cytarabine   

GtoPdb Ligand ID: 4827

Synonyms: Cytosar® | DepoCyte® | U-19920
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.
2D Structure
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Physico-chemical Properties
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
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
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
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
International Nonproprietary Names
INN number INN
1709 cytarabine
Synonyms
Cytosar® | DepoCyte® | U-19920
Database Links
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