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Enocitabine

Enocitabine is a derivative of cytarabine that acts as a nucleoside analog of cytosine. Enocitabine is the a pro-drug of Ara-C and exhibits anticancer chemotherapeutic and antiviral activities. Like other nucleoside analogs, enocitabine is incorporated into DNA, preventing chain elongation and cell growth. Enocitabine is clinically used in some countries and is undergoing clinical trials in others as a potential treatment for leukemias and lymphomas such as acute myelogenous leukemia (AML). Enocitabine also inhibits replication and growth of cytomegalovirus (CMV).

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/1890850

Cas No.

55726-47-1

Purity

≥98%

Formula

C31H55N3O6

Formula Wt.

565.78

IUPAC Name

N-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]docosanamide

Synonym

N4-behenoyl-1-beta-D-arabinofuranosylcytosine; BH-AC

Melting Point

141-142°C

Appearance

Off-white crystalline powder

Ito Y, Wakita A, Takada S, et al. Phase 1 trial of gemtuzumab ozogamicin in combination with enocitabine and daunorubicin for elderly patients with relapsed or refractory acute myeloid leukemia: Japan Adult Leukemia Study Group (JALSG)-GML208 study. Int J Hematol. 2012 Oct;96(4):485-91. PMID: 22956429.

Hamada A, Kawaguchi T, Nakano M. Clinical pharmacokinetics of cytarabine formulations. Clin Pharmacokinet. 2002;41(10):705-18. PMID: 12162758.

Nakamura K, Eizuru Y, Kumura K, et al. Antiviral effect of antileukemic drugs N4-behenoyl-1-beta-D-arabinofuranosylcytosine (BH-AC) and 2,2-anhydro-1-beta-D-arabinofuranosylcytosine (cyclo-C) against human cytomegalovirus. J Med Virol. 1990 Jun;31(2):141-7. PMID: 1696958.

Maehara Y, Kusumoto T, Kusumoto H, et al. In vitro sensitivity of various human tumors to 1-beta-D-arabinofuranosylcytosine and N4-behenoyl-1-beta-D-arabinofuranosylcytosine. Chemotherapy. 1989;35(3):181-6. PMID: 2766858.

Higashigawa M, Ochiai H, Ohkubo T, et al. Incorporation of N4-behenoyl-1-beta-D-arabinofuranosylcytosine into DNA as 1-beta-D-arabinofuranosylcytosine. Med Oncol Tumor Pharmacother. 1988;5(4):265-71. PMID: 2848163.

Ro-3280