Efavirenz
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MedKoo CAT#: 317766

CAS#: 154598-52-4

Description: 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

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Efavirenz
CAS# 154598-52-4

Theoretical Analysis

MedKoo Cat#: 317766
Name: Efavirenz
CAS#: 154598-52-4
Chemical Formula: C14H9ClF3NO2
Exact Mass: 315.02739
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 Quantity
1.0g USD 150.0 2 weeks
2.0g USD 250.0 2 weeks
5.0g USD 450.0 2 weeks
10.0g USD 650.0 2 weeks
20.0g USD 850.0 2 weeks
50.0g USD 1250.0 2 weeks
Bulk inquiry

Synonym: Efavirenz; Sustiva; Stocrin; DMP-266; DMP 266; Merck Sharp and Dohme brand of efavirenz; Stocrin; Sustiva; United Drug brand of efavirenz; L-743,726; 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

Product Data:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.33 121.42
DMF 20.0 63.36
Ethanol 41.5 131.47
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.58

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
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: 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.
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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1: Homkham N, Cressey TR, Ingsrisawang L, Bouazza N, Ngampiyaskul C, Hongsiriwon
S, Srirojana S, Kanjanavanit S, Bhakeecheep S, Coeur SL, Salvadori N, Treluyer
JM, Jourdain G, Urien S. A Population Pharmacokinetic/Pharmacodynamic Model
Predicts Favorable HDL Cholesterol Changes Over the First 5 Years in Children
Treated with Current Efavirenz-Based Regimens. J Clin Pharmacol. 2016 Jan 8. doi:
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2: van Lunzen J, Antinori A, Cohen CJ, Arribas JR, Wohl DA, Rieger A, Rachlis A,
Bloch M, Segal-Maurer S, Garner W, Porter D, Bosse M, Piontkowsky D, Chuck SK,
De-Oertel S. Rilpivirine vs. efavirenz-based single-tablet regimens in
treatment-naive adults: week 96 efficacy and safety from a randomized phase 3b
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PMID: 26684822.

3: Ndolo SM, Sichilongo K, Massele A, Sepako E, Vento S. An Investigation of
Liquid Chromatography-Mass Spectral Attributes and Analytical Performance
Characteristics of Tenofovir, Emtricitabine and Efavirenz in Human Plasma. J Anal
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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
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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
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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
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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,
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mothers and children enrolled under the Option B-Plus approach in Malawi. J
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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
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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
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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
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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
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