CHEBI:63581 - stavudine

ChEBI IDCHEBI:63581
ChEBI Namestavudine
Stars
DefinitionA nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase
Secondary ChEBI IDCHEBI:9253
Last Modified22 February 2017
DownloadsMolfile
FormulaC10H12N2O4
Net Charge0
Average Mass224.216
Monoisotopic Mass224.07971
SMILESCc1cn([C@H]2C=C[C@@H](CO)O2)c(=O)nc1=O
InChIInChI=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
InChIKeyXNKLLVCARDGLGL-JGVFFNPUSA-N
Wikipedia
Roles Classification
Biological Roles:
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor  A DNA polymerase inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need in order to reproduce.
antiviral agent  A substance that destroys or inhibits replication of viruses.
ChEBI Ontology
Outgoing Relation(s)
stavudine (CHEBI:63581) has functional parent thymine (CHEBI:17821)
stavudine (CHEBI:63581) has role antimetabolite (CHEBI:35221)
stavudine (CHEBI:63581) has role antiviral agent (CHEBI:22587)
stavudine (CHEBI:63581) has role EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor (CHEBI:59897)
stavudine (CHEBI:63581) is a dihydrofuran (CHEBI:51659)
stavudine (CHEBI:63581) is a nucleoside analogue (CHEBI:60783)
stavudine (CHEBI:63581) is a organic molecular entity (CHEBI:50860)
IUPAC Name 
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
INNs  Source
estavudinaDrugBank
stavudineKEGG DRUG
stavudinumDrugBank
Synonyms  Source
1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymineChemIDplus
2',3'-Didehydro-3'-deoxythimidineKEGG COMPOUND
3'-Deoxy-2'-thymidineneDrugBank
d4TKEGG COMPOUND
SanilvudineKEGG COMPOUND
StavudineKEGG COMPOUND
Manual XrefsDatabases
2478DrugCentral
C07312KEGG COMPOUND
D00445KEGG DRUG
DB00649DrugBank
EP334368Patent
LSM-5983LINCS
StavudineWikipedia
US5130421Patent
Registry NumbersSources
Reaxys:618327Reaxys
CAS:3056-17-5KEGG COMPOUND
CAS:3056-17-5ChemIDplus