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英语dermatitis herpetiformis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]

达普颂
临床资料
商品名英语Drug nomenclatureAczone及其他商品名
AHFS/Drugs.comMonograph
MedlinePlusa682128
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 (绝大部份由细胞色素P450 2E1英语CYP2E1介导)
生物半衰期20至30小时
排泄途径
识别信息
  • 4-[(4-aminobenzene)sulfonyl]aniline
CAS号80-08-0  checkY
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.001.136 编辑维基数据链接
化学信息
化学式C12H12N2O2S
摩尔质量248.30 g·mol−1
3D模型(JSmol英语JSmol
熔点175至176 °C(347至349 °F)
  • O=S(=O)(c1ccc(N)cc1)c2ccc(N)cc2
  • 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 checkY
  • Key:MQJKPEGWNLWLTK-UHFFFAOYSA-N checkY

使用后的严重副作用有白血球减少症英语Agranulocytosis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[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

感染

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]

目前尚不清楚与乙胺嘧啶联合使用是否有助于预防疟疾[13]

自体免疫性疾病

其他病症

无麸质饮食结合,可治疗疱疹样皮肤炎。[3]

可用于治疗发生坏死棕色遁蛛咬伤。[19]

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英语Erythema elevatum diutinum。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]

于2015年8月发表的一篇评论指出达普颂可有效对抗全身性环状肉芽肿英语generalized granuloma annulare[21]

达普颂已被用于设计为染料吸附聚合物的单体[22]

使用禁忌及注意事项

患有紫质症贫血心脏病肺病HIV感染、G6PD和肝功能不全的人在使用达普颂时,有出现较高不良反应的风险。[9]

不良影响

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英语severe cutaneous adverse reactions(SCAR)中的一种,主要是DRESS症候群英语Drug rash with eosinophilia and systemic symptoms或是DRESS样反应。[25][26]

血液

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英语hemolytic anemia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/达普颂英语Chlorproguanil/dapsone(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,但在预防疟疾英语malaria prophylaxis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英语CO-oximeter)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英语Blood gas test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

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,特别是同功酶细胞色素 P450 2D6细胞色素P450 2B6细胞色素P450 3A4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

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

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英语eosinophilia,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

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

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英语Dihydropteroate synthase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英语respiratory burst杀死细菌过程中,髓过氧化物酶过氧化氢 (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

发现

 
E. Fromm与J. Wittmann提出由4-硝基氯苯合成达普颂的报告(1908年)。[61]

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]然后由法国埃内斯特·富尔诺[63]英国[64]格拉德温·布特尔英语Gladwin Buttle[65]分别独立开发出达普颂。[66]

拟用于抗疟治疗

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

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

达普颂也可用作环氧树脂和亚胺基玻璃体态聚合物英语vitrimers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

参考文献

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外部链接

  • Dapsone. Drug Information Portal. U.S. National Library of Medicine. [2024-03-07]. (原始内容存档于2022-11-22).