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MedKoo Cat#: 598164 | Name: (R)-Efavirenz

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Efavirenz, (R)- is a nonnucleoside HIV-1 reverse transcriptase inhibitor. Efavirenz, (R)- is an antiviral.

Chemical Structure

(R)-Efavirenz
(R)-Efavirenz
CAS#154801-74-8 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 598164

Name: (R)-Efavirenz

CAS#: 154801-74-8 (R-isomer)

Chemical Formula: C14H9ClF3NO2

Exact Mass: 315.0274

Molecular Weight: 315.67

Elemental Analysis: C, 53.27; H, 2.87; Cl, 11.23; F, 18.05; N, 4.44; O, 10.14

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Related CAS #
154801-74-8 (R-isomer) 154598-52-4 (S-isomer) 177530-93-7 (racemic)
Synonym
(R)-Efavirenz; Efavirenz, (R)-; ent Efavirenz; ent-Efavirenz; L 743725; L-743725; L743725;
IUPAC/Chemical Name
(R)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one
InChi Key
XPOQHMRABVBWPR-CYBMUJFWSA-N
InChi Code
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-/m1/s1
SMILES Code
O=C1NC2=CC=C(Cl)C=C2[C@@](C(F)(F)F)(C#CC3CC3)O1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 315.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Gleason RL Jr, Caulk AW, Seifu D, Parker I, Vidakovic B, Getenet H, Assefa G, Amogne W. Current Efavirenz (EFV) or ritonavir-boosted lopinavir (LPV/r) use correlates with elevate markers of atherosclerosis in HIV-infected subjects in Addis Ababa, Ethiopia. PLoS One. 2015 Apr 27;10(4):e0117125. doi: 10.1371/journal.pone.0117125. eCollection 2015. PubMed PMID: 25915208; PubMed Central PMCID: PMC4411122. 2: Arpadi SM, Shiau S, Strehlau R, Patel F, Mbete N, McMahon DJ, Kaufman JJ, Coovadia A, Kuhn L, Yin MT. Efavirenz is associated with higher bone mass in South African children with HIV. AIDS. 2016 Oct 23;30(16):2459-2467. PubMed PMID: 27427876; PubMed Central PMCID: PMC5069169. 3: Imaz A, Llibre JM, Navarro J, Curto J, Clotet B, Crespo M, Ferrer E, Saumoy M, Tiraboschi JM, Murillo O, Podzamczer D. Effectiveness of efavirenz compared with ritonavir-boosted protease-inhibitor-based regimens as initial therapy for patients with plasma HIV-1 RNA above 100,000 copies/ml. Antivir Ther. 2014;19(6):569-77. doi: 10.3851/IMP2736. Epub 2014 Jan 23. PubMed PMID: 24458091. 4: Vesterbacka J, Nowak P, Barqasho B, Abdurahman S, Nyström J, Nilsson S, Funaoka H, Kanda T, Andersson LM, Gisslèn M, Sönnerborg A. Kinetics of microbial translocation markers in patients on efavirenz or lopinavir/r based antiretroviral therapy. PLoS One. 2013;8(1):e55038. doi: 10.1371/journal.pone.0055038. Epub 2013 Jan 28. PubMed PMID: 23383047; PubMed Central PMCID: PMC3557242. 5: Rojas J, Lonca M, Imaz A, Estrada V, Asensi V, Miralles C, Domingo P, Montero M, del Rio L, Fontdevila J, Perez I, Cruceta A, Gatell JM, Arnedo M, Martínez E. Improvement of lipoatrophy by switching from efavirenz to lopinavir/ritonavir. HIV Med. 2016 May;17(5):340-9. doi: 10.1111/hiv.12314. Epub 2015 Sep 10. PubMed PMID: 27089862. 6: Malvestutto CD, Ma Q, Morse GD, Underberg JA, Aberg JA. Lack of pharmacokinetic interactions between pitavastatin and efavirenz or darunavir/ritonavir. J Acquir Immune Defic Syndr. 2014 Dec 1;67(4):390-6. doi: 10.1097/QAI.0000000000000333. PubMed PMID: 25202920; PubMed Central PMCID: PMC4404408. 7: Young J, Schäfer J, Fux CA, Furrer H, Bernasconi E, Vernazza P, Calmy A, Cavassini M, Weber R, Battegay M, Bucher HC; Swiss HIV Cohort Study. Renal function in patients with HIV starting therapy with tenofovir and either efavirenz, lopinavir or atazanavir. AIDS. 2012 Mar 13;26(5):567-75. doi: 10.1097/QAD.0b013e32834f337c. PubMed PMID: 22398568. 8: Song I, Borland J, Chen S, Guta P, Lou Y, Wilfret D, Wajima T, Savina P, Peppercorn A, Castellino S, Wagner D, Hosking L, Mosteller M, Rubio JP, Piscitelli SC. Effects of enzyme inducers efavirenz and tipranavir/ritonavir on the pharmacokinetics of the HIV integrase inhibitor dolutegravir. Eur J Clin Pharmacol. 2014 Oct;70(10):1173-9. doi: 10.1007/s00228-014-1732-8. Epub 2014 Aug 23. PubMed PMID: 25146692; PubMed Central PMCID: PMC4158172. 9: Tiraboschi J, Hamzah L, Teague A, Kulasegaram R, Post F, Jendruleck I, Murray T, Fox J. Short Communication: The Impact of Switching from Atripla to Darunavir/Ritonavir Monotherapy on Neurocognition, Quality of Life, and Sleep: Results from a Randomized Controlled Study. AIDS Res Hum Retroviruses. 