Identification

Name
Efavirenz
Accession Number
DB00625  (APRD00059, DB07709)
Type
Small Molecule
Groups
Approved, Investigational
Description

Efavirenz (brand names Sustiva® and Stocrin®) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1.

For HIV infection that has not previously been treated, efavirenz and lamivudine in combination with zidovudine or tenofovir is the preferred NNRTI-based regimen.

Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regimen to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission.

Structure
Thumb
Synonyms
  • (-)-6-CHLORO-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
  • (S)-6-chloro-4-(Cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
  • (S)-6-chloro-4-Cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[D][1,3]oxazin-2-one
  • 6-chloro-4-(2-Cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[D][1,3]oxazin-2-one
  • Efavirenz
  • Éfavirenz
  • Efavirenzum
External IDs
DMP 266 / L 743726
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AtriplaTablet, film coated600 mg/1OralRemedy Repack2013-03-292014-03-29Us
EfavirenzTablet, film coated600 mg/1OralMylan Laboratories Limited2016-02-17Not applicableUs
StocrinTablet, film coated200 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
StocrinSolution30 mg/mlOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
StocrinCapsule100 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
StocrinTablet, film coated50 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
StocrinCapsule200 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
StocrinCapsule50 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
StocrinTablet, film coated600 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
StocrinCapsule200 mgOralMerck Sharp & Dohme B.V.1999-05-28Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-efavirenzTablet600 mgOralAuro Pharma Inc2014-03-03Not applicableCanada
EfavirenzCapsule50 mg/1OralAurobindo Pharma2017-12-15Not applicableUs
EfavirenzTablet, film coated600 mg/1OralAurobindo Pharma Limited2018-08-30Not applicableUs
EfavirenzTablet, film coated600 mg/1OralCamber Pharmaceuticals2018-04-27Not applicableUs
EfavirenzTablet, film coated600 mg/1OralRemedy Repack2018-02-12Not applicableUs
EfavirenzCapsule200 mg/1OralAurobindo Pharma2017-12-15Not applicableUs
EfavirenzTablet, film coated600 mg/1OralAurobindo Pharma Limited2018-09-21Not applicableUs
EfavirenzTablet600 mg/1OralRemedy Repack2018-04-06Not applicableUs
EfavirenzCapsule200 mg/1OralRising Pharmaceuticals2017-12-15Not applicableUs
EfavirenzCapsule100 mg/1OralAurobindo Pharma2017-12-15Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-efavirenz-emtricitabine-tenofovirEfavirenz (600 mg) + Emtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex CorporationNot applicableNot applicableCanada
AtriplaEfavirenz (600 mg) + Emtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralGilead Sciences, Llc2007-10-23Not applicableCanada
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralGilead Sciences, Llc2006-07-20Not applicableUs
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralRemedy Repack2017-03-29Not applicableUs
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralLake Erie Medical Dba Quality Care Produts Llc2006-07-202014-12-31Us
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUs
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralAvera McKennan Hospital2015-03-062018-06-18Us
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2012-10-16Not applicableUs
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUs
AtriplaEfavirenz (600 mg/1) + Emtricitabine (200 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralDoh Central Pharmacy2009-07-01Not applicableUs
International/Other Brands
E.F (McNeil & Argus) / Efavir (Cipla) / Efavirenz (Aspen Pharmacare) / Efcure (Emcure Pharmaceuticals) / Efferven (Ranbaxy Laboratories) / Estiva (Hetero) / Evirenz (Alkem Laboratories) / Stocrin (Merck & Co.) / Viranz (Aurobindo Pharma)
Categories
UNII
JE6H2O27P8
CAS number
154598-52-4
Weight
Average: 315.675
Monoisotopic: 315.027390859
Chemical Formula
C14H9ClF3NO2
InChI Key
XPOQHMRABVBWPR-ZDUSSCGKSA-N
InChI
InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1
IUPAC Name
(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
SMILES
FC(F)(F)[C@]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1

Pharmacology

Indication

For use in combination treatment of HIV infection (AIDS)

Associated Conditions
Pharmacodynamics

Efavirenz (dideoxyinosine, ddI) is an oral non-nucleoside reverse transcriptase inhibitor (NNRTI). It is a synthetic purine derivative and, similar to zidovudine, zalcitabine, and stavudine. Efavirenz was originally approved specifically for the treatment of HIV infections in patients who failed therapy with zidovudine. Currently, the CDC recommends that Efavirenz be given as part of a three-drug regimen that includes another nucleoside reverse transcriptase inhibitor (e.g., lamivudine, stavudine, zidovudine) and a protease inhibitor or efavirenz when treating HIV infection.

