Stavudine

Stavudine
Clinical data
Trade names	Zerit
Other names	2′,3′-didehydro-2′,3′-dideoxythymidine
AHFS/Drugs.com	Monograph
MedlinePlus	a694033
License data	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: ℞-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.^[3] It is generally recommended for use with other antiretrovirals.^[3] It may be used for prevention after a needlestick injury or other potential exposure.^[3] However, it is not a first-line treatment.^[3] It is given by mouth.^[3]

Common side effects include headache, diarrhea, vomiting, rash, and peripheral nerve problems.^[3] Severe side effects include high blood lactate, pancreatitis, and an enlarged liver.^[3] It is not generally recommended in pregnancy.^[3] Stavudine is in the nucleoside analog reverse-transcriptase inhibitor (NRTI) class of medication.^[3]

Stavudine was first described in 1966 and approved for use in the United States in 1994.^[4] It is available as a generic medication.^[3]

^ Cite error: The named reference Stavudine FDA label was invoked but never defined (see the help page).
^ "Zerit EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 13 October 2020.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Stavudine Monograph for Professionals - Drugs.com". www.drugs.com. Archived from the original on 10 November 2016. Retrieved 9 November 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.

[Stavudine_FDA_label-1] Cite error: The named reference Stavudine FDA label was invoked but never defined (see the help page).

[Zerit_EPAR-2] "Zerit EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 13 October 2020.

[AHFS2016-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Stavudine Monograph for Professionals - Drugs.com". www.drugs.com. Archived from the original on 10 November 2016. Retrieved 9 November 2016.

[4] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.

[1]

[2]

[3]

[4]