:
2200:
2197:
2195:
2192:
2190:
2187:
2185:
2182:
2181:
2179:
2177:
2172:
2168:
2165:
2162:
2158:
2148:
2145:
2144:
2142:
2139:
2135:
2132:
2130:
2125:
2121:
2111:
2107:
2104:
2103:
2101:
2098:
2093:
2087:
2084:
2082:
2079:
2078:
2076:
2072:
2062:
2059:
2057:
2056:Pradofloxacin
2054:
2052:
2049:
2047:
2046:Marbofloxacin
2044:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2023:
2021:
2019:
2015:
2009:
2005:
2004:Trovafloxacin
2002:
2000:
1997:
1995:
1994:Prulifloxacin
1992:
1990:
1987:
1985:
1984:Clinafloxacin
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1965:
1962:
1960:
1957:
1955:
1952:
1951:
1949:
1947:
1943:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1917:
1916:Grepafloxacin
1914:
1912:
1909:
1907:
1904:
1903:
1901:
1899:
1895:
1889:
1886:
1884:
1881:
1879:
1876:
1874:
1870:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1840:Ciprofloxacin
1838:
1837:
1835:
1833:
1829:
1826:
1824:
1820:
1814:
1811:
1809:
1806:
1804:
1801:
1799:
1798:Oxolinic acid
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1780:
1778:
1776:
1772:
1769:
1766:
1759:
1754:
1753:topoisomerase
1748:
1744:
1734:
1731:
1729:
1726:
1724:
1721:
1719:
1718:Acediasulfone
1716:
1715:
1713:
1709:
1703:
1700:
1698:
1695:
1693:
1690:
1688:
1685:
1684:
1682:
1678:
1668:
1665:
1663:
1660:
1658:
1655:
1653:
1650:
1648:
1645:
1643:
1642:Sulfacetamide
1640:
1638:
1635:
1634:
1632:
1628:
1622:
1619:
1617:
1614:
1612:
1611:Sulfamerazine
1609:
1607:
1604:
1602:
1599:
1597:
1594:
1592:
1589:
1587:
1584:
1582:
1579:
1577:
1574:
1573:
1571:
1569:
1565:
1559:
1556:
1554:
1551:
1549:
1546:
1545:
1543:
1541:
1537:
1531:
1530:Sulfathiourea
1528:
1525:
1521:
1517:
1516:Sulfathiazole
1514:
1510:
1507:
1506:
1505:
1504:Sulfanilamide
1502:
1499:
1495:
1494:Sulfafurazole
1492:
1489:
1488:Sulfasalazine
1485:
1484:Sulfapyridine
1482:
1480:
1479:Sulfadimidine
1477:
1475:
1472:
1470:
1467:
1466:
1464:
1462:
1458:
1455:
1452:
1447:
1443:
1435:
1432:
1430:
1427:
1425:
1424:Pyrimethamine
1422:
1420:
1417:
1415:
1412:
1410:
1407:
1406:
1405:
1402:
1401:
1399:
1397:
1393:
1390:
1381:
1375:
1371:
1366:
1362:
1358:
1354:
1347:
1342:
1340:
1335:
1333:
1328:
1327:
1324:
1318:
1315:
1312:
1308:
1305:
1303:
1300:
1297:
1293:
1290:
1288:
1285:
1283:
1280:
1279:
1275:
1266:
1260:
1257:
1252:
1248:
1244:
1240:
1236:
1232:
1229:(7): 856–70.
1228:
1224:
1217:
1214:
1198:
1191:
1184:
1181:
1176:
1172:
1168:
1164:
1160:
1156:
1152:
1148:
1141:
1138:
1133:
1129:
1125:
1121:
1117:
1113:
1106:
1103:
1098:
1094:
1090:
1086:
1082:
1078:
1075:(8): 817–24.
