Identification

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Name
Nevirapine
Accession Number
DB00238  (APRD00705, DB08311)
Type
Small Molecule
Groups
Approved
Description

A potent, non-nucleoside reverse transcriptase inhibitor (NNRTI) used in combination with nucleoside analogues for treatment of Human Immunodeficiency Virus Type 1 (HIV-1) infection and AIDS. [PubChem] Structurally, nevirapine belongs to the dipyridodiazepinone chemical class.

Structure
Thumb
Synonyms
  • 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
  • NEV
  • Nevirapina
  • Nevirapine
  • Nevirapine anhydrous
  • Nevirapine, anhydrous
  • NVP
External IDs
BIRG 0587 / BIRG-0587 / BIRG-587 / NSC-641530
Product Ingredients
IngredientUNIICASInChI Key
Nevirapine hemihydrateB7XF2TD73C220988-26-1KMTLSXAXTLQBKJ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ViramuneTablet, extended release400 mg/1OralBoehringer Ingelheim Pharmaceuticals, Inc.2011-04-11Not applicableUs
ViramuneTablet, extended release50 mgOralBoehringer Ingelheim1998-02-05Not applicableEu
ViramuneTablet, extended release400 mg/1OralA-S Medication Solutions2011-04-11Not applicableUs
ViramuneTablet, extended release400 mgOralBoehringer Ingelheim1998-02-05Not applicableEu
ViramuneTablet200 mg/1OralBoehringer Ingelheim Pharmaceuticals Inc.2001-08-01Not applicableUs0597 004620180907 15195 qhxf1r
ViramuneTablet, extended release400 mg/1OralPhysicians Total Care, Inc.2013-01-23Not applicableUs
ViramuneTablet200 mgOralBoehringer Ingelheim1998-02-05Not applicableEu
ViramuneTablet, extended release400 mgOralBoehringer Ingelheim1998-02-05Not applicableEu
ViramuneSuspension50 mg/5mLOralBoehringer Ingelheim Pharmaceuticals Inc.2001-10-01Not applicableUs
ViramuneTablet200 mg/1OralPhysicians Total Care, Inc.2001-08-012010-06-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-nevirapineTabletOralApotex CorporationNot applicableNot applicableCanada
Apo-nevirapine XRTablet, extended releaseOralApotex Corporation2015-11-24Not applicableCanada
Auro-nevirapineTabletOralAurobindo Pharma Limited (Unit Iii)2010-12-29Not applicableCanada
Jamp NevirapineTabletOralJamp Pharma Corporation2013-06-03Not applicableCanada
Mylan-nevirapineTabletOralMylan Pharmaceuticals2012-06-20Not applicableCanada
NevirapineTablet200 mg/1OralWest-Ward Pharmaceuticals Corp.2012-05-212020-07-11Us
NevirapineTablet, extended release100 mg/1OralSciegen Pharmaceuticals Inc.2017-08-082017-10-01Us
NevirapineTablet, extended release400 mg/1OralAurobindo Pharma Limited2017-02-28Not applicableUs
NevirapineTablet200 mg/1OralCamber Pharmaceuticals2012-05-23Not applicableUs
NevirapineTablet200 mg/1OralSeton Pharmaceuticals2012-05-212014-04-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-zidovudine-lamivudine-nevirapineNevirapine (200 mg) + Lamivudine (150 mg) + Zidovudine (300 mg)TabletOralApotex CorporationNot applicableNot applicableCanada
Lamivudine, Nevirapine, and ZidovudineNevirapine (200 mg/1) + Lamivudine (150 mg/1) + Zidovudine (300 mg/1)Tablet, film coatedOralMicro Labs Limited2018-09-03Not applicableUs
Categories
UNII
99DK7FVK1H
CAS number
129618-40-2
Weight
Average: 266.2979
Monoisotopic: 266.11676109
Chemical Formula
C15H14N4O
InChI Key
NQDJXKOVJZTUJA-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
SMILES
CC1=C2NC(=O)C3=C(N=CC=C3)N(C3CC3)C2=NC=C1

Pharmacology

Indication

For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.

Associated Conditions
Pharmacodynamics

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.

