loading...| Preferred Name |
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|
| Synonyms |
2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine Fludara Fludarabine 5'-monophosphate FAMP Fludarabine monophosphate 2-Fluoro-ARA AMP 9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate 2F-ara-AMP 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate) 2-Fluoroadenine arabinoside 5'-monophosphate 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate |
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| Definitions |
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. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_63599 |
|
| charge |
0 |
|
| database_cross_reference |
KEGG DRUG:D01907 "KEGG DRUG" CiteXplore:20686506 "PubMed citation" CiteXplore:21725721 "PubMed citation" CiteXplore:19567212 "PubMed citation" CiteXplore:20514405 "PubMed citation" ChemIDplus:75607-67-9 "CAS Registry Number" CiteXplore:19862681 "PubMed citation" MeSH:C042382 KEGG DRUG:75607-67-9 "CAS Registry Number" CiteXplore:21909959 "PubMed citation" CiteXplore:21296675 "PubMed citation" Patent:WO2010046917 "Patent" SNOMEDCT:108765002 Reaxys:8167686 "Reaxys Registry Number" Wikipedia:Fludarabine "Wikipedia" CiteXplore:19915381 "PubMed citation" DrugBank:DB01073 "DrugBank" Patent:WO2010133629 "Patent" CiteXplore:21736869 "PubMed citation" CiteXplore:19283354 "PubMed citation" CiteXplore:20215092 "PubMed citation" CiteXplore:20467451 "PubMed citation" NCIt:C1102 PMID:20686506 PMID:19283354 PMID:21909959 PMID:21296675 PMID:8204523 PMID:8651523 PMID:19567212 PMID:10720130 PMID:20215092 Reaxys:8167686 Patent:WO2010046917 Patent:WO2010133629 PMID:21736869 Wikipedia:Fludarabine PMID:21725721 CAS:75607-67-9 KEGG:D01907 PMID:20514405 PMID:19862681 DrugBank:DB01073 PMID:19915381 PMID:8528057 Drug_Central:1189 PMID:20467451 |
|
| definition |
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. |
|
| formula |
C10H13FN5O7P |
|
| has_alternative_id |
CHEBI:31616 |
|
| has_exact_synonym |
2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
Fludara Fludarabine 5'-monophosphate FAMP Fludarabine monophosphate 2-Fluoro-ARA AMP 9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate 2F-ara-AMP 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate) 2-Fluoroadenine arabinoside 5'-monophosphate 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate |
|
| has_role |
http://purl.obolibrary.org/obo/CHEBI_35705 http://purl.obolibrary.org/obo/CHEBI_35610 http://purl.obolibrary.org/obo/CHEBI_35221 |
|
| id |
CHEBI:63599 |
|
| in_subset | ||
| 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 |
|
| inchikey |
GIUYCYHIANZCFB-FJFJXFQQSA-N |
|
| label |
fludarabine phosphate |
|
| mass |
365.21170 |
|
| monoisotopicmass |
365.05366 |
|
| notation |
CHEBI:63599 |
|
| smiles |
Nc1nc(F)nc2n(cnc12)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O |
|
| subClassOf |
http://www.ebi.ac.uk/efo/EFO_0004415 |