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Structure Database (LMSD)

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Common Name

17-phenyl-trinor-PGF2alpha

Systematic Name

9S,11R,15S-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoic acid

Synonyms

17-phenyl-trinor-Prostaglandin F2alpha

LM ID

LMFA03010081

Formula

C₂₃H₃₂O₅

Exact Mass

Calculate m/z

388.224975

Sum Composition

FA 23:7;O3

Status

Curated

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Classification

Biological Context

17-phenyl trinor Prostaglandin F2α (17-phenyl trinor PGF2α) is a metabolically stable analog of PGF2α and is a potent agonist for the FP receptor. It binds to the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF2α.¹ At the rat recombinant FP receptor expressed in CHO cells bimatoprost inhibits PGF2α binding with a Ki of 1.1 nM.² The isopropyl ester of 17-phenyl trinor PGF2α ethyl amide is slightly better than PGF2α isopropyl ester in reducing the intraocular pressure in the cat eye without any irritation.³

This information has been provided by Cayman Chemical

References

1. Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17(8), 691-704 (1992).

2. Lake, S., Gullberg, H., Wahlqvist, J., et al. Cloning of the rat and human prostaglandin F2α receptors and the expression of the rat prostaglandin F2α receptor. FEBS Lett. 355(3), 317-325 (1994).

3. Balapure, A.K., Rexroad, C.E., Jr., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem. Pharmacol. 38(14), 2375-2381 (1989).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Elevation of plasma noradrenaline levels in urethane-anaesthetized rats by activation of central prostanoid EP3 receptors.,
Br J Pharmacol, 1995

Pubmed ID: 7582489

DOI: 10.1111/j.1476-5381.1995.tb14985.x

String Representations

InChiKey (Click to copy)

YFHHIZGZVLHBQZ-KDACTHKWSA-N

InChi (Click to copy)

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

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)O