(S)-Efavirenz | CAS#154598-52-4 | Non-nucleoside Reverse Transcriptase Inhibitor

MedKoo Cat#: 317766 | Name: (S)-Efavirenz

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Description:

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

Efavirenz 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.

Chemical Structure

(S)-Efavirenz

CAS#154598-52-4 (S-isomer)

Theoretical Analysis

MedKoo Cat#: 317766

Name: (S)-Efavirenz

CAS#: 154598-52-4 (S-isomer)

Chemical Formula: C14H9ClF3NO2

Exact Mass: 315.0274

Molecular Weight: 315.67

Elemental Analysis: C, 53.27; H, 2.87; Cl, 11.23; F, 18.06; N, 4.44; O, 10.14

Price and Availability

Size	Price	Availability
1g	USD 150.00	2 weeks
2g	USD 250.00	2 weeks
5g	USD 450.00	2 weeks
25g	USD 850.00	2 weeks

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Related CAS #

154801-74-8 (R-isomer) 154598-52-4 (S-isomer) 177530-93-7 (racemic)

Synonym

Efavirenz; (S)-Efavirenz; Sustiva; Stocrin; DMP-266; DMP 266; DMP266; EFV; L-743726; L743726; L 743726

IUPAC/Chemical Name

(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one

InChi Key

XPOQHMRABVBWPR-ZDUSSCGKSA-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-/m0/s1

SMILES Code

C1CC1C#C[C@]2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F

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, not in water

Shelf Life

>2 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Efavirenz (DMP 266) is an inhibitor of the wild-type HIV-1 reverse transcriptase with a Ki of 2.93 nM.

In vitro activity:

In EFV treated MRC-5 cells, MAD2L2 was significantly upregulated (~2 fold) at 24 h, followed by a –1.34 down-regulation at 48 h. In contrast, CASP3 (~ –1.8 fold) and AURKB (~ –1.5 fold) were down-regulated at 24 h and 48 h, as shown in Figure 5B. In EFV treated A549 lung cancer cells, EFV significantly decreased expression levels of both MAD2L2 (fold changes, ** p < 0.01 and *** p < 0.001) and AURKB (fold changes, p < 0.001) genes at 24 h and 48 h. Reference: Oncotarget. 2020 Oct 13; 11(41): 3737–3748. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7566803/

In vivo activity:

Yet, in MWM test, which assesses the spatial long-term memory and learning, EFV (efavirenz)-treated group displayed a better performance than the control group (Fig. 1b). In fear conditioning tests, EFV-treated mice exhibited a greater postshock freezing (an index of fear memory) during the learning phase of the contextual fear test (Fig. 1c) and also the next day when the actual test was performed (Fig. 1d). However, in the cued fear conditioning, there was no difference between EFV-treated and control mice (Fig. 1e). Thus, EFV treatment improved the spatial long-term memory as well as the short and long-term contextual fear memory but not the spatial short-term working memory or fear cued memory. Reference: Neurotherapeutics. 2019 Jul; 16(3): 710–724. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6694340/

	Solvent	mg/mL	mM
Solubility
	DMSO	38.3	121.42
	DMF	20.0	63.36
	Ethanol	41.5	131.47
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.58

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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

Formulation protocol:

1. Marima R, Hull R, Dlamini Z, Penny C. Efavirenz induces DNA damage response pathway in lung cancer. Oncotarget. 2020 Oct 13;11(41):3737-3748. doi: 10.18632/oncotarget.27725. PMID: 33110481; PMCID: PMC7566803. 2. Malikova J, Zingg T, Fingerhut R, Sluka S, Grössl M, Brixius-Anderko S, Bernhardt R, McDougall J, Pandey AV, Flück CE. HIV Drug Efavirenz Inhibits CYP21A2 Activity with Possible Clinical Implications. Horm Res Paediatr. 2019;91(4):262-270. doi: 10.1159/000500522. Epub 2019 Jun 28. PMID: 31256164. 3. Petrov AM, Lam M, Mast N, Moon J, Li Y, Maxfield E, Pikuleva IA. CYP46A1 Activation by Efavirenz Leads to Behavioral Improvement without Significant Changes in Amyloid Plaque Load in the Brain of 5XFAD Mice. Neurotherapeutics. 2019 Jul;16(3):710-724. doi: 10.1007/s13311-019-00737-0. PMID: 31062296; PMCID: PMC6694340. 4. Gwag T, Meng Z, Sui Y, Helsley RN, Park SH, Wang S, Greenberg RN, Zhou C. Non-nucleoside reverse transcriptase inhibitor efavirenz activates PXR to induce hypercholesterolemia and hepatic steatosis. J Hepatol. 2019 May;70(5):930-940. doi: 10.1016/j.jhep.2018.12.038. Epub 2019 Jan 21. Erratum in: J Hepatol. 2021 Apr;74(4):1003-1004. PMID: 30677459; PMCID: PMC6462244.

