506:
483:
1332:
the hemolysis side effect. This was difficult to accomplish because dapsone is highly insoluble in aqueous solvents. In the early 2000s QLT USA developed Aczone, a 5% dapsone gel that was shown to be effective against acne without causing clinically significant declines in hemoglobin levels, even in subjects with G6PD deficiency. In
February 2016, the FDA approved a 7.5% dapsone gel. This higher strength has the advantage of a once-daily application, versus twice-daily application of the 5% formulation.
1180:(HOCl). HOCl is the most potent oxidant generated by neutrophils, and can cause significant tissue damage during inflammation. Dapsone arrests myeloperoxidase in an inactive intermediate form, reversibly inhibiting the enzyme. This prevents accumulation of hypochlorous acid, and reduces tissue damage during inflammation. Myeloperoxidase inhibition has also been suggested as a neuron-sparing mechanism for reducing inflammation in neurodegenerative diseases such as
1212:
5844:
38:
29:
2476:"Antimalarial chlorproguanil-dapsone (LapDap™) withdrawn following demonstration of post-treatment haemolytic anaemia in G6PD deficient patients in a Phase III trial of chlorproguanil-dapsone-artesunate (Dacart™) versus artemether-lumefantrine (Coartem®) and confirmation of findings in a comparative trial of LapDap™ versus Dacart ™"
2363:
Tempark T, Satapornpong P, Rerknimitr P, Nakkam N, Saksit N, Wattanakrai P, Jantararoungtong T, Koomdee N, Mahakkanukrauh A, Tassaneeyakul W, Suttisai S, Pratoomwun J, Klaewsongkram J, Rerkpattanapipat T, Sukasem C (December 2017). "Dapsone-induced severe cutaneous adverse drug reactions are strongly
866:, as a review found that using oral dapsone alone was effective in 80% of early cases of the disease. However, dapsone can potentially cause severe side effects, meaning that sometimes steroids or other antibiotics should be used instead, although these alternative treatments are much less effective.
1331:
Dapsone had been reported in a few cases to effectively treat acne, but the risk of hemolytic anemia kept it from being widely used for this purpose. For many years scientists attempted to develop a topical formulation of dapsone that would be as effective against acne as oral dapsone, but without
1322:
One advantage of Lapdap was that chlorproguanil and dapsone are both low-cost drugs. Another was that by virtue of being a combination drug, it was less likely to cause drug resistance. However, because dapsone causes hemolytic anemia in patients with G6PD deficiency, and because G6PD deficiency
818:
Idiopathic thrombocytopenic purpura. Dapsone is effective and safe for adjunctive glucocorticoid-sparing treatment of persons with idiopathic thrombocytopenic purpura and is preferred over danazol or interferon alpha in those people with antinuclear
794:
Dapsone by mouth was one of the first medications used to treat moderate to severe acne vulgaris, and is still occasionally prescribed for the treatment of severe cases. A topical form of dapsone is also effective with potentially less side effects.
1323:
affects 10-25% of the population of sub-Saharan Africa, it was discovered that Lapdap is not safe for use in Africa. It was available in many
African countries for four years before GlaxoSmithKline took it off the market in February 2008.
3456:
Diaz-Ruiz A, Zavala C, Montes S, Ortiz-Plata A, Salgado-Ceballos H, Orozco-Suarez S, et al. (November 2008). "Antioxidant, antiinflammatory and antiapoptotic effects of dapsone in a model of brain ischemia/reperfusion in rats".
989:
have been reported by the manufacturer. These toxic reactions may also occur as part of the dapsone hypersensitivity syndrome (a form of SCARs-see above) or dapsone syndrome (see below). Dapsone is metabolized by the
1029:
When used topically, dapsone can cause mild skin irritation, redness, dry skin, burning, and itching. When used together with benzoyl peroxide products, temporary yellow or orange skin discolorations can occur.
832:
Relapsing polychondritis. There are no clinical trials but there are many case reports that dapsone is effective at doses of 25 mg/day to 200 mg/day for treatment of relapsing polychondritis.
2206:
Khazaei A, Kazem-Rostami M, Zare A, Moosavi-Zare AR, Sadeghpour M, Afkhami A (15 September 2013). "Synthesis, characterization, and application of a triazene-based polysulfone as a dye adsorbent".
3337:
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3625:
735:, and a number of types of skin rashes. While the safety of use during pregnancy is not entirely clear some physicians recommend that it be continued in those with leprosy. It is of the
1952:
Antia C, Baquerizo K, Korman A, Alikhan A, Bernstein JA (October 2018). "Urticaria: A comprehensive review: Treatment of chronic urticaria, special populations, and disease outcomes".
939:, leading to the dapsone-containing antimalarial combination Lapdap being withdrawn from clinical use. A case of hemolysis in a neonate from dapsone in breast milk has been reported.
5899:
134:
2328:
Bocquet H, Bagot M, Roujeau JC (December 1996). "Drug-induced pseudolymphoma and drug hypersensitivity syndrome (Drug Rash with
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4395:
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4470:
3386:
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5889:
5422:
1712:
60:
3693:
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4385:
3900:
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724:
602:
2482:
3666:
Buttle G, Stephenson D, Smith S, Dewing T, Foster G (June 1937). "Treatment of streptococcal infections in mice with 4:4'diamino-dipheni-sulphone".
908:
Hypersensitivity reactions occur in 1.4% of persons treated with dapsone, and can be fatal in medical settings with low resources. It is a form of
3302:
Bozeman PM, Learn DB, Thomas EL (August 1992). "Inhibition of the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase by dapsone".
5754:
3613:
957:
occurs in about 15 % of patients treated with long-term dapsone at standard doses (100 mg/day). Only special multi-wavelength oximeters (
927:
is the most prominent side-effect, occurring in about 20 % of patients treated with dapsone, although it is dose-related. It may lead to
5798:
5366:
4463:
4414:
1887:
743:
4577:
3982:
815:
Cutaneous lupus erythematosus. Dapsone is effective and safe in persons with moderate, severe, or refractory cutaneous lupus erythematosus.
3718:
Stotland M, Shalita AR, Kissling RF (June 2009). "Dapsone 5% gel: a review of its efficacy and safety in the treatment of acne vulgaris".
2547:
Sanders SW, Zone JJ, Foltz RL, Tolman KG, Rollins DE (April 1982). "Hemolytic anemia induced by dapsone transmitted through breast milk".
1429:
1664:
1556:
3652:
5864:
5415:
1352:, applications include in printed circuit boards, adhesives and coatings. Its use in epoxy systems typically give a resin with a high
909:
578:
4522:
4400:
3878:
1696:
1658:
1550:
1423:
622:
3267:
Bozeman PM, Learn DB, Thomas EL (January 1990). "Assay of the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase".
1060:(see above). In general, these symptoms will occur within the first six weeks of therapy or not at all, and may be ameliorated by
4456:
3893:
5874:
4390:
3816:"Molecular control over vitrimer-like mechanics - tuneable dynamic motifs based on the Hammett equation in polyimine materials"
943:
occurs rarely when dapsone is used alone but more frequently in combination regimens for malaria prophylaxis. Abnormalities in
280:
174:
92:
2791:
Ganesan S, Sahu R, Walker LA, Tekwani BL (April 2010). "Cytochrome P450-dependent toxicity of dapsone in human erythrocytes".
2475:
870:
2407:
Puavilai S, Chutha S, Polnikorn N, et al. (July 1984). "Incidence of anemia in leprosy patients treated with dapsone".
5769:
5408:
4813:
3202:
1686:
826:
822:
5834:
1466:
5759:
5302:
2120:
Momen SE, Jorizzo J, Al-Niaimi F (December 2014). "Erythema elevatum diutinum: a review of presentation and treatment".
1353:
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5879:
5815:
5383:
4431:
4085:
3886:
2664:
Meyerson MA, Cohen PR (1994). "Dapsone-induced aplastic anemia in a woman with bullous systemic lupus erythematosus".
1769:
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2163:
Lukács J, Schliemann S, Elsner P (August 2015). "Treatment of generalized granuloma annulare - a systematic review".
3697:
5894:
5784:
5749:
863:
727:(G-6-PD), or hypersensitivity. Common side effects include nausea and loss of appetite. Other side effects include
111:
3786:
1041:
reactions occur in some patients. This reaction may be more frequent in patients receiving multiple-drug therapy.
5774:
2853:"Increased incidence in leprosy of hypersensitivity reactions to dapsone after introduction of multidrug therapy"
1619:
1307:, another antimalarial drug, had been developed in the 1980s but was too expensive for large-scale use. This led
1300:
5576:
4828:
4167:
3421:
Kettle AJ, Winterbourn CC (May 1991). "Mechanism of inhibition of myeloperoxidase by anti-inflammatory drugs".
1192:
1125:
841:
709:
2834:
5803:
5371:
4879:
4419:
4053:
4037:
122:
4823:
3614:"Activité du p.aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin"
3153:
Jaffuel D, Lebel B, Hillaire-Buys D, Pene J, Godard P, Michel FB, Blayac JP, Bousquet J, Demolyi P (1998).
