Cytosine arabinoside

Cytarabine
Clinical data


Trade names	Cytosar-U, Depocyt, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682222
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	injectable (intravenous injection or infusion, intrathecal, or subcutaneously)
ATC code	L01BC01 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20% by mouth
Protein binding	13%
Metabolism	liver
Biological half-life	biphasic: 10 min, 1–3 hr
Excretion	kidney
Identifiers
IUPAC name 4-amino-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5- (hydroxymethyl)oxolan-2-yl] pyrimidin-2-one
CAS Number	147-94-4^Y
PubChem CID	6253
IUPHAR/BPS	4827
DrugBank	DB00987^Y
ChemSpider	6017^Y
UNII	04079A1RDZ
KEGG	D00168^Y
ChEBI	CHEBI:28680^Y
ChEMBL	CHEMBL803^Y
PDB ligand	AR3 (PDBe, RCSB PDB)
ECHA InfoCard	100.005.188
Chemical and physical data
Formula	C₉H₁₃N₃O₅
Molar mass	243.217 g/mol
3D model (Jmol)	Interactive image
SMILES O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@@H]2O)CO
InChI 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

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.

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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 4.27 to 5.7 USD per 500 mg vial. This dose in the United Kingdom costs the NHS about 50.00 pounds while the liposomal form is 1,223.75 pounds per 50 mg vial.

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