Structure Database (LMSD)

Common Name
20-ethyl PGF2alpha
Systematic Name
9S,11R,15S-trihydroxy-20a,20b-dihomo-5Z,13E-prostadienoic acid
Synonyms
  • 20-ethyl Prostaglandin F2alpha
  • ICI 74205
LM ID
LMFA03010120
Formula
Exact Mass
Calculate m/z
382.271925
Sum Composition
Status
Curated

Classification

Biological Context

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

This information has been provided by Cayman Chemical

References

1. 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).
2. Haria, M., and Spencer, C.M. Unoprostone (isopropyl unoprostone). Drugs Aging 9(3), 213-218 (1996).
3. 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).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
New antifertility agent--an orally active prostaglandin--ICI 74,205.,
Nature, 1972
Pubmed ID: 4559585

String Representations

InChiKey (Click to copy)
XSDVSOQSNGGUFY-GWSKAPOCSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCCCC)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

CHEBI ID
LIPIDBANK ID
XPR1791
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 412.83
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 4.68
Molar Refractivity 108.91

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Created at
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Updated at
5th Apr 2022