501:
5884:
5255:
4727:
4694:
4666:
4624:
4587:
4572:
4483:
4145:
4042:
3930:
3913:
1181:
1129:
776:
693:
220:
5764:
4650:
4646:
4530:
4448:
4212:
4032:
3366:
2504:
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5779:
5144:
5072:
5024:
4958:
4949:
4901:
4873:
4380:
4058:
1216:
986:
852:
247:
742:
Dapsone was first studied as an antibiotic in 1937. Its use for leprosy began in 1945. It is on the
5619:
4999:
1121:
478:
297:
4773:
5462:
5250:
4722:
3743:
3560:
3482:
3249:
2816:
2607:
2529:
2389:
2305:
2188:
2145:
1977:
1819:
1751:
1706:
1601:
1518:
1493:
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970:
2626:
1413:
5869:
5515:
5500:
4506:
3917:
3909:
3845:
3735:
3552:
3517:
3474:
3438:
3403:
3354:
3319:
3284:
3241:
3184:
3135:
3100:
3065:
3024:
2983:
2942:
2901:
2874:
2808:
2773:
2722:
2681:
2646:
2599:
2564:
2521:
2457:
2416:
2381:
2345:
2297:
2256:
2180:
2137:
2102:
2061:
2026:
1969:
1934:
1883:
1860:
1811:
1743:
1692:
1654:
1648:
1593:
1546:
1540:
1510:
1419:
1264:
1247:(sulfonamidochrysoidine). Further investigation into the involved chemicals opened the way to
1198:
Dapsone is an odorless white to creamy-white crystalline powder with a slightly bitter taste.
1188:
1177:
1148:
1136:
1117:
1018:
962:
954:
932:
732:
189:
50:
2892:
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431:
5652:
5505:
5457:
4995:
4818:
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4674:
3835:
3827:
3727:
3675:
3594:
3544:
3509:
3466:
3430:
3395:
3346:
3311:
3276:
3233:
3174:
3166:
3127:
3092:
3083:
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3055:
3014:
2973:
2932:
2864:
2800:
2763:
2753:
2712:
2673:
2638:
2591:
2556:
2513:
2447:
2373:
2337:
2287:
2246:
2215:
2172:
2129:
2092:
2053:
2016:
2008:
1961:
1924:
1916:
1878:
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1850:
1803:
1735:
1627:
1583:
1502:
1128:, thereby inhibiting nucleic acid synthesis. Though structurally distinct from dapsone, the
1038:
944:
928:
845:
788:
701:
518:
202:
3640:
1243:
for his efforts, made a major breakthrough in 1932 with the discovery of the antibacterial
391:
5848:
4891:
4717:
4208:
4199:
1308:
1268:
991:
948:
940:
897:
716:
371:
230:
210:
3131:
3096:
1572:"Acquired methemoglobinemia: a retrospective series of 138 cases at 2 teaching hospitals"
951:, are rare, yet are the cause of the majority of deaths attributable to dapsone therapy.
3761:
2595:
505:
482:
306:
5809:
5634:
5495:
5377:
5264:
5134:
4934:
4929:
4919:
4783:
4778:
4742:
4600:
4425:
4350:
4094:
3944:
3867:
3840:
3815:
3800:
2768:
2741:
2717:
2700:
2057:
2021:
1996:
1929:
1904:
1903:
Weber E, Reynaud Q, Fort R, Durupt S, Cathébras P, Durieu I, Lega JC (September 2017).
1855:
1838:
1739:
1316:
1236:
1061:
1057:
966:
913:
712:, and various other skin conditions. Dapsone is available both topically and by mouth.
3679:
3513:
2677:
2517:
2341:
1588:
1571:
1227:
was developing theories of selective toxicity based largely on the ability of certain
5858:
5571:
5538:
5490:
5467:
5431:
5232:
5182:
5172:
5130:
5120:
5110:
5042:
4966:
4924:
4844:
4768:
4737:
4656:
4642:
4630:
4620:
4614:
4610:
4605:
4595:
4550:
4284:
4271:
4262:
4176:
4122:
3731:
3434:
3399:
3315:
3280:
3179:
3154:
1256:
1109:
825:. Dapsone is effective and safe for treatment of second-line therapy for people with
799:
780:
705:
697:
589:
494:
84:
3747:
3564:
3253:
2820:
2611:
2533:
2309:
2192:
2149:
1981:
1823:
1755:
1605:
1522:
5677:
5624:
5614:
5609:
5566:
5472:
5452:
5435:
5187:
5177:
5162:
5152:
5125:
5105:
5100:
5095:
5090:
5085:
5080:
5062:
5057:
5052:
5047:
5037:
5032:
4991:
4986:
4788:
4679:
4560:
4491:
4487:
4322:
4255:
4246:
4233:
4112:
4071:
4066:
3921:
3486:
2393:
2012:
1345:
1341:
1260:
1224:
1211:
1191:
and immunomodulatory effects are thought to be its mechanism of action in treating
1053:
784:
747:
157:
152:
147:
142:
2642:
900:, and liver impairment are at higher risks of adverse effects when using dapsone.
630:
InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
2377:
1319:
and dapsone. Lapdap was licensed in the United
Kingdom starting in October 2003.
331:
5713:
5697:
5682:
5590:
5585:
5580:
5556:
5548:
5523:
5482:
5348:
5340:
5320:
5273:
5207:
5167:
5115:
5004:
4854:
4793:
4747:
4707:
4684:
4555:
4535:
4479:
4344:
4310:
4276:
4266:
4189:
4153:
4010:
3963:
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2560:
2452:
2435:
1965:
1462:
1386:
70:
5687:
5444:
5310:
5236:
5223:
5212:
5157:
5014:
5009:
4981:
4914:
4884:
4732:
4545:
4500:
4362:
4338:
4326:
4216:
3995:
3978:
3953:
3598:
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1807:
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in Africa has encouraged the development of new, low-cost antimalarial drugs.
1248:
1152:
764:
681:
677:
554:
362:
5400:
3170:
2921:"Increase in the incidence of dapsone hypersensitivity syndrome—an appraisal"
2758:
869:
An August 2015 review notes that dapsone is reported to be effective against
5733:
5692:
5672:
5647:
5629:
5528:
5330:
5325:
5315:
5297:
4971:
4939:
4909:
4859:
4712:
4635:
4356:
4333:
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1506:
1349:
1244:
1089:
982:
924:
885:
876:
Dapsone has been used as a monomer in the design of dye adsorbent polymers.
728:
720:
260:
64:
3849:
3739:
3521:
3478:
3245:
2946:
2812:
2777:
2525:
2385:
2301:
2260:
2184:
2141:
2106:
2065:
2030:
1973:
1938:
1864:
1815:
1773:
1747:
1624:
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1597:
1514:
1147:-halide-mediated cytotoxic system in polymorphonucleocytes. As part of the
3556:
3442:
3407:
3358:
3323:
3288:
3188:
3139:
3104:
3069:
3028:
2987:
2905:
2878:
2742:"Dapsone-induced methemoglobinemia: "Saturation gap"-The key to diagnosis"
2726:
2685:
2650:
2568:
2461:
2420:
2349:
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2275:
2251:
2234:
5723:
5718:
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4976:
4763:
4540:
4317:
4102:
4000:
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2603:
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1085:
1077:
995:
856:
829:
in those for whom antihistamines and other first-line agents have failed.
342:
106:
1632:
1056:, and is likely to be one manifestation of the SCARs reaction viz., the
351:
20:
5728:
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species that causes malaria, has developed resistance both to
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3641:"Action antistreptococcique des dérivés sulfurés organiques"
3203:"Mechanisms of Action of Dapsone in Dermatological Diseases"
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935:. The side-effect is more common and severe in those with
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2481:. World Health Organization. 4 March 2008. QSM/MC/IEA.1.
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1465:. The American Society of Health-System Pharmacists.
3207:
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1271:
in France and Gladwin Buttle in the United Kingdom.
1132:
group of antibacterial drugs also work in this way.
5742:
5706:
5663:
5600:
5547:
5514:
5481:
5443:
5339:
5296:
5286:
5263:
5249:
5221:
5200:
5143:
5071:
5023:
4957:
4948:
4900:
4872:
4837:
4806:
4756:
4693:
4665:
4586:
4571:
4521:
4499:
4373:
4297:
4232:
4198:
4175:
4166:
4144:
4121:
4093:
4084:
4052:
4024:
3977:
3938:
3929:
3762:"Aczone (dapsone) 7.5% Gel Prescribing Information"
1995:Liang SE, Hoffmann R, Peterson E, Soter NA (2019).
1418:. Lippincott Williams & Wilkins. p. 1142.
1267:(1935), then with that of dapsone independently by
588:
566:
553:
517:
512:
493:
461:
441:
421:
401:
381:
361:
341:
316:
296:
271:
259:
246:
229:
219:
209:
201:
173:
168:
133:
121:
91:
77:
59:
49:
44:
4396:Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim
3639:Fourneau E, Tréfouël TJ, Nitti F, Bovet D (1937).
3612:Tréfouël JT, Nitti F, Bovet D (23 November 1935).
1570:Ash-Bernal R, Wise R, Wright SM (September 2004).
2436:"Side-effects of antileprosy drugs in common use"
1880:Dubois' Lupus Erythematosus and Related Syndromes
1340:4,4-Diaminodiphenyl sulfone also finds uses as a
1303:, two of the most common treatments for malaria.
912:(SCARs) in which a SCARs disorder, primarily the
2746:Journal of Anaesthesiology Clinical Pharmacology
1545:. Jones & Bartlett Publishers. p. 193.
