gemcitabine   Click here for help

GtoPdb Ligand ID: 4793

Synonyms: gemcitabine hydrochloride | Gemzar®
Approved drug PDB Ligand
gemcitabine is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Gemcitabine is a nucleoside analogue chemotherapeutic. Chemically, the hydrogen atoms on the 2' carbon of deoxycytidine are replaced by fluorine atoms.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 110.6
Molecular weight 263.07
XLogP 0.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)(F)F)n1ccc(nc1=O)N
Isomeric SMILES OC[C@H]1O[C@H](C([C@@H]1O)(F)F)n1ccc(nc1=O)N
InChI InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
InChI Key SDUQYLNIPVEERB-QPPQHZFASA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
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,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
International Nonproprietary Names Click here for help
INN number INN
6515 gemcitabine
Synonyms Click here for help
gemcitabine hydrochloride | Gemzar®
Database Links Click here for help
CAS Registry No. 95058-81-4
ChEMBL Ligand CHEMBL888
DrugBank Ligand DB00441
DrugCentral Ligand 1283
GtoPdb PubChem SID 178101495
PubChem CID 60750
RCSB PDB Ligand GEO
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Wikipedia Gemcitabine