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Efavirenz

Catalog No. DB00625 Name DrugBank
CAS Number 154598-52-4 Website http://www.ualberta.ca/
M. F. C14H9ClF3NO2 Telephone (780) 492-3111
M. W. 315.6749696 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 507

SYNONYMS

IUPAC name
(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
IUPAC Traditional name
efavirenz
Brand Name
Stocrin
Sustiva
Synonyms
EFV
efavirenz

DATABASE IDS

PubChem SID 46506827
CAS Number 154598-52-4
PubChem CID 64139

PROPERTIES

Hydrophobicity(logP) 4.6

DETAILS

Description (English)
Item Information
Drug 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.
Indication For use in combination treatment of HIV infection (AIDS)
Pharmacology Efavirenz (dideoxyinosine, ddI) is an oral nucleoside reverse transcriptase inhibitor (NRTI). 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.
Affected Organisms
Human Immunodeficiency Virus
Biotransformation 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.
Half Life 40-55 hours
Protein Binding 99.5-99.75%
Elimination Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.
References
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]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • 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