In vitro protocol:

In vivo protocol:

1. Petrov AM, Lam M, Mast N, Moon J, Li Y, Maxfield E, Pikuleva IA. CYP46A1 Activation by Efavirenz Leads to Behavioral Improvement without Significant Changes in Amyloid Plaque Load in the Brain of 5XFAD Mice. Neurotherapeutics. 2019 Jul;16(3):710-724. doi: 10.1007/s13311-019-00737-0. PMID: 31062296; PMCID: PMC6694340. 2. Gwag T, Meng Z, Sui Y, Helsley RN, Park SH, Wang S, Greenberg RN, Zhou C. Non-nucleoside reverse transcriptase inhibitor efavirenz activates PXR to induce hypercholesterolemia and hepatic steatosis. J Hepatol. 2019 May;70(5):930-940. doi: 10.1016/j.jhep.2018.12.038. Epub 2019 Jan 21. Erratum in: J Hepatol. 2021 Apr;74(4):1003-1004. PMID: 30677459; PMCID: PMC6462244.

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An Investigation of Liquid Chromatography-Mass Spectral Attributes and Analytical Performance Characteristics of Tenofovir, Emtricitabine and Efavirenz in Human Plasma. J Anal Toxicol. 2016 Jan;40(1):49-57. doi: 10.1093/jat/bkv119. Epub 2015 Oct 20. PubMed PMID: 26487641. 4: Sadeghi M, Bayat M, Cheraghi S, Yari K, Heydari R, Dehdashtian S, Shamsipur M. Binding studies of the anti-retroviral drug, efavirenz to calf thymus DNA using spectroscopic and voltammetric techniques. Luminescence. 2016 Feb;31(1):108-17. doi: 10.1002/bio.2931. Epub 2015 May 29. PubMed PMID: 26031412. 5: Sinxadi PZ, McIlleron HM, Dave JA, Smith PJ, Levitt NS, Haas DW, Maartens G. Plasma Efavirenz Concentrations Are Associated With Lipid and Glucose Concentrations. Medicine (Baltimore). 2016 Jan;95(2):e2385. doi: 10.1097/MD.0000000000002385. PubMed PMID: 26765416. 6: Thamrongwonglert P, Chetchotisakd P, Anunnatsiri S, Mootsikapun P. Improvement of lipid profiles when switching from efavirenz to rilpivirine in HIV-infected patients with dyslipidemia. HIV Clin Trials. 2016 Jan 7:1-5. [Epub ahead of print] PubMed PMID: 26739573. 7: De Nardo P, Gentilotti E, Nguhuni B, Vairo F, Chaula Z, Nicastri E, Ippolito G. Efavirenz-based antiretroviral therapy versus nevirapine-including regimens for prevention of mother-to-child transmission of HIV option B plus in resource-limited settings: is there anything missing? Expert Rev Anti Infect Ther. 2016 Jan;14(1):19-27. doi: 10.1586/14787210.2016.1116383. Epub 2015 Dec 3. PubMed PMID: 26559430. 8: Aouri M, Barcelo C, Ternon B, Cavassini M, Anagnostopoulos A, Yerly S, Hugues H, Vernazza P, Günthard HF, Buclin T, Telenti A, Rotger M, Decosterd LA; Swiss HIV Cohort Study. In Vivo Profiling and Distribution of Known and Novel Phase I and Phase II Metabolites of Efavirenz in Plasma, Urine, and Cerebrospinal Fluid. Drug Metab Dispos. 2016 Jan;44(1):151-61. doi: 10.1124/dmd.115.065839. Epub 2015 Nov 9. PubMed PMID: 26553012. 9: Calza L, Magistrelli E, Danese I, Colangeli V, Borderi M, Bon I, Re MC, Mancini R, Conti M, Motta R, Viale P. Changes in Serum Markers of Inflammation and Endothelial Activation in HIV-Infected Antiretroviral Naive Patients Starting A Treatment with Abacavir-Lamivudine or Tenofovir-Emtricitabine Plus Efavirenz. Curr HIV Res. 2016;14(1):61-70. PubMed PMID: 26531764. 10: Weiß M, Kost B, Renner-Müller I, Wolf E, Mylonas I, Brüning A. Efavirenz Causes Oxidative Stress, Endoplasmic Reticulum Stress, and Autophagy in Endothelial Cells. Cardiovasc Toxicol. 2016 Jan;16(1):90-9. doi: 10.1007/s12012-015-9314-2. PubMed PMID: 25666561. 11: Jordaan MA, Singh P, Martincigh BS. A combined TD-DFT and spectroscopic investigation of the solute-solvent interactions of efavirenz. