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Structure Database (LMSD)

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Common Name

15-methyl-15R-PGE2

Systematic Name

9-oxo-11R,15R-dihydroxy-15-methyl-5Z,13E-prostadienoic acid

Synonyms

15-methyl-15R-Prostaglandin E2

LM ID

LMFA03010063

Formula

C₂₁H₃₄O₅

Exact Mass

Calculate m/z

366.240625

Sum Composition

FA 21:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15(R)-15-methyl Prostaglandin E2 (15(R)-15-methyl PGE2) is a prodrug for the potent PGE2 analog 15(S)-15-methyl PGE2 .¹ Acid-catalyzed epimerization in the stomach produces the 15(S)-hydroxy compound which is biologically active.² Oral administration of 15(R)-15-methyl PGE2 to dogs or rats at 10-300 µg/kg results in a dose-dependent inhibition of gastric acid secretion and an increase in the rate of duodenal bicarbonate secretion.^3,4

This information has been provided by Cayman Chemical

References

1. Takanashi, H., Kawabe, Y., and Akima, M. Acid-promoted epimerization of arbaprostil, 15(R)-15-methylprostaglandin E2, elicits gastric antisecretory activities in rats. Jpn. J. Pharmacol. 57, 559-564 (1991).

2. Takanashi, H., and Itoh, Z. Gastric antisecretory activity of 15(R)-15-methylprostaglandin E2, arbaprostil, in dogs. Jpn. J. Pharmacol. 57, 447-451 (1991).

3. Li, J., Nagata, T., Yoshida, M., et al. Effect of 15(R)-15-methyl PGE2 (arbaprostil) on duodenal bicarbonate secretion in rat. Gastroenterol. Jpn. 24, 8-11 (1989).

4. Yankee, E.W., Axen, U., and Bundy, G.L. Total synthesis of 15-methylprostaglandins. J. Am. Chem. Soc. 96, 5865-5876 (1974).

String Representations

InChiKey (Click to copy)

XSGQFHNPNWBVPT-VFXMVCAWSA-N

InChi (Click to copy)

InChI=1S/C21H34O5/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/h5,7,12,14,16-17,19,23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,19-,21-/m1/s1

SMILES (Click to copy)

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