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QuickView for Nevirapine (compound)

Summary
General Info

PubChem

PubChem Compound 4463

PubChem Compound 4463

Name:	Nevirapine
PubChem Compound ID:	4463
Description:	A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS.
Molecular formula:	C₁₅H₁₄N₄O
Molecular weight:	266.298 g/mol
Synonyms:	11-Cyclopropyl-4-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one; Nevirapine; 129618-40-2; Dipyridodiazepinone Nevirapine; AIDS-005653; 11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO[3,2-B:2',3'-E][1,4]DIAZEPIN-6-ONE; Viramune; NVP; BIRG 587; Viramune (TN). show more » 11-Cyclopropyl-4-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one; Nevirapine; 129618-40-2; Dipyridodiazepinone Nevirapine; AIDS-005653; 11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO[3,2-B:2',3'-E][1,4]DIAZEPIN-6-ONE; Viramune; NVP; BIRG 587; Viramune (TN); AIDS-001856; MLS000084585; D00435; NCGC00065890-02; 11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one; SMR000048458; BIRG 0587;BI-RG-587; N11-Cyclopropyl-4-methyl-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e]-[1,4]diazepin-6-one & CD4-immunoadhesin; BI-RG-587; NSC 641530; Nevirapine (JAN/USP); 6H-Dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one, 11-cyclopropyl-5,11-dihydro-4-methyl-; BIRG-0587; Nevirapine & CD4-IgG; HSDB 7164; NSC641530; AIDS005653; BIRG 0587; ZINC00004778; C07263; Nevirapine [USAN:INN]; BIRG-587; NON-NUCLEOSIDE RT INHIBITOR NEVIRAPINE; BI-RG-587 & CD4-IgG; AIDS001856; DRG-0116; NEV show less «

DrugBank

Identification

Name:	Nevirapine
Name (isomeric):	DB00238
Drug Type:	small molecule
Description:	A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS.
Synonyms:	NVP; NEV
Brand:	Viramune
Category:	Anti-HIV Agents, Nonnucleoside Reverse Transcriptase Inhibitors, Reverse Transcriptase Inhibitors
CAS number:	129618-40-2

Pharmacology

Indication:	For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.
Pharmacology:	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 i... show more » 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. show less «
Mechanism of Action:	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.
Absorption:	90% (absolute bioavailability 93 ± 9%)
Protein binding:	60%
Biotransformation:	Hepatic. 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.
Route of elimination:	Thus cytochrome P450 metabolism, glucuronide conjugation, and urinary excretion of glucuronidated metabolites represent the primary route of nevirapine biotransformation and elimination in humans. Only a small fraction (<5%) of the radioactivity in urine (representing <3% of the total dose) was made up of parent compound; therefore, renal excretion plays a minor role in elimination of the parent compound.
Half Life:	45 hours
Toxicity:	Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease.
Affected organisms:	Human Immunodeficiency Virus

Interactions

Food interaction:

Avoid alcohol.

Take without regard to meals.

Drug interaction:

Atazanavir	Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of atazanavir by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of atazanavir if nevirapine is initiated, discontinued or dose changed.
Telithromycin	Nevirapine may decrease the plasma concentration of Telithromycin. Consider alternate therapy.
Trazodone	The CYP3A4 inducer, Nevirapine, may decrease Trazodone efficacy by increasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Nevirapine is initiated, discontinued or dose changed.
Nelfinavir	Nevirapine may decrease the effect of nelfinavir.
St. John's Wort	St. John's Wort decreases nevirapine effect

Atazanavir	Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of atazanavir by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of atazanavir if nevirapine is initiated, discontinued or dose changed.
Telithromycin	Nevirapine may decrease the plasma concentration of Telithromycin. Consider alternate therapy.
Trazodone	The CYP3A4 inducer, Nevirapine, may decrease Trazodone efficacy by increasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Nevirapine is initiated, discontinued or dose changed.
Nelfinavir	Nevirapine may decrease the effect of nelfinavir.
St. John's Wort	St. John's Wort decreases nevirapine effect
Simvastatin	The strong CYP3A4 inducer, nevirapine, may decrase the effect of simvastatin by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of simvastatin if nevirapine is initiated, discontinued or dose changed.
Warfarin	Nevirapine may decrease the anticoagulant effect of warfarin by increasing metabolism of R-warfarin via CYP3A4.
Temsirolimus	Nevirapine may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
Tipranavir	Nevirapine, a CYP3A4 inducer, may decrease the serum concentration of Tipranavir, a CYP3A4 substrate. Monitor for changesin Tipranavir effect if Nevirapine is initiated, discontinued or dose changed.
Lovastatin	The strong CYP3A4 inducer, nevirapine, may decrase the effect of lovastatin by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of lovastatin if nevirapine is initiated, discontinued or dose changed.
Quinupristin	This combination presents an increased risk of toxicity
Ketoconazole	Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of ketoconazole by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of ketoconazole if nevirapine is initiated, discontinued or dose changed.
Anisindione	Nevirapine may decrease the anticoagulant effect of anisindione.
Atorvastatin	Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of atorvastatin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of atorvastatin if nevirapine is initiated, discontinued or dose changed.
Tramadol	Nevirapine may decrease the effect of Tramadol by increasing Tramadol metabolism and clearance.
Acenocoumarol	Nevirapine may decrease the anticoagulant effect of acenocoumarol.
Methadone	The antiretroviral agent decreases the effect of methadone
Dicumarol	Nevirapine may decrease the anticoagulant effect of dicumarol.
Saquinavir	Decreases the effect of saquinavir

Targets

Reverse transcriptase

Enzymes

Cytochrome P450 2B6

Cytochrome P450 3A4

Cytochrome P450 3A5

Cytochrome P450 2C9

Cytochrome P450 2A6

Cytochrome P450 2D6

Cytochrome P450 1A2