Efavirenz

  • CAT Number: A000012
  • CAS Number: 154598-52-4
  • Molecular Formula: C14H9ClF3NO2
  • Molecular Weight: 315.7
  • Purity: ≥95%
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Efavirenz ( CAS 154598-52-4) is a non-nucleoside reverse transcriptase inhibitor, NNRTI. Efavirenz is highly specific and potent allosteric inhibitors of HIV-1 reverse transcriptase. Efavirenz also inhibits the late stages of HIV-1 replication by interfering with HIV-1 Gag-Pol polyprotein processing. It is used as part of highly active antiretroviral therapy for the treatment of a human immunodeficiency virus type 1.

Catalog Number A000012
CAS Number 154598-52-4
Molecular Formula

C14H9ClF3NO2

Purity 95%
Target HIV
Solubility >15.6mg/mL in DMSO
Storage Store at -20C
Overview of Clinical Research

Efavirenz is a non-nucleoside reverse transcriptase inhibitor developed by Merck&Co. It is used to treat HIV-1 infections. 

IUPAC Name (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
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
InChIKey XPOQHMRABVBWPR-UHFFFAOYSA-N
SMILES ClC1=CC=C2C([C@@](C#CC3CC3)(C(F)(F)F)OC(N2)=O)=C1
Reference