1463:"Dapsone (Systemic) Monograph for Professionals"
330:
3694:"Leprosy | 14 History of dapsone and dyes"
1772:. ScienceOfAcne.com. 2012-10-10. Archived from
305:
3587:Berichte der Deutschen Chemischen Gesellschaft
3371:: CS1 maint: DOI inactive as of August 2024 (
1495:Journal of the American Academy of Dermatology
1223:In the early 20th century, the German chemist
5900:World Health Organization essential medicines
5416:
4464:
3894:
763:Dapsone is commonly used in combination with
8:
4386:Ethambutol/isoniazid/pyrazinamide/rifampicin
3226:Bioorganic & Medicinal Chemistry Letters
3003:"Dapsone syndrome occurring in two brothers"
973:result, methemoglobinemia may be suspected.
937:glucose-6-phosphate dehydrogenase deficiency
775:. It is also used to both treat and prevent
725:glucose-6-phosphate dehydrogenase deficiency
110:
19:
3155:"Eosinophilic pneumonia induced by dapsone"
2625:Foucauld J, Uphouse W, Berenberg J (1985).
2233:Lorenz M, Wozel G, Schmitt J (March 2012).
194:In general: â„ž (Prescription only)
5423:
5409:
5401:
5293:
5260:
4954:
4897:
4583:
4518:
4471:
4457:
4449:
4172:
4090:
3935:
3901:
3887:
3879:
2323:
2321:
2319:
1711:: CS1 maint: location missing publisher (
1457:
1455:
1453:
1451:
1449:
1447:
1445:
1443:
1441:
1439:
916:or a DRESS syndrome-like reaction occurs.
504:
481:
370:
36:
27:
3839:
3645:Comptes rendus de l'Académie des sciences
3178:
3059:
3018:
2977:
2936:
2868:
2767:
2757:
2716:
2499:
2497:
2495:
2451:
2291:
2250:
2096:
2020:
1928:
1882:. Edinburgh: Elsevier. pp. 719–726.
1854:
1631:
1587:
1534:
1532:
1488:
1486:
1484:
862:Dapsone is the recommended treatment for
390:
3720:American Journal of Clinical Dermatology
2128:(12). John Wiley & Sons: 1594–1602.
1653:. Oxford University Press. p. 197.
1415:Foye's Principles of Medicinal Chemistry
1210:
1139:, dapsone inhibits the myeloperoxidase-H
5839:
2699:Björkman A, Phillips-Howard PA (1991).
2171:(8). John Wiley & Sons: 1467–1480.
1378:
627:
607:
594:175 to 176 °C (347 to 349 °F)
477:
350:
285:
83:
5755:Clindamycin/adapalene/benzoyl peroxide
3364:
1704:
1013:. Dapsone metabolites produced by the
798:It is unclear if the combination with
495:
18:
5890:Dihydropteroate synthetase inhibitors
2488:from the original on 21 October 2012.
1680:
1678:
1676:
1674:
1626:. Geneva: World Health Organization.
704:. Additionally, it has been used for
450:
430:
69:
7:
3874:. U.S. National Library of Medicine.
3628:from the original on 3 January 2017.
3132:10.1001/archderm.1982.01650190085028
3097:10.1001/archderm.1981.01650010044023
3044:"Dapsone syndrome in a Filipino man"
1259:, the active agent of prontosil, by
156:
146:
3787:"ECHA dapsone registration dossier"
2596:10.5694/j.1326-5377.1977.tb117649.x
1839:"Malaria: prevention in travellers"
1315:, a combination drug consisting of
410:
321:
2208:Journal of Applied Polymer Science
2058:10.1016/j.clindermatol.2006.07.018
1740:10.1111/j.1365-2133.1961.tb14398.x
1728:The British Journal of Dermatology
1275:Proposed use in antimalarial drugs
910:severe cutaneous adverse reactions
715:Severe side effects may include a
680:commonly used in combination with
14:
4401:Rifampicin/isoniazid/pyrazinamide
2835:"Aczone (Dapsone) Package insert"
1796:Expert Opinion on Pharmacotherapy
1589:10.1097/01.md.0000141096.00377.3f
1219:by E. Fromm and J. Wittmann, 1908
1034:Dapsone hypersensitivity syndrome
892:, cardiac disease, lung disease,
880:Contraindications and precautions
5842:
3732:10.2165/00128071-200910040-00002
3655:from the original on 2016-02-20.
3583:"Derivate desp-Nitrothiophenols"
3581:Fromm E, Wittmann J (May 1908).
3459:Journal of Neuroscience Research
3269:Journal of Immunological Methods
3209:. Medscape Today. Archived from
1667:from the original on 2016-03-04.
1559:from the original on 2016-03-04.
1432:from the original on 2016-03-04.
1017:isozyme are associated with the
535:
529:
4391:Ethambutol/isoniazid/rifampicin
2851:Richardus JH, Smith TC (1989).
1685:Rossi S (2006). Rossi S (ed.).
1469:from the original on 2015-01-12
1044:The reaction always involves a
802:is useful in the prevention of
635:Key:MQJKPEGWNLWLTK-UHFFFAOYSA-N
610:O=S(=O)(c1ccc(N)cc1)c2ccc(N)cc2
2013:10.1001/jamadermatol.2018.3715
1387:"Dapsone Use During Pregnancy"
1255:, first with the discovery of
1072:Other adverse effects include
871:generalized granuloma annulare
547:
541:
523:
1:
5770:Erythromycin/benzoyl peroxide
4814:Trimethoprim/sulfamethoxazole
3680:10.1016/S0140-6736(00)75868-5
3514:10.1016/S0151-9638(04)93842-2
2793:Journal of Applied Toxicology
2678:10.1016/s0025-6196(12)65768-1
2643:10.7326/0003-4819-102-1-139_2
2627:"Dapsone and aplastic anemia"
2518:10.1016/S0140-6736(10)60396-0
2366:Pharmacogenetics and Genomics
2342:10.1016/S1085-5629(96)80038-1
1688:Australian Medicines Handbook
1279:The spread of drug-resistant
851:Dapsone may be used to treat
827:chronic spontaneous urticaria
823:Chronic spontaneous urticaria
783:in people unable to tolerate
5760:Clindamycin/benzoyl peroxide
3435:10.1016/0006-2952(91)90565-m
3400:10.1016/0006-2952(93)90010-t
3316:10.1016/0006-2952(92)90449-s
3281:10.1016/0022-1759(90)90020-v
2378:10.1097/FPC.0000000000000306
2081:"Brown recluse spider bites"
1542:Johns Hopkins HIV Guide 2012
1354:glass-transition temperature
969:reading and a high arterial
4819:Ormetoprim/sulfadimethoxine
4285:Thioacetazone (amithiozone)
4086:Protein synthesis inhibitor
2919:Rao PN, Lakshmi TS (2001).
1921:10.1097/MD.0000000000007534
1770:"Dapsone and Acne Vulgaris"
1368:, a more-soluble derivative
779:(PCP). It is also used for
5916:
5785:Tretinoin/benzoyl peroxide
5750:Adapalene/benzoyl peroxide
3238:10.1016/j.bmcl.2018.11.031
3061:10.5935/0305-7518.19950034
3020:10.5935/0305-7518.19860010
2979:10.5935/0305-7518.19850034
2938:10.5935/0305-7518.20010009
2870:10.5935/0305-7518.19890033
2561:10.7326/0003-4819-96-4-465
2453:10.5935/0305-7518.19830032
1966:10.1016/j.jaad.2018.01.023
1837:Croft AM (November 2007).
1215:Synthesis of dapsone from
864:erythema elevatum diutinum
696:and for the prevention of
513:Chemical and physical data
5865:Drugs developed by AbbVie
5793:
5775:Erythromycin/isotretinoin
5361:
4829:Pyrimethamine/sulfadoxine
4409:
3767:. Allergan. February 2016
3599:10.1002/cber.190804102131
2098:10.3122/15572625-13-6-415
1808:10.1517/14656560903002097
1620:World Health Organization
1301:sulfadoxine/pyrimethamine
1021:side effect of the drug.
723:especially in those with
643:
618:
598:
276:
35:
26:
4168:Cell envelope antibiotic
4054:Topoisomerase inhibitors
3423:Biochemical Pharmacology
3388:Biochemical Pharmacology
3304:Biochemical Pharmacology
3171:10.1136/bmj.317.7152.181
2759:10.4103/0970-9185.125710
2705:Bull. World Health Organ
1239:, who would later win a
1193:dermatitis herpetiformis
1126:dihydropteroate synthase
1084:(which are common), and
842:Dermatitis herpetiformis
750:and not very expensive.
721:red blood cell breakdown
710:dermatitis herpetiformis
4146:Polypeptide antibiotics
4038:Calcium aminosalicylate
3872:Drug Information Portal
3353:(inactive 2024-08-26).
