达普颂
此条目需要扩充。 (2016年4月14日) |
达普颂 (英语:Dapsone),也称为4,4'-磺酰二苯胺(SDA) 或二氨基二苯砜(DDS),[2]是一种抗生素(抗细菌药),常与利福平和氯法齐明联合用于治疗痳疯病。[3]它是种治疗和预防肺囊虫肺炎,以及免疫缺陷者于预防弓虫症时使用的二线药物。[3]此外它还用于治疗痤疮、疱疹样皮肤炎和各种其他形式的皮肤病。[4]达普颂有口服形式,也有用于涂抹的凝胶形式(外用药物)。[5]
![]() | |
![]() | |
临床资料 | |
---|---|
商品名 | Aczone及其他商品名 |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682128 |
核准状况 | |
给药途径 | 口服给药, 外用药物 |
ATC码 | |
法律规范状态 | |
法律规范 |
|
药物动力学数据 | |
生物利用度 | 70至80% |
血浆蛋白结合率 | 70至90% |
药物代谢 | 肝脏 (绝大部分由细胞色素P450 2E1介导) |
生物半衰期 | 20至30小时 |
排泄途径 | 肾脏 |
识别信息 | |
| |
CAS号 | 80-08-0 ![]() |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.001.136 |
化学信息 | |
化学式 | C12H12N2O2S |
摩尔质量 | 248.30 g·mol−1 |
3D模型(JSmol) | |
熔点 | 175至176 °C(347至349 °F) |
| |
|
使用后的严重副作用有白血球减少症、溶血反应,尤其是对葡萄糖-6-磷酸去氢酶缺乏症 (G-6-PD) 或对达普颂有过敏反应者。[3]常见的副作用有恶心和食欲不振。[5]其他副作用有肝炎、正铁血红蛋白血症[6]和多种皮疹。[3]虽然怀孕期间的个体使用对胎儿的安全性尚不完全清楚,但一些医生建议麻风病患者继续使用。[3]它是种砜类药物。[3]
达普颂于1937年首次被当作一种抗生素而受到研究。[4]于1945年开始用于治疗麻风病。[4]它被收列于世界卫生组织基本药物标准清单之中。[7]经口服摄取或是局部外用,市面有通用名药物贩售,价格并不昂贵。[3][8]
医疗用途
编辑感染
编辑达普颂通常与利福平与氯法齐明联合用于治疗痳疯病。[3]也用于治疗和预防肺囊虫肺炎 (PCP)。[3][9]它也用于治疗无法耐受含磺胺甲𫫇唑的甲氧苄啶人群的弓虫症。[9]
口服达普颂是最早用于治疗中度至重度寻常性痤疮的药物之一,且仍偶尔会用于治疗严重病例。[10][11]达普颂的外用形式也有效,且有较少的副作用。[12]
自体免疫性疾病
编辑- 圆盘状红斑性狼疮(Cutaneous lupus erythematosis)。达普颂对于中度、重度或难治性圆盘状红斑性狼疮患者有效且使用安全。[14]
- 特发性血小板减少性紫癜。达普颂对于特发性血小板减少性紫癜患者的辅助性减量糖皮质激素治疗有效且使用安全,并且对于治疗具有抗核抗体患者的效果优于达那唑或干扰素α。[15]
- 慢性自发性荨麻疹。对于抗组织胺药和其他一线药物均无疗效的慢性自发性荨麻疹患者,将达普颂用作二线药物,有效且使用安全。[16][17]
- 复发性多发性软骨炎。虽然尚无临床试验证明达普颂可用于治疗复发性多发性软骨炎,但有许多病例报告显示达普颂在25毫克/天至200毫克/天的剂量下,可发挥疗效。[18]
其他病症
编辑一项评论发现单独使用口服达普颂对80%的早期病例有效,而被建议用于治疗慢性隆起性红斑。然而达普颂可能会引起严重副作用,表示有时应该使用类固醇或其他抗生素来代替,但这些替代疗法的效果会差得多。[20]
使用禁忌及注意事项
编辑不良影响
编辑接受达普颂治疗的人中会有1.4%发生敏感反应的案例,在医疗资源匮乏地区可能会因此导致致命结果。[23][24]这种反应是严重皮肤不良反应(SCAR)中的一种,主要是DRESS症候群或是DRESS样反应。[25][26]
血液
