Stavudine

Stavudine
Clinical data
Trade names	Zerit
Other names	2′,3′-didehydro-2′,3′-dideoxythymidine
AHFS/Drugs.com	Monograph
MedlinePlus	a694033
License data	EU EMA: by INN; US DailyMed: Stavudine;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	J05AF04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: WARNINGRx-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	>80%
Protein binding	Negligible
Metabolism	Kidney elimination (~40%)
Elimination half-life	0.8–1.5 hours (in adults)
Identifiers
	IUPAC name 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;
CAS Number	3056-17-5 ;
PubChem CID	18283;
DrugBank	DB00649 ;
ChemSpider	17270 ;
UNII	BO9LE4QFZF;
KEGG	D00445 ;
ChEMBL	ChEMBL991 ;
NIAID ChemDB	000005;
CompTox Dashboard (EPA)	DTXSID1023819 ;
ECHA InfoCard	100.169.180
Chemical and physical data
Formula	C10H12N2O4
Molar mass	224.216 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1/C(=C\N(C(=O)N1)[C@@H]/2O[C@@H](\C=C\2)CO)C;
	InChI InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1 ; Key:XNKLLVCARDGLGL-JGVFFNPUSA-N ;
	(verify)

Stavudine (d4T), sold under the brand name Zerit among others, is an antiretroviral medication used to prevent and treat 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. However, it is not a first-line treatment. It is given by mouth.

Common side effects include headache, diarrhea, vomiting, rash, and peripheral nerve problems. Severe side effects include high blood lactate, pancreatitis, and an enlarged liver. It is not generally recommended in pregnancy. Stavudine is in the nucleoside analog reverse-transcriptase inhibitor (NRTI) class of medication.

Stavudine was first described in 1966 and approved for use in the United States in 1994. It is available as a generic medication.

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