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.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Nevirapine is readily absorbed (greater than 90%) after oral administration in healthy subjects and adults with HIV-1 infection. The absolute bioavailability in healthy adults following a single dose administration is 93 ± 9% (mean ± SD) for a 50 mg tablet and 91 ± 8% for an oral solution. Peak plasma nevirapine concentrations of 2 ± 0.4 mcg/mL (7.5 micromolar) were attained by 4 hours following a single 200 mg dose. Nevirapine tablets and suspension have been shown to be comparably bioavailable and interchangeable at doses up to 200 mg. When the oral tablet is given with a high-fat meal, the extent of absorption is compared to that of the fasted-state.

Volume of distribution
  • 1.21 ± 0.09 L/kg [apparent volume of distribution, healthy adults, IV] Nevirapine is capable of crossing the placenta and is found in breast milk.
Protein binding

60% bound to plasma protein.

Metabolism

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

Clearance
Not Available
Toxicity

Symptoms of overdose include edema, erythema nodosum, fatigue, fever, headache, insomnia, nausea, pulmonaryinfiltrates, rash, vertigo, vomiting, and weight decrease. The most common adverse reaction is rash.

Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategory
Nevirapine Metabolism PathwayDrug metabolism
Nevirapine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Nevirapine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Nevirapine.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Nevirapine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Nevirapine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nevirapine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Nevirapine.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Nevirapine.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Nevirapine.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be increased when combined with Nevirapine.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Nevirapine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

References

Synthesis Reference
US5366972
General References
Not Available
External Links
Human Metabolome Database
HMDB0014383
KEGG Drug
D00435
KEGG Compound
C07263
PubChem Compound
4463
PubChem Substance
46506789
ChemSpider
4308
BindingDB
1434
ChEBI
63613
ChEMBL
CHEMBL57
Therapeutic Targets Database
DAP000184
PharmGKB
PA450616
HET
NVP
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Nevirapine
ATC Codes
J05AG01 — NevirapineJ05AR05 — Zidovudine, lamivudine and nevirapineJ05AR07 — Stavudine, lamivudine and nevirapine
AHFS Codes
  • 08:18.08.16 — Nonnucleoside Reverse Transcriptase Inhibitors
PDB Entries
1fkp / 1jlb / 1jlf / 1lw0 / 1lwc / 1lwe / 1lwf / 1s1u / 1s1x / 1vrt
show 12 more
FDA label
Download (423 KB)
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedNot AvailableHuman Immunodeficiency Virus Type 1 (HIV-1)1
1CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV) Infections1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentHepatic Insufficiency / Impaired Renal Function1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections15
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
1TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
1Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
1, 2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Pf Subclinical Parasitemia1
1, 2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHIV Seropositivity1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections16
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Pediatric AIDS1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionAcquired Immune Deficiency Syndrome (AIDS)1
3CompletedPreventionDisease Transmission, Vertical / Human Immunodeficiency Virus (HIV) Infections / Vertical Human Immunodeficiency Virus Transmission1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections10
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy3
3CompletedTreatmentHIV/TB Co-infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections12
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentCD4 Below 350/µL or Below 15% / Hiv Infection With Antiretroviral Therapy Indication1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections3
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections / Quality of Life1
4CompletedPreventionAntiretroviral Therapies / High Cholesterol / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionCentral Nervous System Diseases / Dementias / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Metabolism, Lipids1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS)2
4CompletedTreatmentHepatic Insufficiency / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections11
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Mitochondrial Toxicity1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis Infection1
4CompletedTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4RecruitingPreventionDiabetes Mellitus (DM) / Human Immunodeficiency Virus (HIV) / Insulin Sensitivity1
4RecruitingPreventionHIV/AIDS and Infections1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
4Unknown StatusPreventionHIV-Associated Lipodystrophy Syndrome / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
Not AvailableCompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS)1
Not AvailableCompletedNot AvailableBreastfeeding / Human Immunodeficiency Virus (HIV) / Pregnancy1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections4
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Kwashiorkor / Marasmus / Severe Acute Malnutrition1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Infant Risk for HIV Infection by MTCT1
Not AvailableCompletedTreatmentEfficacy of Rilpivirine-based Regimens as Switch Therapy1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections9
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Wasting Disease1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingNot AvailableMinor Patient Treated by One or More Antiretroviral and for Which a Blood Test Has Been Performed1
Not AvailableUnknown StatusNot AvailableHCV Viral Load / Hepatitis C Virus (HCV) Infection1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
  • Boehringer ingelheim pharmaceuticals inc
Packagers
  • Boehringer Ingelheim Ltd.
  • Dept Health Central Pharmacy
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Remedy Repack
  • Roxane Labs
Dosage forms
FormRouteStrength
TabletOral
TabletOral
Tablet, film coatedOral
Tablet, coatedOral200 mg/1
Tablet, extended releaseOral100 mg/1
TabletOral100 mg/1
TabletOral400 mg/1
TabletOral200 mg
SuspensionOral50 mg/5ml
TabletOral200 mg/1
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral400 mg
Tablet, extended releaseOral400 mg/1
Tablet, extended releaseOral50 mg
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Viramune 200 mg tablet9.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5366972No1994-11-222012-05-22Us
CA2030056No1995-10-172010-11-15Canada
US8460704No2013-06-112029-03-12Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)196.06Not Available
water solubility0.7046 mg/LNot Available
logP2.5Not Available
Caco2 permeability-4.52ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.105 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.9756
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5606
P-glycoprotein inhibitor INon-inhibitor0.6488
P-glycoprotein inhibitor IINon-inhibitor0.8514
Renal organic cation transporterNon-inhibitor0.7124
CYP450 2C9 substrateNon-substrate0.6179
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.6413
CYP450 1A2 substrateInhibitor0.6175
CYP450 2C9 inhibitorNon-inhibitor0.8009
CYP450 2D6 inhibitorNon-inhibitor0.9451
CYP450 2C19 inhibitorNon-inhibitor0.7971
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5443
Ames testAMES toxic0.5952
CarcinogenicityNon-carcinogens0.9383
BiodegradationNot ready biodegradable0.964
Rat acute toxicity2.6729 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9827
hERG inhibition (predictor II)Non-inhibitor0.8321
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-016r-1390000000-cbb2d729a2b310bf5dd0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-016r-0290000000-64af72aec31bfd168e68
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-3980000000-98e328d2867c43716973

