Cytarabine

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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[1]
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N3O5
Molar mass243.219 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:UHDGCWIWMRVCDJ-CCXZUQQUSA-N checkY
  (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.[2] It is given by injection into a vein, under the skin, or into the cerebrospinal fluid.[2] There is a liposomal formulation for which there is tentative evidence of better outcomes in lymphoma involving the meninges.[2]

Common side effects include bone marrow suppression, vomiting, diarrhea, liver problems, rash, ulcer formation in the mouth, and bleeding.[2] Other serious side effects include loss of consciousness, lung disease, and allergic reactions.[2] Use during pregnancy may harm the baby.[2] Cytarabine is in the antimetabolite and nucleoside analog families of medication.[3] It works by blocking the function of DNA polymerase.[2]

Cytarabine was patented in 1960 and approved for medical use in 1969.[4] 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. ^ 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.
  3. ^ British national formulary: BNF 69 (69 ed.). British Medical Association. 2015. p. 589. ISBN 9780857111562.
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495. 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.