QuickView for Efavirenz (compound)

Summary
General Info

PubChem

PubChem Compound 3203

Name:	efavirenz
PubChem Compound ID:	3203
Molecular formula:	C₁₄H₉ClF₃NO₂
Molecular weight:	315.675 g/mol
Synonyms:	154635-17-3; 2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-; 177530-93-7; 6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one; 2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (+-)-; 6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-3-one; L 741211

DrugBank

Identification

Name:	efavirenz
Name (isomeric):	DB00625
Drug Type:	small molecule
Synonyms:	EFV
Brand:	Sustiva, Stocrin
Category:	Anti-HIV Agents, Nonnucleoside Reverse Transcriptase Inhibitors, Reverse Transcriptase Inhibitors
CAS number:	154598-52-4

Pharmacology

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 tha... show more » 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. show less «
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 tran... show more » 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. show less «
Protein binding:	99.5-99.75%
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.
Route of elimination:	Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.
Half Life:	40-55 hours
Affected organisms:	Human Immunodeficiency Virus

Interactions

Food interaction:

Avoid excessive or chronic alcohol consumption.

Take without regard to meals.

Drug interaction:

Dihydroergotamine	Efavirenze may increase the adverse/toxic effects of dihydroergotamine. Concomitant therapy is contraindicated.
Midazolam	The antiviral agent, efavirenz, may increase the effect and toxicity of the benzodiazepine, midazolam.
Indinavir	Efavirenz decreases the effect of indinavir
Temsirolimus	Efavirenz may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
Trazodone	The CYP3A4 inhibitor and inducer, Efavirenz, may alter Trazodone efficacy/toxicity by altering Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Efavirenz is initiated, discontinued or dose changed.

Dihydroergotamine	Efavirenze may increase the adverse/toxic effects of dihydroergotamine. Concomitant therapy is contraindicated.
Midazolam	The antiviral agent, efavirenz, may increase the effect and toxicity of the benzodiazepine, midazolam.
Indinavir	Efavirenz decreases the effect of indinavir
Temsirolimus	Efavirenz may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
Trazodone	The CYP3A4 inhibitor and inducer, Efavirenz, may alter Trazodone efficacy/toxicity by altering Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Efavirenz is initiated, discontinued or dose changed.
Ergotamine	The antiretroviral agent may increase the ergot derivative toxicity
Atorvastatin	Efavirenz may decrease the serum concentration of atorvastatin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of atorvastatin if efavirenz is initiated, discontinued or dose changed.
Simvastatin	Efavirenz may decrease the serum concentration of simvastatin. Monitor for changes in the therapeutic and adverse effects of simvastatin if efavirenz is initiated, discontinued or dose changed.
Methadone	Efavirenz may decrease the serum concentration of methadone by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of methadone if efavirenz is initiated, discontinued or dose changed.
Triazolam	The antiviral agent, efavirenz, may increase the effect and toxicity of the benzodiazepine, triazolam.
Voriconazole	Efavirenze may decrease the serum concentration of voriconazole likely by increasing its metabolism. Voriconazole may increase the serum concentration of efavirenz by decreasing its metabolism. Consider alternate therapy or adjust doses and monitor for reduced voriconazole efficacy and increased efavirenz adverse effects during concomitant therapy.
Atazanavir	Efavirenz decreases the levels/effects of atazanavir
Tamsulosin	Efavirenz, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Efavirenz is initiated, discontinued, or dose changed.
Dihydroergotoxine	The antiretroviral agent may increase the ergot derivative toxicity
St. John's Wort	St. John's Wort decreases the antiretroviral effect
Methylergonovine	The antiretroviral agent may increase the ergot derivative toxicity
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Lovastatin	Efavirenz may decrease the serum concentration of lovastatin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of lovastatin if efavirenz is initiated, discontinued or dose changed.
Saquinavir	Efavirenz decreases the effect of saquinavir
Astemizole	Increased risk of cardiotoxicity and arrhythmias
Methysergide	The antiretroviral agent may increase the ergot derivative toxicity
Tramadol	Efavirenz may decrease the effect of Tramadol by increasing Tramadol metabolism and clearance.
Tipranavir	Efavirenz may alter the serum concentration Tipranavir. Monitor for changes in Tipranavir therapeutic and adverse effects if Efavirenz is initiated, discontinued or dose changed.
Tolterodine	Efavirenz may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Alprazolam	The antiviral agent, efavirenz, may increase the effect and toxicity of the benzodiazepine, alprazolam.
Cyclosporine	Efavirenz decreases the levels of cyclosporine
Clarithromycin	Efavirenz decreases levels of clarithromycin
Cisapride	Increased risk of cardiotoxicity and arrhythmias
Telithromycin	Efavirenz may decrease the plasma concentration of Telithromycin. Consider alternate therapy.

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Targets

Reverse transcriptase

Enzymes