2016 Dec;32(12):1198-1201. Epub 2016 Aug 22. PubMed PMID: 27216134. 10: Metzger IF, Quigg TC, Epstein N, Aregbe AO, Thong N, Callaghan JT, Flockhart DA, Nguyen AT, Stevens CK, Gupta SK, Desta Z. Substantial effect of efavirenz monotherapy on bilirubin levels in healthy volunteers. Curr Ther Res Clin Exp. 2014 Sep 27;76:64-9. doi: 10.1016/j.curtheres.2014.05.002. eCollection 2014 Dec. PubMed PMID: 25352936; PubMed Central PMCID: PMC4209507. 11: Kwara A, Cao L, Yang H, Poethke P, Kurpewski J, Tashima KT, Mahjoub BD, Court MH, Peloquin CA. Factors associated with variability in rifampin plasma pharmacokinetics and the relationship between rifampin concentrations and induction of efavirenz clearance. Pharmacotherapy. 2014 Mar;34(3):265-71. doi: 10.1002/phar.1388. Epub 2014 Jan 13. PubMed PMID: 24420746; PubMed Central PMCID: PMC3947488. 12: Torres B, Rallón NI, Loncá M, Díaz A, Alós L, Martínez E, Cruceta A, Arnaiz JA, Leal L, Lucero C, León A, Sánchez M, Negredo E, Clotet B, Gatell JM, Benito JM, Garcia F. Immunological function restoration with lopinavir/ritonavir versus efavirenz containing regimens in HIV-infected patients: a randomized clinical trial. AIDS Res Hum Retroviruses. 2014 May;30(5):425-33. doi: 10.1089/AID.2013.0185. Epub 2014 Feb 10. PubMed PMID: 24380397; PubMed Central PMCID: PMC4010173. 13: Gleason RL Jr, Caulk AW, Seifu D, Rosebush JC, Shapiro AM, Schwartz MH, Eckard AR, Amogne W, Abebe W. Efavirenz and ritonavir-boosted lopinavir use exhibited elevated markers of atherosclerosis across age groups in people living with HIV in Ethiopia. J Biomech. 2016 Sep 6;49(13):2584-2592. doi: 10.1016/j.jbiomech.2016.05.018. Epub 2016 May 21. PubMed PMID: 27270208. 14: Yin K, Meng X, Dong P, Ding T, Shen L, Zhang L, Zhang R, Cai W, Lu H. A simple, rapid, economical, and practical method for the determination of efavirenz in plasma of Chinese AIDS patients by reverse phase high-performance liquid chromatography with ultraviolet detector. Biosci Trends. 2014 Aug;8(4):227-34. PubMed PMID: 25224629. 15: Taniguchi T, Grubb JR, Nurutdinova D, Önen NF, Shacham E, Donovan M, Overton ET. Efavirenz outperforms boosted atazanavir among treatment-naive HIV-1-infected persons in routine clinical care. J Int Assoc Provid AIDS Care. 2013 Mar-Apr;12(2):138-41. doi: 10.1177/1545109712467057. Epub 2012 Dec 26. PubMed PMID: 23269514. 16: Honório Tda S, Pinto EC, Rocha HV, Esteves VS, dos Santos TC, Castro HC, Rodrigues CR, de Sousa VP, Cabral LM. In vitro-in vivo correlation of efavirenz tablets using GastroPlus®. AAPS PharmSciTech. 2013 Sep;14(3):1244-54. doi: 10.1208/s12249-013-0016-4. Epub 2013 Aug 14. PubMed PMID: 23943401; PubMed Central PMCID: PMC3755163. 17: Jiang F, Desta Z, Shon JH, Yeo CW, Kim HS, Liu KH, Bae SK, Lee SS, Flockhart DA, Shin JG. Effects of clopidogrel and itraconazole on the disposition of efavirenz and its hydroxyl metabolites: exploration of a novel CYP2B6 phenotyping index. Br J Clin Pharmacol. 2013 Jan;75(1):244-53. doi: 10.1111/j.1365-2125.2012.04314.x. Erratum in: Br J Clin Pharmacol. 2013 Apr;75(4):1171. PubMed PMID: 22554354; PubMed Central PMCID: PMC3555064. 18: Wang Q, Young J, Bernasconi E, Vernazza P, Calmy A, Cavassini M, Furrer H, Fehr J, Bucher HC, Battegay M; Swiss HIV Cohort Study. Virologic and immunologic responses in treatment-naive patients to ritonavir-boosted atazanavir or efavirenz with a common backbone. HIV Clin Trials. 2014 May-Jun;15(3):92-103. doi: 10.1310/hct1503-92. PubMed PMID: 24947533. 19: Meyer zu Schwabedissen HE, Oswald S, Bresser C, Nassif A, Modess C, Desta Z, Ogburn ET, Marinova M, Lütjohann D, Spielhagen C, Nauck M, Kroemer HK, Siegmund W. Compartment-specific gene regulation of the CAR inducer efavirenz in vivo. Clin Pharmacol Ther. 2012 Jul;92(1):103-11. doi: 10.1038/clpt.2012.34. Epub 2012 May 16. Erratum in: Clin Pharmacol Ther. 2013 Jan;93(1):129. Dosage error in article text. PubMed PMID: 22588604; PubMed Central PMCID: PMC3667667. 20: Calderón MM, Penzak SR, Pau AK, Kumar P, McManus M, Alfaro RM, Kovacs JA. Efavirenz but Not Atazanavir/Ritonavir Significantly Reduces Atovaquone Concentrations in HIV-Infected Subjects. Clin Infect Dis. 2016 Apr 15;62(8):1036-1042. doi: 10.1093/cid/ciw028. Epub 2016 Jan 20. PubMed PMID: 26797214; PubMed Central PMCID: PMC4803107.

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