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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14N4O
Molecular Weight 266.2984
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEVIRAPINE

SMILES

Cc1ccnc2c1N=C(c3cccnc3N2C4CC4)O

InChI

InChIKey=NQDJXKOVJZTUJA-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H14N4O
Molecular Weight 266.2984
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/nevirapine.html

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

Curator's Comment:: Nevirapine (NVP) crosses well the BBB

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL614530
239.0 µM [EC50]
0.31 nM [EC50]
250.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Viramune

Approved Use

VIRAMUNE is an NNRTI indicated for combination antiretroviral treatment of HIV-1 infection

Launch Date

8.2036798E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2060 ng/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEVIRAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
82000 ng × h/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
NEVIRAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
96700 ng × h/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
NEVIRAPINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
161000 ng × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEVIRAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
45 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEVIRAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEVIRAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 8-days-old
n = 1
Health Status: unhealthy
Age Group: 8-days-old
Sex: F
Population Size: 1
Sources:
Other AEs: Neutropenia, Hyperlactatemia...
Other AEs:
Neutropenia (mild)
Hyperlactatemia
Sources:
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Disc. AE: Rash, Stevens-Johnson syndrome...
AEs leading to
discontinuation/dose reduction:
Rash (2%)
Stevens-Johnson syndrome (1%)
Transaminases increased (1%)
ALT increased (1%)
GGT increased (<1%)
AST increased (<1%)
Hepatic enzyme increased (<1%)
Hepatitis (1%)
Hepatotoxicity (1%)
Hepatitis acute (<1%)
Hepatitis toxic (<1%)
Nausea (1%)
Malaise (1%)
Pyrexia (1%)
Fatigue (1%)
Vascular disorders (<1%)
Sources: Page: p. 56
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Disc. AE: Rash, Drug rash with eosinophilia and systemic symptoms...
AEs leading to
discontinuation/dose reduction:
Rash (2%)
Drug rash with eosinophilia and systemic symptoms (<1%)
Transaminases increased (1%)
ALT increased (<1%)
GGT increased (<1%)
AST increased (<1%)
Hepatic enzyme increased (<1%)
Hepatitis (1%)
Hepatotoxicity (<1%)
Hepatitis acute (<1%)
Hepatitis toxic (<1%)
Nausea (<1%)
Malaise (<1%)
Pyrexia (<1%)
Fatigue (<1%)
Vascular disorders (<1%)
Musculoskeletal and connective tissue disorders (<1%)
Sources: Page: p. 56
800 mg 1 times / day multiple, oral
Overdose
Dose: 800 mg, 1 times / day
Route: oral
Route: multiple
Dose: 800 mg, 1 times / day
Sources:
unhealthy, adult
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Hepatotoxicity, Reaction skin...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (grade 5)
Reaction skin (severe)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hyperlactatemia
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 8-days-old
n = 1
Health Status: unhealthy
Age Group: 8-days-old
Sex: F
Population Size: 1
Sources:
Neutropenia mild
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 8-days-old
n = 1
Health Status: unhealthy
Age Group: 8-days-old
Sex: F
Population Size: 1
Sources:
ALT increased 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Fatigue 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Hepatitis 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Hepatotoxicity 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Malaise 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Nausea 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Pyrexia 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Stevens-Johnson syndrome 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Transaminases increased 1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Rash 2%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
AST increased <1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
GGT increased <1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Hepatic enzyme increased <1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Hepatitis acute <1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Hepatitis toxic <1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Vascular disorders <1%
Disc. AE
200 mg 2 times / day steady, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: steady
Dose: 200 mg, 2 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 506
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 506
Sources: Page: p. 56
Hepatitis 1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Transaminases increased 1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Rash 2%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
ALT increased <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
AST increased <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Drug rash with eosinophilia and systemic symptoms <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Fatigue <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
GGT increased <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Hepatic enzyme increased <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Hepatitis acute <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Hepatitis toxic <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Hepatotoxicity <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Malaise <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Musculoskeletal and connective tissue disorders <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Nausea <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Pyrexia <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Vascular disorders <1%
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources: Page: p. 56
unhealthy, >18 years
n = 505
Health Status: unhealthy
Age Group: >18 years
Sex: M+F
Population Size: 505
Sources: Page: p. 56
Hepatotoxicity grade 5
Disc. AE
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, adult
Reaction skin severe
Disc. AE
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, adult
PubMed

