Ancitabine

ChEBI: An organic heterotricyclic compound resulting from the formal condensation of the oxo group of cytidine to the 2' position with loss of water to give the corresponding cyclic ether. A prodrug, it is metabolised to the antineoplastic agent cytarabine, so is used to maintain a more constant antineoplastic action.

Ancitabine is an organic heterotricyclic compound resulting from the formal condensation of the oxo group of cytidine to the 2' position with loss of water to give the corresponding cyclic ether. A prodrug, it is metabolised to the antineoplastic agent cytarabine, so is used to maintain a more constant antineoplastic action. It has a role as a prodrug, an antimetabolite and an antineoplastic agent. It is an organic heterotricyclic compound and a diol. It is a conjugate base of an ancitabine(1+).|Ancitabine is a cytarabine congener prodrug with antineoplastic activity. Upon administration, ancitabine is slowly hydrolyzed into cytarabine, which is converted to the active triphosphate form and competes with deoxycytidine triphosphate 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. This agent also inhibits DNA and RNA polymerases, resulting in a decrease in cell growth. 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.|Congener of CYTARABINE that is metabolized to cytarabine and thereby maintains a more constant antineoplastic action.

Molecular Weight:225.20
XLogP3:-2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:225.07495584
Monoisotopic Mass:225.07495584
Topological Polar Surface Area:98.4
Heavy Atom Count:16
Complexity:394
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes