9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate
5-Monophosphate · ludarabine phosphate · Fludarabine phosphate 75607-67-9 · FAMP · Fludura · F-ara-AMP · -F-ara-AMP · 2-fluoro-araamp
Identifikatoren & physikalische Daten
| CAS No. | 75607-67-9 |
|---|---|
| Summenformel | C10H13FN5O7P |
| Durchschnittliche Molmasse | 365,21 g/mol |
| Monoisotopische Masse | 365,05366293 g/mol |
| SMILES | Nc1nc(F)nc2c1ncn2C1OC(COP(=O)(O)O)C(O)C1O |
| InChIKey | GIUYCYHIANZCFB-UHFFFAOYSA-N |
| PubChem CID | 3368 |
| ChEMBL | CHEMBL1965242 |
Chemische & physikalische Eigenschaften
| 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 |
| Schmelzpunkt | 203°C(dec.)(lit.) |
| Siedepunkt | 864.2±75.0 °C(Predicted) |
| Dichte | 2.39±0.1 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO: soluble1mg/mLSoluble in DMSO or water at 5mg/ml |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 1.86±0.10(Predicted) |
| Farbe | white |
| Merck | 14,4126 |
| Stabilität | 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 |
| CAS Datenbank | 75607-67-9(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| Zollcode | 2934990002 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Muta. 2Repr. 2 |
Anwendungen & Verwendung
Beschreibung
Fludarabine 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.
Verwenden
Fludarabine 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.