fludarabine phosphate

CHEBI:63599 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Once incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used for the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to, or whose disease has progressed during, treatment with at least one standard alkylating-agent containing regimenas. — 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:37143
Label unavailable CHEBI:37514
Label unavailable CHEBI:60783

Chemical structure

Computed structure properties
Molecular formula	C10H13FN5O7P
Charge	0
Average mass	365.214 Da
Monoisotopic mass	365.05366 Da
Source	ChEBI
InChIKey	GIUYCYHIANZCFB-FJFJXFQQSA-N

SMILES

Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O

InChI

InChI=1S/C10H13FN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6+,9-/m1/s1

Also called

Fludara (BRAND_NAME)— chebi
2-fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amine (EXACT_SYNONYM)— chebi
2-Fluoro-ARA AMP (EXACT_SYNONYM)— chebi
2-Fluoroadenine arabinoside 5'-monophosphate (EXACT_SYNONYM)— chebi
2F-ara-AMP (EXACT_SYNONYM)— chebi
9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate (EXACT_SYNONYM)— chebi
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate) (EXACT_SYNONYM)— chebi
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate (EXACT_SYNONYM)— chebi
FAMP (EXACT_SYNONYM)— chebi
Fludarabine 5'-monophosphate (EXACT_SYNONYM)— chebi
Fludarabine monophosphate (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.

cas:75607-67-9
reaxys:8167686

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

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:63599`	fludarabine phosphate	`antibioticmech:chebi-2e091683c4`	2026-08-30

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:59517 (DNA synthesis 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

Provenance

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

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