cytarabine   Click here for help

GtoPdb Ligand ID: 4827

Synonyms: Cytosar® | DepoCyte® | U-19920
Approved drug PDB Ligand
cytarabine is an approved drug (FDA (1969), EMA (2001))
Compound class: Synthetic organic
Comment: Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 130.83
Molecular weight 243.09
XLogP -0.98
No. Lipinski's rules broken 0
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Canonical SMILES OCC1OC(C(C1O)O)n1ccc(nc1=O)N
Isomeric SMILES OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1ccc(nc1=O)N
InChI InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
No information available.
Summary of Clinical Use Click here for help
Cytarabine is used to treat some types of leukemia including leukemia associated with meningitis. In August 2017 the US FDA approved a fixed-dose combination of cytarabine and daunorubicin (Vyxeos®) for the treatment of adults with two types of acute myeloid leukemia (AML): newly diagnosed therapy-related AML (t-AML) or AML with myelodysplasia-related changes (AML-MRC).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cytarabine is toxic to proliferating mammalian cells as it causes DNA damage during the S phase of cell division, most likely by inhibiting the activity of DNA polymerases. Some evidence suggests direct incorporation of cytarabine into DNA and RNA, again leading to nucleic acid damage. Due to the complex and varied nature of nucleic acids we do not include DNA or RNA as targets on this database.
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