编辑溶血反应是最为突出的副作用,使用达普颂治疗的患者中约有20%会发生此种反应,[27]通常与使用剂量有关。它可能导致溶血性贫血和正铁血红蛋白血症。[28]这种副作用在G-6-PD患者中更为常见,且状况严重,导致含达普颂的抗疟疾复方药物氯丙胍/达普颂(品牌名称Lapdap)因此退出临床使用。[29][30]据报导有一新生儿因母乳中含有达普颂而发生溶血反应的案例。[31]单独使用达普颂时很少发生白血球减少症,但在预防疟疾的联合治疗方案中较为常见。[32]白血球形成异常(包括再生不良性贫血)很少见,但却是利用达普颂治疗导致多起死亡的原因。[33][34][35]
长期接受标准剂量(100毫克/天)治疗的患者中约15%会出现正铁血红蛋白血症。只有特殊的多波长血氧仪(一氧化碳脉搏血氧计)才能直接检测出此种病症。当一般脉搏血氧饱和仪读数较低与动脉血氧分析结果较高之间存在"饱和差距"时,就可能有正铁血红蛋白血症存在的嫌疑。[36]
肝脏
编辑药厂报告有用药后毒性肝炎和黄疸案例出现。这些毒性反应也可能是达普颂超敏症候群(SCAR)或达普颂症候群(见下文)中的一种。[25]达普颂由细胞色素P450系统代谢,特别是同功酶如细胞色素 P450 2D6、细胞色素P450 2B6、细胞色素P450 3A4和细胞色素P450 2C19。[37]使用此药物,与细胞色素P450产生的代谢物作用而导致的正铁血红蛋白血症有关联。[38]
皮肤
编辑达普颂凝胶于局部使用时会引起轻度皮肤不适、发红、干燥、灼热感和发痒。与名为benzoyl peroxide(治疗痤疮用产品)一起使用时,可能皮肤会出现暂时性的黄色或橙色。[39]
达普颂超敏症候群
编辑部分患者会出现敏感反应。这种反应在接受多种药物治疗的患者中可能会更常见。[40][41][42]
反应包含有皮疹,也可能包含发烧、黄疸和嗜酸性粒细胞增多症,且可能是SCAR反应中的一种。[25][43][44][45][46][47]一般来说,这些症状会在治疗的前六周内出现,或根本不会出现,可透过皮质类固醇治疗以改善。[9]
其他不良影响
编辑其他不良反应有恶心、头痛和皮疹(此为常见反应)、失眠、思觉失调和周边神经病变。对肺部的影响甚少发生,但有的话可能会很严重,但通常可经治疗改善。[48]
作用机转
编辑达普颂是种抗细菌药,会透过与对氨基苯甲酸竞争二氢叶酸合成酶的活性位点,抑制细菌合成二氢叶酸,而抑制核酸合成。[49]磺胺类药物在结构上与达普颂不同,但也以相同方式发挥作用。[50]
达普颂有抑制发炎的作用,可抑制多形核细胞中髓过氧化物酶-H2O2-卤化物介导的细胞毒性系统。[51]嗜中性球透过呼吸爆发杀死细菌过程中,髓过氧化物酶将过氧化氢 (H2O2) 转化为次氯酸 (HOCl)。 HOCl是嗜中性球产生的最有效的氧化剂,在发炎过程中也会造成严重的组织损伤。达普颂以无活性的中间体形式阻止髓过氧化物酶,而可逆地抑制该酶,而可防止次氯酸积聚,并减少发炎期间的组织损伤。[52][53][54][55][56]髓过氧化物酶抑制也被认为是一种神经元保护机制,可减少阿兹海默症和中风等神经退化性疾病中的发炎。[57]
达普颂的抗发炎和免疫调节作用[58]被认为是其治疗疱疹样皮肤炎的作用机制。[59]
达普颂是一种无臭的白色至乳白色结晶粉末,味微苦。[60]
历史
编辑发现
编辑20世纪初,德国化学家保罗·埃尔利希利用基于某些染料具有杀死微生物的能力而发展出选择性毒性理论。德国病理学家与细菌学家格哈德·多马克于1932年取得重大突破,发现抗菌剂百浪多息(磺酰胺基雷索定(sulfonamidochrysoidine)),后来因其成就而获得诺贝尔奖。对相关化学物质作进一步研究为磺胺类药物和砜疗法开辟道路,首先由达尼埃尔·博韦和他在巴斯德研究所的团队于1935年发现磺胺(百浪多息的活性剂),[62]然后由法国的埃内斯特·富尔诺[63]和英国[64]的格拉德温·布特尔[65]分别独立开发出达普颂。[66]
拟用于抗疟治疗
