Name: Ancitabine hydrochloride
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HIT ID:HIT103483274
Cas No:10212-25-6
Common Name:Ancitabine hydrochloride
alias:NSC 145668 HCl, Cyclocytidine hydrochloride, Cyclocytidine HCl, Cyclo-CMP hydrochloride, Cyclo-C HCl
alias:NSC 145668 HCl, Cyclocytidine hydrochloride, Cyclocytidine HCl, Cyclo-CMP hydrochloride, Cyclo-C HCl
IUPAC:(2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.0^{2,6}]dodeca-8,11-dien-5-ol hydrochloride
IUPAC:(2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.0^{2,6}]dodeca-8,11-dien-5-ol hydrochloride
InChIKey:KZOWNALBTMILAP-HCVDSKSXSA-N

Molecular Formula:C9H12ClN3O4
Molecular Weight:261.66
Hydrogen Bond Donor (HBD):3
Hydrogen Bond Acceptor (HBA):7
LogP:-2.755000000000000e+000
SMILES:Cl.OC[C@H]1O[C@@H]2[C@@H](Oc3nc(=N)ccn23)[C@@H]1O
SMILES:Cl.OC[C@H]1O[C@@H]2[C@@H](Oc3nc(=N)ccn23)[C@@H]1O

Ancitabine hydrochloride (NSC 145668 HCl) is the hydrochloride salt of a cytarabine congener prodrug with antineoplastic activity. Upon administration, ancitabine is slowly hydrolyzed into cytarabine. Subsequently, cytarabine is converted to the triphosphate form within the cell and then competes with cytidine for incorporation into DNA. Because the arabinose sugar sterically hinders the rotation of the molecule within DNA, DNA replication ceases, specifically during the S phase of the cell cycle. Cytarabine agent also inhibits DNA polymerase, resulting in a decrease in DNA replication and repair. Compared to cytarabine, a more prolonged, consistent cytarabine-mediated therapeutic effect may be achieved with ancitabine because of the slow hydrolytic conversion of ancitabine to cytarabine.

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