1507:10.1067/mjd.2001.114733
1124:for the active site of
1120:, via competition with
717:decrease in blood cells
670:diaminodiphenyl sulfone
5875:Anti-acne preparations
4728:Sulfamethoxypyridazine
4043:Sodium aminosalicylate
3931:Nucleic acid inhibitor
3914:tuberculosis treatment
1220:
844:in combination with a
777:pneumocystis pneumonia
694:pneumocystis pneumonia
662:4,4'-sulfonyldianiline
5765:Clindamycin/tretinoin
5201:Newer non-fluorinated
4838:Other DHPS inhibitors
4824:Pyrimethamine/dapsone
4651:Succinylsulfathiazole
4647:Phthalylsulfathiazole
4531:2,4-Diaminopyrimidine
4213:arabinosyltransferase
4033:4-Aminosalicylic acid
3502:Ann Dermatol Venereol
2293:10.1056/NEJMoa1213096
2252:10.2340/00015555-1268
1954:J. Am. Acad. Dermatol
1843:BMJ Clinical Evidence
1286:Plasmodium falciparum
1214:
1094:peripheral neuropathy
1068:Other adverse effects
994:system, specifically
947:formation, including
771:for the treatment of
688:for the treatment of
16:Antibiotic medication
5780:Sulfacetamide/sulfur
4625:Acetyl sulfisoxazole
4484:inhibit nucleic acid
4381:Ethambutol/isoniazid
2330:Semin Cutan Med Surg
1909:Medicine (Baltimore)
1647:Greenwood D (2008).
1217:4-nitrochlorobenzene
1015:cytochrome P450 2C19
987:cholestatic jaundice
853:brown recluse spider
702:poor immune function
5620:Cyproterone acetate
5000:Alalevonadifloxacin
4667:Intermediate-acting
4249:synth. inhibition:
3001:Jamrozik K (1986).
2434:Jopling WH (1983).
2239:Acta Derm. Venereol
1539:Gallant JE (2008).
1344:for materials like
1182:Alzheimer's disease
1112:, dapsone inhibits
1104:Mechanism of action
1048:, may also include
23:
5880:Antileprotic drugs
5820:Never to phase III
5468:Blue light therapy
5463:8-Hydroxyquinoline
5434:-treating agents (
5388:Never to phase III
4889:thereby inhibiting
4877:(inhibit bacterial
4723:Sulfametoxydiazine
4511:thereby inhibiting
4504:(inhibit bacterial
4436:Never to phase III
3918:leprostatic agents
3910:Antimycobacterials
3832:10.1039/d0sc05458e
3549:10.1042/bss0610163
3537:Biochem. Soc. Symp
2960:Joseph MS (1985).
1393:. 11 November 2019
1221:
1122:para-aminobenzoate
971:blood gas analysis
855:bites that become
810:Autoimmune disease
729:liver inflammation
700:in those who have
5895:German inventions
5830:
5829:
5539:Red light therapy
5516:Anti-inflammatory
5398:
5397:
5357:
5356:
5282:
5281:
5245:
5244:
5196:
5195:
4868:
4867:
4802:
4801:
4507:purine metabolism
4446:
4445:
4293:
4292:
4283:Others/unsorted:
4162:
4161:
4080:
4079:
3471:10.1002/jnr.21775
3465:(15): 3410–3419.
3429:(10): 1485–1492.
3394:(10): 2003–2010.
3351:10.1159/000233335
2220:10.1002/app.39069
2177:10.1111/jdv.12976
2134:10.1111/jdv.12566
2079:Forks TP (2000).
1889:978-0-323-47927-1
1412:Lemke TL (2008).
1265:Pasteur Institute
1189:anti-inflammatory
1178:hypochlorous acid
1149:respiratory burst
1137:anti-inflammatory
1118:dihydrofolic acid
1096:. Effects on the
1019:methemoglobinemia
963:methemoglobinemia
955:Methemoglobinemia
933:methemoglobinemia
733:methemoglobinemia
655:
654:
579:Interactive image
463:CompTox Dashboard
187:
129:By mouth, topical
104:
5907:
5847:
5846:
5845:
5838:
5653:Ethinylestradiol
5506:Benzoyl peroxide
5458:Benzoyl peroxide
5425:
5418:
5411:
5402:
5294:
5261:
4996:Levonadifloxacin
4955:
4950:Fluoroquinolones
4898:
4703:Sulfadimethoxine
4675:Sulfamethoxazole
4596:Sulfaisodimidine
4584:
4519:
4473:
4466:
4459:
4450:
4173:
4091:
3936:
3903:
3896:
3889:
3880:
3875:
3854:
3853:
3843:
3820:Chemical Science
3811:
3805:
3804:
3797:
3791:
3790:
3783:
3777:
3776:
3774:
3772:
3766:
3758:
3752:
3751:
3715:
3709:
3708:
3706:
3705:
3696:. Archived from
3690:
3684:
3683:
3674:(5936): 1331–4.
3663:
3657:
3656:
3636:
3630:
3629:
3609:
3603:
3602:
3593:(2): 2264–2273.
3575:
3569:
3568:
3532:
3526:
3525:
3497:
3491:
3490:
3453:
3447:
3446:
3418:
3412:
3411:
3383:
3377:
3376:
3370:
3362:
3334:
3328:
3327:
3299:
3293:
3292:
3264:
3258:
3257:
3221:
3215:
3214:
3213:on May 17, 2011.
3199:
3193:
3192:
3182:
3150:
3144:
3143:
3115:
3109:
3108:
3080:
3074:
3073:
3063:
3039:
3033:
3032:
3022:
2998:
2992:
2991:
2981:
2957:
2951:
2950:
2940:
2916:
2910:
2909:
2889:
2883:
2882:
2872:
2848:
2842:
2841:
2839:
2831:
2825:
2824:
2805:10.1002/jat.1493
2788:
2782:
2781:
2771:
2761:
2737:
2731:
2730:
2720:
2696:
2690:
2689:
2661:
2655:
2654:
2631:Ann. Intern. Med
2622:
2616:
2615:
2579:
2573:
2572:
2544:
2538:
2537:
2512:(9742): 739–41.
2501:
2490:
2489:
2487:
2480:
2472:
2466:
2465:
2455:
2431:
2425:
2424:
2409:J Med Assoc Thai
2404:
2398:
2397:
2360:
2354:
2353:
2325:
2314:
2313:
2295:
2271:
2265:
2264:
2254:
2230:
2224:
2223:
2214:(6): 3439–3446.
2203:
2197:
2196:
2160:
2154:
2153:
2117:
2111:
2110:
2100:
2076:
2070:
2069:
2041:
2035:
2034:
2024:
1992:
1986:
1985:
1949:
1943:
1942:
1932:
1900:
1894:
1893:
1875:
1869:
1868:
1858:
1834:
1828:
1827:
1802:(9): 1515–1521.
1791:
1785:
1784:
1782:
1781:
1766:
1760:
1759:
1723:
1717:
1716:
1710:
1702:
1682:
1669:
1668:
1644:
1638:
1637:
1635:
1616:
1610:
1609:
1591:
1567:
1561:
1560:
1536:
1527:
1526:
1490:
1479:
1478:
1476:
1474:
1459:
1434:
1433:
1409:
1403:
1402:
1400:
1398:
1383:
1348:and imine-based
1263:and his team at
1175:
1174:
1173:
1165:
1164:
1052:, jaundice, and
1039:Hypersensitivity
945:white blood cell
929:hemolytic anemia
846:gluten-free diet
789:sulfamethoxazole
660:, also known as
651:
650:
581:
561:
549:
543:
537:
531:
525:
508:
497:
486:
485:
471:
469:
454:
434:
414:
394:
374:
354:
334:
324:
323:
309:
251:
185:
182:
160:
150:
114:
103:
100:
87:
73:
40:
31:
24:
22:
5915:
5914:
5910:
5909:
5908:
5906:
5905:
5904:
5855:
5854:
5853:
5843:
5841:
5833:
5831:
5826:
5825:
5810:Clinical trials
5789:
5738:
5702:
5659:
5596:
5543:
5510:
5477:
5439:
5429:
5399:
5394:
5393:
5378:Clinical trials
5353:
5335:
5301:
5278:
5254:
5241:
5217:
5192:
5139:
5067:
5019:
4944:
4892:DNA replication
4890:
4888:
4882:
4878:
4876:
4864:
4833:
4798:
4757:Other/ungrouped
4752:
4718:Sulfametomidine
4689:
4661:
4575:
4567:
4514:
4512:
4510:
4505:
4503:
4495:
4477:
4447:
4442:
4441:
4426:Clinical trials
4405:
4369:
4289:
4228:
4209:Ethylenediamine
4200:Arabinogalactan
4194:
4158:
4140:
4117:
4095:Aminoglycosides
4076:
4057:
4048:
4020:
3973:
3943:
3925:
3907:
3866:
3863:
3858:
3857:
3813:
3812:
3808:
3799:
3798:
3794:
3785:
3784:
3780:
3770:
3768:
3764:
3760:
3759:
3755:
3717:
3716:
3712:
3703:
3701:
3692:
3691:
3687:
3665:
3664:
3660:
3638:
3637:
3633:
3611:
3610:
3606:
3580:
3578:
3576:
3572:
3534:
3533:
3529:
3508:(12): 1062–73.
3499:
3498:
3494:
3455:
3454:
3450:
3420:
3419:
3415:
3385:
3384:
3380:
3363:
3336:
3335:
3331:
3301:
3300:
3296:
3266:
3265:
3261:
3223:
3222:
3218:
3201:
3200:
3196:
3152:
3151:
3147:
3117:
3116:
3112:
3082:
3081:
3077:
3041:
3040:
3036:
3000:
2999:
2995:
2959:
2958:
2954:
2918:
2917:
2913:
2891:
2890:
2886:
2850:
2849:
2845:
2837:
2833:
2832:
2828:
2790:
2789:
2785:
2739:
2738:
2734:
2698:
2697:
2693:
2672:(12): 1159–62.
