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Bending the Curve Trial by Trial
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Pyrimidine analogues and fluoropyrimidinesUsed in a few countriesDerivative of an earlier drugNeeds review

Ancitabine (cyclocytidine)

Also known as cyclocytidine, 2,2'-O-cyclocytidine, cyclo-C, 2,2'-anhydro-1-beta-D-arabinofuranosylcytosine

A 2,2'-anhydro derivative of cytarabine, a prodrug that converts to cytarabine in aqueous solution. A 2002 review lists it among cytarabine derivatives used clinically in Japan.

From discovery to approval

  1. 1971 · First described

    A 1971 paper in Gan by Hoshi and colleagues is titled as describing 2,2'-O-cyclocytidine as an antitumour cytidine analogue resistant to cytidine deaminase (title only). A 1990 paper gives ancitabine as cyclo-C, 2,2'-anhydro-ara-C; the match to the 1971 name rests on nomenclature.[2][1][3][4]

  2. No approval is recorded on this site.

How it works

It is a prodrug that converts to cytarabine quantitatively in aqueous solution, in a 1984 kinetic study; cytarabine then acts as described for that drug.[1]

Where it came from and why

The 1971 title says the analogue resists cytidine deaminase. A 2002 review says cytarabine's rapid deamination to an inactive metabolite is the reason for the search for derivatives.

Cancers

  • Leukaemia

    A 1990 paper calls ancitabine (cyclo-C) an antileukemic drug; a 2002 review says it has been used clinically in Japan.[4]

Family and partners

Derived from: Cytarabine

Worth knowing

  • A 1990 paper names 2,2'-anhydro-1-beta-D-arabinofuranosylcytosine as ancitabine (cyclo-C) and N4-behenoyl-1-beta-D-arabinofuranosylcytosine as enocitabine (BH-AC), and describes both, with cytarabine, as antileukemic drugs.[4]
  • A 2002 review lists ancitabine (cyclocytidine), enocitabine and cytarabine ocfosfate as cytarabine derivatives that have been used clinically in Japan.[3]
  • In a 1984 kinetic study the prodrug ancitabine was quantitatively converted to cytarabine under all aqueous conditions tested, and a solution at pH 4 or below at 30 degrees C was calculated to keep 90% of its concentration for 12 days.[1]

References

  1. Kirsch LE, Notari RE. Aqueous conversion kinetics and mechanisms of ancitabine, a prodrug of the antileukemic agent cytarabine. J Pharm Sci. 1984;73(7):896-902. PubMedDOI
  2. Hoshi A, Kanazawa F, Kuretani K, Saneyoshi M, Arai Y. 2,2'-O-cyclocytidine, an antitumor cytidine analog resistant to cytidine deaminase. Gan. 1971;62(2):145-6. PubMed
  3. Hamada A, Kawaguchi T, Nakano M. Clinical pharmacokinetics of cytarabine formulations. Clin Pharmacokinet. 2002;41(10):705-18. PubMedDOI
  4. Nakamura K, Eizuru Y, Kumura K, Minamishima Y. 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;31(2):141-7. PubMedDOI