Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML0536

Sigma-Aldrich

Efavirenz

≥98% (HPLC)

Synonym(s):

Efavirenz, (4S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C14H9ClF3NO2
CAS Number:
154598-52-4
Molecular Weight:
315.67
MDL number:
MFCD05662344
UNSPSC Code:
12352200
PubChem Substance ID:
329825539
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -90 to -100°, c = 1 in methanol

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

ClC1=CC=C2C([C@@](C#CC3CC3)(C(F)(F)F)OC(N2)=O)=C1

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

InChI key

XPOQHMRABVBWPR-ZDUSSCGKSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Efavirenz, commercially known as Sustiva™ is a polycyclic aromatic hydrocarbon with benzene and oxazinan-2-one chromophores.

Application

Efavirenz has been used:
  • to assess its anti-porcine endogenous retrovirus (PERV) activity
  • in cytotoxicity assay
  • to investigate the solute-solvent effects of efavirenz by means combined time-dependent density functional theory (TD-DFT) and spectroscopic calculations

Biochem/physiol Actions

Efavirenz is a nonnucleoside reverse transcriptase inhibitor (NNRTI). It is an anti-HIV drug, commonly used in combination therapy for AIDs treatment. It is part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Legal Information

Sustiva is a trademark of E. I. du Pont de Nemours and Company

Signal Word

Danger

Hazard Statements

H302,H360,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Lawrence S U Lee et al.
Annals of the Academy of Medicine, Singapore, 41(12), 559-562 (2013-01-11)
Efavirenz is an inducer of drug metabolism enzymes. We studied the effect of efavirenz and ritonavir-boosted darunavir on serum unconjugated and conjugated bilirubin, as probes for UGT1A1 and bile transporters. Healthy volunteers were enrolled in a clinical trial. There were
Rochelle P Walensky et al.
Annals of internal medicine, 158(2), 84-92 (2013-01-16)
U.S. HIV treatment guidelines recommend branded once-daily, 1-pill efavirenz-emtricitabine-tenofovir as first-line antiretroviral therapy (ART). With the anticipated approval of generic efavirenz in the United States, a once-daily, 3-pill alternative (generic efavirenz, generic lamivudine, and tenofovir) will decrease cost but may
L B Avery et al.
Antimicrobial agents and chemotherapy, 57(3), 1409-1414 (2013-01-09)
Efavirenz (EFV) is one of the most commonly prescribed antiretroviral drugs (ARVs) for the treatment of HIV. Highly protein-bound drugs, like EFV, have limited central nervous system (CNS) penetration when measured using total drug concentration gradients between blood plasma (BP)
A combined TD-DFT and spectroscopic investigation of the solute?solvent interactions of efavirenz.
Jordaan M A, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 157, 204-210 (2016)
Gregory P Bisson et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 56(8), 1165-1173 (2013-01-31)
The burden of Cryptococcus neoformans in cerebrospinal fluid (CSF) predicts clinical outcomes in human immunodeficiency virus (HIV)-associated cryptococcal meningitis (CM) and is lower in patients on antiretroviral therapy (ART). This study tested the hypothesis that initiation of ART during initial
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service