Structure via PubChem · Public domain (PubChem)
cytarabine
Sign in to saveAlso known as Cytosar®, DepoCyte®, U-19920, 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone, 1-beta-D-Arabinofuranosylcytosine, cytosine-beta-D-arabinofuranoside, cytosine arabinoside
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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 460111587
- Drug.image
- Cytarabin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Cytarabine ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Cytosar-U, Depocyt, others
- Drug.MedlinePlus
- a682222
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- injectable (intravenous injection or infusion, intrathecal, or subcutaneously)
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- BC01
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- 20% by mouth
- Drug.protein_bound
- 13%
- Drug.metabolism
- Liver
- Drug.elimination_half life
- biphasic: 10 min, 1–3 hr
via Wikipedia infobox
Chemical data
- Formula
- C9H13N3O5
- Molecular weight
- 243.22 g/mol
- IUPAC name
- 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- SMILES
- C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
- InChIKey
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N
- XLogP
- -2.1
- Polar surface area
- 129 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
20,221 papers- Cytarabine and neurologic toxicity.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 1991
- Daunorubicin/Cytarabine Liposome: A Review in Acute Myeloid Leukaemia.Drugs · 2018
- The toxicity of cytarabine.Drug safety · 1990
- Cytarabine (Cytosar).Clinical pharmacology and therapeutics · 1970
- Cytarabine.Journal of pediatric oncology nursing : official journal of the Association of Pediatric Oncology Nurses · 1990
via PubMed
~7 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Side effects
- Mechanism of action
- History
- Names
- References
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.
Excerpted from Wikipedia’s “cytarabine” article, available under the CC BY-SA 4.0 licence.