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Cytarabine

Catalog No. DB00987 Name DrugBank
CAS Number 147-94-4 Website http://www.ualberta.ca/
M. F. C9H13N3O5 Telephone (780) 492-3111
M. W. 243.21662 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 861

SYNONYMS

IUPAC name
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
IUPAC Traditional name
cytarabine
Brand Name
Depocyt
Udicil
Arabitin
Cytosar-U
AR3
Alexan
Arafcyt
Cytarbel
Cytosar
Depocyt (liposomal)
Erpalfa
Iretin
Spongocytidine
Tarabine
Synonyms
Beta-cytosine arabinoside
Aracytidine
Ara-C
Arabinofuranosylcytosine
Arabinocytidine
AraC
Aracytine
Cytarabinoside
Cytosine beta-D-arabinoside
Cytosine arabinose
Cytosine, beta-D-arabinoside
Cytosine-beta-arabinoside
Cytosine-beta-D-arabinofuranoside
cytarabine liposome injection
Arabinosylcytosine
Aracytin
beta-Arabinosylcytosine
beta-D-Arabinosylcytosine
Citarabina [INN-Spanish]
Cytarabina
Cytarabin
Cytarabinum [INN-Latin]
Cytosine 1-beta-D-arabinofuranoside
Cytosine arabinoside
Cytosine arabinofuranoside
Cytosine-1-beta-D-arabinofuranoside

DATABASE IDS

PubChem SID 46505879
CAS Number 147-94-4
PubChem CID 6253

PROPERTIES

Hydrophobicity(logP) -2.8
Solubility Freely soluble

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)
Indication For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia.
Pharmacology Cytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Cytarabine is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle.
Toxicity Cytarabine syndrome may develop - it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Less than 20% of the orally administered dose is absorbed from the gastrointestinal tract.
Half Life 10 minutes
Protein Binding 13%
Elimination The primary route of elimination of cytarabine is metabolism to the inactive compound ara-U, followed by urinary excretion of ara-U.
External Links
Wikipedia
RxList
Drugs.com

REFERENCES