Structure Database (LMSD)
Common Name
PGF2alpha methyl ester
Systematic Name
methyl 9S,11R,15S-trihydroxy-5Z,13E-prostadienoate
Synonyms
- Prostaglandin F2alpha methyl ester
LM ID
LMFA03010115
Formula
Exact Mass
Calculate m/z
368.256275
Sum Composition
Status
Curated
3D model of PGF2alpha methyl ester
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Prostaglandin F2α methyl ester (PGF2α methyl ester) is an analog of PGF2α in which the C-1 carboxyl group has been esterified as the methyl ester. PGF2α methyl ester was one of the first PG esters shown to have ocular hypotensive activity.1 This compound continues to be a standard by which other ocular hypotensive PG prodrugs are evaluated. The methyl ester is about 4-5 times more potent than the free acid, PGF2α. This difference is attributed to improved corneal penetration, and a depot effect of prolonged retention of the ester form of the compound in ocular tissue. A 2.5 µg dose of PGF2α-OMe applied to the eyes of cats results in a 6-8 mm Hg reduction in IOP.1
This information has been provided by Cayman Chemical
References
1. Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. Exp. Eye Res. 38(2), 181-184 (1984).
String Representations
InChiKey (Click to copy)
PJDMFGSFLLCCAO-NVRZHKMMSA-N
InChi (Click to copy)
InChI=1S/C21H36O5/c1-3-4-7-10-16(22)13-14-18-17(19(23)15-20(18)24)11-8-5-6-9-12-21(25)26-2/h5,8,13-14,16-20,22-24H,3-4,6-7,9-12,15H2,1-2H3/b8-5-,14-13+/t16-,17+,18+,19-,20+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)OC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
1
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
395.53
Topological Polar Surface Area
86.99
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.99
Molar Refractivity
104.06
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