bimatoprost   Click here for help

GtoPdb Ligand ID: 1958

Synonyms: AGN 192024 | LS-181817 | Lumigan®
Approved drug PDB Ligand
bimatoprost is an approved drug (FDA (2001), EMA (2002))
Compound class: Synthetic organic
Comment: Bimatoprost is a prostaglandin analogue which binds to the prostanoid FP receptor. It has been demonstrated that bimatoprost is also a prodrug that is metabolised in vivo to its free acid form [1-2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 89.79
Molecular weight 415.27
XLogP 3.15
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCNC(=O)CCCC=CCC1C(O)CC(C1C=CC(CCc1ccccc1)O)O
Isomeric SMILES CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](CCc1ccccc1)O)O
InChI InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1
InChI Key AQOKCDNYWBIDND-FTOWTWDKSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2001), EMA (2002))
Is prodrug? Yes
Active form bimatoprost (free acid form)
IUPAC Name Click here for help
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
International Nonproprietary Names Click here for help
INN number INN
8035 bimatoprost
Synonyms Click here for help
AGN 192024 | LS-181817 | Lumigan®
Database Links Click here for help
CAS Registry No. 155206-00-1 (source: Scifinder)
ChEBI CHEBI:51230
ChEMBL Ligand CHEMBL1200963
DrugBank Ligand DB00905
DrugCentral Ligand 371
GtoPdb PubChem SID 135649995
PubChem CID 5311027
RCSB PDB Ligand 15M
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Wikipedia Bimatoprost