2666:Mayo Clin. Proc
2663:
2662:
2658:
2624:
2623:
2619:
2581:
2580:
2576:
2546:
2545:
2541:
2503:
2502:
2493:
2485:
2478:
2474:
2473:
2469:
2433:
2432:
2428:
2406:
2405:
2401:
2372:(12): 429–437.
2362:
2361:
2357:
2327:
2326:
2317:
2273:
2272:
2268:
2232:
2231:
2227:
2205:
2204:
2200:
2162:
2161:
2157:
2119:
2118:
2114:
2078:
2077:
2073:
2043:
2042:
2038:
1994:
1993:
1989:
1951:
1950:
1946:
1902:
1901:
1897:
1890:
1877:
1876:
1872:
1836:
1835:
1831:
1793:
1792:
1788:
1779:
1777:
1768:
1767:
1763:
1734:(10): 367–370.
1725:
1724:
1720:
1703:
1699:
1684:
1683:
1672:
1661:
1646:
1645:
1641:
1618:
1617:
1613:
1569:
1568:
1564:
1553:
1538:
1537:
1530:
1492:
1491:
1482:
1472:
1470:
1461:
1460:
1437:
1426:
1411:
1410:
1406:
1396:
1394:
1385:
1384:
1380:
1375:
1362:
1338:
1329:
1309:GlaxoSmithKline
1277:
1269:Ernest Fourneau
1253:sulfone therapy
1209:
1204:
1172:
1169:
1168:
1167:
1163:
1160:
1159:
1158:
1156:
1146:
1142:
1106:
1070:
1036:
1027:
992:Cytochrome P450
979:
949:aplastic anemia
941:Agranulocytosis
922:
906:
904:Adverse effects
898:G6PD deficiency
882:
839:
812:
761:
756:
646:
644:
639:
636:
631:
626:
625:
614:
611:
606:
605:
584:
559:
546:
540:
534:
528:
489:
465:
457:
437:
417:
397:
377:
357:
337:
320:
312:
292:
289:
284:
283:
249:
221:Protein binding
211:Bioavailability
203:Pharmacokinetic
197:
164:
124:
117:
17:
12:
11:
5:
5913:
5911:
5903:
5902:
5897:
5892:
5887:
5882:
5877:
5872:
5867:
5857:
5856:
5852:
5851:
5828:
5827:
5824:
5823:
5822:
5821:
5818:
5807:
5801:
5795:
5794:
5791:
5790:
5788:
5787:
5782:
5777:
5772:
5767:
5762:
5757:
5752:
5746:
5744:
5740:
5739:
5737:
5736:
5731:
5726:
5721:
5716:
5710:
5708:
5704:
5703:
5701:
5700:
5695:
5690:
5685:
5680:
5675:
5669:
5667:
5661:
5660:
5658:
5657:
5656:
5655:
5650:
5640:
5639:
5638:
5635:Spironolactone
5632:
5627:
5622:
5617:
5606:
5604:
5598:
5597:
5595:
5594:
5588:
5583:
5574:
5569:
5564:
5559:
5553:
5551:
5545:
5544:
5542:
5541:
5536:
5531:
5526:
5520:
5518:
5512:
5511:
5509:
5508:
5503:
5498:
5496:Salicylic acid
5493:
5487:
5485:
5479:
5478:
5476:
5475:
5470:
5465:
5460:
5455:
5449:
5447:
5441:
5440:
5430:
5428:
5427:
5420:
5413:
5405:
5396:
5395:
5392:
5391:
5390:
5389:
5386:
5375:
5369:
5363:
5362:
5359:
5358:
5355:
5354:
5352:
5351:
5345:
5343:
5337:
5336:
5334:
5333:
5328:
5323:
5318:
5313:
5307:
5305:
5303:RNA polymerase
5291:
5284:
5283:
5280:
5279:
5277:
5276:
5270:
5268:
5265:Nitroimidazole
5258:
5247:
5246:
5243:
5242:
5240:
5239:
5233:Aminocoumarins
5229:
5227:
5219:
5218:
5216:
5215:
5210:
5204:
5202:
5198:
5197:
5194:
5193:
5191:
5190:
5185:
5180:
5175:
5170:
5165:
5160:
5155:
5149:
5147:
5141:
5140:
5138:
5137:
5135:Alatrofloxacin
5128:
5123:
5118:
5113:
5108:
5103:
5098:
5093:
5088:
5083:
5077:
5075:
5073:4th generation
5069:
5068:
5066:
5065:
5060:
5055:
5050:
5045:
5040:
5035:
5029:
5027:
5025:3rd generation
5021:
5020:
5018:
5017:
5012:
5007:
5002:
4989:
4984:
4979:
4974:
4969:
4963:
4961:
4959:2nd generation
4952:
4946:
4945:
4943:
4942:
4937:
4935:Piromidic acid
4932:
4930:Pipemidic acid
4927:
4922:
4920:Nalidixic acid
4917:
4912:
4906:
4904:
4902:1st generation
4895:
4870:
4869:
4866:
4865:
4863:
4862:
4857:
4852:
4847:
4841:
4839:
4835:
4834:
4832:
4831:
4826:
4821:
4816:
4810:
4808:
4804:
4803:
4800:
4799:
4797:
4796:
4791:
4786:
4784:Sulfaguanidine
4781:
4779:Sulfadicramide
4776:
4771:
4766:
4760:
4758:
4754:
4753:
4751:
4750:
4745:
4743:Sulfaphenazole
4740:
4735:
4730:
4725:
4720:
4715:
4710:
4705:
4699:
4697:
4691:
4690:
4688:
4687:
4682:
4677:
4671:
4669:
4663:
4662:
4660:
4659:
4654:
4640:
4639:
4638:
4628:
4618:
4608:
4603:
4601:Sulfamethizole
4598:
4592:
4590:
4581:
4578:DHPS inhibitor
4569:
4568:
4566:
4565:
4564:
4563:
4558:
4553:
4548:
4543:
4538:
4527:
4525:
4523:DHFR inhibitor
4516:
4497:
4496:
4480:Antibacterials
4478:
4476:
4475:
4468:
4461:
4453:
4444:
4443:
4440:
4439:
4438:
4437:
4434:
4423:
4417:
4411:
4410:
4407:
4406:
4404:
4403:
4398:
4393:
4388:
4383:
4377:
4375:
4371:
4370:
4368:
4367:
4351:Nitroimidazole
4347:
4342:
4330:
4314:
4301:
4299:
4295:
4294:
4291:
4290:
4288:
4287:
4280:
4279:
4274:
4269:
4263:Thiocarbamides
4259:
4258:
4253:
4239:
4237:
4230:
4229:
4227:
4226:
4220:
4219:
4205:
4203:
4196:
4195:
4193:
4192:
4182:
4180:
4170:
4164:
4163:
4160:
4159:
4157:
4156:
4150:
4148:
4142:
4141:
4139:
4138:
4133:
4127:
4125:
4119:
4118:
4116:
4115:
4110:
4105:
4099:
4097:
4088:
4082:
4081:
4078:
4077:
4075:
4074:
4069:
4063:
4061:
4050:
4049:
4047:
4046:
4040:
4028:
4026:
4022:
4021:
4019:
4018:
4013:
4008:
4003:
3998:
3993:
3987:
3985:
3975:
3974:
3972:
3971:
3966:
3961:
3956:
3950:
3948:
3945:RNA polymerase
3933:
3927:
3926:
3908:
3906:
3905:
3898:
3891:
3883:
3877:
3876:
3862:
3861:External links
3859:
3856:
3855:
3826:(1): 293–302.
3806:
3803:. 3 June 2017.
3801:"LAPOX ASH-10"
3792:
3778:
3753:
3726:(4): 221–227.
3710:
3685:
3658:
3631:
3604:
3570:
3527:
3492:
3448:
3413:
3378:
3345:(3): 277–284.
3329:
3310:(3): 553–563.
3294:
3275:(1): 125–133.
3259:
3216:
3194:
3145:
3110:
3075:
3034:
2993:
2952:
2911:
2884:
2843:
2826:
2799:(3): 271–275.
2783:
2732:
2711:(3): 297–304.
2691:
2656:
2617:
2574:
2549:Ann Intern Med
2539:
2491:
2467:
2426:
2399:
2355:
2315:
2286:(17): 1620–8.
2266:
2225:
2198:
2155:
2112:
2091:(6): 415–423.
2071:
2046:Clin. Dermatol
2036:
1987:
1960:(4): 617–633.
1944:
1895:
1888:
1870:
1829:
1786:
1761:
1718:
1697:
1670:
1659:
1639:
1611:
1582:(5): 265–273.
1562:
1551:
1528:
1501:(3): 420–434.