Mechanism of action

Similar to zidovudine, efavirenz inhibits the activity of viral RNA-directed DNA polymerase (i.e., reverse transcriptase). Antiviral activity of efavirenz is dependent on intracellular conversion to the active triphosphorylated form. The rate of efavirenz phosphorylation varies, depending on cell type. It is believed that inhibition of reverse transcriptase interferes with the generation of DNA copies of viral RNA, which, in turn, are necessary for synthesis of new virions. Intracellular enzymes subsequently eliminate the HIV particle that previously had been uncoated, and left unprotected, during entry into the host cell. Thus, reverse transcriptase inhibitors are virustatic and do not eliminate HIV from the body. Even though human DNA polymerase is less susceptible to the pharmacologic effects of triphosphorylated efavirenz, this action may nevertheless account for some of the drug's toxicity.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

99.5-99.75%

Metabolism

Efavirenz is principally metabolized by the cytochrome P450 system to hydroxylated metabolites with subsequent glucuronidation of these hydroxylated metabolites. These metabolites are essentially inactive against HIV-1.

Route of elimination

Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.

Half life

40-55 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategory
Efavirenz Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2B6CYP2B6*6Not AvailableG > T / A > GEffect Directly StudiedThe presence of this polymorphism in CYP2B6 is associated with reduction in efavirenz metabolism.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Efavirenz.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Efavirenz.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Efavirenz is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Efavirenz is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Efavirenz.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Efavirenz is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Efavirenz.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Efavirenz is combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Efavirenz.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Efavirenz is combined with 5-methoxy-N,N-dimethyltryptamine.
Food Interactions
  • Avoid excessive or chronic alcohol consumption.
  • Take without regard to meals.

References

Synthesis Reference

John Doney, "Amorphous efavirenz and the production thereof." U.S. Patent US20070026073, issued February 01, 2007.

