Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Stavudine [USAN:USP:INN:BAN]
RN: 3056-17-5
UNII: BO9LE4QFZF
InChIKey: XNKLLVCARDGLGL-JGVFFNPUSA-N

Note

  • A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.

Molecular Formula

  • C10-H12-N2-O4

Molecular Weight

  • 224.2148
 

Classification Codes

  • Anti-HIV Agents
  • Anti-Infective Agents
  • Anti-Retroviral Agents
  • Antimetabolites
  • Antiviral
  • Antiviral Agents
  • Enzyme Inhibitors
  • Mutation Data
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Reverse Transcriptase Inhibitors

Names and Synonyms

Name of Substance

  • Stavudine
  • Stavudine [USAN:USP:INN:BAN]

MeSH Heading

  • Stavudine

Synonyms

  • 1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine
  • 2',3'-Didehydro-3'-deoxythymidine
  • 3'-Deoxy-2',3'-didehydrothymidine
  • BMY 27857
  • BMY-27857
  • BRN 0618327
  • d 4T
  • d 4T (nucleoside)
  • d4T
  • Estavudina
  • Estavudina [INN-Spanish]
  • HSDB 7338
  • NSC 163661
  • Sanilvudine
  • Stavudine
  • Stavudinum
  • Stavudinum [INN-Latin]
  • UNII-BO9LE4QFZF
  • Zerit
  • Zerit XR
  • Zerut XR

Systematic Names

  • 2'-Thymidinene, 3'-deoxy-
  • Thymidine, 2',3'-didehydro-3'-deoxy-
  • Thymine, 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)- (7CI,8CI)

Registry Numbers

CAS Registry Number

  • 3056-17-5

FDA UNII

  • BO9LE4QFZF

Other Registry Number

  • 132425-31-1

System Generated Number

  • 0003056175

Structure Descriptors

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

InChIKey

XNKLLVCARDGLGL-JGVFFNPUSA-N

Smiles

Cc1cn(c(=O)[nH]c1=O)[C@H]2C=C[C@H](O2)CO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD intravenous > 1680mg/kg (1680mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
dog LD oral > 2gm/kg (2000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
mouse LD50 intravenous 1gm/kg (1000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
mouse LD50 oral 1gm/kg (1000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
rat LD50 intravenous > 1200mg/kg (1200mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.
rat LD50 oral 4gm/kg (4000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 1944, 1998.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.72 (none)   EXP
Water Solubility 6600 mg/L 25 EST
Vapor Pressure 2.82E-12 mm Hg 25 EST
Henry's Law Constant 2.31E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.21E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.