Structure Database (LMSD)
Common Name
17-phenyl-trinor-PGF2alpha isopropyl ester
Systematic Name
isopropyl 9S,11R,15S-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate
Synonyms
- 17-phenyl-trinor-Prostaglandin F2alpha isopropyl ester
- Bimatoprost isopropyl ester
LM ID
LMFA03010124
Formula
Exact Mass
Calculate m/z
430.271925
Sum Composition
Status
Curated
3D model of 17-phenyl-trinor-PGF2alpha isopropyl ester
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
17-phenyl trinor PGF2α N-ethyl amide is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost.1 The N-ethyl amide prostaglandin prodrugs are converted to the active free acid more slowly than the analogous prostaglandin ester prodrugs such as latanoprost.2 This product is the isopropyl ester of the free acid prostaglandin which corresponds to Bimatoprost. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist.3 In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. The 17-phenyl trinor PGF2α isopropyl ester derivative was examined for IOP-lowering activity during the development of latanoprost.4 At the dose of 3 μg/eye in the monkey, 17-phenyl trinor PGF2α isopropyl ester was the most potent analog tested in reducing IOP, lowering the IOP 1.3 mm Hg below the level achieved by latanoprost. However, this derivative was also significantly more irritating to the eye than latanoprost.4
This information has been provided by Cayman Chemical
References
1. Maxey, K.M., Johnson, J., and LaBrecque, J. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv. Ophthalmol. 47(Suppl. 1), S34-S40 (2002).
2. Resul, B., Stjernschantz, J., Selén, G., et al. Structure-activity relationships and receptor profiles of some ocular hypotensive prostanoids. Surv. Ophthalmol. 41(Suppl. 2), S47-S52 (1997).
3. Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of bimatoprost (Lumigan™). Surv. Ophthalmol. 45(Suppl. 4), S337-S345 (2001).
References
String Representations
InChiKey (Click to copy)
JGZRPRSJSQLFBO-FWPUOYPASA-N
InChi (Click to copy)
InChI=1S/C26H38O5/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/h3,5-8,10-11,16-17,19,21-25,27-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t21-,22+,23+,24-,25+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCC2C=CC=CC=2)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)OC(C)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
31
Rings
2
Aromatic Rings
1
Rotatable Bonds
13
Van der Waals Molecular Volume
450.85
Topological Polar Surface Area
86.99
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
5.11
Molar Refractivity
124.40
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Created at
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Updated at
2nd Feb 2024