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Alkyldiarylamines
Alternative Parents
Pyridodiazepines / Methylpyridines / 1,4-diazepines / Imidolactams / Vinylogous amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Alkyldiarylamine / Pyrido-para-diazepine / Para-diazepine / Methylpyridine / Imidolactam / Pyridine / Heteroaromatic compound / Vinylogous amide / Carboxamide group / Lactam
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dipyridodiazepine (CHEBI:63613)

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Not Available
Gene Name
pol
Uniprot ID
Q72547
Uniprot Name
Reverse transcriptase/RNaseH
Molecular Weight
65223.615 Da
References
  1. Ambrose Z, Herman BD, Sheen CW, Zelina S, Moore KL, Tachedjian G, Nissley DV, Sluis-Cremer N: The human immunodeficiency virus type 1 nonnucleoside reverse transcriptase inhibitor resistance mutation I132M confers hypersensitivity to nucleoside analogs. J Virol. 2009 Apr;83(8):3826-33. doi: 10.1128/JVI.01968-08. Epub 2009 Feb 4. [PubMed:19193782]
  2. Nikolenko GN, Delviks-Frankenberry KA, Pathak VK: A novel molecular mechanism of dual resistance to nucleoside and nonnucleoside reverse transcriptase inhibitors. J Virol. 2010 May;84(10):5238-49. doi: 10.1128/JVI.01545-09. Epub 2010 Mar 10. [PubMed:20219933]
  3. Ghosn J, Chaix ML, Delaugerre C: HIV-1 resistance to first- and second-generation non-nucleoside reverse transcriptase inhibitors. AIDS Rev. 2009 Jul-Sep;11(3):165-73. [PubMed:19654858]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Paganotti GM, Russo G, Sobze MS, Mayaka GB, Muthoga CW, Tawe L, Martinelli A, Romano R, Vullo V: CYP2B6 poor metaboliser alleles involved in efavirenz and nevirapine metabolism: CYP2B6*9 and CYP2B6*18 distribution in HIV-exposed subjects from Dschang, Western Cameroon. Infect Genet Evol. 2015 Oct;35:122-6. doi: 10.1016/j.meegid.2015.08.003. Epub 2015 Aug 4. [PubMed:26247717]
  3. Hedrich WD, Hassan HE, Wang H: Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. doi: 10.1016/j.apsb.2016.07.016. Epub 2016 Aug 9. [PubMed:27709010]
  4. Viramune (Nevirapine) FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Fichtenbaum CJ, Gerber JG: Interactions between antiretroviral drugs and drugs used for the therapy of the metabolic complications encountered during HIV infection. Clin Pharmacokinet. 2002;41(14):1195-211. doi: 10.2165/00003088-200241140-00004. [PubMed:12405866]
  3. Mouly S, Rizzo-Padoin N, Simoneau G, Verstuyft C, Aymard G, Salvat C, Mahe I, Bergmann JF: Effect of widely used combinations of antiretroviral therapy on liver CYP3A4 activity in HIV-infected patients. Br J Clin Pharmacol. 2006 Aug;62(2):200-9. doi: 10.1111/j.1365-2125.2006.02637.x. [PubMed:16842395]
  4. Indiana University - Department of Medicine Clinical Pharmacology [Link]
  5. Lexicomp database [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
There are limited data on the literature supporting this enzyme action, with the exception of some case reports.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Liedtke MD, Rathbun RC: Warfarin-antiretroviral interactions. Ann Pharmacother. 2009 Feb;43(2):322-8. doi: 10.1345/aph.1L497. Epub 2009 Feb 5. [PubMed:19196837]
