Fludarabine is a purine analogue and antineoplastic agent. It is generally used as its 5-O-phosphorylated form known as fludarabine phosphate,
sold under the brand name Fludara among others. It is a chemotherapy medication used in the treatment of leukemia and lymphoma.[3] These include chronic lymphocytic leukemia, non-Hodgkin's lymphoma, acute myeloid leukemia, and acute lymphocytic leukemia.[3] It is given by injection into a vein or by mouth.[3]
Quick Facts Clinical data, Trade names ...
Fludarabine |
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Trade names | Fludara, others |
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AHFS/Drugs.com | Monograph |
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MedlinePlus | a692003 |
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Routes of administration | Intravenous, by mouth |
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Bioavailability | 55% |
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Protein binding | 19 to 29% |
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Elimination half-life | 20 hours |
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Excretion | Kidney |
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(2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
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CAS Number | |
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CompTox Dashboard (EPA) | |
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ECHA InfoCard | 100.123.703 |
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Formula | C10H12FN5O4 |
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Molar mass | 285.235 g·mol−1 |
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3D model (JSmol) | |
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Fc1nc(c2ncn(c2n1)[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)CO)N
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InChI=1S/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-/m1/s1 YKey:HBUBKKRHXORPQB-FJFJXFQQSA-N Y
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Common side effects include nausea, diarrhea, fever, rash, shortness of breath, numbness, vision changes, and feeling tired.[3] Severe side effects include brain dysfunction, low blood cell counts, and lung inflammation.[3] Use in pregnancy will likely result in harm to the fetus.[3] Fludarabine is in the purine analog family of medications and works by interfering with the duplication of DNA.[3][4]
Fludarabine was approved for medical use in the United States in 1991.[3] It is on the World Health Organization's List of Essential Medicines.[5]
Fludarabine is a purine analog, and can be given both orally and intravenously. Fludarabine inhibits DNA synthesis by interfering with ribonucleotide reductase and DNA polymerase. It is active against both dividing and resting cells. Being phosphorylated, fludarabine is ionized at physiologic pH and is effectually trapped in blood. This provides some level of specificity for blood cells, both cancerous and healthy.
Fludarabine is generally administered as its 5-O-phosphorylated form known as fludarabine phosphate, which is rapidly dephosphorylated to fludarabine in the plasma.
World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. Gonzalez H, Leblond V, Azar N, Sutton L, Gabarre J, Binet JL, et al. (June 1998). "Severe autoimmune hemolytic anemia in eight patients treated with fludarabine". Hematology and Cell Therapy. 40 (3): 113–118. PMID 9698219. Sneader W (2005). Drug discovery: a history. New York: Wiley. p. 258. ISBN 0-471-89979-8.