Structure via PubChem · Public domain (PubChem)
fludarabine phosphate
Sign in to saveAlso known as Oforta, Fludarabine 5'-monophosphate, Fludarabine monophosphate, 2-Fluoro-ara AMP, 2F-Ara-AMP, 2-Fluoroadenine arabinoside 5'-monophosphate, 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)
Chemical data
- Formula
- C10H13FN5O7P
- Molecular weight
- 365.21 g/mol
- IUPAC name
- [(2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- SMILES
- C1=NC2=C(N=C(N=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)F)N
- InChIKey
- GIUYCYHIANZCFB-FJFJXFQQSA-N
- XLogP
- -3.1
- Polar surface area
- 186 Ų
- H-bond donors
- 5
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1991
- Admin. routes
- oral, parenteral
- Indications
- chronic lymphocytic leukemia, lymphoma, acute myeloid leukemia, neoplasm
via ChEMBL · EBI
Research
291 papers- Fludarabine phosphate: a synthetic purine antimetabolite with significant activity against lymphoid malignancies.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 1991
- Fludarabine phosphate in the treatment of chronic lymphocytic leukemia: biology, clinical impact, and future directions.Cancer treatment and research · 1993
- Fludarabine phosphate. A new anticancer drug with significant activity in patients with chronic lymphocytic leukemia and in patients with lymphoma.Investigational new drugs · 1994
- Fludarabine phosphate (Fludara).Journal of pediatric oncology nursing : official journal of the Association of Pediatric Oncology Nurses · 1992
- Fludarabine phosphate in the treatment of chronic lymphocytic leukemia.Seminars in oncology · 1990
via PubMed
Wikidata facts
- Mass
- 365.054
- Has use
- medication
Show 6 more facts
- chemical formula
- C₁₀H₁₃FN₅O₇P
- isomeric SMILES
- C1=NC2=C(N1[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N=C(N=C2N)F
- canonical SMILES
- C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)O)O)O)N=C(N=C2N)F
- subject has role
- essential medicine
- Commons category
- Fludarabine
- legal status (medicine)
- boxed warning
Sources (6)
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- History
- Names
- References
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. These include chronic lymphocytic leukemia, non-Hodgkin's lymphoma, acute myeloid leukemia, and acute lymphocytic leukemia. It is given by injection into a vein or by mouth.
Common side effects include nausea, diarrhea, fever, rash, shortness of breath, numbness, vision changes, and feeling tired. Severe side effects include brain dysfunction, low blood cell counts, and lung inflammation. Use in pregnancy will likely result in harm to the fetus. Fludarabine is in the purine analog family of medications and works by interfering with the duplication of DNA.
Excerpted from Wikipedia’s “fludarabine phosphate” article, available under the CC BY-SA 4.0 licence.