20-ethyl Prostaglandin F2alpha

20-ethyl Prostaglandin F2alpha (20-ethyl PGF2alpha) is an analog of PGF2alpha in which the omega-chain has been extended by the addition of two more methylene carbon atoms. It is therefore a modified version of the clinically approved glaucoma medication unoprostone. Unoprostone also contains lower side chain modifications (13,14-dihydro-15-keto) which severely limit its affinity for FP receptors, contributing to its lack of potency as a medication. 20-ethyl PGF2alpha retains the natural 15(S) allylic hydroxyl in the lower side chain, which may improve its potency as an intraocular hypotensive agent compared to unoprostone. The 2 carbon extension in 20-ethyl-PGF2alpha increases the Ki (120 nM) for the FP receptor from bovine corpus luteum only about 2.5-fold compared to PGF2alpha (50 nM). In vivo effects may be prolonged using 20-ethyl PGF2alpha, as the activity of 15-hydroxy PGDH using 20-ethyl PGF2alpha as a substrate is only 35% of the activity observed with PGF2alpha.Formal Name: 9alpha,11alpha,15S-trihydroxy-20a,20b-dihomoprosta-5Z,13E-dien-1-oic acid. CAS Number: 36950-85-3. Synonyms: ICI 74205, 20-ethyl PGF2alpha. Molecular Formula: C22H38O5. Formula Weight: 382.5. Purity: >98%. Formulation: (Request formulation change), A solution in methyl acetate. Solubility: DMF: 33 mg/ml, DMSO: 14 mg/ml, Ethanol: 33 mg/ml, PBS (pH 7.2): 3 mg/ml. SMILES: O[C@@H]1C[C@H](O)[C@H](C/C=C\CCCC(O)=O)[C@H]1/C=C/[C@@H](O)CCCCCCC. InChi Code: InChI=1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,14-15,17-21,23-25H,2-5,7-8,10-13,16H2,1H3,(H,26,27)/b9-6-,15-14+/t17-,18+,19+,20-,21+/m0/s1. InChi Key: XSDVSOQSNGGUFY-GWSKAPOCSA-N.