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Fludarabine information


Fludarabine
Clinical data
Trade namesFludara, others
AHFS/Drugs.comMonograph
MedlinePlusa692003
Routes of
administration
Intravenous, by mouth
ATC code
  • L01BB05 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only[2]
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only
Pharmacokinetic data
Bioavailability55%
Protein binding19 to 29%
Elimination half-life20 hours
ExcretionKidney
Identifiers
IUPAC name
  • (2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CAS Number
  • 21679-14-1 ☒N
PubChem CID
  • 657237
IUPHAR/BPS
  • 4802
DrugBank
  • DB01073 checkY
ChemSpider
  • 571392 checkY
UNII
  • P2K93U8740
KEGG
  • D01907 checkY
ChEBI
  • CHEBI:63599 ☒N
ChEMBL
  • ChEMBL1568 checkY
CompTox Dashboard (EPA)
  • DTXSID2023060 Edit this at Wikidata
ECHA InfoCard100.123.703 Edit this at Wikidata
Chemical and physical data
FormulaC10H12FN5O4
Molar mass285.235 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • Fc1nc(c2ncn(c2n1)[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)CO)N
InChI
  • 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 checkY
  • Key:HBUBKKRHXORPQB-FJFJXFQQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

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]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
  3. ^ a b c d e f g h "Fludarabine Phosphate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  4. ^ Helms RA, Quan DJ (2006). Textbook of Therapeutics: Drug and Disease Management. Lippincott Williams & Wilkins. p. 2309. ISBN 9780781757348. Archived from the original on 2016-12-20.
  5. ^ 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.

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Fludarabine

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Fludarabine is a purine analogue and antineoplastic agent. It is generally used as its 5-O-phosphorylated form known as fludarabine phosphate, sold under...

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Chronic lymphocytic leukemia

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survival than single agents: FC (fludarabine with cyclophosphamide) FR (fludarabine with rituximab) FCR (fludarabine, cyclophosphamide, and rituximab)...

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Purine analogue

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are used primarily to treat hairy cell leukemia. Nucleotide analogues Fludarabine inhibits multiple DNA polymerases, DNA primase, and DNA ligase I, and...

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Leukemia

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Hensel M, Steinbrecher C, et al. (February 2006). "Fludarabine plus cyclophosphamide versus fludarabine alone in first-line therapy of younger patients with...

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Treosulfan

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healthy blood cells. It is used together with another medicine called fludarabine in adults and children from one month of age with blood cancers as well...

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Lumiliximab

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et al. (January 2010). "Phase 1/2 study of lumiliximab combined with fludarabine, cyclophosphamide, and rituximab in patients with relapsed or refractory...

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MALT lymphoma

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not to be active in t(11;18) disease. The purine nucleoside analogs fludarabine and cladribine also demonstrate activity, the latter conferring a CR...

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Encephalopathy

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recessive neonatal encephalopathy. Chemotherapy medication, for example, fludarabine can cause a permanent severe global encephalopathy. Ifosfamide can cause...

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Sanofi

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(Sodium ferric gluconate complex), for iron deficiency anemia. Fludara (Fludarabine), for leukemia. Mozobil (Plerixafor), for macrocycle, approved by the...

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Antimetabolite

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6-Mercaptopurine (6-MP) Capecitabine (Xeloda®) Cytarabine (Ara-C®) Floxuridine Fludarabine Gemcitabine (Gemzar®) Hydroxycarbamide Methotrexate Pemetrexed (Alimta®)...

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Alemtuzumab

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people who have been treated with alkylating agents and who have failed fludarabine therapy. It is an unconjugated antibody, thought to work via the activation...

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Chemotherapy regimen

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cancer FCM or FMC fludarabine, cyclophosphamide, mitoxantrone B cell non-Hodgkin lymphoma FCM-R or R-FCM or R-FMC or FMC-R fludarabine, cyclophosphamide...

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List of antileukemic drugs

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Cyclophosphamide Cytosine arabinoside Dasatinib Daunorubicin Decitabine Etoposide Fludarabine Gemtuzumab ozogamicin Idarubicin Imatinib mesylate Interferon-α Interleukin-2...

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Busulfan

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used in pediatrics and adults in combination with cyclophosphamide or fludarabine/clofarabine as a conditioning agent prior to bone marrow transplantation...

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Chemotherapy

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analogues include cytarabine, gemcitabine, decitabine, azacitidine, fludarabine, nelarabine, cladribine, clofarabine, and pentostatin. The thiopurines...

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Tretinoin

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Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine# Tioguanine#) Pyrimidine Thymidylate...

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Methotrexate

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Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine# Tioguanine#) Pyrimidine Thymidylate...

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Chlorambucil

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tolerated by most patients, though chlorambucil has been largely replaced by fludarabine as first-line treatment in younger patients. It can be used for treating...

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Parvovirus B19

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to persistent parvovirus B19 infection after immunochemotherapy with fludarabine/cyclophosphamide and rituximab for relapsed B cell lymphoma". Haematologica...

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Cancer immunotherapy

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anti-CD52 humanized IgG1 monoclonal antibody indicated for the treatment of fludarabine-refractory chronic lymphocytic leukemia (CLL), cutaneous T-cell lymphoma...

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Arabinosyl nucleoside

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used as cytostatics or virostatics. Cytarabine Vidarabine Nelarabine Fludarabine Clofarabine Sorivudine Clevudine Cohen, Seymour S. (1966). Introduction...

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Nitrogen mustard

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Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine# Tioguanine#) Pyrimidine Thymidylate...

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Bendamustine

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sole therapy and in combination with other agents including etoposide, fludarabine, mitoxantrone, methotrexate, prednisone, rituximab, vincristine and 90Y-ibritumomab...

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Ibrutinib

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open-label, actively controlled trial of ibrutinib with rituximab compared to fludarabine, cyclophosphamide, and rituximab (FCR) in 529 adult subjects 70 years...

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Fluorouracil

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Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine# Tioguanine#) Pyrimidine Thymidylate...

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Hydroxycarbamide

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Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine# Tioguanine#) Pyrimidine Thymidylate...

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Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine# Tioguanine#) Pyrimidine Thymidylate...

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