1480:
1435:
1424:
1404:
1377:
1376:
1374:
1371:
1370:
1369:
1361:
1358:
1337:
1334:
1328:
1325:
1317:chlorproguanil
1276:
1273:
1237:Gerhard Domagk
1208:
1205:
1203:
1200:
1170:
1161:
1144:
1140:
1105:
1102:
1069:
1066:
1062:corticosteroid
1058:DRESS syndrome
1035:
1032:
1026:
1023:
978:
975:
967:pulse oximeter
921:
918:
914:DRESS syndrome
905:
902:
881:
878:
838:
835:
834:
833:
830:
820:
816:
811:
808:
760:
757:
755:
752:
653:
652:
641:
640:
638:
637:
634:
632:
629:
621:
620:
619:
616:
615:
613:
612:
609:
601:
600:
599:
596:
595:
592:
586:
585:
583:
582:
574:
572:
564:
563:
557:
551:
550:
544:
538:
532:
526:
521:
515:
514:
510:
509:
499:
491:
490:
488:
487:
474:
472:
459:
458:
456:
455:
447:
445:
439:
438:
436:
435:
427:
425:
419:
418:
416:
415:
407:
405:
399:
398:
396:
395:
387:
385:
379:
378:
376:
375:
367:
365:
359:
358:
356:
355:
347:
345:
339:
338:
336:
335:
327:
325:
314:
313:
311:
310:
302:
300:
294:
293:
291:
290:
287:
279:
278:
277:
274:
273:
269:
268:
263:
257:
256:
255:20 to 30 hours
253:
244:
243:
233:
227:
226:
223:
217:
216:
213:
207:
206:
199:
198:
196:
195:
192:
179:
177:
171:
170:
166:
165:
163:
162:
139:
137:
131:
130:
127:
125:administration
119:
118:
116:
115:
97:
95:
89:
88:
81:
75:
74:
67:
57:
56:
55:Aczone, others
53:
47:
46:
42:
41:
33:
32:
15:
13:
10:
9:
6:
4:
3:
2:
5912:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5885:Benzosulfones
5883:
5881:
5878:
5876:
5873:
5871:
5868:
5866:
5863:
5862:
5860:
5850:
5840:
5836:
5819:
5817:
5814:
5813:
5811:
5808:
5805:
5802:
5800:
5797:
5796:
5792:
5786:
5783:
5781:
5778:
5776:
5773:
5771:
5768:
5766:
5763:
5761:
5758:
5756:
5753:
5751:
5748:
5747:
5745:
5741:
5735:
5732:
5730:
5727:
5725:
5722:
5720:
5717:
5715:
5712:
5711:
5709:
5705:
5699:
5696:
5694:
5691:
5689:
5686:
5684:
5681:
5679:
5676:
5674:
5671:
5670:
5668:
5666:
5662:
5654:
5651:
5649:
5646:
5645:
5644:
5641:
5636:
5633:
5631:
5628:
5626:
5623:
5621:
5618:
5616:
5613:
5612:
5611:
5610:Antiandrogens
5608:
5607:
5605:
5603:
5599:
5592:
5589:
5587:
5584:
5582:
5578:
5577:Tetracyclines
5575:
5573:
5572:Sulfacetamide
5570:
5568:
5565:
5563:
5560:
5558:
5555:
5554:
5552:
5550:
5546:
5540:
5537:
5535:
5532:
5530:
5527:
5525:
5522:
5521:
5519:
5517:
5513:
5507:
5504:
5502:
5499:
5497:
5494:
5492:
5491:Glycolic acid
5489:
5488:
5486:
5484:
5480:
5474:
5471:
5469:
5466:
5464:
5461:
5459:
5456:
5454:
5451:
5450:
5448:
5446:
5445:Antibacterial
5442:
5437:
5433:
5426:
5421:
5419:
5414:
5412:
5407:
5406:
5403:
5387:
5385:
5382:
5381:
5379:
5376:
5373:
5370:
5368:
5365:
5364:
5360:
5350:
5347:
5346:
5344:
5342:
5338:
5332:
5329:
5327:
5324:
5322:
5319:
5317:
5314:
5312:
5309:
5308:
5306:
5304:
5299:
5295:
5292:
5289:
5285:
5275:
5272:
5271:
5269:
5266:
5262:
5259:
5257:
5252:
5248:
5238:
5234:
5231:
5230:
5228:
5225:
5220:
5214:
5211:
5209:
5206:
5205:
5203:
5199:
5189:
5186:
5184:
5183:Pradofloxacin
5181:
5179:
5176:
5174:
5173:Marbofloxacin
5171:
5169:
5166:
5164:
5161:
5159:
5156:
5154:
5151:
5150:
5148:
5146:
5142:
5136:
5132:
5131:Trovafloxacin
5129:
5127:
5124:
5122:
5121:Prulifloxacin
5119:
5117:
5114:
5112:
5111:Clinafloxacin
5109:
5107:
5104:
5102:
5099:
5097:
5094:
5092:
5089:
5087:
5084:
5082:
5079:
5078:
5076:
5074:
5070:
5064:
5061:
5059:
5056:
5054:
5051:
5049:
5046:
5044:
5043:Grepafloxacin
5041:
5039:
5036:
5034:
5031:
5030:
5028:
5026:
5022:
5016:
5013:
5011:
5008:
5006:
5003:
5001:
4997:
4993:
4990:
4988:
4985:
4983:
4980:
4978:
4975:
4973:
4970:
4968:
4967:Ciprofloxacin
4965:
4964:
4962:
4960:
4956:
4953:
4951:
4947:
4941:
4938:
4936:
4933:
4931:
4928:
4926:
4925:Oxolinic acid
4923:
4921:
4918:
4916:
4913:
4911:
4908:
4907:
4905:
4903:
4899:
4896:
4893:
4886:
4881:
4880:topoisomerase
4875:
4871:
4861:
4858:
4856:
4853:
4851:
4848:
4846:
4845:Acediasulfone
4843:
4842:
4840:
4836:
4830:
4827:
4825:
4822:
4820:
4817:
4815:
4812:
4811:
4809:
4805:
4795:
4792:
4790:
4787:
4785:
4782:
4780:
4777:
4775:
4772:
4770:
4769:Sulfacetamide
4767:
4765:
4762:
4761:
4759:
4755:
4749:
4746:
4744:
4741:
4739:
4738:Sulfamerazine
4736:
4734:
4731:
4729:
4726:
4724:
4721:
4719:
4716:
4714:
4711:
4709:
4706:
4704:
4701:
4700:
4698:
4696:
4692:
4686:
4683:
4681:
4678:
4676:
4673:
4672:
4670:
4668:
4664:
4658:
4657:Sulfathiourea
4655:
4652:
4648:
4644:
4643:Sulfathiazole
4641:
4637:
4634:
4633:
4632:
4631:Sulfanilamide
4629:
4626:
4622:
4621:Sulfafurazole
4619:
4616:
4615:Sulfasalazine
4612:
4611:Sulfapyridine
4609:
4607:
4606:Sulfadimidine
4604:
4602:
4599:
4597:
4594:
4593:
4591:
4589:
4585:
4582:
4579:
4574:
4570:
4562:
4559:
4557:
4554:
4552:
4551:Pyrimethamine
4549:
4547:
4544:
4542:
4539:
4537:
4534:
4533:
4532:
4529:
4528:
4526:
4524:
4520:
4517:
4508:
4502:
4498:
4493:
4489:
4485:
4481:
4474:
4469:
4467:
4462:
4460:
4455:
4454:
4451:
4435:
4433:
4430:
4429:
4427:
4424:
4421:
4418:
4416:
4413:
4412:
4408:
4402:
4399:
4397:
4394:
4392:
4389:
4387:
4384:
4382:
4379:
4378:
4376:
4372:
4365:
4364:
4359:
4358:
4353:
4352:
4348:
4346:
4343:
4340:
4336:
4335:
4331:
4328:
4324:
4320:
4319:
4315:
4312:
4308:
4307:
4303:
4302:
4300:
4298:Other/unknown
4296:
4286:
4282:
4281:
4278:
4275:
4273:
4272:Prothionamide
4270:
4268:
4264:
4261:
4260:
4257:
4254:
4252:
4248:
4244:
4241:
4240:
4238:
4235:
4231:
4225:
4222:
4221:
4218:
4214:
4210:
4207:
4206:
4204:
4201:
4197:
4191:
4187:
4184:
4183:
4181:
4178:
4177:Peptidoglycan
4174:
4171:
4169:
4165:
4155:
4152:
4151:
4149:
4147:
4143:
4137:
4134:
4132:
4129:
4128:
4126:
4124:
4120:
4114:
4111:
4109:
4106:
4104:
4101:
4100:
4098:
4096:
4092:
4089:
4087:
4083:
4073:
4070:
4068:
4065:
4064:
4062:
4060:
4055:
4051:
4044:
4041:
4039:
4035:
4034:
4030:
4029:
4027:
4023:
4017:
4014:
4012:
4009:
4007:
4004:
4002:
3999:
3997:
3994:
3992:
3989:
3988:
3986:
3984:
3980:
3976:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3951:
3949:
3946:
3941:
3937:
3934:
3932:
3928:
3923:
3919:
3915:
3911:
3904:
3899:
3897:
3892:
3890:
3885:
3884:
3881:
3873:
3869:
3865:
3864:
3860:
3851:
3847:
3842:
3837:
3833:
3829:
3825:
3821:
3817:
3810:
3807:
3802:
3796:
3793:
3788:
3782:
3779:
3763:
3757:
3754:
3749:
3745:
3741:
3737:
3733:
3729:
3725:
3721:
3714:
3711:
3700:on 2009-02-12
3699:
3695:
3689:
3686:
3681:
3677:
3673:
3669:
3662:
3659:
3654:
3650:
3647:(in French).
3646:
3642:
3635:
3632:
3627:
3623:
3620:(in French).
