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12-Hydroxynevirapine

CAT: 0804-HY-148642-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-148642-01Size:1 mg
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Description
12-Hydroxynevirapine (12-hydroxy-NVP; 12-OH-NVP) is a major oxidative metabolite of Nevirapine. 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].
CAS Number
133627-24-4
Product Name Alternative
12-hydroxy-NVP; 12-OH-NVP
UNSPSC
12352005
Target
Drug Metabolite
Type
Reference compound
Related Pathways
Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/12-hydroxynevirapine.html
Purity
96.04
Solubility
10 mM in DMSO
Smiles
O=C1NC2=C(CO)C=CN=C2N(C3CC3)C4=NC=CC=C14
Molecular Formula
C15H14N4O2
Molecular Weight
282.30
References & Citations
[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.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

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

12-hydroxynevirapine is a dipyridodiazepine that is nevirapine in which one of the hydrogens of the methyl group has been substituted by a hydroxy group. It is a metabolite of the anti-HIV drug, nevirapine. It has a role as a drug metabolite. It is an aromatic primary alcohol, a member of cyclopropanes and a dipyridodiazepine. It is functionally related to a nevirapine.

CAS Number133627-24-4
PubChem CID453338
IUPAC Name2-cyclopropyl-7-(hydroxymethyl)-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
Molecular FormulaC15H14N4O2
Molecular Weight282.30
XLogP0.7
Topological Polar Surface Area78.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Heavy Atom Count21
Formal Charge0
Complexity414
SMILES
C1CC1N2C3=C(C=CC=N3)C(=O)NC4=C(C=CN=C42)CO
InChI
InChI=1S/C15H14N4O2/c20-8-9-5-7-17-14-12(9)18-15(21)11-2-1-6-16-13(11)19(14)10-3-4-10/h1-2,5-7,10,20H,3-4,8H2,(H,18,21)
InChIKey
SEBABOMFNCVZGF-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 11-Cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
CAS: 133627-24-4
CID: 453338
Formula: C15H14N4O2
MW: 282.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight282.30
XLogP30.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass282.11167570
Monoisotopic Mass282.11167570
Topological Polar Surface Area78.4 Ų
Heavy Atom Count21
Formal Charge0
Complexity414
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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