Structure via PubChem · Public domain (PubChem)
stavudine
Sign in to saveAlso known as Zerit Xr, D4T, 1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine, 3'-Deoxy-2'-thymidinene, Sanilvudine, 2',3'-Didehydro-3'-deoxythimidine, STV, BMY-27857
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.
Key facts
- Drug.verifiedrevid
- 477173315
- Drug.image
- Stavudine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 180
- Drug.image2
- Stavudine ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Zerit
- Drug.MedlinePlus
- a694033
- Drug.DailyMedID
- Stavudine
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- J05
- Drug.ATC_suffix
- AF04
- Drug.legal_AU
- S4
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- >80%
via Wikipedia infobox
Chemical data
- Formula
- C10H12N2O4
- Molecular weight
- 224.21 g/mol
- IUPAC name
- 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
- SMILES
- CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO
- InChIKey
- XNKLLVCARDGLGL-JGVFFNPUSA-N
- XLogP
- -0.8
- Polar surface area
- 78.9 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
3,093 papers- Stavudine once daily.Drugs · 2002
- Stavudine: an update of its use in the treatment of HIV infection.Drugs · 1999
- Stavudine.Acta crystallographica. Section C, Crystal structure communications · 2005
- Stavudine extended release (once-daily, Bristol-Myers Squibb) for the treatment of HIV/AIDS.Expert opinion on pharmacotherapy · 2013
- Stavudine: a review of its pharmacodynamic and pharmacokinetic properties and clinical potential in HIV infection.Drugs · 1996
via PubMed
Wikidata facts
- Mass
- 224.079707
Show 7 more facts
- chemical formula
- C₁₀H₁₂N₂O₄
- canonical SMILES
- CC1=CN(C(=O)NC1=O)C2C=CC(O2)CO
- isomeric SMILES
- CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO
- defined daily dose
- 80
- World Health Organisation international non-proprietary name
- stavudine
- MCN code
- 2934.99.27
- Commons category
- Stavudine
via Wikidata · CC0
~9 min read
Article
10 sectionsContents
- Medical uses
- Pregnancy and breastfeeding
- Children
- Elderly
- Adverse effects
- Mechanism of action
- Pharmacokinetics
- Drug interactions
- History
- References
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.