<br />
1: Homkham N, Cressey TR, Ingsrisawang L, Bouazza N, Ngampiyaskul C, Hongsiriwon<br />
S, Srirojana S, Kanjanavanit S, Bhakeecheep S, Coeur SL, Salvadori N, Treluyer<br />
JM, Jourdain G, Urien S. A Population Pharmacokinetic/Pharmacodynamic Model<br />
Predicts Favorable HDL Cholesterol Changes Over the First 5 Years in Children<br />
Treated with Current Efavirenz-Based Regimens. J Clin Pharmacol. 2016 Jan 8. doi:<br />
10.1002/jcph.701. [Epub ahead of print] PubMed PMID: 26749102.<br />
2: van Lunzen J, Antinori A, Cohen CJ, Arribas JR, Wohl DA, Rieger A, Rachlis A,<br />
Bloch M, Segal-Maurer S, Garner W, Porter D, Bosse M, Piontkowsky D, Chuck SK,<br />
De-Oertel S. Rilpivirine vs. efavirenz-based single-tablet regimens in<br />
treatment-naive adults: week 96 efficacy and safety from a randomized phase 3b<br />
study. AIDS. 2016 Jan;30(2):251-9. doi: 10.1097/QAD.0000000000000911. PubMed<br />
PMID: 26684822.<br />
3: Ndolo SM, Sichilongo K, Massele A, Sepako E, Vento S. An Investigation of<br />
Liquid Chromatography-Mass Spectral Attributes and Analytical Performance<br />
Characteristics of Tenofovir, Emtricitabine and Efavirenz in Human Plasma. J Anal<br />
Toxicol. 2016 Jan;40(1):49-57. doi: 10.1093/jat/bkv119. Epub 2015 Oct 20. PubMed<br />
PMID: 26487641.<br />
4: Sadeghi M, Bayat M, Cheraghi S, Yari K, Heydari R, Dehdashtian S, Shamsipur M.<br />
Binding studies of the anti-retroviral drug, efavirenz to calf thymus DNA using<br />
spectroscopic and voltammetric techniques. Luminescence. 2016 Feb;31(1):108-17.<br />
doi: 10.1002/bio.2931. Epub 2015 May 29. PubMed PMID: 26031412.<br />
5: Sinxadi PZ, McIlleron HM, Dave JA, Smith PJ, Levitt NS, Haas DW, Maartens G.<br />
Plasma Efavirenz Concentrations Are Associated With Lipid and Glucose<br />
Concentrations. Medicine (Baltimore). 2016 Jan;95(2):e2385. doi:<br />
10.1097/MD.0000000000002385. PubMed PMID: 26765416.<br />
6: Thamrongwonglert P, Chetchotisakd P, Anunnatsiri S, Mootsikapun P. Improvement<br />
of lipid profiles when switching from efavirenz to rilpivirine in HIV-infected<br />
patients with dyslipidemia. HIV Clin Trials. 2016 Jan 7:1-5. [Epub ahead of<br />
print] PubMed PMID: 26739573.<br />
7: De Nardo P, Gentilotti E, Nguhuni B, Vairo F, Chaula Z, Nicastri E, Ippolito<br />
G. Efavirenz-based antiretroviral therapy versus nevirapine-including regimens<br />
for prevention of mother-to-child transmission of HIV option B plus in<br />
resource-limited settings: is there anything missing? Expert Rev Anti Infect<br />
Ther. 2016 Jan;14(1):19-27. doi: 10.1586/14787210.2016.1116383. Epub 2015 Dec 3.<br />
PubMed PMID: 26559430.<br />
8: Aouri M, Barcelo C, Ternon B, Cavassini M, Anagnostopoulos A, Yerly S, Hugues<br />
H, Vernazza P, G&uuml;nthard HF, Buclin T, Telenti A, Rotger M, Decosterd LA; Swiss<br />
HIV Cohort Study. In Vivo Profiling and Distribution of Known and Novel Phase I<br />
and Phase II Metabolites of Efavirenz in Plasma, Urine, and Cerebrospinal Fluid.<br />
Drug Metab Dispos. 2016 Jan;44(1):151-61. doi: 10.1124/dmd.115.065839. Epub 2015<br />
Nov 9. PubMed PMID: 26553012.<br />
9: Calza L, Magistrelli E, Danese I, Colangeli V, Borderi M, Bon I, Re MC,<br />
Mancini R, Conti M, Motta R, Viale P. Changes in Serum Markers of Inflammation<br />
and Endothelial Activation in HIV-Infected Antiretroviral Naive Patients Starting<br />
A Treatment with Abacavir-Lamivudine or Tenofovir-Emtricitabine Plus Efavirenz.<br />
Curr HIV Res. 2016;14(1):61-70. PubMed PMID: 26531764.<br />
10: Wei&szlig; M, Kost B, Renner-M&uuml;ller I, Wolf E, Mylonas I, Br&uuml;ning A. Efavirenz<br />
Causes Oxidative Stress, Endoplasmic Reticulum Stress, and Autophagy in<br />
Endothelial Cells. Cardiovasc Toxicol. 2016 Jan;16(1):90-9. doi:<br />
10.1007/s12012-015-9314-2. PubMed PMID: 25666561.<br />
11: Jordaan MA, Singh P, Martincigh BS. A combined TD-DFT and spectroscopic<br />