1074:
1070:
1063:
1060:
1047:
1041:
1038:
1034:
1029:
1026:
1021:
1017:
1013:
1009:
1005:
1001:
994:
987:
984:
971:
970:
964:
957:
954:
941:
937:
931:
928:
915:
911:
905:
902:
890:
886:
880:
877:
872:
868:
861:
858:
854:
853:2-228-88108-2
850:
846:
840:
837:
832:
826:
822:
821:
813:
810:
805:
801:
796:
791:
787:
783:
779:
772:
769:
764:
758:
754:
747:
744:
741:
740:9780321735515
737:
733:
727:
724:
711:
705:
703:
699:
686:
680:
677:
672:
668:
663:
658:
654:
650:
646:
642:
638:
631:
628:
621:
617:
614:
612:
609:
606:
603:
601:
598:
596:
593:
592:
588:
586:
584:
580:
576:
572:
568:
564:
560:
556:
551:
545:
542:
538:
537:
536:
533:
531:
530:cotrimoxazole
525:
521:
519:
515:
511:
507:
503:
499:
495:
491:
477:
469:
462:
450:
447:
439:
437:
435:
431:
427:
423:
419:
411:
409:
405:
394:
389:
387:
386:first-aid kit
383:
379:
375:
371:
367:
363:
359:
355:
350:
348:
347:sulfanilamide
344:
340:
336:
332:
328:
324:
320:
316:
310:
307:
303:
299:
294:
293:coal-tar dyes
290:
286:
282:
278:
270:
268:
266:
262:
261:Sulfasalazine
258:
256:
252:
248:
244:
240:
239:sulfonylureas
236:
235:acetazolamide
232:
228:
224:
220:
216:
212:
208:
205:
197:
192:
188:
182:
178:
174:
170:
164:
156:
154:
151:
149:
145:
141:
137:
135:
131:
130:sulfonylureas
127:
124:
120:
116:
115:antimicrobial
112:
108:
104:
103:sulphonamides
100:
96:
93:(a part of a
92:
88:
81:
77:
70:
66:
59:
55:
51:
45:
41:
37:
33:
19:
4004:Sulfonamides
3994:Hepatotoxins
3884:
3841:
3810:
3734:Nonsteroidal
3732:
3701:
3666:ESC blockers
3633:Quinethazone
3560:Polythiazide
3368:Sulfonamides
3367:
3309:Tirbanibulin
3263:Tromantadine
3172:Sulfonamides
3171:
3134:Fusidic acid
3130:
3102:Nadifloxacin
3050:Tetracycline
3026:Tetracycline
2898:Fenfluramine
2878:Brivaracetam
2827:Sulfonamides
2825:
2760:
2745:
2742:Phensuximide
2732:Ethosuximide
2727:Succinimides
2725:
2705:
2664:
2644:Carboxamides
2642:
2622:
2597:
2584:Fosphenytoin
2572:
2533:
2523:
2486:
2441:
2391:
2376:
2348:Barbexaclone
2343:Barbiturates
2341:
2214:Lipiarmycins
2061:Sarafloxacin
2051:Orbifloxacin
2036:Enrofloxacin
2026:Danofloxacin
1999:Sitafloxacin
1979:Moxifloxacin
1974:Gemifloxacin
1969:Finafloxacin
1964:Gatifloxacin
1959:Delafloxacin
1954:Besifloxacin
1936:Tosufloxacin
1931:Temafloxacin
1926:Sparfloxacin
1921:Pazufloxacin
1911:Balofloxacin
1906:Levofloxacin
1865:Nadifloxacin
1860:Lomefloxacin
1680:Combinations
1662:Sulfametrole
1647:Sulfaclozine
1553:Sulfadiazine
1461:Short-acting
1446:Sulfonamides
1445:
1434:Trimethoprim
1310:
1264:
1259:
1226:
1222:
1216:
1204:. Retrieved
1197:the original
1183:
1150:
1146:
1140:
1115:
1111:
1105:
1072:
1068:
1062:
1050:. Retrieved
1040:
1028:
1003:
999:
986:
974:. Retrieved
967:
956:
944:. Retrieved
940:the original
930:
918:. Retrieved
913:
904:
892:. Retrieved
888:
879:
870:
866:
860:
844:
839:
819:
812:
785:
781:
771:
752:
746:
731:
726:
714:. Retrieved
689:. Retrieved
679:
644:
640:
630:
552:
549:
534:
526:
522:
494:haemopoietic
487:
466:Person with
451:Side effects
426:trimethoprim
415:
406:
390:
370:World War II
351:
327:Daniel Bovet
315:streptococci
311:
306:Josef Klarer
274:
259:
201:
166:
152:
138:
111:sulpha drugs
110:
106:
102:
86:
85:
36:
3984:Dermatoxins
3947:from market
3910:Cicletanine
3905:Theobromine
3899:Meralluride
3876:Isopropanol
3684:Triamterene
3603:Clorexolone
3593:Clofenamide
3577:(primarily
3448:Indacrinone
3278:Ibacitabine
3233:Idoxuridine
3228:Penciclovir
3144:Tyrothricin
3017:Antibiotics
2996:Antibiotics
2938:from market
2888:Carisbamate
2883:Cannabidiol
2769:Lamotrigine
2673:Lamotrigine
2624:Fatty acids
2619:Pheneturide
2614:Phenacemide
2589:Mephenytoin
2488:Fatty acids
2469:Stiripentol
2464:Paraldehyde
2428:Nimetazepam
2408:Clorazepate
2353:Metharbital
2247:from market
2222:Fidaxomicin
2194:Rifapentine
2147:Secnidazole
2140:derivatives
2081:Nemonoxacin
2041:Ibafloxacin
1989:Garenoxacin
1878:Norfloxacin
1728:Solasulfone
1667:Sulfanitran
1621:Sulfamazone
1581:Sulfadoxine
1568:Long-acting
1558:Sulfamoxole
1429:Tetroxoprim
1409:Brodimoprim
1386:DNA and RNA
1374:Antifolates
1147:Drug Safety
532:allergy").
