Basic information
- CAS
75607-67-9- Standard SMILES
Nc1nc(F)nc2c1ncn2C1OC(COP(=O)(O)O)C(O)C1O- InChIKey
GIUYCYHIANZCFB-UHFFFAOYSA-N- Molecular formula
- C10H13FN5O7P
- Average molar mass
- 365.21 g/mol
- Monoisotopic mass
- 365.05366293
Overview
See also: Fludarabine (annotation moved to); Fludarabine Phosphate (annotation moved to).
Names & identifiers
- Preferred name
- 9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate
- IUPAC
- [5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- English name
- Fludarabine phosphate
- Molecular formula
- C10H13FN5O7P
- Molecular weight
- 365.21
Names & synonyms
FAMPC10H13FN5O7PFluduraNSC3128879H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-.beta.-D-arabinofuranosyl)-NSC 328002Fludara (Berlex)Fluclarabine phosphateSCHEMBL1650192Fludarabine Phosphate (Fludara)9-.beta.-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)CHEMBL1965242
Show more names
5-Monophosphateludarabine phosphateFludarabine phosphate 75607-67-9F-ara-AMP-F-ara-AMP2-fluoro-araampfludarabine hclfludara Phosphate
GIUYCYHIANZCFB-UHFFFAOYSA-NHMS3654F05HMS5079I19{[(2R,3S,4R,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acids1229Fludarabine (NSC 118218) Phosphate[5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphateNCI60_002698
Database identifiers
- CAS
75607-67-9
Properties
Computed structural properties
- XLogP
- -3.1
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 514
Physicochemical properties
- Melting point
- 203 °C · 203°C(dec.)(lit.)
- alpha
- 20 · [α]D20 +10～+14゜(c=0.5,H2O)
- Boiling point
- 864.2 · 864.2±75.0 °C(Predicted)
- Density
- 2.39 · 2.39±0.1 g/cm3(Predicted)
- RTECS
- 7440900 · UO7440900
- storage temp.
- 2 · 2-8°C
- solubility
- 1 mg/mL · DMSO: soluble1mg/mL
- form
- Powder
- pka
- 1.86 · 1.86±0.10(Predicted)
- color
- white
- Water Solubility
- 5 mg/ml · Soluble in DMSO or water at 5mg/ml
- Merck
- 14 · 14,4126
- Stability
- Hygroscopic
- 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)
- InChIKey
- GIUYCYHIANZCFB-GFRUICAKSA-N
- SMILES
- Fc1nc2[n](cnc2c(n1)[N+H3])C3OC(C(C3O)O)CO[P](=O)([O-])O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- hs_code
- 2934990002
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H341-H361d
- Hazard Classifications
- Muta. 2Repr. 2
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
Chemistry & industry
Applications
DescriptionFludarabine phosphate is an antimetabolite indicated for the treatment of B cell lymphocytic leukemia. It is reportedly effective in patients refractory to other therapies. Fludarabine phosphate acts by inhibiting primer RNA synthesis. Its side effects include bone marrow suppression, anemia, thrombocytopenia and neutropenia.
UsesFludarabine phosphate is used for the treatment of chronic lymphatic leukemia and low-grade lymphoma. In the circulation,fludarabine phosphate is immediately dephosphorylated to the nucleoside fludarabine. About 30-40% of nucleoside fludarabine is excreted into the urine. In addition, fludarabine is metabolized into a hypoxanthine metabolite also excreted in the urine.Intracellularly,fludarabine is stepwise rephosphorylated to the active triphosphate. Deoxycytidine kinase is the dominant, if not the exclusive,enzyme for the formation of the monophosphate. Adenylate kinase and nucleoside diphosphate kinase are believed to be involved in the formation of the diphosphate and triphosphate,respectively.
Usesanticonvulsant
Upstream & downstream products
Upstream raw materials
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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