Cytarabine

Cytarabine
Clinical data
Trade names	Cytosar-U, Depocyt, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682222
Pregnancy; category	AU: D;
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
Elimination half-life	biphasic: 10 min, 1–3 hr
Excretion	Kidney
Identifiers
	IUPAC name 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5- (hydroxymethyl)oxolan-2-yl] pyrimidin-2-one;
CAS Number	147-94-4 ;
PubChem CID	6253;
IUPHAR/BPS	4827;
DrugBank	DB00987 ;
ChemSpider	6017 ;
UNII	04079A1RDZ;
KEGG	D00168 ;
ChEBI	CHEBI:28680 ;
ChEMBL	ChEMBL803 ;
PDB ligand	AR3 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3022877 ;
ECHA InfoCard	100.005.188
Chemical and physical data
Formula	C9H13N3O5
Molar mass	243.219 g·mol−1
3D model (JSmol)	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 ; Key:UHDGCWIWMRVCDJ-CCXZUQQUSA-N ;
	(verify)

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.^[1] It is given by injection into a vein, under the skin, or into the cerebrospinal fluid.^[1] There is a liposomal formulation for which there is tentative evidence of better outcomes in lymphoma involving the meninges.^[1]

Common side effects include bone marrow suppression, vomiting, diarrhea, liver problems, rash, ulcer formation in the mouth, and bleeding.^[1] Other serious side effects include loss of consciousness, lung disease, and allergic reactions.^[1] Use during pregnancy may harm the baby.^[1] Cytarabine is in the antimetabolite and nucleoside analog families of medication.^[2] It works by blocking the function of DNA polymerase.^[1]

Cytarabine was patented in 1960 and approved for medical use in 1969.^[3] It is on the World Health Organization's List of Essential Medicines.^[4]

^ ^a ^b ^c ^d ^e ^f ^g "Cytarabine". The American Society of Health-System Pharmacists. Archived from the original on 11 June 2016. Retrieved 8 December 2016.
^ British national formulary: BNF 69 (69 ed.). British Medical Association. 2015. p. 589. ISBN 9780857111562.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495. Archived from the original on 2016-12-20.
^ 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.