3619:
3615:
3608:
3605:
3600:
3596:
3592:
3588:
3584:
3574:
3571:
3566:
3562:
3558:
3554:
3550:
3546:
3542:
3538:
3531:
3528:
3523:
3519:
3515:
3511:
3507:
3504:(in French).
3503:
3496:
3493:
3488:
3484:
3480:
3476:
3472:
3468:
3464:
3460:
3452:
3449:
3444:
3440:
3436:
3432:
3428:
3424:
3417:
3414:
3409:
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3401:
3397:
3393:
3389:
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3379:
3374:
3368:
3360:
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3352:
3348:
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3340:
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3330:
3325:
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3317:
3313:
3309:
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3298:
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3290:
3286:
3282:
3278:
3274:
3270:
3263:
3260:
3255:
3251:
3247:
3243:
3239:
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3227:
3220:
3217:
3212:
3208:
3204:
3198:
3195:
3190:
3186:
3181:
3176:
3172:
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3165:(7152): 181.
3164:
3160:
3156:
3149:
3146:
3141:
3137:
3133:
3129:
3125:
3121:
3120:Arch Dermatol
3114:
3111:
3106:
3102:
3098:
3094:
3090:
3086:
3085:Arch Dermatol
3079:
3076:
3071:
3067:
3062:
3057:
3054:(4): 307–13.
3053:
3049:
3045:
3038:
3035:
3030:
3026:
3021:
3016:
3012:
3008:
3004:
2997:
2994:
2989:
2985:
2980:
2975:
2972:(4): 315–20.
2971:
2967:
2963:
2956:
2953:
2948:
2944:
2939:
2934:
2930:
2926:
2922:
2915:
2912:
2907:
2903:
2899:
2895:
2894:Indian J Lepr
2888:
2885:
2880:
2876:
2871:
2866:
2863:(4): 267–73.
2862:
2858:
2854:
2847:
2844:
2836:
2830:
2827:
2822:
2818:
2814:
2810:
2806:
2802:
2798:
2794:
2787:
2784:
2779:
2775:
2770:
2765:
2760:
2755:
2751:
2747:
2743:
2736:
2733:
2728:
2724:
2719:
2714:
2710:
2706:
2702:
2695:
2692:
2687:
2683:
2679:
2675:
2671:
2667:
2660:
2657:
2652:
2648:
2644:
2640:
2636:
2632:
2628:
2621:
2618:
2613:
2609:
2605:
2601:
2597:
2593:
2590:(8): 247–51.
2589:
2585:
2578:
2575:
2570:
2566:
2562:
2558:
2554:
2550:
2543:
2540:
2535:
2531:
2527:
2523:
2519:
2515:
2511:
2507:
2500:
2498:
2496:
2492:
2484:
2477:
2471:
2468:
2463:
2459:
2454:
2449:
2446:(4): 261–70.
2445:
2441:
2437:
2430:
2427:
2422:
2418:
2414:
2410:
2403:
2400:
2395:
2391:
2387:
2383:
2379:
2375:
2371:
2367:
2359:
2356:
2351:
2347:
2343:
2339:
2335:
2331:
2324:
2322:
2320:
2316:
2311:
2307:
2303:
2299:
2294:
2289:
2285:
2281:
2277:
2270:
2267:
2262:
2258:
2253:
2248:
2244:
2240:
2236:
2229:
2226:
2221:
2217:
2213:
2209:
2202:
2199:
2194:
2190:
2186:
2182:
2178:
2174:
2170:
2166:
2159:
2156:
2151:
2147:
2143:
2139:
2135:
2131:
2127:
2123:
2116:
2113:
2108:
2104:
2099:
2094:
2090:
2086:
2082:
2075:
2072:
2067:
2063:
2059:
2055:
2051:
2047:
2040:
2037:
2032:
2028:
2023:
2018:
2014:
2010:
2006:
2002:
2001:JAMA Dermatol
1998:
1991:
1988:
1983:
1979:
1975:
1971:
1967:
1963:
1959:
1955:
1948:
1945:
1940:
1936:
1931:
1926:
1922:
1918:
1915:(37): e7534.
1914:
1910:
1906:
1899:
1896:
1891:
1885:
1881:
1874:
1871:
1866:
1862:
1857:
1852:
1848:
1844:
1840:
1833:
1830:
1825:
1821:
1817:
1813:
1809:
1805:
1801:
1797:
1790:
1787:
1776:on 2012-07-29
1775:
1771:
1765:
1762:
1757:
1753:
1749:
1745:
1741:
1737:
1733:
1729:
1722:
1719:
1714:
1708:
1700:
1698:0-9757919-2-3
1694:
1690:
1689:
1681:
1679:
1677:
1675:
1671:
1666:
1662:
1660:9780199534845
1656:
1652:
1651:
1643:
1640:
1634:
1629:
1625:
1621:
1615:
1612:
1607:
1603:
1599:
1595:
1590:
1585:
1581:
1577:
1573:
1566:
1563:
1558:
1554:
1552:9781449619794
1548:
1544:
1543:
1535:
1533:
1529:
1524:
1520:
1516:
1512:
1508:
1504:
1500:
1496:
1489:
1487:
1485:
1481:
1468:
1464:
1458:
1456:
1454:
1452:
1450:
1448:
1446:
1444:
1442:
1440:
1436:
1431:
1427:
1425:9780781768795
1421:
1417:
1416:
1408:
1405:
1392:
1388:
1382:
1379:
1372:
1367:
1364:
1363:
1359:
1357:
1355:
1351:
1347:
1343:
1335:
1333:
1326:
1324:
1320:
1318:
1314:
1310:
1306:
1302:
1298:
1294:
1293:
1289:, one of the
1288:
1287:
1282:
1274:
1272:
1270:
1266:
1262:
1258:
1257:sulfanilamide
1254:
1250:
1246:
1245:prontosil red
1242:
1238:
1234:
1230:
1226:
1218:
1213:
1206:
1201:
1199:
1196:
1194:
1190:
1185:
1183:
1179:
1154:
1150:
1138:
1133:
1131:
1127:
1123:
1119:
1116:synthesis of
1115:
1111:
1110:antibacterial
1103:
1101:
1099:
1095:
1091:
1087:
1083:
1079:
1075:
1067:
1065:
1063:
1059:
1055:
1051:
1047:
1042:
1040:
1033:
1031:
1024:
1022:
1020:
1016:
1012:
1008:
1004:
1000:
997:
993:
988:
984:
976:
974:
972:
968:
964:
961:) can detect
960:
956:
952:
950:
946:
942:
938:
934:
930:
926:
919:
917:
915:
911:
903:
901:
899:
895:
891:
887:
879:
877:
874:
872:
867:
865:
860:
858:
854:
849:
847:
843:
836:
831:
828:
824:
821:
817:
814:
813:
809:
807:
805:
801:
800:pyrimethamine
796:
792:
790:
786:
782:
781:toxoplasmosis
778:
774:
770:
766:
758:
753:
751:
749:
745:
740:
738:
734:
730:
726:
722:
718:
713:
711:
707:
703:
699:
698:toxoplasmosis
695:
691:
687:
683:
679:
675:
671:
667:
663:
659:
649:
642:
633:
628:
624:
617:
608:
604:
597:
593:
591:
590:Melting point
587:
580:
576:
575:
573:
570:
565:
558:
556:
552:
522:
520:
516:
511:
507:
503:
500:
498:
496:ECHA InfoCard
492:
484:
480:
479:DTXSID4020371
476:
475:
473:
464:
460:
453:
449:
448:
446:
444:
440:
433:
429:
428:
426:
424:
420:
413:
409:
408:
406:
404:
400:
393:
389:
388:
386:
384:
380:
373:
369:
368:
366:
364:
360:
353:
349:
348:
346:
344:
340:
333:
329:
328:
326:
319:
315:
308:
304:
303:
301:
299:
295:
286:
282:
275:
270:
267:
264:
262:
258:
254:
252:
245:
241:
237:
234:
232:
228:
224:
222:
218:
214:
212:
208:
204:
200:
193:
191:
181:
180:
178:
176:
172:
167:
159:
154:
149:
144:
141:
140:
138:
136:
132:
128:
126:
120:
113:
108:
99:
98:
96:
94:
90:
86:
82:
80:
76:
72:
68:
66:
62:
58:
54:
52:
48:
45:Clinical data
43:
39:
34:
30:
25:
5743:Combinations
5678:Isotretinoin
5625:Drospirenone
5615:Bicalutamide
5567:Erythromycin
5561:
5473:Tea tree oil
5453:Azelaic acid
5341:Lipiarmycins
5188:Sarafloxacin
5178:Orbifloxacin
5163:Enrofloxacin
5153:Danofloxacin
5126:Sitafloxacin
5106:Moxifloxacin
5101:Gemifloxacin
5096:Finafloxacin
5091:Gatifloxacin
5086:Delafloxacin
5081:Besifloxacin
5063:Tosufloxacin
5058:Temafloxacin
5053:Sparfloxacin
5048:Pazufloxacin
5038:Balofloxacin
5033:Levofloxacin
4992:Nadifloxacin
4987:Lomefloxacin
4849:
4807:Combinations
4789:Sulfametrole
4774:Sulfaclozine
4680:Sulfadiazine
4588:Short-acting
4573:Sulfonamides
4561:Trimethoprim
4374:Combinations
4361:
4355:
4349:
4332:
4323:Pyrazinamide
4316:
4304:
4256:Methaniazide
4247:mycolic acid
4234:Mycolic acid
4113:Streptomycin
4072:Moxifloxacin
4067:Gatifloxacin
4031:
3990:
3912:, including
3871:
3823:
3819:
3809:
3795:
3781:
3769:. Retrieved
3756:
3723:
3719:
3713:
3702:. Retrieved
3698:the original
3688:
3671:
3667:
3661:
3648:
3644:
3634:
3621:
3617:
3607:
3590:
3586:
3573:
3540:
3536:
3530:
3505:
3501:
3495:
3462:
3458:
3451:
3426:
3422:
3416:
3391:
3387:
3381:
3367:cite journal
3342:
3338:
3332:
3307:
3303:
3297:
3272:
3268:
3262:
3229:
3225:
3219:
3211:the original
3206:
3197:
3162:
3158:
3148:
3126:(7): 531–2.
