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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:32 UTC
HMDB IDHMDB0014383
Secondary Accession Numbers
  • HMDB14383
Metabolite Identification
Common NameNevirapine
DescriptionNevirapine, also known as viramune or NEV, belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group. Nevirapine is a drug which is used for use in combination with other antiretroviral drugs in the ongoing treatment of hiv-1 infection. In vivo studies in humans and in vitro studies with human liver microsomes have shown that nevirapine is extensively biotransformed via cytochrome P450 3A4 metabolism to several hydroxylated metabolites. A potent, non-nucleoside reverse transcriptase inhibitor (NNRTI) used in combination with nucleoside analogues for treatment of Human Immunodeficiency Virus Type 1 (HIV-1) infection and AIDS. Nevirapine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Nevirapine is a very strong basic compound (based on its pKa). Within humans, nevirapine participates in a number of enzymatic reactions. In particular, nevirapine can be converted into 3-hydroxynevirapine through its interaction with the enzyme cytochrome P450 2B6. In addition, nevirapine can be converted into 8-hydroxynevirapine; which is catalyzed by the enzymes cytochrome P450 3A4, cytochrome P450 2B6, and cytochrome P450 2D6. In humans, nevirapine is involved in nevirapine metabolism pathway. The most common adverse reaction is rash. HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by nevirapine. Structurally, nevirapine belongs to the dipyridodiazepinone chemical class.
Structure
Data?1582753172
Synonyms
ValueSource
11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-oneChEBI
NEVChEBI
NVPChEBI
ViramuneChEBI
Nevirapine hemihydrateHMDB
BI RG 587HMDB
BIRG587HMDB
Hemihydrate, nevirapineHMDB
BI-RG-587HMDB
Chemical FormulaC15H14N4O
Average Molecular Weight266.2979
Monoisotopic Molecular Weight266.11676109
IUPAC Name2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
Traditional Namenevirapine
CAS Registry Number129618-40-2
SMILES
CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1
InChI Identifier
InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
InChI KeyNQDJXKOVJZTUJA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAlkyldiarylamines
Alternative Parents
Substituents
  • Alkyldiarylamine
  • Pyrido-para-diazepine
  • Para-diazepine
  • Methylpyridine
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196.06 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 g/LNot Available
LogP2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP1.75ALOGPS
logP2.49ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.37ChemAxon
pKa (Strongest Basic)5.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.48 m³·mol⁻¹ChemAxon
Polarizability27.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01s9-0890000000-c2ef64541073a1c774c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-016r-1390000000-cbb2d729a2b310bf5dd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-016r-0290000000-64af72aec31bfd168e68Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-3980000000-98e328d2867c43716973Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-e341212035575baee47cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1090000000-aa8be82ca660a3a1654dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9240000000-96f26abab0ca2960a8d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-5ff2e0be399277e2d1e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0090000000-e6562b6940dd28d0a37bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-1890000000-d60a9db4a4fef99e1ca5Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00238 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00238 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00238
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4308
KEGG Compound IDC07263
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNevirapine
METLIN IDNot Available
PubChem Compound4463
PDB IDNVP
ChEBI ID63613
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). FDA label . .