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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-09-25 12:10:30 UTC
HMDB IDHMDB0014383
Secondary Accession Numbers
  • HMDB14383
StatusExpected but not Quantified
Metabolite Identification
Common NameNevirapine
DescriptionNevirapine is only found in individuals that have used or taken this drug. It is a potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates.
Structure
Thumb
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 hemihydrateMeSH
BI RG 587MeSH
BIRG587MeSH
Hemihydrate, nevirapineMeSH
BI-RG-587MeSH
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
DescriptionThis compound 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
Process
Naturally occurring process:
Biological process:
Biochemical pathway:
Disposition
Biological Location:
Subcellular:
Biofluid and excreta:
Role
Industrial application:
Pharmaceutical industry:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point196.06 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.05e-01 g/LNot Available
LogP2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.48 m3·mol-1ChemAxon
Polarizability27.8 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-016r-1390000000-cbb2d729a2b310bf5dd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-016r-0290000000-64af72aec31bfd168e68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-3980000000-98e328d2867c43716973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Nevirapine Action PathwayPw000720Pw000720 greyscalePw000720 simpleNot Available
Nevirapine Metabolism PathwayPw000618Pw000618 greyscalePw000618 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4308
KEGG Compound IDC07263
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNevirapine
NuGOwiki LinkHMDB0014383
METLIN IDNot Available
PubChem Compound4463
PDB IDNVP
ChEBI ID63613
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). FDA label . .