Cytarabine

Cytarabine, also known as cytosine arabinoside (ara-C), is a chemotherapy medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and non-Hodgkin's lymphoma. It is given by injection into a vein, under the skin, or into the cerebrospinal fluid. There is a liposomal formulation for which there is tentative evidence of better outcomes in lymphoma involving the meninges.

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Cytarabine
Clinical data
Trade namesCytosar-U, Depocyt, others
AHFS/Drugs.comMonograph
MedlinePlusa682222
Pregnancy
category
  • AU: D
Routes of
administration		injectable (intravenous injection or infusion, intrathecal, or subcutaneously)
ATC code
Legal status
Legal status
  • US: WARNING
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20% by mouth
Protein binding13%
MetabolismLiver
Elimination half-lifebiphasic: 10 min, 1–3 hr
ExcretionKidney
Identifiers
  • 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5- (hydroxymethyl)oxolan-2-yl] pyrimidin-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.005.188
Chemical and physical data
FormulaC9H13N3O5
Molar mass243.219 g·mol−1
3D model (JSmol)
SMILES
  • O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@@H]2O)CO
  • InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1 Y
  • Key:UHDGCWIWMRVCDJ-CCXZUQQUSA-N Y
  (verify)

Common side effects include bone marrow suppression, vomiting, diarrhea, liver problems, rash, ulcer formation in the mouth, and bleeding. Other serious side effects include loss of consciousness, lung disease, and allergic reactions. Use during pregnancy may harm the baby. Cytarabine is in the antimetabolite and nucleoside analog families of medication. It works by blocking the function of DNA polymerase.

Cytarabine was patented in 1960 and approved for medical use in 1969. It is on the World Health Organization's List of Essential Medicines.

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