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
SMILES / InChI / InChIKey
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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
InChI Key UHDGCWIWMRVCDJ-CCXZUQQUSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1969), EMA (2001))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
International Nonproprietary Names Click here for help
INN number INN
1709 cytarabine
Synonyms Click here for help
Cytosar® | DepoCyte® | U-19920
Database Links Click here for help
CAS Registry No. 147-94-4 (source: Scifinder)
ChEMBL Ligand CHEMBL803
DrugBank Ligand DB00987
DrugCentral Ligand 770
GtoPdb PubChem SID 178101529
PubChem CID 6253
RCSB PDB Ligand AR3
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Wikipedia Cytarabine