US20070026073
General References
  1. Ren J, Bird LE, Chamberlain PP, Stewart-Jones GB, Stuart DI, Stammers DK: Structure of HIV-2 reverse transcriptase at 2.35-A resolution and the mechanism of resistance to non-nucleoside inhibitors. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14410-5. Epub 2002 Oct 17. [PubMed:12386343]
  2. Robertson SM, Penzak SR, Lane J, Pau AK, Mican JM: A potentially significant interaction between efavirenz and phenytoin: a case report and review of the literature. Clin Infect Dis. 2005 Jul 15;41(2):e15-8. doi: 10.1086/431208. Epub 2005 Jun 7. [PubMed:15983905]
  3. Michaud V, Ogburn E, Thong N, Aregbe AO, Quigg TC, Flockhart DA, Desta Z: Induction of CYP2C19 and CYP3A activity following repeated administration of efavirenz in healthy volunteers. Clin Pharmacol Ther. 2012 Mar;91(3):475-82. doi: 10.1038/clpt.2011.249. Epub 2012 Feb 8. [PubMed:22318618]
External Links
Human Metabolome Database
HMDB0014763
KEGG Drug
D00896
KEGG Compound
C08088
PubChem Compound
64139
PubChem Substance
46506827
ChemSpider
57715
BindingDB
2483
ChEBI
119486
ChEMBL
CHEMBL223228
Therapeutic Targets Database
DAP000709
PharmGKB
PA449441
HET
EFZ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Efavirenz
ATC Codes
J05AR06 — Emtricitabine, tenofovir disoproxil and efavirenzJ05AG03 — EfavirenzJ05AR11 — Lamivudine, tenofovir disoproxil and efavirenz
AHFS Codes
  • 08:18.08.16 — Nonnucleoside Reverse Transcriptase Inhibitors
PDB Entries
1fk9 / 1fko / 1ikv / 1ikw / 1jkh / 4b3o / 6bsg / 6bsh / 6bsi / 6bsj
FDA label
Download (154 KB)
MSDS
Download (57.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedOtherHealthy Volunteers1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Protease Inhibitors1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Substance Abuse1
1CompletedNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedBasic ScienceDrug Drug Interaction (DDI) / Intestinal Transporter Expression / Pharmacodynamics / Pharmacokinetics1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceTuberculosis Infection1
1CompletedDiagnosticCytochrome / Pharmacokinetics1
1CompletedDiagnosticHuman Volunteers1
1CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV) Infections1
1CompletedOtherHIV-DDI1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV) Infections / Pharmacokinetics1
1CompletedTreatmentHIV Seronegativity / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers / Infections, Human Immunodeficiency Virus and Herpesviridae1
1CompletedTreatmentHepatic Impairment / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis Infection1
1CompletedTreatmentNon-Hodgkin's Lymphoma (NHL) / Tumors, Solid1
1CompletedTreatmentTuberculosis Infection1
1Not Yet RecruitingOtherAlzheimer's Disease, Early Onset1
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
1SuspendedTreatmentHuman Immunodeficiency Virus (HIV)1
1Unknown StatusNot AvailableHuman Immunodeficiency Virus (HIV) / Hyperlipidemias1
1Unknown StatusTreatmentCytochrome P-450 CYP2B6 / Efavirenz / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
1, 2CompletedTreatmentInfection, Human Immunodeficiency Virus I / Pf Subclinical Parasitemia1
2Active Not RecruitingTreatmentAcute HIV Infection / HIV CNS Involvement1
2Active Not RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHIV Seropositivity1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAntiretroviral Naive / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections26
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lymphoma, AIDS Related1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
2CompletedTreatmentInfection, Human Immunodeficiency Virus I4
2TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
2TerminatedTreatmentInfection, Human Immunodeficiency Virus I1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2Unknown StatusTreatmentMalignant Neoplasm of Pancreas1
2Unknown StatusTreatmentProstate Cancer1
2WithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHIV-1-infection / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2, 3Not Yet RecruitingTreatmentSeverely Immunocompromised HIV Patients1
2, 3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus-type 1 Infection1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I2
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I / Kaposi s Sarcoma (KS)1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I / Tuberculosis Infection1
3CompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
3CompletedScreeningHuman Immunodeficiency Virus (HIV)1
3CompletedScreeningHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
3CompletedTreatmentHIV/TB Co-infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections30
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I3
3RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
3SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3WithdrawnPreventionBreastfeeding / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
4Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedPreventionCentral Nervous System Diseases / Dementias / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
4CompletedTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentCardiovascular Disease (CVD)1
4CompletedTreatmentHCV Coinfection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)6
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections11
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
4CompletedTreatmentInfection, Human Immunodeficiency Virus I2
4RecruitingSupportive CareHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentHIV-1-infection1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedOtherDrug Drug Interaction (DDI)1
4TerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mitochondrial Dysfunction1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection3
4Unknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections5
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
4WithdrawnTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableActive Not RecruitingTreatmentAnti-Retroviral Agents / Dyslipidemias / Efavirenz / HIV-1-infection / Rilpivirine / Sustained Virologic Response1
Not AvailableCompletedNot AvailableBreastfeeding / Human Immunodeficiency Virus (HIV) / Pregnancy1
Not AvailableCompletedNot AvailableCD4 Cell Counts / Treatment Failure, HIV or AIDS1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV)2
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedScreeningEfavirenz, Metabolism and Pharmacokinetics Changes1
Not AvailableCompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentAcute HIV Infection1
Not AvailableCompletedTreatmentAntiretroviral Treatment Outcomes1
Not AvailableCompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections12
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection2
Not AvailableCompletedTreatmentSleep disorders and disturbances1
Not AvailableNo Longer AvailableNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableNot Yet RecruitingTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableRecruitingNot AvailableChild Behavior / Cognitive Symptom / Drug-Related Side Effects and Adverse Reactions / Efavirenz / Medication Adherence1
Not AvailableRecruitingNot AvailableContraceptive Usage / Drug Drug Interaction (DDI) / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Tuberculosis Infection1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableUnknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Immune Reconstitution Inflammatory Syndrome1
Not AvailableUnknown StatusTreatmentHBV Coinfection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculous Meningitis1
Not AvailableWithdrawnBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1

