Efavirenz

Efavirenz
Clinical data
Pronunciation	/ɪˈfævɪrɛnz/ i-FAV-i-renz or /ˌɛfəˈvaɪrɛnz/ EF-ə-VY-renz
Trade names	Sustiva, Stocrin, others
Other names	EFV
AHFS/Drugs.com	Monograph
MedlinePlus	a699004
License data	US DailyMed: Efavirenz;
Pregnancy; category	AU: D;
Routes of; administration	By mouth (capsules, tablets)
ATC code	J05AG03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	40–45% (under fasting conditions)
Protein binding	99.5–99.75%
Metabolism	Liver (CYP2A6 and CYP2B6-mediated)
Onset of action	3–5 hours
Elimination half-life	Single-dose: 52–76 h; Multi-dose: 40–55 h
Excretion	Kidney (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 ;
PubChem CID	64139;
DrugBank	DB00625 ;
ChemSpider	57715 ;
UNII	JE6H2O27P8;
KEGG	D00896 ;
ChEBI	CHEBI:119486 ;
ChEMBL	ChEMBL223228 ;
NIAID ChemDB	032934;
PDB ligand	EFZ (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID9046029 ;
ECHA InfoCard	100.149.346
Chemical and physical data
Formula	C14H9ClF3NO2
Molar mass	315.68 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1Nc2ccc(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1;
	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 ; Key:XPOQHMRABVBWPR-ZDUSSCGKSA-N ;
	(verify)

Efavirenz (EFV), sold under the brand names Sustiva among others, is an antiretroviral medication used to treat and prevent HIV/AIDS.^[1] It is generally recommended for use with other antiretrovirals.^[1] It may be used for prevention after a needlestick injury or other potential exposure.^[1] It is sold both by itself and in combination as efavirenz/emtricitabine/tenofovir.^[1] It is taken by mouth.^[1]

Common side effects include rash, nausea, headache, feeling tired, and trouble sleeping.^[1] Some of the rashes may be serious such as Stevens–Johnson syndrome.^[1] Other serious side effects include depression, thoughts of suicide, liver problems, and seizures.^[1] It is not safe for use during pregnancy.^[1] It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and works by blocking the function of reverse transcriptase.^[1]

Efavirenz was approved for medical use in the United States in 1998,^[1] and in the European Union in 1999.^[4] It is on the World Health Organization's List of Essential Medicines.^[6] As of 2016, it is available as a generic medication.^[7]^[8]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l "Efavirenz". The American Society of Health-System Pharmacists. Archived from the original on 17 November 2016. Retrieved 28 November 2016.
^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
^ Cite error: The named reference Sustiva FDA label was invoked but never defined (see the help page).
^ ^a ^b "Stocrin EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 15 October 2020.
^ ^a ^b Cite error: The named reference Sustiva-Label was invoked but never defined (see the help page).
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ Cite error: The named reference Efavirenz Drug Profile was invoked but never defined (see the help page).
^ Cite error: The named reference Efavirenz generic approval was invoked but never defined (see the help page).

[AHFS2016-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l "Efavirenz". The American Society of Health-System Pharmacists. Archived from the original on 17 November 2016. Retrieved 28 November 2016.

[2] "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.

[Sustiva_FDA_label-3] Cite error: The named reference Sustiva FDA label was invoked but never defined (see the help page).

[Stocrin_EPAR-4] "Stocrin EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 15 October 2020.

[Sustiva-Label-5] Cite error: The named reference Sustiva-Label was invoked but never defined (see the help page).

[WHO21st-6] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[Efavirenz_Drug_Profile-7] Cite error: The named reference Efavirenz Drug Profile was invoked but never defined (see the help page).

[Efavirenz_generic_approval-8] Cite error: The named reference Efavirenz generic approval was invoked but never defined (see the help page).

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