latanoprost (isopropyl ester)   Click here for help

GtoPdb Ligand ID: 1961

Synonyms: PHXA-41 | XA-41 | Xalatan®
Approved drug
latanoprost (isopropyl ester) is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Latanoprost is administered in the isopropyl ester form shown here, which is then hydrolysed in vivo in to active metabolite lanoprost free acid.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 86.99
Molecular weight 432.29
XLogP 4.4
No. Lipinski's rules broken 1
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Canonical SMILES OC(CCc1ccccc1)CCC1C(O)CC(C1CC=CCCCC(=O)OC(C)C)O
Isomeric SMILES O[C@@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)OC(C)C)O
InChI InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1
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Summary of Clinical Use Click here for help
Opthalmic solution applied topically to the eye to control the progression of glaucoma or ocular hypertension.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Latonoprost is metabolised to its active free acid form in vivo, which is a selective agonist of the FP receptor. This agonism results in a reduction in interocular pressure by means of increased outflow of aqueous fluid from the eyes.