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11-Cyclopropyl-5,11-dihydro-4-(hydroxyMethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Names

[ CAS No. ]:
133627-24-4

[ Name ]:
11-Cyclopropyl-5,11-dihydro-4-(hydroxyMethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

[Synonym ]:
4-hydroxymethyl-nevirapine
12-hydroxynevirapine
Nevirapin 4-substituted deriv. 2
11-cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one
N11-Cyclopropyl-4-hydroxymethyl-5,11-dihydro-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
11-cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one

Biological Activity

[Description]:

12-Hydroxynevirapine (12-hydroxy-NVP; 12-OH-NVP) is a major oxidative metabolite of Nevirapine (HY-10570). Nevirapine is a non-nucleoside reverse transcriptase inhibitor indicated for the HIV-1 infections. Nevirapine causes idiosyncratic hepatotoxicity and mild-to-severe skin rashes. 12-Hydroxynevirapine, a non-reactive metabolite, can be bioactivated by sulphotransferases (SULTs) in the liver and skin, yielding the reactive species 12-Sulphoxy-nevirapine[1][2].

[Related Catalog]:

Research Areas >> Infection

[References]

[1]. Amy M Sharma, et al. 12-OH-nevirapine sulfate, formed in the skin, is responsible for nevirapine-induced skin rash. Chem Res Toxicol. 2013 May 20;26(5):817-27.  

[2]. Aline T Marinho, et al. Differences in nevirapine biotransformation as a factor for its sex-dependent dimorphic profile of adverse drug reactions. J Antimicrob Chemother. 2014 Feb;69(2):476-82.  

Chemical & Physical Properties

[ Density]:
1.45g/cm3

[ Boiling Point ]:
482.6ºC at 760 mmHg

[ Molecular Formula ]:
C15H14N4O2

[ Molecular Weight ]:
282.29700

[ Flash Point ]:
245.6ºC

[ Exact Mass ]:
282.11200

[ PSA ]:
81.84000

[ LogP ]:
1.71970

[ Vapour Pressure ]:
4.01E-10mmHg at 25°C

[ Index of Refraction ]:
1.701

Synthetic Route

Click to get detail synthetic route

Related Compounds