Fludarabine Phosphate

Identifikatoren & physikalische Daten

CAS No.	75607-67-9
Summenformel	C10H13FN5O7P
Durchschnittliche Molmasse	365,21 g/mol
Monoisotopische Masse	365,05366261 g/mol
SMILES	Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O
InChIKey	GIUYCYHIANZCFB-FJFJXFQQSA-N
PubChem CID	30751
ChEMBL	CHEMBL1096882
ChEBI	CHEBI:63599
EC No.	616-242-0
DTXSID	DTXSID2023060

XLogP	-3,1
Polarare Oberfläche (TPSA)	186
H-Brücken-Donoren	5
H-Brücken-Akzeptoren	12
Frei drehbare Bindungen	4
Schwere Atome	24
Formalladung	0
Komplexität	514
LogP (Verteilungskoeffizient)	-2.8
Löslichkeit	2.97e+00 g/LWater 9.2 (mg/mL)pH 4 buffer 27.6 (mg/mL)pH 9 buffer 57 (mg/mL)
Human Drugs	FDA approved drugs -> Active ingredient
Schmelzpunkt	260 °C
Optical Rotation	(c = 0.5, H2O) [a]21D = 12 ± 2°
Physical Description	Solid
Stability/Shelf Life	Bulk: Based on HPLC analysis, the sample is stable for at least one month when stored as the bulk chemical at room temperature and 60 °C. Solution: A 2 mg/mL aqueous solution is stable for at least 48 hours at room temperature and laboratory illumination (HPLC).
Collision Cross Section	168.8 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]

GHS-Einstufung	DangerH341 (97.6%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]P203, P260, P264, P270, P280, P318, P319, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 82 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard Classes and Categories	Muta. 2 (97.6%)
Expositionspfade	Bioavailability is 55% following oral administration.
Toxizitätsübersicht	Fludarabine 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.
Carcinogen Classification	No indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury	Drug Induced Liver Injury Rank (DILIrank 2.0)Fludarabine phosphatevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015
Toxicity Data	Mouse(iv): LD50: 1236 mg/kg