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Peroxidation of the antimalarial drug primaquine: characterization of a benzidine-like metabolite with methaemoglobin-forming activity.

作者信息

Morais M da S, Augusto O

机构信息

Department of Biochemistry, Universidade de São Paulo, Brazil.

出版信息

Xenobiotica. 1993 Feb;23(2):133-9. doi: 10.3109/00498259309059369.

DOI:10.3109/00498259309059369
PMID:8498077
Abstract
  1. An organic solvent-extractable product was obtained from incubations of primaquine (70 mM) with H2O2 (70mM) and horseradish peroxidase (0.5 mg/ml) in acetate buffer, pH4.2. 2. The metabolite was characterized as 5,5-di-(8-[(4-amino-1-methylbutyl)amino]-6-methoxyquinoline) by 1H-n.m.r., mass, FT-i.r. and u.v.-visible spectroscopy. 3. Incubations of rat erythrocytes with 5,5-di-(8-[(4-amino-1-methylbutyl)amino]-6-methoxyquinoline) led to the formation of methaemoglobin in a time- and metabolite concentration-dependent manner.
摘要

相似文献

1
Peroxidation of the antimalarial drug primaquine: characterization of a benzidine-like metabolite with methaemoglobin-forming activity.
Xenobiotica. 1993 Feb;23(2):133-9. doi: 10.3109/00498259309059369.
2
Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes.
J Med Chem. 1984 Mar;27(3):407-10. doi: 10.1021/jm00369a031.
3
Direct ESR detection of a free radical intermediate during the peroxidase-catalyzed oxidation of the antimalarial drug primaquine.在抗疟药伯氨喹的过氧化物酶催化氧化过程中对自由基中间体的直接电子自旋共振检测
Biochem Pharmacol. 1988 Jul 15;37(14):2791-7. doi: 10.1016/0006-2952(88)90042-1.
4
Studies on the mechanisms of oxidation in the erythrocyte by metabolites of primaquine.伯氨喹代谢产物对红细胞氧化机制的研究。
Biochem Pharmacol. 1988 Jul 1;37(13):2683-90. doi: 10.1016/0006-2952(88)90263-8.
5
Oxidative activity of primaquine metabolites on rat erythrocytes in vitro and in vivo.伯氨喹代谢产物对大鼠红细胞的体外和体内氧化活性。
Biochem Pharmacol. 1994 Jan 20;47(2):309-16. doi: 10.1016/0006-2952(94)90022-1.
6
In vitro metabolism of the antimalarial agent primaquine by mouse liver enzymes and identification of a methemoglobin-forming metabolite.抗疟药伯氨喹在小鼠肝脏酶作用下的体外代谢及一种形成高铁血红蛋白代谢物的鉴定。
Drug Metab Dispos. 1984 Jan-Feb;12(1):35-44.
7
Methemoglobin formation resulting from administration of candidate 8-aminoquinoline antiparasitic drugs in the dog.
Fundam Appl Toxicol. 1988 Feb;10(2):270-5. doi: 10.1016/0272-0590(88)90311-9.
8
Metabolism of 8-aminoquinoline antimalarial agents.8-氨基喹啉抗疟药的代谢
Bull World Health Organ. 1981;59(3):413-25.
9
A simple and rapid evaluation of methemoglobin toxicity of 8-aminoquinolines and related compounds.8-氨基喹啉及相关化合物高铁血红蛋白毒性的简单快速评估
Ecotoxicol Environ Saf. 2000 Mar;45(3):236-9. doi: 10.1006/eesa.1999.1868.
10
[Methemoglobin formation in the erythrocytes of mice as affected by primaquine metabolites and the protective action of antioxidants].[伯氨喹代谢产物对小鼠红细胞高铁血红蛋白形成的影响及抗氧化剂的保护作用]
Med Parazitol (Mosk). 1984 Jul-Aug(4):22-4.

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1
Tafenoquine and NPC-1161B require CYP 2D metabolism for anti-malarial activity: implications for the 8-aminoquinoline class of anti-malarial compounds.他非诺喹和NPC-1161B需要CYP 2D代谢以发挥抗疟活性：对8-氨基喹啉类抗疟化合物的启示。
Malar J. 2014 Jan 3;13:2. doi: 10.1186/1475-2875-13-2.
2
Drug-induced methaemoglobinaemia. Treatment issues.药物性高铁血红蛋白血症。治疗问题。
Drug Saf. 1996 Jun;14(6):394-405. doi: 10.2165/00002018-199614060-00005.