20-ethyl Prostaglandin F

Cayman Chemical Item Number 16940

20-ethyl PGF; ICI 74205 (CAS 36950-85-3)

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Description

20-ethyl Prostaglandin F (20-ethyl PGF) is an analog of PGF in which the ω-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.1 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 PGF 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-PGF increases the Ki (120 nM) for the FP receptor from bovine corpus luteum only about 2.5-fold compared to PGF (50 nM).2 In vivo effects may be prolonged using 20-ethyl PGF, as the activity of 15-hydroxy PGDH using 20-ethyl PGF as a substrate is only 35% of the activity observed with PGF.3,2

1. Haria, M., and Spencer, C.M. Unoprostone (isopropyl unoprostone). Drugs Aging 9 213-218 (1996).

2. Powell, W.S., Hammarström, S., Samuelsson, B., et al. Interactions between prostaglandin analogues and a receptor in bovine Corpora lutea. Correlation of dissociation constants with luteolytic potencies in hamsters. Eur J Biochem 59 271-276 (1975).

3. Sun, F.F., Armour, S.B., Bockstanz, V.R., et al. Studies on 15-hydroxyprostaglandin dehydrogenase from monkey lung. Adv Prostaglandin Thromboxane Res 1 163-169 (1976).

Synonyms
  • 20-ethyl PGF
  • ICI 74205
Formal Name 9α,​11α,​15S-​trihydroxy-​20a,​20b-​dihomoprosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 36950-85-3
Molecular Formula C22H38O5
Formula Weight 382.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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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
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​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
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XSDVSOQSNGGUFY-GWSKAPOCSA-N

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20-ethyl Prostaglandin F is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $51.00 $0.00
5 mg $230.00 $0.00
10 mg $408.00 $0.00
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Pricing updated 2015-05-23. Prices are subject to change without notice.

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Related Products

Prostaglandin F
Unoprostone
Unoprostone isopropyl ester

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