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Details

Stereochemistry ACHIRAL
Molecular Formula 2C15H14N4O.H2O
Molecular Weight 550.611
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEVIRAPINE HEMIHYDRATE

SMILES

O.CC1=CC=NC2=C1NC(=O)C3=C(N=CC=C3)N2C4CC4.CC5=CC=NC6=C5NC(=O)C7=C(N=CC=C7)N6C8CC8

InChI

InChIKey=KMTLSXAXTLQBKJ-UHFFFAOYSA-N
InChI=1S/2C15H14N4O.H2O/c2*1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10;/h2*2-3,6-8,10H,4-5H2,1H3,(H,18,20);1H2

HIDE SMILES / InChI

Description

Nevirapine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by nevirapine. Nevirapine is, in general, only prescribed after the immune system has declined and infections have become evident. It is always taken with at least one other HIV medication such as Retrovir or Videx. The virus can develop resistance to nevirapine if the drug is taken alone, although even if used properly, nevirapine is effective for only a limited time. 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. Nevirapine is used for use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
239.0 µM [EC50]
0.31 nM [EC50]
250.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Viramune

Cmax

ValueDoseCo-administeredAnalytePopulation
2060 ng/mL
400 mg single, oral
NEVIRAPINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
161000 ng × h/mL
400 mg single, oral
NEVIRAPINE plasma
Homo sapiens
82000 ng × h/mL
400 mg 1 times / day multiple, oral
NEVIRAPINE plasma
Homo sapiens
96700 ng × h/mL
400 mg 1 times / day multiple, oral
NEVIRAPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
45 h
400 mg single, oral
NEVIRAPINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
400 mg single, oral
NEVIRAPINE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dose for Nevirapine is one 200 mg tablet daily for the first 14 days, followed by one 200 mg tablet twice daily, in combination with other antiretroviral agents.
Route of Administration: Oral
In Vitro Use Guide
The IC50 value for inhibition by nevirapine against immunodeficiency virus type 1 (HIV) nucleoside reverse transcriptase (RT) in removal assay was 3 uM