An analog of PGF2α with an extended ω-chain
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20-ethyl Prostaglandin F2α

Item No. 16940

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-20a,20b-dihomoprosta-5Z,13E-dien-1-oic acid
CAS Number
36950-85-3
Synonyms
  • ICI 74205
  • 20-ethyl PGF2α
Molecular Formula
C22H38O5
Formula Weight
382.5
Purity
≥98%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 14 mg/mlEthanol: 33 mg/mlPBS (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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

    $547

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    Product Description

    20-ethyl Prostaglandin F2α (20-ethyl PGF2α) is an analog of PGF2α 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 PGF2α 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-PGF2α increases the Ki (120 nM) for the FP receptor from bovine corpus luteum only about 2.5-fold compared to PGF2α (50 nM).2 In vivo effects may be prolonged using 20-ethyl PGF2α, as the activity of 15-hydroxy PGDH using 20-ethyl PGF2α as a substrate is only 35% of the activity observed with PGF2α.3,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Haria, M., and Spencer, C.M. Unoprostone (isopropyl unoprostone). Drugs Aging 9(3), 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(1), 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).