基本情報
- 標準SMILES
Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O- InChIKey
GIUYCYHIANZCFB-FJFJXFQQSA-N- 分子式
- C10H13FN5O7P
- 平均分子量
- 365.21 g/mol
- 単同位体質量
- 365.05366261
概要
Fludarabine phosphate is 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. It has a role as an antiviral agent, an antimetabolite, an antineoplastic agent, an immunosuppressive agent, a prodrug and a DNA synthesis inhibitor. It is an organofluorine compound, a purine arabinonucleoside monophosphate and a nucleoside analogue. It is functionally related to a 2-fluoroadenine.
名称と識別子
- 優先名称
- Fludarabine Phosphate
- IUPAC
- [(2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
名称と別名
名称をさらに表示
データベース識別子
- CAS
75607-67-9- PubChem CID
- 30751
- DTXSID
DTXSID2023060- ChEMBL
CHEMBL1096882- ChEBI
CHEBI:63599- UNII
- 1X9VK9O1SC
- EC Number
- 616-242-0
- Nikkaji
- J535.382C
物性
構造計算による物性
- XLogP
- -3.1
- 極性表面積
- 186 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 12
- 回転可能結合数
- 4
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 514
実験および物理化学的性質
Solubility
2.97e+00 g/L
Water 9.2 (mg/mL)
pH 4 buffer 27.6 (mg/mL)
pH 9 buffer 57 (mg/mL)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
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).
安全と法規制
GHS分類
GHS Classification
Danger
H341 (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.
危険有害性情報
毒性情報
Toxicity Summary
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.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Fludarabine phosphate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
化学と産業
薬理情報
FDA Pharmacological Classification
FLUDARABINE PHOSPHATE
Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]
MeSH Pharmacological Classification
Antimetabolites that are useful in cancer chemotherapy.
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
用途と製造
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