Product Name

Cytarabine

CAS Number

147-94-4

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Product Name:
Cytarabine
CAS Number:
147-94-4
Indication:
For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia.
Mode of Action:

Cytarabine acts through direct DNA damage and incorporation into DNA. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. It exhibits cell phase specificity, primarily killing cells undergoing DNA synthesis (S-phase) and under certain conditions blocking the progression of cells from the G1 phase to the S-phase. Although the mechanism of action is not completely understood, it appears that cytarabine acts through the inhibition of DNA polymerase. A limited, but significant, incorporation of cytarabine into both DNA and RNA has also been reported.

Pharmacodynamics:

Cytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Anti-metabolites masquerade as purine or pyrimidine – which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Cytarabine is metabolized intracellularly into its active triphosphateplas form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle.

Metabolism:

Hepatic.

Toxicity:

Cytarabine syndrome may develop – it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise.

IUPAC:
4-amino-1-[(2R, 3S, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1, 2-dihydropyrimidin-2-one
ATC:
L01BC01
PubChem:
6253
DrugBank:
DB00987 (APRD00499)
Formula:
C3H2F6O
Molecular Mass:
243.2166
Synonyms:
Ara-C Arabinocytidine Arabinofuranosylcytosine Arabinosylcytosine AraC Aracytidine Aracytin Aracytine beta-Arabinosylcytosine Beta-cytosine arabinoside beta-D-Arabinosylcytosine Citarabina [INN-Spanish] Cytarabin Cytarabina cytarabine liposome injection Cytarabinoside Cytarabinum [INN-Latin] Cytosine 1-beta-D-arabinofuranoside Cytosine arabinofuranoside Cytosine arabinose Cytosine arabinoside Cytosine beta-D-arabinoside Cytosine-1-beta-D-arabinofuranoside Cytosine-beta-arabinoside Cytosine-beta-D-arabinofuranoside Cytosine, beta-D-arabinoside
SMILES:
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
AHFS Code:
10:00.0
InChi:
UHDGCWIWMRVCDJ-CCXZUQQUSA-N

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