Stavudine

Stavudine
Clinical data
Trade namesZerit
Other names2′,3′-didehydro-2′,3′-dideoxythymidine
AHFS/Drugs.comMonograph
MedlinePlusa694033
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: WARNING[1]Rx-only[2]
  • EU: Rx-only[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability>80%
Protein bindingNegligible
MetabolismKidney elimination (~40%)
Elimination half-life0.8–1.5 hours (in adults)
Identifiers
  • 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.169.180 Edit this at Wikidata
Chemical and physical data
FormulaC10H12N2O4
Molar mass224.216 g·mol−1
3D model (JSmol)
  • O=C1/C(=C\N(C(=O)N1)[C@@H]/2O[C@@H](\C=C\2)CO)C
  • 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 checkY
  • Key:XNKLLVCARDGLGL-JGVFFNPUSA-N checkY
  (verify)

Stavudine (d4T), sold under the brand name Zerit among others, is an antiretroviral medication used to prevent and treat HIV/AIDS.[4] It is generally recommended for use with other antiretrovirals.[4] It may be used for prevention after a needlestick injury or other potential exposure.[4] However, it is not a first-line treatment.[4] It is given by mouth.[4]

Common side effects include headache, diarrhea, vomiting, rash, and peripheral nerve problems.[4] Severe side effects include high blood lactate, pancreatitis, and an enlarged liver.[4] It is not generally recommended in pregnancy.[4] Stavudine is in the nucleoside analog reverse-transcriptase inhibitor (NRTI) class of medication.[4]

Stavudine was first described in 1966 and approved for use in the United States in 1994.[5] It is available as a generic medication.[4]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ Cite error: The named reference Stavudine FDA label was invoked but never defined (see the help page).
  3. ^ "Zerit EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 13 October 2020.
  4. ^ 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.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.