Efavirenz

Efavirenz
Clinical data


Pronunciation	e-FAV-irr-enz
Trade names	Atripla, Sustiva, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699004
Pregnancy category	US: D (Evidence of risk)
Routes of administration	By mouth (capsules, tablets)
ATC code	J05AG03 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	40–45% (under fasting conditions)
Protein binding	99.5–99.75%
Metabolism	Hepatic (CYP2A6 and CYP2B6-mediated)
Onset of action	3–5 hours
Biological half-life	40–55 hours
Excretion	Urine (14–34%) and feces (16–61%)
Identifiers
IUPAC name (4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
CAS Number	154598-52-4^Y
PubChem (CID)	64139
DrugBank	DB00625^Y
ChemSpider	57715^Y
UNII	JE6H2O27P8^Y
KEGG	D00896^Y
ChEBI	CHEBI:119486^Y
ChEMBL	CHEMBL223228^Y
NIAID ChemDB	032934
PDB ligand ID	EFZ (PDBe, RCSB PDB)
ECHA InfoCard	100.149.346
Chemical and physical data
Formula	C₁₄H₉ClF₃NO₂
Molar mass	315.675 g/mol
3D model (Jmol)	Interactive image
SMILES FC(F)([C@]1(OC(NC2=CC=C(C=C21)Cl)=O)C#CC3CC3)F
InChI 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^Y Key:XPOQHMRABVBWPR-ZDUSSCGKSA-N^Y

Efavirenz (EFV), sold under the brand names Sustiva among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needlestick injury or other potential exposure. It is sold both by itself and in combination as efavirenz/emtricitabine/tenofovir. It is taken by mouth once a day.

Common side effects include rash, nausea, headache, feeling tired, and trouble sleeping. Some of the rashes may be serious such as Stevens-Johnson syndrome. Other serious side effects include depression, thoughts of suicide, liver problems, and seizures. It is not safe for use during pregnancy. It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and works by blocking the function of reverse transcriptase.

Efavirenz was approved for medical use in the United States in 1998. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. As of 2015 it is not available as a generic medication. The wholesale cost in the developing world is about 3.27 to 9.15 USD per month. As of 2015 the cost for a typical month of medication in the United States is more than 200 USD.

For HIV infection that has not previously been treated, the United States Department of Health and Human Services Panel on Antiretroviral Guidelines recommends the use of efavirenz in combination with tenofovir/emtricitabine (Truvada) as one of the preferred NNRTI-based regimens in adults and adolescents and children.

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