CHEBI:63581 - stavudine

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ChEBI Name stavudine
ChEBI ID CHEBI:63581
Definition A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:9253
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Formula C10H12N2O4
Net Charge 0
Average Mass 224.21330
Monoisotopic Mass 224.07971
InChI 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@@H]2O[C@H](CO)C=C2)c(=O)[nH]c1=O
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
estavudina DrugBank
stavudine KEGG DRUG
stavudinum DrugBank
Synonyms Sources
1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine ChemIDplus
2',3'-Didehydro-3'-deoxythimidine KEGG COMPOUND
3'-Deoxy-2'-thymidinene DrugBank
d4T KEGG COMPOUND
Sanilvudine KEGG COMPOUND
Stavudine KEGG COMPOUND
STV DrugBank
Manual Xrefs Databases
2478 DrugCentral
C07312 KEGG COMPOUND
D00445 KEGG DRUG
DB00649 DrugBank
EP334368 Patent
LSM-5983 LINCS
Stavudine Wikipedia
US5130421 Patent
View more database links
Registry Numbers Types Sources
3056-17-5 CAS Registry Number KEGG COMPOUND
3056-17-5 CAS Registry Number ChemIDplus
618327 Reaxys Registry Number Reaxys
Last Modified
22 February 2017