  2. Stolbach A, Paziana K, Heverling H, Pham P: A Review of the Toxicity of HIV Medications II: Interactions with Drugs and Complementary and Alternative Medicine Products. J Med Toxicol. 2015 Sep;11(3):326-41. doi: 10.1007/s13181-015-0465-0. [PubMed:26036354]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Wen B, Chen Y, Fitch WL: Metabolic activation of nevirapine in human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4. Drug Metab Dispos. 2009 Jul;37(7):1557-62. doi: 10.1124/dmd.108.024851. Epub 2009 Apr 13. [PubMed:19364830]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. von Moltke LL, Greenblatt DJ, Granda BW, Giancarlo GM, Duan SX, Daily JP, Harmatz JS, Shader RI: Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. J Clin Pharmacol. 2001 Jan;41(1):85-91. doi: 10.1177/00912700122009728. [PubMed:11225565]
  2. Heil SG, van der Ende ME, Schenk PW, van der Heiden I, Lindemans J, Burger D, van Schaik RH: Associations between ABCB1, CYP2A6, CYP2B6, CYP2D6, and CYP3A5 alleles in relation to efavirenz and nevirapine pharmacokinetics in HIV-infected individuals. Ther Drug Monit. 2012 Apr;34(2):153-9. doi: 10.1097/FTD.0b013e31824868f3. [PubMed:22354160]
  3. Wen B, Chen Y, Fitch WL: Metabolic activation of nevirapine in human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4. Drug Metab Dispos. 2009 Jul;37(7):1557-62. doi: 10.1124/dmd.108.024851. Epub 2009 Apr 13. [PubMed:19364830]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. von Moltke LL, Greenblatt DJ, Granda BW, Giancarlo GM, Duan SX, Daily JP, Harmatz JS, Shader RI: Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. J Clin Pharmacol. 2001 Jan;41(1):85-91. doi: 10.1177/00912700122009728. [PubMed:11225565]
  2. Mhandire D, Lacerda M, Castel S, Mhandire K, Zhou D, Swart M, Shamu T, Smith P, Musingwini T, Wiesner L, Stray-Pedersen B, Dandara C: Effects of CYP2B6 and CYP1A2 Genetic Variation on Nevirapine Plasma Concentration and Pharmacodynamics as Measured by CD4 Cell Count in Zimbabwean HIV-Infected Patients. OMICS. 2015 Sep;19(9):553-62. doi: 10.1089/omi.2015.0104. [PubMed:26348712]
  3. Nevirapine [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Torimoto N, Ishii I, Toyama K, Hata M, Tanaka K, Shimomura H, Nakamura H, Ariyoshi N, Ohmori S, Kitada M: Helices F-G are important for the substrate specificities of CYP3A7. Drug Metab Dispos. 2007 Mar;35(3):484-92. doi: 10.1124/dmd.106.011304. Epub 2006 Dec 18. [PubMed:17178770]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [PubMed:15814459]
  2. Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [PubMed:16336266]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Inhibition data supported only by 1 in vitro study.
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Moss DM, Liptrott NJ, Siccardi M, Owen A: Interactions of antiretroviral drugs with the SLC22A1 (OCT1) drug transporter. Front Pharmacol. 2015 Apr 10;6:78. doi: 10.3389/fphar.2015.00078. eCollection 2015. [PubMed:25914645]

Drug created on June 13, 2005 07:24 / Updated on November 12, 2019 22:30