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

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:26440
Label unavailable CHEBI:38315
Label unavailable 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

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.

wikipedia.en:Cytarabine

Activity roles

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

antiviral agent 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

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

Provenance

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

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