Rac-Efavirenz | CAS#177530-93-7 | Efavirenz

MedKoo Cat#: 596695 | Name: Rac-Efavirenz

Description:

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

Rac-Efavirenz is a non stereospecific structure of Efavirenz.

Chemical Structure

Rac-Efavirenz

CAS#177530-93-7 (racemic)

Theoretical Analysis

MedKoo Cat#: 596695

Name: Rac-Efavirenz

CAS#: 177530-93-7 (racemic)

Chemical Formula: C14H9ClF3NO2

Exact Mass: 315.0274

Molecular Weight: 315.68

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

Rac-Efavirenz; Racemic-Efavirenz; (+/-)-Efavirenz; Rac L741211; L 741211; L-741211; Rac DMP-266; DMP 266; DMP266; Rac-EFV;

IUPAC/Chemical Name

6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one

InChi Key

XPOQHMRABVBWPR-UHFFFAOYSA-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)

SMILES Code

O=C1NC2=CC=C(Cl)C=C2C(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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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:

Rac-Efavirenz is a non stereospecific structure of efavirenz. Efavirenz is a potent inhibitor of the wild-type HIV-1 reverse transcriptase with a Ki of 2.93 nM and exhibits an IC95 of 1.5 nM for the inhibition of HIV-1 replicative spread in cell culture.

In vitro activity:

This study found that efavirenz induced growth in MCF-7 cells by binding directly to the estrogen receptor at a roughly 1000-fold higher concentration than observed with 17β-oestradiol. This suggests that efavirenz-induced gynaecomastia may be caused, at least in part, by drug-induced estrogen receptor activation in breast tissues. Reference: HIV Med. 2010 Oct 1;11(9):603-7. https://pubmed.ncbi.nlm.nih.gov/20408889/

In vivo activity:

This study found that the combination treatment of zidovudine and efavirenz almost entirely blocked tumorigenesis. The combination was very well tolerated in mice, implying that the combination therapy could be a potential course to treat colorectal tumors and metastasis to the liver. Reference: Viruses. 2021 Nov 30;13(12):2396. https://pubmed.ncbi.nlm.nih.gov/34960665/

	Solvent	mg/mL	mM
Solubility
	To be determined	0.0	0.00
	To be determined	0.0	0.00
	To be determined	0.0	0.00
	To be determined	0.0	0.00
	To be determined	0.0	0.00
	To be determined	0.0	0.00
	To be determined	0.0	0.00
	To be determined	0.0	0.00

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 315.68 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. Correia CA, Gilmore K, McQuade DT, Seeberger PH. A concise flow synthesis of efavirenz. Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4945-8. doi: 10.1002/anie.201411728. Epub 2015 Feb 27. PMID: 25727078. 2. Sikora MJ, Rae JM, Johnson MD, Desta Z. Efavirenz directly modulates the oestrogen receptor and induces breast cancer cell growth. HIV Med. 2010 Oct 1;11(9):603-7. doi: 10.1111/j.1468-1293.2010.00831.x. Epub 2010 Jun 28. PMID: 20408889; PMCID: PMC2943013. 3. Buzibye A, Wools-Kaloustian K, Olagunju A, Twinomuhwezi E, Yiannoutsos C, Owen A, Neary M, Matovu J, Banturaki G, Castelnuovo B, Lamorde M, Khoo S, Waitt C, Kiragga A. Relating CYP2B6 genotype and efavirenz resistance among post-partum women living with HIV with high viremia in Uganda: a nested cross-sectional study. AIDS Res Ther. 2023 Mar 31;20(1):20. doi: 10.1186/s12981-023-00514-2. PMID: 37004096; PMCID: PMC10064798. 4. Schneider MA, Buzdin AA, Weber A, Clavien PA, Borger P. Combination of Antiretroviral Drugs Zidovudine and Efavirenz Impairs Tumor Growths in a Mouse Model of Cancer. Viruses. 2021 Nov 30;13(12):2396. doi: 10.3390/v13122396. PMID: 34960665; PMCID: PMC8703283.

In vitro protocol:

In vivo protocol:

1. Buzibye A, Wools-Kaloustian K, Olagunju A, Twinomuhwezi E, Yiannoutsos C, Owen A, Neary M, Matovu J, Banturaki G, Castelnuovo B, Lamorde M, Khoo S, Waitt C, Kiragga A. Relating CYP2B6 genotype and efavirenz resistance among post-partum women living with HIV with high viremia in Uganda: a nested cross-sectional study. AIDS Res Ther. 2023 Mar 31;20(1):20. doi: 10.1186/s12981-023-00514-2. PMID: 37004096; PMCID: PMC10064798. 2. Schneider MA, Buzdin AA, Weber A, Clavien PA, Borger P. Combination of Antiretroviral Drugs Zidovudine and Efavirenz Impairs Tumor Growths in a Mouse Model of Cancer. Viruses. 2021 Nov 30;13(12):2396. doi: 10.3390/v13122396. PMID: 34960665; PMCID: PMC8703283.

1: Correia CA, Gilmore K, McQuade DT, Seeberger PH. A concise flow synthesis of efavirenz. Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4945-8. doi: 10.1002/anie.201411728. Epub 2015 Feb 27. PubMed PMID: 25727078.