AntibioticMech

cytarabine

CHEBI:28680 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A pyrimidine nucleoside in which cytosine is attached to D-arabinofuranose via a β-N1-glycosidic bond. Used mainly in the treatment of leukaemia, especially acute non-lymphoblastic leukaemia, cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. It also has antiviral and immunosuppressant properties. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:26440 CHEBI:26440
• CHEBI:38315 CHEBI:38315
• CHEBI:63367 CHEBI:63367

Chemical structure

Computed structure properties

Molecular formula	C9H13N3O5
Charge	0
Average mass	243.219 Da
Monoisotopic mass	243.08552 Da
Source	ChEBI
InChIKey	UHDGCWIWMRVCDJ-CCXZUQQUSA-N

SMILES

Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1

InChI

InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1

Also called

• citarabina (INN)— chebi
• cytarabinum (INN)— chebi
• 4-amino-1-β-D-arabinofuranosylpyrimidin-2(1H)-one (EXACT_SYNONYM)— chebi
• 1-beta-D-Arabinofuranosylcytosine (EXACT_SYNONYM)— chebi
• 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone (EXACT_SYNONYM)— chebi
• Arabinoside C (EXACT_SYNONYM)— chebi
• Cytarabine (EXACT_SYNONYM)— chebi
• Cytosine arabinoside (EXACT_SYNONYM)— chebi
• Cytosine-1-beta-D-arabinofuranoside (EXACT_SYNONYM)— chebi
• ara-C (EXACT_SYNONYM)— chebi
• arabinocytosine (EXACT_SYNONYM)— chebi
• cytosine-β-D-arabinofuranoside (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:147-94-4
• drugbank:DB00987
• drugcentral:770
• hmdb:HMDB0015122
• kegg.compound:C02961
• kegg.drug:D00168
• lincs.smallmolecule:LSM-5470
• pdb-ccd:AR3
• reaxys:89175
• wikipedia.en:Cytarabine

Activity roles

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

• CHEBI:22587 CHEBI:22587

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:28680	cytarabine	antibioticmech:chebi-c0f393ff1a	2026-08-30

Mechanism summary

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.