stavudine

CHEBI:63581 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:51659
Label unavailable CHEBI:60783

Chemical structure

Computed structure properties
Molecular formula	C10H12N2O4
Charge	0
Average mass	224.216 Da
Monoisotopic mass	224.07971 Da
Source	ChEBI
InChIKey	XNKLLVCARDGLGL-JGVFFNPUSA-N

SMILES

Cc1cn([C@H]2C=C[C@@H](CO)O2)c(=O)nc1=O

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

Also called

estavudina (INN)— chebi
stavudinum (INN)— chebi
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (EXACT_SYNONYM)— chebi
1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine (EXACT_SYNONYM)— chebi
2',3'-Didehydro-3'-deoxythimidine (EXACT_SYNONYM)— chebi
3'-Deoxy-2'-thymidinene (EXACT_SYNONYM)— chebi
STV (EXACT_SYNONYM)— chebi
Sanilvudine (EXACT_SYNONYM)— chebi
Stavudine (EXACT_SYNONYM)— chebi
d4T (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antiviral agent CHEBI:22587
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor CHEBI:59897

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:63581`	stavudine	`antibioticmech:chebi-b4d69f4518`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION host shared target — Assigned from ChEBI role CHEBI:59897 (EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.
Clinical status: APPROVED

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-28 · seed_from_sources
Re-seeded; changed: genotype_resistance_score_rules (HIVDB_HIVFACTS be1c11a5145fea9073fdb71801919d4a34265336). Upstream retrieval date 2026-08-30, unchanged.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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