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Structure Database (LMSD)

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Common Name

15-methyl-15R-PGF2alpha methyl ester

Systematic Name

methyl 9S,11R,15S-trihydroxy-15-methyl-5Z,13E-prostadienoate

Synonyms

15-methyl-15R-Prostaglandin F2alpha methyl ester

LM ID

LMFA03010122

Formula

C₂₂H₃₈O₅

Exact Mass

Calculate m/z

382.271926

Sum Composition

FA 22:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15(S)-15-methyl Prostaglandin F2α methyl ester (15(S)-15-methyl PGF2α methyl ester) is a derivative of 15(S)-15-methyl PGF2α with increased membrane permeability.^1,2 Hydrolysis of the methyl ester in vivo releases the biologically active 15(S)-15-methyl PGF2α, which is a potent uterine stimulant and abortifacient.^3,4,5

This information has been provided by Cayman Chemical

References

1. Adaikan, P.G., Prasad, R.N.V., Kottegoda, S.R., et al. Effect of indomethacin on the injection-abortion interval of 15(S)15 methyl PGF2α-induced mid-trimester abortions - a randomized study. Prostaglandins Leukot. Med. 27(2-3), 161-167 (1987).

2. Lindblom, B., Källfelt, B., Hahlin, M., et al. Local prostaglandin F2α injection for termination of ectopic pregnancy. Lancet 1(8536), 776-777 (1987).

3. Roseman, T.J., Biermacher, J.J., Bennett, R.M., et al. Design criteria for controlled release delivery systems of carboprost methyl. J. Control. Release 3(1-4), 25-37 (1986).

4. Halstead, G.W., and Theis, D.L. Drug release testing of a prostaglandin containing controlled-release vaginal device: Development of a semi-automated method. J. Pharm. Sci. 74(10), 1086-1090 (1985).

5. Carlan, S.J., Gushwa, J.P., O'Brien, W.F., et al. Effect of intramuscular 15-methyl prostaglandin F2α after second-trimester delivery. Obstet. Gynecol. 89(1), 5-9 (1997).

String Representations

InChiKey (Click to copy)

QQCOAAFKJZXJFP-XAYIDPIISA-N

InChi (Click to copy)

InChI=1S/C22H38O5/c1-4-5-10-14-22(2,26)15-13-18-17(19(23)16-20(18)24)11-8-6-7-9-12-21(25)27-3/h6,8,13,15,17-20,23-24,26H,4-5,7,9-12,14,16H2,1-3H3/b8-6-,15-13+/t17-,18-,19+,20-,22+/m1/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@](C)(O)CCCCC)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)OC