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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

Molecular Formula C15H14N4O
Molecular Weight 266.2979
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
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
Drug resistance and drug combination features of the human immunodeficiency virus inhibitor, BCH-10652 [(+/-)-2'-deoxy-3'-oxa-4'-thiocytidine, dOTC].
2000 Jul
Computer-assisted design, synthesis and biological evaluation of novel pyrrolyl heteroaryl sulfones targeted at HIV-1 reverse transcriptase as non-nucleoside inhibitors.
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
A single amino acid change at Leu-188 in the reverse transcriptase of HIV-2 and SIV renders them sensitive to non-nucleoside reverse transcriptase inhibitors.
2001
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.
2001
Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription.
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
[Highly active antiretroviral therapy with nevirapine. Therapy compliance determines success].
2001 Apr 2
[Results of the AIDS-In-Europe Study. Non-nucleoside reverse transcriptase inhibitor does not equal non-nucleoside reverse transcriptase inhibitor].
2001 Apr 2
Antiviral drugs: current state of the art.
2001 Aug
South Africa cuts agreement for one AIDS drug but ignores another.
2001 Feb
Revised nevirapine insert.
2001 Feb
Stevens-Johnson syndrome caused by the antiretroviral drug nevirapine.
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
Simple and rapid determination of nevirapine in human serum by reversed-phase high-performance liquid chromatography.
2001 Feb 25
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.
2001 Feb 26
Prevention of nevirapine-associated rash.
2001 Feb 3
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
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
Serious adverse events attributed to nevirapine regimens for postexposure prophylaxis after HIV exposures--worldwide, 1997-2000.
2001 Jan 5
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
Development of drug resistance in patients receiving combinations of zidovudine, didanosine and nevirapine.
2001 Jul 6
Hepatotoxicity in HIV-1-infected patients receiving nevirapine-containing antiretroviral therapy.
2001 Jul 6
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.
2001 Jun
The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study.
2001 Jun 1
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
High exposure to nevirapine in plasma is associated with an improved virological response in HIV-1-infected individuals.
2001 Jun 15
Analysis of human immunodeficiency virus type 1 drug resistance in children receiving nucleoside analogue reverse-transcriptase inhibitors plus nevirapine, nelfinavir, or ritonavir (Pediatric AIDS Clinical Trials Group 377).
2001 Jun 15
2-Amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1.
2001 Jun 7
[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
Jaundice and hepatocellular damage associated with nevirapine therapy.
2001 May
An in vivo model for HIV resistance development.
2001 May 1
HIV in body fluids during primary HIV infection: implications for pathogenesis, treatment and public health.
2001 May 4
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 Thu Jul 06 04:09:12 UTC 2023
Edited
by admin
on Thu Jul 06 04:09:12 UTC 2023
Record UNII
B7XF2TD73C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEVIRAPINE HEMIHYDRATE
USP-RS   WHO-DD   WHO-IP  
Common Name English
NEVIRAPINE HEMIHYDRATE [WHO-IP]
Common Name English
NEVIRAPINE HEMIHYDRATE [EP MONOGRAPH]
Common Name English
Nevirapine hemihydrate [WHO-DD]
Common Name English
NEVIRAPINE HEMIHYDRATE [USP-RS]
Common Name English
NEVIRAPINUM HEMIHYDRATE [WHO-IP LATIN]
Common Name English
NEVIRAPINE HEMIHYDRATE [USP MONOGRAPH]
USP-RS  
Common Name English
6H-DIPYRIDO(3,2-B:2',3'-E)(1,4)DIAZEPIN-6-ONE, 11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-, HYDRATE (2:1)
Systematic Name English
Code System Code Type Description
RS_ITEM_NUM
1460714
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
DRUG BANK
DBSALT002723
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
SMS_ID
100000127941
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NEVIRAPINE HEMIHYDRATE
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
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.
PUBCHEM
9959243
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
RXCUI
2462459
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID30176606
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
DAILYMED
B7XF2TD73C
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
FDA UNII
B7XF2TD73C
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
EVMPD
SUB34149
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
CAS
220988-26-1
Created by admin on Thu Jul 06 04:09:12 UTC 2023 , Edited by admin on Thu Jul 06 04:09:12 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
ANHYDROUS->SOLVATE
Related Record Type Details
IMPURITY -> PARENT
Amount Not Specified
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
Amount Not Specified
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY