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化合物简介

Pretomanid (PA-824) is an experimental anti-tuberculosis drug. Pretomanid is a bicyclic nitroimidazole-like molecule with a very complex mechanism of action. It is active against both replicating and hypoxic, non-replicating Mycobacterium tuberculosis. Microarray analysis of the mode of action of pretomanid showed a puzzling mixed effect both on genes responsive to both cell wall inhibition (like isoniazid) and respiratory poisoning (like cyanide). The aerobic killing mechanism of this drug appears to involve inhibition of cell wall mycolic acid biosynthesis through an as yet unknown molecular mechanism.The respiratory poisoning through nitric oxide release seemed to be a crucial element of anaerobic activity by pretomanid. The effect of pretomanid on the respiratory complex under hypoxic non-replicating conditions was also manifested in a rapid drop in intracellular ATP levels, again similar to that observed by cyanide treatment. Pretomanid recently was shown to be safe, well tolerated, and efficacious at doses of 100–200mg daily in a dose-ranging study among drug-sensitive, sputum smear–positive, adult pulmonary TB patients

基本信息

CAS:187235-37-6
中文别名
英文别名:Pretomanid (PA-824);PA-824;UNII-2XOI31YC4N;(S)-6-(4-(trifluoromethoxy)benzyloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine;(6S)-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine;
分子式:C14H12F3N3O5
分子量:359.257
精确质量:359.073
Psa:91.33
Logp:3.1909

编号系统

MDL号:MFCD06809939

物化性质

密度:1.58g/cm3
沸点:462.3ºC at 760 mmHg
闪点:233.4ºC
折射率:1.588
蒸汽压:1E-08mmHg at 25°C

安全信息

海关编码:2934999090
危险性防范说明:P280; P304 + P340 + P312; P305 + P351 + P338; P337 + P313
危险标志:GHS07
危险性描述:H315; H319; H335
信号词:Warning

生产方法及用途

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图谱

1H NMR : Predict


13C NMR : Predict


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