investigation of the solute-solvent interactions of efavirenz. Spectrochim Acta A<br />
Mol Biomol Spectrosc. 2015 Dec 8;157:204-210. doi: 10.1016/j.saa.2015.12.008.<br />
[Epub ahead of print] PubMed PMID: 26773263.<br />
12: Gervasoni C, ChemD SB, Cerea M, Cenderello G, Bini T, Vimercati S, Iardino<br />
MR, Gazzaniga A, D/&#39;Arminio Monforte A, Clementi E, Cattaneo D. Comparison of the<br />
in vivo pharmacokinetics and in vitro dissolution of branded versus generic<br />
efavirenz formulation in HIV-infected patients. Ther Drug Monit. 2015 Dec 30.<br />
[Epub ahead of print] PubMed PMID: 26727626.<br />
13: Dickinson L, Amin J, Else L, Boffito M, Egan D, Owen A, Khoo S, Back D,<br />
Orrell C, Clarke A, Losso M, Phanuphak P, Carey D, Cooper DA, Emery S, Puls R.<br />
Comprehensive Pharmacokinetic, Pharmacodynamic and Pharmacogenetic Evaluation of<br />
Once-Daily Efavirenz 400 and 600 mg in Treatment-Na&iuml;ve HIV-Infected Patients at<br />
96 Weeks: Results of the ENCORE1 Study. Clin Pharmacokinet. 2015 Dec 29. [Epub<br />
ahead of print] PubMed PMID: 26715213.<br />
14: Shelton JD. Reduced Effectiveness of Contraceptive Implants for Women Taking<br />
the Antiretroviral Efavirenz (EFV): Still Good Enough and for How Long? Glob<br />
Health Sci Pract. 2015 Dec 8;3(4):528-31. doi: 10.9745/GHSP-D-15-00356. PubMed<br />
PMID: 26681700; PubMed Central PMCID: PMC4682578.<br />
15: Palombi L, Pirillo MF, Marchei E, Jere H, Sagno JB, Luhanga R, Floridia M,<br />
Andreotti M, Galluzzo CM, Pichini S, Mwenda R, Mancinelli S, Marazzi MC, Vella S,<br />
Liotta G, Giuliano M. Concentrations of tenofovir, lamivudine and efavirenz in<br />
mothers and children enrolled under the Option B-Plus approach in Malawi. J<br />
Antimicrob Chemother. 2015 Dec 17. pii: dkv435. [Epub ahead of print] PubMed<br />
PMID: 26679247.<br />
16: Wilkins E, Fisher M, Brogan AJ, Talbird SE, La EM. Cost-effectiveness<br />
analysis of tenofovir/emtricitabine and abacavir/lamivudine in combination with<br />
efavirenz or atazanavir/ritonavir for treatment-na&iuml;ve adults with HIV-1 infection<br />
in the UK, based on the AIDS Clinical Trials Group 5202 clinical trial. HIV Med.<br />
2015 Dec 9. doi: 10.1111/hiv.12349. [Epub ahead of print] PubMed PMID: 26663715.<br />
17: R&ouml;hrich CR, Dr&ouml;gem&ouml;ller BI, Ikediobi O, Gandhi M, Van der Merwe L, Grobbelaar<br />
N, Wright GE, Huang Y, McGregor N, Aouizerat B, Warnich L. CYP2B6*6 and CYP2B6*18<br />
predict long-term efavirenz exposure measured in hair samples in HIV-positive<br />
South African women. AIDS Res Hum Retroviruses. 2015 Dec 13. [Epub ahead of<br />
print] PubMed PMID: 26655325.<br />
18: Cusato J, Tomasello C, Simiele M, Calcagno A, Bonora S, Marinaro L, Leggieri<br />
A, Allegra S, Di Perri G, D/&#39;Avolio A. Efavirenz pharmacogenetics in a cohort of<br />
Italian patients. Int J Antimicrob Agents. 2015 Dec 18. pii:<br />
S0924-8579(15)00404-5. doi: 10.1016/j.ijantimicag.2015.11.012. [Epub ahead of<br />
print] PubMed PMID: 26774523.<br />
19: Rotzinger A, Locatelli I, Bugnon O, Fayet Mello A, Parienti JJ, Cavassini M,<br />
Schneider MP. Switching from a two-tablet regimen of tenofovir/emtricitabine and<br />
efavirenz to a one-tablet regimen may affect patients/&#39; perceptions and drug<br />
management. HIV Med. 2015 Dec 21. doi: 10.1111/hiv.12345. [Epub ahead of print]<br />
PubMed PMID: 26688004.<br />
20: Lortholary O, Roussillon C, Boucherie C, Padoin C, Chaix ML, Breton G, Rami<br />
A, Veziris N, Patey O, Caumes E, May T, Molina JM, Robert J, Tod M, Fagard C,<br />
Ch&ecirc;ne G; ANRS 129 BKVIR Trial Group. Tenofovir DF/emtricitabine and efavirenz<br />
combination therapy for HIV infection in patients treated for tuberculosis: the<br />
ANRS 129 BKVIR trial. J Antimicrob Chemother. 2015 Dec 17. pii: dkv384. [Epub<br />
ahead of print] PubMed PMID: 26679250.<br />
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