编辑由于抗药性疟疾在非洲蔓延,促使各方积极开发新型低成本抗疟疾药物。恶性疟原虫是引起疟疾的疟原虫之一,对氯化奎宁和磺胺多辛/乙胺嘧啶(两种最常见的疟疾治疗药物)产生抗药性。有一名为青蒿素的抗疟药于20世纪80年代开发成功,但因价格昂贵,无法大规模使用,而促使葛兰素史克开发出一种由氯丙胍/达普颂组成的复方药物 - Lapdap,并于2003年10月在英国获准用于医疗用途。[30]
Lapdap的优点之一是氯丙胍和达普颂均为低成本药物。另一个原因是由于它是复方药物,不太容易引起抗药性。然而因达普颂会导致G6PD患者发生溶血性贫血,并且因撒哈拉以南非洲地区人口中有10-25%有G6PD的状况,使用Lapdap并不安全。葛兰素史克于2008年2月将其撤下,而当时此种药物在许多非洲国家中已销售四年。[30]
达普颂凝胶
编辑据报导达普颂在少数病例中可有效治疗痤疮,但因溶血性贫血风险使其无法广泛使用。科学家历经多年尝试,开发出一种达普颂外用制剂,可与口服达普颂一样有效对抗痤疮,且无溶血副作用。由于达普颂极难溶于水性溶剂,开发困难。生物制剂公司QLT USA于2000年开发出Aczone,是种含5%达普颂的凝胶,可有效治疗痤疮,即使对有G6PD的使用者也不会导致血红蛋白水平显著下降。[67]美国食品药物管理局(FDA)于2016年2月核准含7.5%达普颂凝胶作治疗用途。这种含有更高浓度达普颂的凝胶有每日只需使用一次的优势(含5%浓度的需每日使用两次)。[68]
其他用途
编辑达普颂也可用作环氧树脂和亚胺基玻璃体态聚合物等材料的固化剂,可应用于印刷电路板、黏合剂和涂料。[69][70][71]它在环氧树脂体系中的应用通常会产生具有高玻璃转化温度的树脂。
参见
编辑- 普罗敏,一种易溶于水的达普颂衍生物
参考文献
编辑- ^ Dapsone Use During Pregnancy. Drugs.com. 2019-11-11 [2020-05-17]. (原始内容存档于2021-01-20).
- ^ Lemke TL. Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. 2008: 1142. ISBN 9780781768795. (原始内容存档于2016-03-04).
- ^ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 Dapsone (Systemic) Monograph for Professionals. The American Society of Health-System Pharmacists. [2015-01-12]. (原始内容存档于2015-01-12).
- ^ 4.0 4.1 4.2 Zhu YI, Stiller MJ. Dapsone and sulfones in dermatology: overview and update. Journal of the American Academy of Dermatology. September 2001, 45 (3): 420–434. PMID 11511841. S2CID 39874987. doi:10.1067/mjd.2001.114733.
- ^ 5.0 5.1 Gallant JE. Johns Hopkins HIV Guide 2012. Jones & Bartlett Publishers. 2008: 193. ISBN 9781449619794. (原始内容存档于2016-03-04).
- ^ Ash-Bernal R, Wise R, Wright SM. Acquired methemoglobinemia: a retrospective series of 138 cases at 2 teaching hospitals. Medicine. September 2004, 83 (5): 265–273. PMID 15342970. S2CID 40957843. doi:10.1097/01.md.0000141096.00377.3f .
