bimatoprost (free acid form)   Click here for help

GtoPdb Ligand ID: 1959

Synonyms: 17-phenyl-ω-trinor-PGF
Compound class: Synthetic organic
Comment: Formed from the in vivo metabolism of the prodrug bimatoprost.
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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 11
Topological polar surface area 97.99
Molecular weight 388.22
XLogP 2.94
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)CCCC=CCC1C(O)CC(C1C=CC(CCc1ccccc1)O)O
Isomeric SMILES OC(=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/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1
InChI Key YFHHIZGZVLHBQZ-KDACTHKWSA-N
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Summary of Clinical Use Click here for help
Administered as the prodrug bimatoprost which is used in the management of open angle glaucoma or ocular hypertension.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Prodrug bimatoprost and the free acid from resulting from the drug's in vivo metabolism decrease the pressure within the eye by mimicking the action of prostaglandin PGF in increasing the outflow of aqueous humor from the eyeball.