PubMed

TitleDatePubMed
A novel genotype encoding a single amino acid insertion and five other substitutions between residues 64 and 74 of the HIV-1 reverse transcriptase confers high-level cross-resistance to nucleoside reverse transcriptase inhibitors. Abacavir CNA2007 International Study Group.
1999 Oct 1
Didanosine-induced hepatitis.
2000 Aug
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.
2000 Aug
Increasing cerebrospinal fluid chemokine concentrations despite undetectable cerebrospinal fluid HIV RNA in HIV-1-infected patients receiving antiretroviral therapy.
2000 Dec 15
Drug resistance and drug combination features of the human immunodeficiency virus inhibitor, BCH-10652 [(+/-)-2'-deoxy-3'-oxa-4'-thiocytidine, dOTC].
2000 Jul
Presence of 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"-oxath iole-2",2"-dioxide) (TSAO)-resistant virus strains in TSAO-inexperienced HIV patients.
2000 Jun 10
Non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis and biological evaluation of novel quinoxalinylethylpyridylthioureas as potent antiviral agents.
2000 Mar
Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors.
2000 May 18
Synthesis and antiviral activity of 4-benzyl pyridinone derivatives as potent and selective non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors.
2000 Oct 19
Piperidinylethyl, phenoxyethyl and fluoroethyl bromopyridyl thiourea compounds with potent anti-HIV activity.
2000 Sep
Computer-assisted design, synthesis and biological evaluation of novel pyrrolyl heteroaryl sulfones targeted at HIV-1 reverse transcriptase as non-nucleoside inhibitors.
2000 Sep
The tolerability of efavirenz after nevirapine-related adverse events.
2000 Sep
Stereochemistry of halopyridyl and thiazolyl thiourea compounds is a major determinant of their potency as nonnucleoside inhibitors of HIV-1 reverse transcriptase.
2000 Sep 18
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.
2001
Rwanda to receive cheaper anti-HIV drugs for chronic treatment and free viramune to prevent viral transmission from mother to child.
2001 Apr
Long-term safety and efficacy of nevirapine, stavudine and lamivudine in a real-world setting.
2001 Apr 13
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.
2001 Apr 15
Long-term follow-up of antiretroviral-naive HIV-positive patients treated with nevirapine.
2001 Apr 15
Revised nevirapine insert.
2001 Feb
Stevens-Johnson syndrome caused by the antiretroviral drug nevirapine.
2001 Feb
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.
2001 Feb
SJ-3366, a unique and highly potent nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 (HIV-1) that also inhibits HIV-2.
2001 Feb
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.
2001 Feb 10
South Africa's AIDS activists say new neviripine programme is not enough.
2001 Feb 10
Indian company offers cheap anti-AIDS drugs.
2001 Feb 15
Drug interaction between St John's wort and nevirapine.
2001 Feb 16
Nevirapine and postexposure prophylaxis for human immunodeficiency virus.
2001 Feb 21
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.
2001 Feb 26
Further views by the Erice working group on mother-to-child transmission of HIV type 1.
2001 Jan
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.
2001 Jan
Pharmacokinetic of nevirapine in haemodialysis.
2001 Jan
Ritonavir-induced carbamazepine toxicity.
2001 Jan
Sex differences in nevirapine rash.
2001 Jan
Estimation of binding affinities for HEPT and nevirapine analogues with HIV-1 reverse transcriptase via Monte Carlo simulations.
2001 Jan 18
Efficacy, tolerance, and pharmacokinetics of the combination of stavudine, nevirapine, nelfinavir, and saquinavir as salvage regimen after ritonavir or indinavir failure.
2001 Jan 20
Nevirapine should not be prescribed for needlestick injuries.
2001 Jan 20
From the Centers for Disease Control and Prevention. Serious adverse events attributed to nevirapine regimens for postexposure prophylaxis after HIV exposures--worldwide, 1997-2000.
2001 Jan 24-31
Need for increased dose of warfarin in HIV patients taking nevirapine.
2001 Jan 26
Sequence-specific detection of individual DNA strands using engineered nanopores.
2001 Jul
Distribution of K103N and/or Y181C HIV-1 mutations by exposure to zidovudine and non-nucleoside reverse transcriptase inhibitors.
2001 Jul
The steady-state pharmacokinetics of efavirenz and nevirapine when used in combination in human immunodeficiency virus type 1-infected persons.
2001 Jul 1
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.
2001 Jun
Phenotypic hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in treatment-experienced HIV-infected patients: impact on virological response to efavirenz-based therapy.
2001 Jun 15
South Africa in crisis on HIV/AIDS treatment.
2001 Jun 29
[Nevirapine and clinical withdrawal syndrome].
2001 Mar
Pharmacokinetics of ritonavir and nevirapine in peritoneal dialysis.
2001 Mar
International perspectives on antiretroviral resistance. Nonnucleoside reverse transcriptase inhibitor resistance.
2001 Mar 1
Indinavir, nevirapine, stavudine, and lamivudine for human immunodeficiency virus-infected, amprenavir-experienced subjects: AIDS Clinical Trials Group protocol 373.
2001 Mar 1
Efficiency comparisons of rank and permutation tests based on summary statistics computed from repeated measures data.
2001 Mar 15
Prophylaxis with a nevirapine-containing triple regimen after exposure to HIV-1.
2001 Mar 3
Patents