- ^ World Health Organization. World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. hdl:10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
- ^ Greenwood D. Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. Oxford University Press. 2008: 197. ISBN 9780199534845. (原始内容存档于2016-03-04).
- ^ 9.0 9.1 9.2 9.3 Rossi S. Rossi S , 编. Australian Medicines Handbook. Adelaide. 2006. ISBN 0-9757919-2-3.
- ^ Ross CM. The treatment of acne vulgaris with dapsone. The British Journal of Dermatology. October 1961, 73 (10): 367–370. PMID 14494150. S2CID 36293895. doi:10.1111/j.1365-2133.1961.tb14398.x.
- ^ Dapsone and Acne Vulgaris. ScienceOfAcne.com. 2012-10-10 [2012-08-17]. (原始内容存档于2012-07-29).
- ^ Pickert A, Raimer S. An evaluation of dapsone gel 5% in the treatment of acne vulgaris. Expert Opinion on Pharmacotherapy. June 2009, 10 (9): 1515–1521. PMID 19505219. S2CID 11880942. doi:10.1517/14656560903002097.
- ^ Croft AM. Malaria: prevention in travellers. BMJ Clinical Evidence. November 2007, 2007. PMC 2943798 . PMID 19450348.
- ^ Chong B, Werth V. Management of Cutaneous Lupus Erythematosus. Wallace D (编). Dubois' Lupus Erythematosus and Related Syndromes. Edinburgh: Elsevier. 2019: 719–726. ISBN 978-0-323-47927-1.
- ^ Weber E, Reynaud Q, Fort R, Durupt S, Cathébras P, Durieu I, Lega JC. Immunomodulatory treatments for persistent and chronic immune thrombocytopenic purpura: A PRISMA-compliant systematic review and meta-analysis of 28 studies. Medicine (Baltimore). September 2017, 96 (37): e7534. PMC 5604622 . PMID 28906353. doi:10.1097/MD.0000000000007534.
- ^ Antia C, Baquerizo K, Korman A, Alikhan A, Bernstein JA. Urticaria: A comprehensive review: Treatment of chronic urticaria, special populations, and disease outcomes. J. Am. Acad. Dermatol. October 2018, 79 (4): 617–633. PMID 30241624. S2CID 52312492. doi:10.1016/j.jaad.2018.01.023.
- ^ Liang SE, Hoffmann R, Peterson E, Soter NA. Use of Dapsone in the Treatment of Chronic Idiopathic and Autoimmune Urticaria. JAMA Dermatol. 2019, 155 (1): 90–95. PMC 6439569 . PMID 30476976. doi:10.1001/jamadermatol.2018.3715.
- ^ Rapini RP, Warner NB. Relapsing polychondritis. Clin. Dermatol. 2006, 24 (6): 482–5. PMID 17113965. doi:10.1016/j.clindermatol.2006.07.018.
- ^ Forks TP. Brown recluse spider bites. The Journal of the American Board of Family Practice. 2000, 13 (6): 415–423. PMID 11117338. doi:10.3122/15572625-13-6-415 .
- ^ Momen SE, Jorizzo J, Al-Niaimi F. Erythema elevatum diutinum: a review of presentation and treatment. Journal of the European Academy of Dermatology and Venereology (John Wiley & Sons). December 2014, 28 (12): 1594–1602. PMID 25288365. S2CID 30029976. doi:10.1111/jdv.12566.
- ^ Lukács J, Schliemann S, Elsner P. Treatment of generalized granuloma annulare - a systematic review. Journal of the European Academy of Dermatology and Venereology (John Wiley & Sons). August 2015, 29 (8): 1467–1480. PMID 25651003. S2CID 20884856. doi:10.1111/jdv.12976.
- ^ Khazaei A, Kazem-Rostami M, Zare A, Moosavi-Zare AR, Sadeghpour M, Afkhami A. Synthesis, characterization, and application of a triazene-based polysulfone as a dye adsorbent. Journal of Applied Polymer Science. 2013-09-15, 129 (6): 3439–3446. doi:10.1002/app.39069.
- ^ Lorenz M, Wozel G, Schmitt J. Hypersensitivity reactions to dapsone: a systematic review. Acta Derm. Venereol. March 2012, 92 (2): 194–9. PMID 22307940. doi:10.2340/00015555-1268 .
- ^ Zhang FR, Liu H, Irwanto A, et al. HLA-B*13:01 and the dapsone hypersensitivity syndrome.. N Engl J Med. October 2013, 369 (17): 1620–8. PMID 24152261. S2CID 34708642. doi:10.1056/NEJMoa1213096 .
- ^ 25.0 25.1 25.2 Bocquet H, Bagot M, Roujeau JC. Drug-induced pseudolymphoma and drug hypersensitivity syndrome (Drug Rash with Eosinophilia and Systemic Symptoms: DRESS). Semin Cutan Med Surg. December 1996, 15 (4): 250–7. PMID 9069593. doi:10.1016/S1085-5629(96)80038-1.
- ^ 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. Dapsone-induced severe cutaneous adverse drug reactions are strongly linked with HLA-B*13: 01 allele in the Thai population. Pharmacogenetics and Genomics. December 2017, 27 (12): 429–437. PMID 28885988. S2CID 4283457. doi:10.1097/FPC.0000000000000306.
- ^ Puavilai S, Chutha S, Polnikorn N, et al. Incidence of anemia in leprosy patients treated with dapsone. J Med Assoc Thai. July 1984, 67 (7): 404–7. PMID 6512448.
- ^ Jopling WH. Side-effects of antileprosy drugs in common use. Lepr Rev. 1983, 54 (4): 261–70. PMID 6199637. doi:10.5935/0305-7518.19830032 .
- ^ 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 ™ (PDF). World Health Organization. 2008-03-04. QSM/MC/IEA.1. (原始内容存档 (PDF)于2012-10-21).
- ^ 30.0 30.1 30.2 Luzzatto L. The rise and fall of the antimalarial Lapdap: a lesson in pharmacogenetics. Lancet. August 2010, 376 (9742): 739–41. PMID 20599264. S2CID 34866078. doi:10.1016/S0140-6736(10)60396-0.
- ^ Sanders SW, Zone JJ, Foltz RL, Tolman KG, Rollins DE. Hemolytic anemia induced by dapsone transmitted through breast milk.. Ann Intern Med. April 1982, 96 (4): 465–6. PMID 7065565. doi:10.7326/0003-4819-96-4-465.
- ^ Firkin FC, Mariani AF. Agranulocytosis due to dapsone. Med. J. Aust. 1977, 2 (8): 247–51. PMID 909500. S2CID 34641425. doi:10.5694/j.1326-5377.1977.tb117649.x.
- ^ Foucauld J, Uphouse W, Berenberg J. Dapsone and aplastic anemia. Ann. Intern. Med. 1985, 102 (1): 139 [2024-03-07]. PMID 3966740. doi:10.7326/0003-4819-102-1-139_2. (原始内容存档于2023-11-15).
- ^ Meyerson MA, Cohen PR. Dapsone-induced aplastic anemia in a woman with bullous systemic lupus erythematosus. Mayo Clin. Proc. 1994, 69 (12): 1159–62. PMID 7967777. doi:10.1016/s0025-6196(12)65768-1.
- ^ Björkman A, Phillips-Howard PA. Adverse reactions to sulfa drugs: implications for malaria chemotherapy. Bull. World Health Organ. 1991, 69 (3): 297–304. PMC 2393107 . PMID 1893504.
- ^ Singh S, Sethi N, Pandith S, Ramesh GS. Dapsone-induced methemoglobinemia: "Saturation gap"-The key to diagnosis. Journal of Anaesthesiology Clinical Pharmacology. January 2014, 30 (1): 86–88. PMC 3927300 . PMID 24574600. doi:10.4103/0970-9185.125710 .
- ^ Ganesan S, Sahu R, Walker LA, Tekwani BL. Cytochrome P450-dependent toxicity of dapsone in human erythrocytes. Journal of Applied Toxicology. April 2010, 30 (3): 271–275. PMID 19998329. S2CID 33330708. doi:10.1002/jat.1493.
- ^ Ganesan, Shobana; Sahu, Rajnish. Cytochrome P450-dependent toxicity of dapsone in human erythrocytes. Journal of Applied Toxicology. January 2009, 30 (3): 271–5 [2024-02-27]. doi:10.1002/jat.1493.
