AntibioticMech

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

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:37143 CHEBI:37143
• CHEBI:37514 CHEBI:37514
• CHEBI:60783 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

Equivalent identifiers for this same structure in other resources.

• cas:75607-67-9
• drugbank:DB01073
• drugcentral:1189
• kegg.drug:D01907
• patent:WO2010046917
• patent:WO2010133629
• reaxys:8167686
• wikipedia.en:Fludarabine

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: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

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.