An active metabolite of cytarabine
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Cytarabine 5′-monophosphate

Item No. 36496

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-1-(5-O-phosphono-β-D-arabinofuranosyl)-2(1H)-pyrimidinone
CAS Number
7075-11-8
Synonyms
  • ara-CMP
  • 1-β-D-Arabinofuranosylcytosine 5'-monophosphate
  • Cytosine Arabinoside monophosphate
  • NSC 99445
Molecular Formula
C9H14N3O8P
Formula Weight
323.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
OP(OC[C@@H]1[C@@H](O)[C@H](O)[C@]([H])(N2C(N=C(N)C=C2)=O)O1)(O)=O
InChi Code
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7+,8-/m1/s1
InChi Key
IERHLVCPSMICTF-CCXZUQQUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Cytarabine 5′-monophosphate (ara-CMP) is an active metabolite of the nucleoside analog cytarabine (Item No. 16069).1 It is formed from cytarabine by deoxycytidine kinase.2 ara-CMP is incorporated into DNA by DNA polymerase α, which slows the rate of DNA synthesis by approximately 2,000-fold in a cell-free assay.3 It inhibits nuclear and mitochondrial DNA replication in S. cerevisiae when used at a concentration of 15 mM.4 ara-CMP (3.5-75.1 mg/kg) improves survival in an L1210 murine leukemia model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, S., Liu, L., Liu, X., et al. Development and application of a rapid and sensitive liquid chromatography-mass spectrometry method for simultaneous analysis of cytarabine, cytarabine monophosphate, cytarabine diphosphate and cytarabine triphosphate in the cytosol and nucleus. J. Pharm. Biomed. Anal. 211, 114582 (2022).

    2. Momparler, R.L., and Fischer, G.A. Mammalian deoxynucleoside kinases. I. Deoxycytidine kinase: Purification, properties, and kinetic studies with cytosine arabinoside. The Journal of Biological Chemisty 243(16), 4298-4304 (1968).

    3. Perrino, F.W., and Mekosh, H.L. Incorporation of cytosine arabinoside monophosphate into DNA at internucleotide linkages by human DNA polymerase α. The Journal of Biological Chemisty 267(32), 23043-23051 (1992).

    4. Mcintosh, E.M., Kunz, B.A., and Haynes, R.H. Inhibition of DNA replication in Saccharomyces cerevisiae by araCMP. Curr. Genet. 10(8), 579-585 (1986).

    5. Schrecker, A.W., and Goldin, A. Antitumor effect and mode of action of 1-β-D-arabinofuranosylcytosine 5'-phosphate in leukemia L1210. Cancer Res. 28(4), 802-803 (1968).