- ^ Aczone (Dapsone) Package insert. (PDF). Irvine CA: Allergan Inc. 2016 [2024-03-07]. (原始内容存档 (PDF)于2021-05-15) –通过U.S. Food and Drug Administration.
- ^ Richardus JH, Smith TC. Increased incidence in leprosy of hypersensitivity reactions to dapsone after introduction of multidrug therapy. Lepr Rev. 1989, 60 (4): 267–73. PMID 2491425. doi:10.5935/0305-7518.19890033 .
- ^ Kumar RH, Kumar MV, Thappa DM. Dapsone syndrome—a five year retrospective analysis. Indian J Lepr. 1998, 70 (3): 271–6. PMID 9801899.
- ^ Rao PN, Lakshmi TS. Increase in the incidence of dapsone hypersensitivity syndrome—an appraisal. Lepr Rev. 2001, 72 (1): 57–62. PMID 11355519. doi:10.5935/0305-7518.20010009 .
- ^ Joseph MS. Hypersensitivity reaction to dapsone. Four case reports. Lepr Rev. 1985, 56 (4): 315–20. PMID 4079634. doi:10.5935/0305-7518.19850034 .
- ^ Jamrozik K. Dapsone syndrome occurring in two brothers. Lepr Rev. 1986, 57 (1): 57–62. PMID 3702581. doi:10.5935/0305-7518.19860010 .
- ^ Hortaleza AR, Salta-Ramos NG, Barcelona-Tan J, Abad-Venida L. Dapsone syndrome in a Filipino man. Lepr Rev. 1995, 66 (4): 307–13. PMID 8637384. doi:10.5935/0305-7518.19950034 .
- ^ Tomecki KJ, Catalano CJ. Dapsone hypersensitivity. The sulfone syndrome revisited. Arch Dermatol. 1981, 117 (1): 38–9. PMID 6450569. doi:10.1001/archderm.1981.01650010044023.
- ^ Kromann NP, Vilhelmsen R, Stahl D. The dapsone syndrome. Arch Dermatol. 1982, 118 (7): 531–2. PMID 7092282. doi:10.1001/archderm.1982.01650190085028.
- ^ Jaffuel D, Lebel B, Hillaire-Buys D, Pene J, Godard P, Michel FB, Blayac JP, Bousquet J, Demolyi P. Eosinophilic pneumonia induced by dapsone. BMJ. 1998, 317 (7152): 181. PMC 28611 . PMID 9665900. doi:10.1136/bmj.317.7152.181.
- ^ Mechanisms of Action of Dapsone in Dermatological Diseases. Dapsone: Clinical Uses in Various Cutaneous Diseases. Medscape Today. (原始内容存档于2011-05-17).
- ^ Mechanisms of Antibacterial Drugs. Microcology. [2024-02-27]. (原始内容存档于2024-02-27).
- ^ Galijasevic S. The development of myeloperoxidase inhibitors. Bioorganic & Medicinal Chemistry Letters. January 2019, 29 (1): 1–7. PMID 30466896. S2CID 53721156. doi:10.1016/j.bmcl.2018.11.031.
- ^ Bozeman PM, Learn DB, Thomas EL. Assay of the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase. Journal of Immunological Methods. January 1990, 126 (1): 125–133. PMID 2154520. doi:10.1016/0022-1759(90)90020-v.
- ^ Bozeman PM, Learn DB, Thomas EL. Inhibition of the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase by dapsone. Biochemical Pharmacology. August 1992, 44 (3): 553–563. PMID 1324677. doi:10.1016/0006-2952(92)90449-s.
- ^ Stendahl O, Molin L, Lindroth M. Granulocyte-mediated release of histamine from mast cells. Effect of myeloperoxidase and its inhibition by antiinflammatory sulfone compounds. International Archives of Allergy and Applied Immunology. March 1983, 70 (3): 277–284. PMID 6186607. doi:10.1159/000233335.
