bimatoprost   

GtoPdb Ligand ID: 1958

Synonyms: AGN 192024 | LS-181817 | Lumigan®
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
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
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
Compound class Synthetic organic
Approved drug? Yes (FDA (2001), EMA (2002))
Is prodrug? Yes
Active form bimatoprost (free acid form)
IUPAC Name
(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
INN number INN
8035 bimatoprost
Synonyms
AGN 192024 | LS-181817 | Lumigan®
Comments
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].
Database Links
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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Search UniChem for chemical match using the InChIKey AQOKCDNYWBIDND-FTOWTWDKSA-N
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Wikipedia Bimatoprost