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Structure Database (LMSD)

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Common Name

15-methyl-15S-PGF2alpha

Systematic Name

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

Synonyms

15-methyl-15S-Prostaglandin F2alpha
Carboprost

LM ID

LMFA03010080

Formula

C₂₁H₃₆O₅

Exact Mass

Calculate m/z

368.256275

Sum Composition

FA 21:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15(S)-15-methyl Prostaglandin F2α (15(S)-15-methyl PGF2α) is a metabolically stable analog of PGF2α. It is a potent uterine stimulant and abortifacient which can be administered intramuscularly to induce labor.^1,2,3 It induces luteolysis and reduces serum progesterone concentrations when given as an intramuscular injection in non-pregnant rhesus monkeys.⁴

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. Wilks, J.W. Inhibition of the monkey corpus luteum with 15-methyl prostaglandins. Prostaglandins 20(5), 793-805 (1980).

4. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Total synthesis of 15-methylprostaglandins.,
J Am Chem Soc, 1974

Pubmed ID: 4416671

String Representations

InChiKey (Click to copy)

DLJKPYFALUEJCK-IIELGFQLSA-N

InChi (Click to copy)

InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/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)O