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

Item No. 29014

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3R,3aS,9aR)-tetrahydro-3-hydroxy-6-imino-6H-furo[2′,3′:4,5]oxazolo[3,2-a]pyrimidine-2-methanol, monohydrochloride
CAS Number
10212-25-6
Synonyms
  • Ancitabine hydrochloride
  • NSC 145668
  • 2,2′-O-Cyclocytidine hydrochloride
Molecular Formula
C9H11N3O4 • HCl
Formula Weight
261.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: Partially solubleDMSO: Partially solubleEthanol: Partially solublePBS (pH 7.2): 10 mg/ml
λmax
235, 266 nm
SMILES
N=C1C=CN(C(O2)=N1)[C@@]3([H])[C@]2([H])[C@H](O)[C@@H](CO)O3.Cl
InChi Code
InChI=1S/C9H11N3O4.ClH/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8;/h1-2,4,6-8,10,13-14H,3H2;1H/t4-,6-,7+,8-;/m1./s1
InChi Key
KZOWNALBTMILAP-JBMRGDGGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 g

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    Product Description

    Cyclocytidine is a prodrug form of cytarabine (Item No. 16069) that is hydrolyzed to cytarabine in vivo.1 It inhibits the growth of L5178Y leukemia cells in vitro (IC50 = 0.041 µg/ml) and inhibits DNA synthesis by inhibiting thymidine incorporation into DNA (IC50 = 110 µg/ml).2 It increases lifespan in an L1210 mouse model of leukemia when administered at doses ranging from 3 to 1,000 mg/kg per day.1 Cyclocytidine transiently increases blood pressure in dogs, cats, and rats when administered at doses ranging from 5 to 100 mg/kg and induces postural hypotension in dogs, an effect that can be blocked by the α-adrenergic receptor antagonist phentolamine (Item No. 16135).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoshi, A., Kanazawa, F., Kuretani, K., et al. 2,2'-O-cyclocytidine, an antitumor cytidine analog resistant to cytidine deaminase. Gan. 62(2), 145-146 (1971).

    2. Hoshi, A., Yoshida, M., Kanzawa, F., et al. Inhibition by cyclocytidine of nucleic acid biosynthesis in cultured cells (L5178Y). Chem. Pharm. Bull. (Tokyo) 21(7), 1446-1450 (1973).

    3. Burks, T.F., Loo, T.L., and Grubb, M.N. Mechanism of the cardiovascular actions of cyclocytidine. Proc. Soc. Exp. Biol. Med. 159(3), 374-379 (1978).