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Dec 8;157:204-210. doi: 10.1016/j.saa.2015.12.008. [Epub ahead of print] PubMed PMID: 26773263. 12: Gervasoni C, ChemD SB, Cerea M, Cenderello G, Bini T, Vimercati S, Iardino MR, Gazzaniga A, D'Arminio Monforte A, Clementi E, Cattaneo D. Comparison of the in vivo pharmacokinetics and in vitro dissolution of branded versus generic efavirenz formulation in HIV-infected patients. Ther Drug Monit. 2015 Dec 30. [Epub ahead of print] PubMed PMID: 26727626. 13: Dickinson L, Amin J, Else L, Boffito M, Egan D, Owen A, Khoo S, Back D, Orrell C, Clarke A, Losso M, Phanuphak P, Carey D, Cooper DA, Emery S, Puls R. Comprehensive Pharmacokinetic, Pharmacodynamic and Pharmacogenetic Evaluation of Once-Daily Efavirenz 400 and 600 mg in Treatment-Naïve HIV-Infected Patients at 96 Weeks: Results of the ENCORE1 Study. Clin Pharmacokinet. 2015 Dec 29. [Epub ahead of print] PubMed PMID: 26715213. 14: Shelton JD. Reduced Effectiveness of Contraceptive Implants for Women Taking the Antiretroviral Efavirenz (EFV): Still Good Enough and for How Long? Glob Health Sci Pract. 2015 Dec 8;3(4):528-31. doi: 10.9745/GHSP-D-15-00356. PubMed PMID: 26681700; PubMed Central PMCID: PMC4682578. 15: Palombi L, Pirillo MF, Marchei E, Jere H, Sagno JB, Luhanga R, Floridia M, Andreotti M, Galluzzo CM, Pichini S, Mwenda R, Mancinelli S, Marazzi MC, Vella S, Liotta G, Giuliano M. Concentrations of tenofovir, lamivudine and efavirenz in mothers and children enrolled under the Option B-Plus approach in Malawi. J Antimicrob Chemother. 2015 Dec 17. pii: dkv435. [Epub ahead of print] PubMed PMID: 26679247. 16: Wilkins E, Fisher M, Brogan AJ, Talbird SE, La EM. Cost-effectiveness analysis of tenofovir/emtricitabine and abacavir/lamivudine in combination with efavirenz or atazanavir/ritonavir for treatment-naïve adults with HIV-1 infection in the UK, based on the AIDS Clinical Trials Group 5202 clinical trial. HIV Med. 2015 Dec 9. doi: 10.1111/hiv.12349. [Epub ahead of print] PubMed PMID: 26663715. 17: Röhrich CR, Drögemöller BI, Ikediobi O, Gandhi M, Van der Merwe L, Grobbelaar N, Wright GE, Huang Y, McGregor N, Aouizerat B, Warnich L. CYP2B6*6 and CYP2B6*18 predict long-term efavirenz exposure measured in hair samples in HIV-positive South African women. AIDS Res Hum Retroviruses. 2015 Dec 13. [Epub ahead of print] PubMed PMID: 26655325. 18: Cusato J, Tomasello C, Simiele M, Calcagno A, Bonora S, Marinaro L, Leggieri A, Allegra S, Di Perri G, D'Avolio A. Efavirenz pharmacogenetics in a cohort of Italian patients. Int J Antimicrob Agents. 2015 Dec 18. pii: S0924-8579(15)00404-5. doi: 10.1016/j.ijantimicag.2015.11.012. [Epub ahead of print] PubMed PMID: 26774523. 19: Rotzinger A, Locatelli I, Bugnon O, Fayet Mello A, Parienti JJ, Cavassini M, Schneider MP. Switching from a two-tablet regimen of tenofovir/emtricitabine and efavirenz to a one-tablet regimen may affect patients' perceptions and drug management. HIV Med. 2015 Dec 21. doi: 10.1111/hiv.12345. [Epub ahead of print] PubMed PMID: 26688004. 20: Lortholary O, Roussillon C, Boucherie C, Padoin C, Chaix ML, Breton G, Rami A, Veziris N, Patey O, Caumes E, May T, Molina JM, Robert J, Tod M, Fagard C, Chêne G; ANRS 129 BKVIR Trial Group. Tenofovir DF/emtricitabine and efavirenz combination therapy for HIV infection in patients treated for tuberculosis: the ANRS 129 BKVIR trial. J Antimicrob Chemother. 2015 Dec 17. pii: dkv384. [Epub ahead of print] PubMed PMID: 26679250.