496:disorders,
412:Preparation
241:(including
209:(including
119:sulfonamide
107:sulfa drugs
87:Sulfonamide
32:Sulfonamide
18:Sulfa drugs
3978:Categories
3828:Satavaptan
3823:Mozavaptan
3818:Conivaptan
3740:Finerenone
3719:Eplerenone
3628:Metolazone
3613:Indapamide
3608:Fenquizone
3550:Mebutizide
3473:Torasemide
3463:Piretanide
3453:Muzolimine
3433:Bumetanide
3423:Furosemide
3248:Resiquimod
3215:Antivirals
3139:Bacitracin
3098:Quinolones
3086:Gentamicin
3066:Amphenicol
2913:Perampanel
2903:Ganaxolone
2893:Etiracetam
2852:Zonisamide
2847:Topiramate
2797:Retigabine
2779:Zonisamide
2774:Topiramate
2757:Pregabalin
2752:Gabapentin
2737:Mesuximide
2688:Zonisamide
2683:Topiramate
2678:Rufinamide
2668:Lacosamide
2634:Valpromide
2574:Hydantoins
2556:modulators
2508:Vigabatrin
2498:Valpromide
2433:Nitrazepam
2403:Clonazepam
2383:Cenobamate
2378:Carbamates
2318:GABAergics
2184:Rifampicin
2171:Rifamycins
2129:inhibitors
2110:Novobiocin
2086:Ozenoxacin
2031:Difloxacin
2018:Veterinary
1888:Rufloxacin
1883:Pefloxacin
1855:Fleroxacin
1788:Flumequine
1758:DNA gyrase
1747:Quinolones
1606:Sulfaperin
1419:Ormetoprim
1388:synthesis)
1206:7 February
1188:Veroni M.
1052:26 October
1020:1066656753
1006:(1): 147.
920:17 January
894:17 January
716:17 January
691:17 January
622:References
393:protonated
366:penicillin
323:erysipelas
227:bumetanide
223:furosemide
219:indapamide
215:metolazone
183:(vitamin B
148:penicillin
69:Furosemide
3957:Phase III
3945:Withdrawn
3833:Tolvaptan
3714:Canrenone
3674:Amiloride
3623:Meticrane
3618:Mefruside
3598:Clopamide
3535:Epitizide
3483:Thiazides
3458:Ozolinone
3428:Azosemide
3355:Diuretics
3258:Docosanol
3243:Imiquimod
3238:Edoxudine
3223:Aciclovir
3149:Mupirocin
3124:Rifaximin
3120:Rifamycin
2948:Phase III
2936:Withdrawn
2873:Beclamide
2764:Imepitoin
2712:Ethadione
2629:Valproate
2594:Phenytoin
2540:Tiagabine
2530:Progabide
2493:Valproate
2459:Imepitoin
2438:Temazepam
2423:Midazolam
2418:Lorazepam
2388:Felbamate
2373:Primidone
2257:Phase III
2245:Withdrawn
2204:Rifalazil
2199:Rifaximin
2189:Rifabutin
2163:synthesis
2124:Anaerobic
2095:Related (
1845:Ofloxacin
1813:Rosoxacin
1783:Cinoxacin
1733:Sulfoxone
1586:Sulfalene
1509:Prontosil
1012:2063-6997
543:reaction.