- ^ Kettle AJ, Gedye CA, Winterbourn CC. Superoxide is an antagonist of antiinflammatory drugs that inhibit hypochlorous acid production by myeloperoxidase. Biochemical Pharmacology. May 1993, 45 (10): 2003–2010. PMID 8390258. doi:10.1016/0006-2952(93)90010-t.
- ^ Kettle AJ, Winterbourn CC. Mechanism of inhibition of myeloperoxidase by anti-inflammatory drugs. Biochemical Pharmacology. May 1991, 41 (10): 1485–1492. PMID 1850278. doi:10.1016/0006-2952(91)90565-m.
- ^ Diaz-Ruiz A, Zavala C, Montes S, Ortiz-Plata A, Salgado-Ceballos H, Orozco-Suarez S, et al. Antioxidant, antiinflammatory and antiapoptotic effects of dapsone in a model of brain ischemia/reperfusion in rats. Journal of Neuroscience Research. November 2008, 86 (15): 3410–3419. PMID 18615706. S2CID 5837071. doi:10.1002/jnr.21775.
- ^ Begon E, Chosidow O, Wolkenstein P. [Disulone]. Ann Dermatol Venereol. December 2004, 131 (12): 1062–73. PMID 15692440. doi:10.1016/S0151-9638(04)93842-2 (法语).
- ^ Uetrecht JP. Myeloperoxidase as a generator of drug free radicals. Biochem. Soc. Symp. 1995, 61: 163–70. PMID 8660393. S2CID 12471553. doi:10.1042/bss0610163.
- ^ Dapsone. National Library of Medicine. [2024-02-27]. (原始内容存档于2024-02-27).
- ^ Derivatives of p-Nitrothiophenols, by E. Fromm and J. Wittmann
Reports of the German Chemical Society Mai–August 1908 Fromm E, Wittmann J. Derivate desp-Nitrothiophenols. Berichte der Deutschen Chemischen Gesellschaft. May 1908, 41 (2): 2264–2273. doi:10.1002/cber.190804102131. - ^ Tréfouël JT, Nitti F, Bovet D. Activité du p.aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin. Comptes rendus des séances de la Société de biologie et de ses filiales. 23 November 1935, 120: 756. (原始内容存档于3 January 2017) (法语).
- ^ Fourneau E, Tréfouël TJ, Nitti F, Bovet D. Action antistreptococcique des dérivés sulfurés organiques. Comptes rendus de l'Académie des sciences. 1937, 204: 1763. (原始内容存档于2016-02-20) (法语).
- ^ Buttle G, Stephenson D, Smith S, Dewing T, Foster G. Treatment of streptococcal infections in mice with 4:4'diamino-dipheni-sulphone. Lancet. June 1937, 229 (5936): 1331–4. doi:10.1016/S0140-6736(00)75868-5.
- ^ Buttle G, Stephenson D, Smith S, Dewing T, Foster G. Treatment of streptococcal infections in mice with 4:4'diamino-dipheni-sulphone. Lancet. June 1937, 229 (5936): 1331–4. doi:10.1016/S0140-6736(00)75868-5.
- ^ Leprosy | 14 History of dapsone and dyes. [2009-02-24]. (原始内容存档于2009-02-12).
- ^ Stotland M, Shalita AR, Kissling RF. Dapsone 5% gel: a review of its efficacy and safety in the treatment of acne vulgaris. American Journal of Clinical Dermatology. June 2009, 10 (4): 221–227. PMID 19489655. S2CID 19485887. doi:10.2165/00128071-200910040-00002.
- ^ Aczone (dapsone) 7.5% Gel Prescribing Information (PDF). Allergan. February 2016 [2016-06-23]. (原始内容存档 (PDF)于2022-10-08).
- ^ ECHA dapsone registration dossier. [2024-03-07]. (原始内容存档于2021-08-28).
- ^ LAPOX ASH-10. 2017-06-03 [2024-03-07]. (原始内容存档于2020-11-24).
- ^ Schoustra SK, Dijksman JA, Zuilhof H, Smulders MM. Molecular control over vitrimer-like mechanics - tuneable dynamic motifs based on the Hammett equation in polyimine materials. Chemical Science. November 2020, 12 (1): 293–302. PMC 8178953 . PMID 34163597. doi:10.1039/d0sc05458e.