AntibioticMech

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

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:51659 CHEBI:51659
• CHEBI:60783 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

Equivalent identifiers for this same structure in other resources.

• cas:3056-17-5
• drugbank:DB00649
• drugcentral:2478
• kegg.compound:C07312
• kegg.drug:D00445
• lincs.smallmolecule:LSM-5983
• patent:EP334368
• patent:US5130421
• reaxys:618327
• wikipedia.en:Stavudine

Activity roles

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

• CHEBI:22587 CHEBI:22587
• CHEBI:59897 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

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

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