498:porphyria
440:Varieties
289:IG Farben
277:Prontosil
255:celecoxib
247:glyburide
243:glipizide
231:torsemide
207:diuretics
140:Allergies
3895:Mersalyl
3778:Glycerol
3773:Mannitol
3679:Benzamil
3638:Xipamide
3515:Butizide
3505:Altizide
3443:Etozolin
3273:Lysozyme
3190:Mafenide
3091:Amikacin
3081:Neomycin
2868:Albutoin
2842:Sultiame
2579:Ethotoin
2413:Diazepam
2398:Clobazam
1850:Enoxacin
1637:Mafenide
1414:Iclaprim
1251:25623592
1243:15303450
1175:20386434
1167:11330653
1132:15242722
1089:11549195
976:28 March
671:16350088
589:See also
279:, was a
204:thiazide
157:Function
126:sultiame
95:molecule
58:thiazide
3872:Ethanol
3812:Vaptans
3410:Na-K-Cl
3268:Inosine
2761:Others:
2665:Others:
2599:Ureides
2554:Channel
2445:Bromide
2442:Others:
1756:and/or
1723:Dapsone
1097:8493824
946:4 April
804:3525495
341:at the
331:Jacques
281:prodrug
271:History
253:(e.g.,
3940:WHO-EM
3843:Others
3283:Lysine
3131:other:
3059:Others
2931:WHO-EM
2861:Others
2810:Others
2517:Others
2240:WHO-EM
1298:, 1939
1249:
1241:
1173:
1165:
1130:
1095:
1087:
1018:
1010:
873:: 756.
851:
827:
802:
759:
738:
669:
662:440870
659:
380:) and
321:, and
229:, and
217:, and
181:folate
128:. The
3865:Other
3487:Na-Cl
3371:(and
3292:Other
3006:use (
1355:that
1247:S2CID
1200:(PDF)
1193:(PDF)
1171:S2CID
1093:S2CID
996:(PDF)
559:hives
285:Bayer
99:drugs
89:is a
3880:2M2B
3800:and
3783:Urea
3654:(at
3406:Loop
3385:(at
3002:for
2998:and
2334:PAMs
2327:GABA
1365:J01M
1361:J01E
1239:PMID
1208:2014
1163:PMID
1128:PMID
1085:PMID
1054:2013
1016:OCLC
1008:ISSN
978:2014
969:Time
948:2014
922:2014
896:2014
849:ISBN
825:ISBN
800:PMID
757:ISBN
736:ISBN
718:2014
693:2014
667:PMID
611:PABA
557:and
555:rash
333:and
196:PABA
132:and
3798:DCT
3579:DCT
3491:DCT
3489:at
3412:at
3359:C03
3008:D06
2309:N03
2161:RNA
2126:DNA
1231:doi
1155:doi
1120:doi
1077:doi
871:120
790:doi
657:PMC
649:doi
257:).
233:),
109:or
3980::
3953::
3897:,
3893:,
3878:,
3874:,
3802:CD
3764:DL
3762:,
3760:PT
3656:CD
3414:AL
3387:PT
3122::
3111::
3100::
3079::
3068::
2944::
2759:;
2744:;
2730::
2724:;
2663:;
2641:;
2621:;
2596:;
2532:;
2528::
2451:,
2440:;
2396::
2390:;
2381::
2375:;
2253::
2108::
2097:DG
1522:,
1363:,
1309:.
1294:,
1245:.
1237:.
1227:24
1225:.
1169:.
1161:.
1151:24
1149:.
1126:.
1116:24
1114:.
1091:.
1083:.
1073:94
1071:.
1014:.
1002:.
998:.
966:.
912:.
887:.
869:.
855:).
823:.
798:.
786:17
784:.
780:.
701:^
665:.
655:.
643:.
639:.
577:,
573:,
569:,
565:,
508:,
400:pK
267:.
245:,
237:,
225:,
213:,
105:,
3901:)
3889:(
3804:)
3796:(
3766:)
3758:(
3658:)
3581:)
3498:)
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3485:(
3416:)
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3389:)
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3361:)
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2749::
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2646::
2626::
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2329:A
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1518:(
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Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