3123:
3119:
3113:
3088:
3084:
3078:
3051:
3047:
3037:
3013:(1): 57–62.
3010:
3006:
2996:
2969:
2965:
2955:
2931:(1): 57–62.
2928:
2924:
2914:
2900:(3): 271–6.
2897:
2893:
2887:
2860:
2856:
2846:
2829:
2796:
2792:
2786:
2752:(1): 86–88.
2749:
2745:
2735:
2708:
2704:
2694:
2669:
2665:
2659:
2634:
2630:
2620:
2587:
2584:Med. J. Aust
2583:
2577:
2555:(4): 465–6.
2552:
2548:
2542:
2509:
2505:
2470:
2443:
2439:
2429:
2415:(7): 404–7.
2412:
2408:
2402:
2369:
2365:
2358:
2336:(4): 250–7.
2333:
2329:
2283:
2280:N Engl J Med
2279:
2269:
2245:(2): 194–9.
2242:
2238:
2228:
2211:
2207:
2201:
2168:
2164:
2158:
2125:
2121:
2115:
2088:
2084:
2074:
2052:(6): 482–5.
2049:
2045:
2039:
2007:(1): 90–95.
2004:
2000:
1990:
1957:
1953:
1947:
1912:
1908:
1898:
1879:
1873:
1846:
1842:
1832:
1799:
1795:
1789:
1778:. Retrieved
1774:the original
1764:
1731:
1727:
1721:
1691:. Adelaide.
1687:
1649:
1642:
1633:10665/325771
1623:
1614:
1579:
1575:
1565:
1541:
1498:
1494:
1471:. Retrieved
1414:
1407:
1395:. Retrieved
1390:
1381:
1346:epoxy resins
1342:curing agent
1339:
1330:
1321:
1290:
1284:
1278:
1261:Daniel Bovet
1225:Paul Ehrlich
1222:
1197:
1186:
1184:and stroke.
1134:
1107:
1071:
1054:eosinophilia
1043:
1037:
1028:
980:
959:CO-oximeters
953:
923:
907:
884:People with
883:
875:
868:
861:
850:
840:
797:
793:
785:trimethoprim
762:
754:Medical uses
748:generic drug
741:
714:
673:
669:
665:
661:
657:
656:
645:
248:Elimination
175:Legal status
169:Legal status
93:License data
5806:from market
5714:Epristeride
5698:Trifarotene
5683:Motretinide
5591:Doxycycline
5586:Minocycline
5581:Lymecycline
5557:Clindamycin
5549:Antibiotics
5524:Niacinamide
5483:Keratolytic
5374:from market
5349:Fidaxomicin
5321:Rifapentine
5274:Secnidazole
5267:derivatives
5208:Nemonoxacin
5168:Ibafloxacin
5116:Garenoxacin
5005:Norfloxacin
4855:Solasulfone
4794:Sulfanitran
4748:Sulfamazone
4708:Sulfadoxine
4695:Long-acting
4685:Sulfamoxole
4556:Tetroxoprim
4536:Brodimoprim
4513:DNA and RNA
4501:Antifolates
4422:from market
4345:Bedaquiline
4311:Clofazimine
4277:Thiocarlide
4267:Ethionamide
4215:inhibitor:
4190:Cycloserine
4154:Capreomycin
4123:Oxazolidone
4011:Solasulfone
3979:Antifolates
3964:Rifapentine
3091:(1): 38–9.
1473:January 12,
1327:Dapsone gel
1311:to develop
1305:Artemisinin
1297:chloroquine
1241:Nobel Prize
1153:neutrophils
1130:sulfonamide
896:infection,
819:antibodies.
769:clofazimine
686:clofazimine
562: g·mol
502:100.001.136
272:Identifiers
79:MedlinePlus
51:Trade names
5859:Categories
5688:Tazarotene
5311:Rifampicin
5298:Rifamycins
5256:inhibitors
5237:Novobiocin
5213:Ozenoxacin
5158:Difloxacin
5145:Veterinary
5015:Rufloxacin
5010:Pefloxacin
4982:Fleroxacin
4915:Flumequine
4885:DNA gyrase
4874:Quinolones
4733:Sulfaperin
4546:Ormetoprim
4515:synthesis)
4363:Pretomanid
4339:Terizidone
4327:Morinamide
4243:Hydrazides
4217:Ethambutol
4188:analogue:
4059:quinolones
3996:Acedapsone
3954:Rifampicin
3940:Rifamycins
3704:2009-02-24
3543:: 163–70.
3232:(1): 1–7.
2637:(1): 139.
1780:2012-08-17
1373:References
1336:Other uses
1292:Plasmodium
1249:sulfa drug
1187:Dapsone's
765:rifampicin
759:Infections
682:rifampicin
678:antibiotic
567:3D model (
555:Molar mass
452:ChEMBL1043
432:CHEBI:4325
392:8W5C518302
363:ChemSpider
298:CAS Number
281:IUPAC name
242:-mediated)
231:Metabolism
5816:Phase III
5804:Withdrawn
5734:Tioxolone
5693:Tretinoin
5673:Adapalene
5665:Retinoids
5648:Estradiol
5643:Estrogens
5630:Flutamide
5529:Ibuprofen
5384:Phase III
5372:Withdrawn
5331:Rifalazil
5326:Rifaximin
5316:Rifabutin
5290:synthesis
5251:Anaerobic
5222:Related (
4972:Ofloxacin
4940:Rosoxacin
4910:Cinoxacin
4860:Sulfoxone
4713:Sulfalene
4636:Prontosil
4432:Phase III
4420:Withdrawn
4357:Delamanid
4334:Isoxazole
4306:Phenazine
4251:Isoniazid
4136:Sutezolid
4131:Linezolid
4108:Kanamycin
4016:Sulfoxone
3969:Rifalazil
3959:Rifabutin
3947:inhibitor
3868:"Dapsone"
1707:cite book
1391:Drugs.com
1350:vitrimers
1207:Discovery
1114:bacterial
1090:psychosis
1064:therapy.
983:hepatitis
925:Hemolysis
886:porphyria
676:), is an
288:4-aniline
261:Excretion
250:half-life
225:70 to 90%
215:70 to 80%
123:Routes of
71:Monograph
65:Drugs.com
5870:Anilines
5849:Medicine
5724:Pelretin
5719:Mesulfen
5602:Hormonal
4977:Enoxacin
4764:Mafenide
4541:Iclaprim
4318:Pyrazine
4103:Amikacin
4001:Diucifon
3850:34163597
3748:19485887
3740:19489655
3653:Archived
3651:: 1763.
3626:Archived
3565:12471553
3522:15692440
3479:18615706
3254:53721156
3246:30466896
3048:Lepr Rev
3007:Lepr Rev
2966:Lepr Rev
2947:11355519
2925:Lepr Rev
2857:Lepr Rev
2821:33330708
2813:19998329
2778:24574600
2612:34641425
2534:34866078
2526:20599264
2483:Archived
2440:Lepr Rev
2386:28885988
2310:34708642
2302:24152261
2261:22307940
2193:20884856
2185:25651003
2150:30029976
2142:25288365
2107:11117338
2066:17113965
2031:30476976
1982:52312492
1974:30241624
1939:28906353
1865:19450348
1824:11880942
1816:19505219
1756:36293895
1748:14494150
1665:Archived
1622:(2019).
1606:40957843
1598:15342970
1576:Medicine
1557:Archived
1523:39874987
1515:11511841
1467:Archived
1430:Archived
1360:See also
1233:microbes
1231:to kill
1086:insomnia
1078:headache
996:isozymes
857:necrotic
648:(verify)
343:DrugBank
238:(mostly
135:ATC code
107:DailyMed
5729:Stridex
5562:Dapsone
5534:Aspirin
4883:and/or
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3189:9665900
3140:7092282
3105:6450569
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2651:3966740
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2462:6199637
2421:6512448
2394:4283457
2350:9069593
2022:6439569
1930:5604622
1856:2943798
1281:malaria
1202:History
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1011:CYP2C19
804:malaria
773:leprosy
739:class.
737:sulfone
690:leprosy
658:Dapsone
519:Formula
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318:PubChem
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1080:, and
1074:nausea
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1007:CYP3A4
1003:CYP2B6
999:CYP2D6
981:Toxic
890:anemia
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560:248.30
443:ChEMBL
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266:Kidney
240:CYP2E1
190:â„ž-only
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4202:layer
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2608:S2CID
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2306:S2CID
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1820:S2CID
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920:Blood
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423:ChEBI
236:Liver
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3846:PMID
3773:2016
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