17-PHENYL TRINOR PGF2ALPHA-IPR Chemical Properties

Boiling point:

573.4±50.0 °C(Predicted)

Density 

1.141

storage temp. 

Store at -20°C

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 50 mg/ml; Ethanol:PBS (pH 7.2) (1:1): 1 mg/ml

pka

14.25±0.20(Predicted)

form 

Solid

color 

White to off-white

InChIKey

JGZRPRSJSQLFBO-FWPUOYPASA-N

SMILES

C(OC(C)C)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCC1=CC=CC=C1

17-PHENYL TRINOR PGF2ALPHA-IPR Usage And Synthesis

Description

17-phenyl trinor PGF_2α 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. The N-ethyl amide prostaglandin prodrugs are converted to the active free acid more slowly than the analogous prostaglandin ester prodrugs such as latanoprost. This product is the isopropyl ester of the free acid prostaglandin which corresponds to Bimatoprost. The free acid, 17-phenyl trinor PGF_2α, is a potent FP receptor agonist. In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. The 17-phenyl trinor PGF_2α isopropyl ester derivative was examined for IOP-lowering activity during the development of latanoprost. At the dose of 3 μg/eye in the monkey, 17-phenyl trinor PGF_2α 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.

Uses

PhDH 100A can be useful in the determination of prostaglandin analogs in cosmetic products by high performance liquid chromatography with tandem mass spectrometry.

Definition

ChEBI: 17-phenyl-trinor-PGF2alpha isopropyl ester is a prostanoid.

References

[1] MARK ABRAMOVITZ . The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2000, 1483 2: Pages 285-293. DOI: 10.1016/s1388-1981(99)00164-x
[2] D.F WOODWARD PHD. The Pharmacology of Bimatoprost (Lumigan?)[J]. Survey of ophthalmology, 2001, 45: Pages S337-S345. DOI: 10.1016/s0039-6257(01)00224-7
[3] BAHRAM RESUL PHD  Johan S M, PHD  Laszlo B P  Goran Selén Phd. Structure-activity relationships and receptor profiles of some ocular hypotensive prostanoids[J]. Survey of ophthalmology, 1997, 41: Pages S47-S52. DOI: 10.1016/s0039-6257(97)80007-0
[4] KIRK M MAXEY MD  Jennifer L B  Jennifer L Johnson MS. The Hydrolysis of Bimatoprost in Corneal Tissue Generates a Potent Prostanoid FP Receptor Agonist[J]. Survey of ophthalmology, 2002, 47: Pages S34-S40. DOI: 10.1016/s0039-6257(02)00323-5

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