A prodrug form of cytarabine
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Active Metabolite(s)
16069Cytarabine
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Enocitabine

Item No. 36538

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(1-β-D-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-docosanamide
CAS Number
55726-47-1
Synonyms
  • Behenoyl-ara-C
  • N4-Behenoyl-1-β-D-arabinofuranosylcytosine
  • behenoyl Cytarabine
  • NSC 239336
Molecular Formula
C31H55N3O6
Formula Weight
565.8
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly soluble upon heatingMethanol: slightly soluble upon heatingTHF: slightly soluble upon heating
SMILES
O[C@@H]1[C@@](N2C(N=C(C=C2)NC(CCCCCCCCCCCCCCCCCCCCC)=O)=O)([H])O[C@@H]([C@H]1O)CO
InChi Code
InChI=1S/C31H55N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(36)32-26-22-23-34(31(39)33-26)30-29(38)28(37)25(24-35)40-30/h22-23,25,28-30,35,37-38H,2-21,24H2,1H3,(H,32,33,36,39)/t25-,28-,29+,30-/m1/s1
InChi Key
SAMRUMKYXPVKPA-VFKOLLTISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $73

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    25 mg

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    50 mg

    $538

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    Product Description

    Enocitabine is a lipophilic prodrug form of the nucleoside analog cytarabine (Item No. 16069) that contains a docosanoic acid (Item No. 9000338) moiety.1 It is resistant to deamination by cytidine deaminase.2 Enocitabine reduces the virus yield in the supernatant of CMV-infected Vero cells (EC90 = 0.5 µg/ml) and inhibits viral DNA synthesis when used at a concentration of 5 µg/ml.3 It increases survival in an L1210 murine skin lymphocytic leukemia model in a dose-dependent manner.2 Formulations containing enocitabine have been used in the treatment of acute myeloid leukemia (AML).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Higashigawa, M., Ochiai, H., Ohkubo, T., et al. Incorporation of N4-behenoyl-1-β-ᴅ-arabinofuranosylcytosine into DNA as 1-β-ᴅ-arabinofuranosylcytosine. Med. Oncol. Tumor Pharmacother. 5(4), 265-271 (1988).

    2. Aoshima, M., Tsukagoshi, S., Sakurai, Y., et al. N4-Behenoyl-1-β-ᴅ-arabinofuranosylcytosine as a potential new antitumor agent. Cancer Res. 37(8 Pt. 1), 2481-2486 (1977).

    3. 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. 31(2), 141-147 (1990).