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
The IC50 value for inhibition by nevirapine against immunodeficiency virus type 1 (HIV) nucleoside reverse transcriptase (RT) in removal assay was 3 uM
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:56:11 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:11 UTC 2021
Record UNII
99DK7FVK1H
Record Status Validated (UNII)
Record Version
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Name Type Language
NEVIRAPINE
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
NEVIRAPINE ANHYDROUS [USP-RS]
Common Name English
VIRAMUNE
Brand Name English
NEVIRAPINE [MI]
Common Name English
NEVIRAPINE, ANHYDROUS [EP]
Common Name English
NEVIRAPINE [EP MONOGRAPH]
Common Name English
NEVIRAPINE [USP]
Common Name English
NEVIRAPINE TEVA
Brand Name English
NEVIRAPINUM ANHYDROUS [WHO-IP LATIN]
Common Name English
NSC-641530
Code English
NEVIRAPINE [MART.]
Common Name English
NEVIRAPINE [INN]
Common Name English
NEVIRAPINE ANHYDROUS [WHO-IP]
Common Name English
NEVIRAPINE, ANHYDROUS
EP  
Common Name English
BIRG-0587
Code English
NEVIRAPINE [EMA EPAR]
Common Name English
NEVIRAPINE [VANDF]
Common Name English
BIRG 0587
Code English
NEVIRAPINE [JAN]
Common Name English
11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO(3,2-B:2',3'-E)(1,4)DIAZEPIN-6-ONE
Systematic Name English
NEVIRAPINE [USP MONOGRAPH]
Common Name English
6H-DIPYRIDO(3,2-B:2',3'-E)(1,4)DIAZEPIN-6-ONE, 11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-
Systematic Name English
NEVIRAPINE [WHO-DD]
Common Name English
NEVIRAPINE [HSDB]
Common Name English
NEVIRAPINE [USAN]
Common Name English
NEVIRAPINE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS NEVIRAPINE TEVA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
NCI_THESAURUS C97453
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-ATC J05AR05
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-VATC QJ05AG01
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
NDF-RT N0000175463
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
EMA ASSESSMENT REPORTS VIRAMUNE (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
LIVERTOX 679
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.2
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-VATC QJ05AR07
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
NDF-RT N0000009948
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
NDF-RT N0000175460
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/STA)
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-ATC J05AG01
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
FDA ORPHAN DRUG 293409
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LAM/NEV/ZID)
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-VATC QJ05AR05
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
WHO-ATC J05AR07
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
Code System Code Type Description
EVMPD
SUB09214MIG
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
NDF-RT
N0000190118
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY Cytochrome P450 3A Inducers [MoA]
EPA CompTox
129618-40-2
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
RXCUI
53654
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY RxNorm
LACTMED
Nevirapine
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
EVMPD
SUB25191
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
INN
6815
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
WIKIPEDIA
NEVIRAPINE
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL57
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
MESH
D019829
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
MERCK INDEX
M7845
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY Merck Index
CAS
129618-40-2
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
USP_CATALOG
1460703
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY USP-RS
WHO INTERNATIONAL PHARMACOPEIA
NEVIRAPINE
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY Description: A white to almost white powder. Solubility: Practically insoluble in water, sparingly to slightly soluble in dichloromethane R, slightly soluble in methanol R. Category: Antiretroviral (Non-Nucleoside Reverse Transcriptase Inhibitor). Storage: Nevirapine should be kept in a well-closed container. Labelling: The designation on the container should state whether the substance is the hemihydrate or is in the anhydrous form. Definition: Nevirapine contains not less than 98.0% and not more than 102.0% of nevirapine (C15H14N4O), calculated with reference to the anhydrous substance.
DRUG BANK
DB00238
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
DRUG CENTRAL
1904
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
NCI_THESAURUS
C29277
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
PUBCHEM
4463
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
HSDB
7164
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
NDF-RT
N0000187064
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
FDA UNII
99DK7FVK1H
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
SUBSTANCE->BASIS OF STRENGTH
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount NOT SPECIFIED
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
The test is not valid unless the resolution between nevirapine and nevirapine impurity B RS is not less than 5. In the chromatogram obtained with solution (3) the peak due to impurity (B) is eluted at a relative retention of about 0.7 with reference to nevirapine (retention time about 7.6 minutes).
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Amount NOT SPECIFIED
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC