フルダラビン

化学名:フルダラビン

CAS番号.21679-14-1

英語名:Fludarabine

CBNumberCB8188247

MFC10H12FN5O4

MW285.23

MOL File21679-14-1.mol

别名

6-アミノ-2-フルオロ-9-β-D-アラビノフラノシル-9H-プリン

フルダラビン

9-β-D-アラビノフラノシル-2-フルオロ-9H-プリン-6-アミン

フルダラビン物理性質

融点	265-268°C
比旋光度	D25 +17 ±2.5° (c = 0.1 in ethanol)
沸点	747.3±70.0 °C(Predicted)
比重(密度)	2.17±0.1 g/cm3(Predicted)
貯蔵温度	2-8°C
溶解性	DMF：20～mg/mL、透明、微黄色
外見	粉
酸解離定数(Pka)	13.05±0.70(Predicted)
色	白色～淡黄色
水溶解度	DMF、DMSO、メタノール、エタノールに可溶。水に溶けにくい
Merck	13,4152
BRN	1225932
安定性：	-20°C の DMSO 溶液で最大 3 か月間保存できます。
InChI	InChI=1/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/s3
InChIKey	HBUBKKRHXORPQB-VOSPVXAENA-N
SMILES	C12N=C(N=C(N)C=1N=CN2[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1)F \|&1:10,11,13,15,r\|
CAS データベース	21679-14-1(CAS DataBase Reference)

安全性情報

主な危険性	Xn
Rフレーズ	23/24/25-36/37/38-39/23/24/25-39-22
Sフレーズ	26-36/37-45-36
WGK Germany	3
RTECS 番号	AU6207000
F	10
HSコード	29349990
有毒物質データの	21679-14-1(Hazardous Substances Data)

危険有害性情報のコード(GHS)

フルダラビン価格

製品番号	包装	価格	製品説明	購入
富士フイルム和光純薬株式会社(wako) W01MAS076060	1g	￥322000		購入
富士フイルム和光純薬株式会社(wako) W01TRCF425000	50mg	￥37400	フルダラビン	購入
Sigma-Aldrich Japan F2773	5mg	￥24900	2-フルオロアデニン-9-β-D-アラビノフラノシド DNA synthesis and methylation inhibitor	購入
Sigma-Aldrich Japan F2773	10mg	￥44700	2-フルオロアデニン-9-β-D-アラビノフラノシド DNA synthesis and methylation inhibitor	購入
富士フイルム和光純薬株式会社(wako) W01TRCF425000	10mg	￥25800	フルダラビン	購入

MSDS Information

フルダラビン化学特性,用途語,生産方法

外観
白色～ほとんど白色粉末～結晶
効能
抗悪性腫瘍薬, 代謝拮抗薬
化学的特性
White Solid
使用
Fludarabine is not one of the most used drugs in pediatric oncology area. It is used in combination with other drugs to treat AML in children, mostly those who are receiving second-line therapy. It is commonly sold as 10 mg film-coated tablets and IV vial containing 50mg.
適応症
Fludarabine (Fludara) is a fluorinated purine analogue of the antiviral agent vidarabine.The active metabolite, 2-fluoro-ara-adenosine triphosphate, inhibits various enzymes involved in DNA synthesis, including DNA polymerase-α, ribonucleotide reductase, and DNA primase. Unlike most antimetabolites, it is toxic to nonproliferating as well as dividing cells, primarily lymphocytes and lymphoid cancer cells.
The drug is highly active in the treatment of chronic lymphocytic leukemia, with approximately 40% of patients achieving remissions after previous therapy with alkylating agents has failed. Activity is also seen in the low-grade lymphomas.
The major side effect is myelosuppression, which contributes to fevers and infections in as many as half of treated patients. Nausea and vomiting are mild. Occasional neurotoxicity has been noted at higher doses, with agitation, confusion, and visual disturbances.
一般的な説明
The drug is available as the phosphate salt in a 50-mg vialfor IV use. Fludarabine is used to treat chronic lymphocyticleukemia and non-Hodgkin’s lymphoma. The mechanism ofaction involves the triphosphate metabolite and its inhibitionof DNA chain elongation. The 2-fluoro group on the adeninering renders fludarabine resistant to breakdown byadenosine deaminase. The drug is rapidly dephosphorylatedto 2-fluoro-ara-adenosine (F-ara-A) after administration. Fara-A is taken into the cell and subsequently re-phosphorylatedto yield the triphosphate (F-ara-ATP), the active drugspecies. Resistance can occur via decreased expression ofthe activating enzymes and decreased drug transport.Fludarabine is orally bioavailable and is distributed throughoutthe body reaching high levels in liver, kidney, andspleen. The drug is metabolized to F-ara-A, which enterscells via the nucleoside transport system and is rephosphorylatedby deoxycytidine kinase to fludarabine monophosphateand finally fludarabine triphosphate, the activespecies. About 25% of F-ara-A is excreted unchanged inurine. Drug interactions include an increased incidence offatal pulmonary toxicity when fludarabine is used in combinationwith pentostatin. Additionally, fludarabine may potentiate the effects of several other anticancer drugs includingcytarabine, cyclophosphamide, and cisplatin.Toxicities include myelosuppression, immunosuppression,fever, nausea, and vomiting.
生物活性
Purine analog that inhibits DNA synthesis. Exhibits antiproliferative activity (IC 50 = 1.54 μ M in RPMI cells) and triggers apoptosis through increasing Bax and decreasing Bid, XIAP and survivin expression. Displays anticancer activity against hematological malignancies in vivo .
Mode of action
Fludarabine is a fluorinated analogue of adenine that is relatively resistant to deamination by adenosine deaminase. Fludarabine phosphate is a prodrug that is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active metabolite triphosphate 2-fluoro-ara-ATP. Fludarabine inhibits the DNA synthesis via inhibition of ribonucleotide reductase, DNA polymerase (α, δ, and ε), DNA primase, and DNA ligase. The action mechanism also is by partial inhibition of RNA polymerase II, causing reduction in protein synthesis. It is believed that effects on DNA, RNA, and protein synthesis contribute to the inhibition of cell growth, mostly by inhibition of DNA synthesis. Lymphocytes of CLL when exposed, in vitro, to the compound 2-fluoro-ara-A lead to extensive DNA fragmentation and apoptosis.

フルダラビン上流と下流の製品情報

フルダラビン生産企業

フルダラビンスペクトルデータ(¹HNMR)

21679-14-1, フルダラビンキーワード

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フルダラビン

危険有害性情報のコード(GHS)

フルダラビン 価格

MSDS Information

フルダラビン 化学特性,用途語,生産方法

フルダラビン 上流と下流の製品情報

フルダラビン 生産企業

フルダラビン スペクトルデータ(1HNMR)

21679-14-1, フルダラビン キーワード

フルダラビン価格

フルダラビン化学特性,用途語,生産方法

フルダラビン上流と下流の製品情報

フルダラビン生産企業

フルダラビンスペクトルデータ(¹HNMR)

21679-14-1, フルダラビンキーワード