You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Database of hazardous chemicals.
Record Information
Version1.0
Creation Date2014-09-11 05:15:56 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003729
Identification
Common NameStavudine
ClassSmall Molecule
DescriptionA dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Anti-HIV Agent
  • Antimetabolite
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Reverse Transcriptase Inhibitor
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymineChEBI
2',3'-Didehydro-3'-deoxythimidineChEBI
3'-Deoxy-2'-thymidineneChEBI
d4TChEBI
EstavudinaChEBI
SanilvudineChEBI
StavudinumChEBI
STVChEBI
ZeritKegg
1-(2,3-Dideoxy-b-D-glycero-pent-2-enofuranosyl)thymineGenerator
1-(2,3-Dideoxy-β-D-glycero-pent-2-enofuranosyl)thymineGenerator
2',3'-Didehydro-2',3'-dideoxythmidineHMDB
2',3' Didehydro 3' deoxythymidineHMDB
2',3'-Didehydro-3'-deoxythymidineHMDB
Bristol-myers squibb brand OF stavudineHMDB
Bristol-myers brand OF stavudineHMDB
Stavudine, monosodium saltHMDB
Chemical FormulaC10H12N2O4
Average Molecular Mass224.213 g/mol
Monoisotopic Mass224.080 g/mol
CAS Registry Number3056-17-5
IUPAC Name1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Namestavudine
SMILESCC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O
InChI IdentifierInChI=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
InChI KeyXNKLLVCARDGLGL-JGVFFNPUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassNot Available
Direct ParentNucleoside and nucleotide analogues
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • Pyrimidine
  • Dihydrofuran
  • Vinylogous amide
  • Heteroaromatic compound
  • Lactam
  • Urea
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point159-160°C
Boiling PointNot Available
Solubility5-10 g/100 mL at 21°C
Predicted Properties
PropertyValueSource
Water Solubility40.5 g/LALOGPS
logP-0.73ALOGPS
logP-0.23ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.87 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.32 m³·mol⁻¹ChemAxon
Polarizability21.33 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-004i-9710000000-ec1b8accee7609d895afView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-0fi9-9710000000-a08eaef1e27e4362b56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-a15778802feedb7e8702View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-5900000000-1e77dd699ba1244d96ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7j-9600000000-42ce2a756eceb750ac46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00c0-2940000000-3e2b43ac1b4b3b11d540View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01di-3920000000-0a634444532bc0df9549View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-5a3e9da67f3d054c39c8View in MoNA
Toxicity Profile
Route of ExposureFollowing oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).
Mechanism of ToxicityStavudine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.
MetabolismPhosphorylated intracellularly to stavudine triphosphate, the active substrate for HIV-reverse transcriptase. Half Life: 0.8-1.5 hours (in adults)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of human immunovirus (HIV) infections.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSide effects include peripheral neuropathy tingling, burning, numbness, or pain in the hands or feet), fatal lactic acidosis has been reported in patients treated with stavudine (ZERIT) in combination with other antiretroviral agents, severe liver enlargement, inflammation (pain and swelling) of the liver, and liver failure.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00649
HMDB IDHMDB0014787
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkStavudine
Chemspider ID17270
ChEBI ID63581
PubChem Compound ID18283
Kegg Compound IDC07312
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Purna Chandra Ray, Jagan Mohana Chary Tummanapalli, Seeta Ramanjaneyulu Gorantla, “Process for the Large Scale Production of Stavudine.” U.S. Patent US20080312428, issued December 18, 2008.

MSDSLink
General ReferencesNot Available