Nevirapine

Nevirapine
Clinical data
Trade names	Viramune
AHFS/Drugs.com	Monograph
MedlinePlus	a600035
License data	US DailyMed: Nevirapine;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	J05AG01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	93% ± 9%
Metabolism	Liver
Elimination half-life	45 hours
Excretion	Kidney: <6% (Parent drug) ; Bile duct <5% (Parent drug)
Identifiers
	IUPAC name 11-cyclopropyl-4-methyl-5,11-dihydro-6H- dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one;
CAS Number	129618-40-2 ;
PubChem CID	4463;
DrugBank	DB00238 ;
ChemSpider	4308 ;
UNII	99DK7FVK1H;
KEGG	D00435 ;
ChEMBL	ChEMBL57 ;
NIAID ChemDB	001856;
CompTox Dashboard (EPA)	DTXSID7031797 ;
ECHA InfoCard	100.117.250
Chemical and physical data
Formula	C15H14N4O
Molar mass	266.304 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2Nc1c(ccnc1N(c3ncccc23)C4CC4)C;
	InChI InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20) ; Key:NQDJXKOVJZTUJA-UHFFFAOYSA-N ;
	(verify)

Nevirapine (NVP), sold under the brand name Viramune among others, is a medication used to treat and prevent HIV/AIDS, specifically HIV-1.^[4] It is generally recommended for use with other antiretroviral medications.^[4] It may be used to prevent mother to child spread during birth but is not recommended following other exposures.^[4] It is taken by mouth.^[4]

Common side effects include rash, headache, nausea, feeling tired, and liver problems.^[4] The liver problems and skin rash may be severe and should be checked for during the first few months of treatment.^[4]^[5] It appears to be safe for use during pregnancy.^[4] It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and works by blocking the function of reverse transcriptase.^[4]

Nevirapine was approved for medical use in the United States in 1996.^[4] It is on the World Health Organization's List of Essential Medicines.^[6] It is available as a generic medication.^[4]

^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ Cite error: The named reference Viramune FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Viramune XR FDA label was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Nevirapine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 3 December 2016.
^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 63. ISBN 9781284057560.
^ 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.

[1] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[Viramune_FDA_label-2] Cite error: The named reference Viramune FDA label was invoked but never defined (see the help page).

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

[AHFS2016-4] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Nevirapine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 3 December 2016.

[Ric2015-5] Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 63. ISBN 9781284057560.

[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.

[1]

[2]

[3]

[4]

[5]

[6]