Pharmacoeconomics

Manufacturers
  • Bristol myers squibb co
  • Bristol myers squibb pharma co
Packagers
  • Apotheca Inc.
  • Bristol-Myers Squibb Co.
  • Lake Erie Medical and Surgical Supply
  • Physicians Total Care Inc.
  • Remedy Repack
Dosage forms
FormRouteStrength
Tablet, film coatedOral
CapsuleOral100 mg/1
CapsuleOral200 mg/1
CapsuleOral50 mg/1
TabletOral600 mg/1
SolutionOral30 mg/ml
Tablet, film coatedOral200 mg
Tablet, film coatedOral50 mg
Tablet, film coatedOral600 mg
Capsule, gelatin coatedOral200 mg/1
Capsule, gelatin coatedOral50 mg/1
Tablet, film coatedOral600 mg/1
CapsuleOral100 mg
CapsuleOral200 mg
CapsuleOral50 mg
TabletOral600 mg
TabletOral
Prices
Unit descriptionCostUnit
Sustiva 600 mg tablet21.68USD tablet
Sustiva 200 mg capsule7.37USD capsule
Sustiva 100 mg capsule3.34USD capsule
Sustiva 50 mg capsule1.84USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5811423No1998-09-222012-08-07Us
CA2279198No2009-04-142018-02-02Canada
CA2101572No2001-08-282013-07-29Canada
US5914331Yes1999-06-222018-01-02Us
US6043230Yes2000-03-282018-01-25Us
US5814639Yes1998-09-292017-03-29Us
US6555133Yes2003-04-292019-10-06Us
US6939964Yes2005-09-062018-07-20Us
US6639071Yes2003-10-282018-08-14Us
US6238695Yes2001-05-292019-10-06Us
US6642245Yes2003-11-042021-05-04Us
US6703396Yes2004-03-092021-09-09Us
US5922695Yes1999-07-132018-01-25Us
US5935946Yes1999-08-102018-01-25Us
US5977089Yes1999-11-022018-01-25Us
US8592397No2013-11-262024-01-13Us
US8716264No2014-05-062024-01-13Us
US9018192No2015-04-282026-06-13Us
US8598185No2013-12-032028-05-01Us
US9545414No2017-01-172026-06-13Us
US9457036No2016-10-042024-01-13Us
US9744181No2017-08-292024-01-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)139-141 °CNot Available
logP4.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00855 mg/mLALOGPS
logP3.89ALOGPS
logP4.46ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.52ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.34 m3·mol-1ChemAxon
Polarizability26.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.9182
Caco-2 permeable+0.5553
P-glycoprotein substrateNon-substrate0.7617
P-glycoprotein inhibitor INon-inhibitor0.7451
P-glycoprotein inhibitor IINon-inhibitor0.9557
Renal organic cation transporterNon-inhibitor0.9157
CYP450 2C9 substrateNon-substrate0.8033
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6037
CYP450 1A2 substrateInhibitor0.6996
CYP450 2C9 inhibitorNon-inhibitor0.6975
CYP450 2D6 inhibitorNon-inhibitor0.8699
CYP450 2C19 inhibitorNon-inhibitor0.5291
CYP450 3A4 inhibitorNon-inhibitor0.7577
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6705
Ames testNon AMES toxic0.6991
CarcinogenicityNon-carcinogens0.8997
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5416 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9617
hERG inhibition (predictor II)Non-inhibitor0.9098
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-1059000000-f599b397bafd1974176e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014l-5090000000-b807e6fcee57f8b27cb6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9040000000-260d9ba8c55987cd2b0e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9010000000-459e48522e8275e941f8
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9000000000-531ef8f962aff7837863
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9000000000-9574533b450f3724a645
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03dl-0098000000-f0d050ef36094b37e62d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fxx-0091000000-8ab690a60877e8476640
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0frx-0190000000-deeefb25f97b767955b2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0giu-0390000000-7a682b484377bc11de1b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01b9-0790000000-a789e578dcf6568d7eb9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0930000000-a1dae29a53e6be48d87f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014r-0910000000-70a86e64f2e50ce28b18
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00xu-0390000000-d7561e61b30a86d9a480
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0giu-1290000000-c402be3d2864520be5fb

