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

Modify Date: 2024-01-02 22:15:07

11-Cyclopropyl-5,11-dihydro-4-(hydroxyMethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one Structure
11-Cyclopropyl-5,11-dihydro-4-(hydroxyMethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one structure
Common Name 11-Cyclopropyl-5,11-dihydro-4-(hydroxyMethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
CAS Number 133627-24-4 Molecular Weight 282.29700
Density 1.45g/cm3 Boiling Point 482.6ºC at 760 mmHg
Molecular Formula C15H14N4O2 Melting Point N/A
MSDS N/A Flash Point 245.6ºC

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


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].

 Names

Name 11-cyclopropyl-4-(hydroxymethyl)-5H-dipyrido[2,3-e:2',3'-f][1,4]diazepin-6-one
Synonym More Synonyms

  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
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

 Synonyms

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
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