(-)-Cyclocytidine hydrochloride, CAS No. 10212-25-6

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10212-25-6

Catalog No. EBD46123

CAS 10212-25-6

Name (-)-Cyclocytidine hydrochloride

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Basic Information

Synonyms: Cyclocytidinehydrochloride (2R,3R,3aS,6E,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol (6E)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol 2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol 2,2'-dihydro-1-beta-D-arabinofuranosylcytosinehydrochloride 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosinehydrochloride 2,2'-O-CyclocytidineHydrochloride (-)-cyclocytidinehydrochloride o2-2'-cyclocytidinehydrochloride 1-beta-d-arabinofuranosyl-2,2’-anhydro-cytosinhydrochloride 2,2’-anhydro-1-beta-d-arabinofuranosylcytosinhydrochloride 2,2’-anhydroarabinosylcytosinehydrochloride 2,2’-anhydrocytarabinehydrochloride 2,2’-cyclocytidinehydrochloride 2,2’-o-cyclocytidinehydrochloride 3’:4,5)oxazolo(3,2-a)-pyrimidine-2-methanol,2,3,3a,9a-tetrahydro-3-6h-furo(2 Ancitabinehydrochloride

Molecular Formula: C9H12ClN3O4

Molecular Weight: 261.66

MDL Number: MFCD00012636

Categories: Medicinal Chemistry > APIs and Their Salts > Antineoplastic Agents Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides

Product Description:

(-)-Cyclocytidine hydrochloride is a hydrochloride salt of cyclocytidine, a cytidine analogue where the ribose sugar is replaced by a cyclopentane ring. This structural modification confers metabolic stability and alters its biological activity profile compared to the parent nucleoside. Its primary and most significant application is as an antineoplastic (anticancer) agent. Cyclocytidine acts as a prodrug; following administration, it is converted intracellularly into cytarabine (Ara-C), a well-established antimetabolite used in the treatment of acute myeloid leukemia (AML) and other hematologic malignancies. As a prodrug, cyclocytidine hydrochloride was developed to improve the pharmacokinetic properties, such as oral bioavailability and duration of action, compared to cytarabine itself. It functions by inhibiting DNA synthesis after being phosphorylated to its active triphosphate form, which incorporates into DNA and halts chain elongation. While its direct clinical use may have been superseded by newer formulations or analogues in some regions, cyclocytidine hydrochloride remains a compound of historical and research importance in oncology and nucleoside chemistry. It serves as a key reference standard and a tool for studying nucleoside metabolism and anticancer mechanisms.

Physical Properties

Melting Point: 269-270 °C (dec.)(lit.)

Boiling Point: 442 °C at 760 mmHg

Flash Point: 221.1 °C

Density: 2.01 g/cm3

Analytical Data

Appearance: white fine crystalline powder