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxazines
Sub Class
Not Available
Direct Parent
Benzoxazines
Alternative Parents
Ynones / Benzenoids / Aryl chlorides / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Organochlorides
show 2 more
Substituents
Benzoxazine / Aryl chloride / Aryl halide / Ynone / Benzenoid / Oxacycle / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Azacycle / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, organochlorine compound, cyclopropanes, acetylenic compound, benzoxazine (CHEBI:119486)

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. Gazzard BG: Efavirenz in the management of HIV infection. Int J Clin Pract. 1999 Jan-Feb;53(1):60-4. [PubMed:10344069]
  2. Adkins JC, Noble S: Efavirenz. Drugs. 1998 Dec;56(6):1055-64; discussion 1065-6. [PubMed:9878993]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Michaud V, Ogburn E, Thong N, Aregbe AO, Quigg TC, Flockhart DA, Desta Z: Induction of CYP2C19 and CYP3A activity following repeated administration of efavirenz in healthy volunteers. Clin Pharmacol Ther. 2012 Mar;91(3):475-82. doi: 10.1038/clpt.2011.249. Epub 2012 Feb 8. [PubMed:22318618]
  3. Michaud V, Kreutz Y, Skaar T, Ogburn E, Thong N, Flockhart DA, Desta Z: Efavirenz-mediated induction of omeprazole metabolism is CYP2C19 genotype dependent. Pharmacogenomics J. 2014 Apr;14(2):151-9. doi: 10.1038/tpj.2013.17. Epub 2013 Apr 30. [PubMed:23629159]
  4. Xu C, Desta Z: In vitro analysis and quantitative prediction of efavirenz inhibition of eight cytochrome P450 (CYP) enzymes: major effects on CYPs 2B6, 2C8, 2C9 and 2C19. Drug Metab Pharmacokinet. 2013;28(4):362-71. Epub 2013 Feb 5. [PubMed:23385314]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. Xu C, Desta Z: In vitro analysis and quantitative prediction of efavirenz inhibition of eight cytochrome P450 (CYP) enzymes: major effects on CYPs 2B6, 2C8, 2C9 and 2C19. Drug Metab Pharmacokinet. 2013;28(4):362-71. Epub 2013 Feb 5. [PubMed:23385314]
  2. Efavirenz FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Hesse LM, von Moltke LL, Shader RI, Greenblatt DJ: Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion. Drug Metab Dispos. 2001 Feb;29(2):100-2. [PubMed:11159797]
  3. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  5. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  6. Fahmi OA, Shebley M, Palamanda J, Sinz MW, Ramsden D, Einolf HJ, Chen L, Wang H: Evaluation of CYP2B6 Induction and Prediction of Clinical Drug-Drug Interactions: Considerations from the IQ Consortium Induction Working Group-An Industry Perspective. Drug Metab Dispos. 2016 Oct;44(10):1720-30. doi: 10.1124/dmd.116.071076. Epub 2016 Jul 15. [PubMed:27422672]
  7. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Efavirenz FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
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. Flockhart Table - Indiana University [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
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. Flockhart Table - Indiana University [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
The FDA label states that this enzyme inhibition occurs in vitro and is unlikely to occur at therapeutic concentrations.
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Efavirenz FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:11225565]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inducer
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Interactions [Link]

Carriers

Kind
Protein
Organism
Human
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
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2018 10:03