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药品详细

Efavirenz (依法韦仑 )

化学结构式图
中文名
依法韦仑
英文名
Efavirenz
分子式
Not Available
化学名
(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
分子量
Average: 315.675
Monoisotopic: 315.027390859
CAS号
154598-52-4
ATC分类
J05A Direct acting antivirals
药物类型
small molecule
阶段
商品名
Stocrin;Sustiva;
同义名
efavirenz;EFV;
基本介绍

Efavirenz (brand names Sustiva庐 and Stocrin庐) 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.

生产厂家
  • Bristol myers squibb co
  • Bristol myers squibb pharma co
封装厂家
参考
Synthesis Reference Not Available
General Reference
  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
剂型
Form Route Strength
Capsule Oral
Tablet Oral
规格
Unit description Cost Unit
Sustiva 600 mg tablet 21.68 USD tablet
Sustiva 200 mg capsule 7.37 USD capsule
Sustiva 100 mg capsule 3.34 USD capsule
Sustiva 50 mg capsule 1.84 USD capsule
化合物类型
Type small molecule
Classes
  • Benzyl Alcohols and Derivatives
  • Carbamates and Derivatives
  • Halobenzenes
  • Anilines
Substructures
  • Benzyl Alcohols and Derivatives
  • Alkynes
  • Carbamates and Derivatives
  • Cyclopropane and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Heterocyclic compounds
  • Aromatic compounds
  • Anilines
适应症
ANTIVIRALS 抗病毒;
药理
Indication For use in combination treatment of HIV infection (AIDS)
Pharmacodynamics 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.
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.
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 Not Available
理化性质
Properties
State solid
Melting point 139-141 oC
Experimental Properties
Property Value Source
logP 4.6 PhysProp
Predicted Properties
Property Value Source
water solubility 8.55e-03 g/l ALOGPS
logP 3.89 ALOGPS
logP 4.46 ChemAxon Molconvert
logS -4.57 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 38.33 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 71.34 ChemAxon Molconvert
polarizability 26.81 ChemAxon Molconvert
药物相互作用
Drug Interaction
Alprazolam The antiviral agent, efavirenz, may increase the effect and toxicity of the benzodiazepine, alprazolam.
Astemizole Increased risk of cardiotoxicity and arrhythmias
Atazanavir Efavirenz decreases the levels/effects of atazanavir
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.
Cisapride Increased risk of cardiotoxicity and arrhythmias
Clarithromycin Efavirenz decreases levels of clarithromycin
Cyclosporine Efavirenz decreases the levels of cyclosporine
Dihydroergotamine Efavirenze may increase the adverse/toxic effects of dihydroergotamine. Concomitant therapy is contraindicated.
Dihydroergotoxine The antiretroviral agent may increase the ergot derivative toxicity
Ergotamine The antiretroviral agent may increase the ergot derivative toxicity
Indinavir Efavirenz decreases the effect of indinavir
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.
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.
Methylergonovine The antiretroviral agent may increase the ergot derivative toxicity
Methysergide The antiretroviral agent may increase the ergot derivative toxicity
Midazolam The antiviral agent, efavirenz, may increase the effect and toxicity of the benzodiazepine, midazolam.
Saquinavir Efavirenz decreases the effect of saquinavir
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.
St. John's Wort St. John's Wort decreases the antiretroviral effect
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.
Telithromycin Efavirenz may decrease the plasma concentration of Telithromycin. Consider alternate therapy.
Temsirolimus Efavirenz may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
Terfenadine Increased risk of cardiotoxicity and arrhythmias
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.
Tramadol Efavirenz may decrease the effect of Tramadol by increasing Tramadol metabolism and clearance.
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.
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.
食物相互作用
  • Avoid excessive or chronic alcohol consumption.
  • Take without regard to meals.

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