Fludarabine (CHEM003693)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2014-09-11 05:14:03 UTC
Update Date2026-03-26 21:33:38 UTC
Accession NumberCHEM003693
Identification
Common NameFludarabine
ClassSmall Molecule
DescriptionFludarabine (marketed as fludarabine phosphate under the trade name Fludara) is a chemotherapy drug used in the treatment of hematological malignancies.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antineoplastic Agent
  • Drug
  • Ether
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Fluoro-ara AMPChEBI
2-Fluoroadenine arabinoside 5'-monophosphateChEBI
2F-Ara-AMPChEBI
9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphateChEBI
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)ChEBI
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphateChEBI
FAMPChEBI
FludaraChEBI
Fludarabine 5'-monophosphateChEBI
Fludarabine monophosphateChEBI
2-Fluoroadenine arabinoside 5'-monophosphoric acidGenerator
9-b-Arabinofuranosyl-2-fluoroadenine-5'-phosphateGenerator
9-b-Arabinofuranosyl-2-fluoroadenine-5'-phosphoric acidGenerator
9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphoric acidGenerator
9-Β-arabinofuranosyl-2-fluoroadenine-5'-phosphateGenerator
9-Β-arabinofuranosyl-2-fluoroadenine-5'-phosphoric acidGenerator
9-b-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)Generator
9-b-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphoric acid)Generator
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphoric acid)Generator
9-Β-D-arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)Generator
9-Β-D-arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphoric acid)Generator
9-b-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphateGenerator
9-b-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphoric acidGenerator
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphoric acidGenerator
9-Β-D-arabinofuranosyl-2-fluoroadenine 5'-monophosphateGenerator
9-Β-D-arabinofuranosyl-2-fluoroadenine 5'-monophosphoric acidGenerator
Fludarabine 5'-monophosphoric acidGenerator
Fludarabine monophosphoric acidGenerator
Fludarabine phosphateHMDB
FaraAMPHMDB
BeneflurHMDB
9 beta-D-Arabinofuranosyl-2-fluoroadenine monophosphateHMDB
F-Ara-AMPHMDB
Fluoro-ara-AMPHMDB
Fludarabine phosphoric acidGenerator
Chemical FormulaC10H13FN5O7P
Average Molecular Mass365.212 g/mol
Monoisotopic Mass365.054 g/mol
CAS Registry Number75607-67-9
IUPAC Name{[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Namefludarabine
SMILESNC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]3O)C2=NC(F)=N1
InChI IdentifierInChI=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
InChI KeyGIUYCYHIANZCFB-FJFJXFQQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Halopyrimidine
  • 2-halopyrimidine
  • Monoalkyl phosphate
  • Imidolactam
  • Alkyl phosphate
  • Aryl fluoride
  • Aryl halide
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organohalogen compound
  • Primary amine
  • Amine
  • Organofluoride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point260°C
Boiling PointNot Available
Solubility3.53 mg/ml
Predicted Properties
PropertyValueSource
Water Solubility2.97 g/LALOGPS
logP-2.5ALOGPS
logP-3.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.34ChemAxon
pKa (Strongest Basic)0.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.93 m³·mol⁻¹ChemAxon
Polarizability28.88 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9623000000-df7fef014b7ed6f138caSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01vk-9412300000-a8e2be4c7ab19ccd3280Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0913000000-80f61b17aa4ad7d3fce9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-e0aa5e8a08f61ff3d3b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0900000000-0bba10c09fa50579ea86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0i29-4409000000-1d1175238eed452b53c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-8900000000-b0d8f9f14834a2ff1f97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-b33283ba6688bd6f3e24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0946000000-3a07161a0ba92c58de3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-aa1b46adc5cdd97f9294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0900000000-19d5fbe69fb7f606a97aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2009000000-acf04284a548ec80568eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9102000000-d93a2baa104d5742de76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-c74fcde8d9f9eae4249bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureBioavailability is 55% following oral administration.
Mechanism of ToxicityFludarabine phosphate is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. This metabolite appears to act by inhibiting DNA polymerase alpha, ribonucleotide reductase and DNA primase, thus inhibiting DNA synthesis. The mechanism of action of this antimetabolite is not completely characterized and may be multi-faceted.
MetabolismHalf Life: 20 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor 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 regimen
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000425
HMDB IDHMDB0015206
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFludarabine
Chemspider ID28532
ChEBI ID63599
PubChem Compound ID30751
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

John G. Bauman, Randolph C. Wirsching, “Process for the preparation of fludarabine or fludarabine phosphate from guanosine.” U.S. Patent US5602246, issued January, 1992.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10720130
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19283354
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19567212
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19862681
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19915381
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20215092
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20467451
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20514405
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20686506
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21296675
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21725721
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21736869
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21909959
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8204523
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=8528057
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=8651523
17. Gonzalez H, Leblond V, Azar N, Sutton L, Gabarre J, Binet JL, Vernant JP, Dighiero G: Severe autoimmune hemolytic anemia in eight patients treated with fludarabine. Hematol Cell Ther. 1998 Jun;40(3):113-8.
18. Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7.
19. Tournilhac O, Cazin B, Lepretre S, Divine M, Maloum K, Delmer A, Grosbois B, Feugier P, Maloisel F, Villard F, Villemagne B, Bastit D, Belhadj K, Azar N, Michallet M, Manhes G, Travade P: Impact of frontline fludarabine and cyclophosphamide combined treatment on peripheral blood stem cell mobilization in B-cell chronic lymphocytic leukemia. Blood. 2004 Jan 1;103(1):363-5. Epub 2003 Sep 11.