Tìm theo
Efavirenz
Các tên gọi khác (7 ) :
  • (-)-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
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 154598-52-4
ATC: J05AG03
ĐG : Apotheca Inc.
CTHH: C14H9ClF3NO2
PTK: 315.675
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.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C14H9ClF3NO2
Phân tử khối
315.675
Monoisotopic mass
315.027390859
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
InChI Key
InChIKey=XPOQHMRABVBWPR-ZDUSSCGKSA-N
IUPAC Name
(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
Traditional IUPAC Name
efavirenz
SMILES
FC(F)(F)[C@]1(OC(=O)NC2=C1C=C(Cl)C=C2)C#CC1CC1
Độ tan chảy
139-141 °C
Độ hòa tan
8.55e-03 g/l
logP
4.6
logS
-4.6
pKa (strongest acidic)
12.52
pKa (Strongest Basic)
-1.5
PSA
38.33 Å2
Refractivity
71.34 m3·mol-1
Polarizability
26.81 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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. 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.
Dược Động Học :

▧ 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
Chỉ Định : For use in combination treatment of HIV infection (AIDS)
Tương Tác Thuốc :
  • 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.
  • Eltrombopag Affects hepatic enzyme CYP2C9/10 metabolism and may increase the level of eltrombopag.
  • Ergotamine The antiretroviral agent may increase the ergot derivative toxicity
  • Estradiol valerate/Dienogest Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
  • Etravirine Etravirine, when used concomitantly with Efavirenz, may experience a significant decrease in plasma levels and a loss of efficacy. Combination of two NNRTIs has not been demonstrated to be of benefit to HIV therapy. It is recommended to avoid this combination.
  • 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.
  • Methylergometrine 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.
  • Rilpivirine Concentration of rilpivirine decreases by affecting CYP3A4 metabolism. Concomitant use is contraindicated. Rilpivirine should not be used with other NNRTI's.
  • Roflumilast Affects CYP3A4 metabolism, decreases level or effect of roflumilast.
  • 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.
  • Telaprevir Inducers of CYP3A enzymes will decrease telaprevir levels.
  • 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.
  • Vandetanib Decreases levels of vandetanib by affecting CYP3A4 metabolism. Contraindicated.
  • 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.
Liều Lượng & Cách Dùng : Capsule - Oral
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Sustiva 50 mg capsule
    Giá bán buôn : USD >1.84
    Đơn vị tính : capsule
  • Biệt dược thương mại : Sustiva 100 mg capsule
    Giá bán buôn : USD >3.34
    Đơn vị tính : capsule
  • Biệt dược thương mại : Sustiva 200 mg capsule
    Giá bán buôn : USD >7.37
    Đơn vị tính : capsule
  • Biệt dược thương mại : Sustiva 600 mg tablet
    Giá bán buôn : USD >21.68
    Đơn vị tính : tablet
Nhà Sản Xuất
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00625
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=64139
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506827
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C08088
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00896
ChemSpider
http://www.chemspider.com/Chemical-Structure.57715.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=2483
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0056-0474-92
PharmGKB
http://www.pharmgkb.org/drug/PA449441
Wikipedia
http://en.wikipedia.org/wiki/Efavirenz
RxList
http://www.rxlist.com/cgi/generic/efaviren.htm
Drugs.com
http://www.drugs.com/cdi/efavirenz.html
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