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Enprostil

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Enprostil
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • methyl 7-[(1S,2S,3S)-3-hydroxy-2-[(3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC23H28O6
Molar mass400.471 g·mol−1
3D model (JSmol)
  • COC(=O)CCC=C=CC[C@@H]1[C@H]([C@@H](CC1=O)O)/C=C/[C@H](COc2ccccc2)O
  • InChI=1S/C23H28O6/c1-28-23(27)12-8-3-2-7-11-19-20(22(26)15-21(19)25)14-13-17(24)16-29-18-9-5-4-6-10-18/h3-7,9-10,13-14,17,19-20,22,24,26H,8,11-12,15-16H2,1H3/b14-13 /t2?,17-,19-,20-,22-/m1/s1
  • Key:PTOJVMZPWPAXER-VFJVYMGBSA-N
  (verify)

Enprostil is a synthetic prostaglandin designed to resemble dinoprostone. Enprostil was found to be a highly potent inhibitor of gastric HCl secretion.[1] It is an analog of prostaglandin E2 but unlike this prostaglandin, which binds to and activates all four cellular receptors viz., EP1, EP2, EP3, and EP4 receptors, enprostil is a more selective receptor agonist in that it binds to and activates primarily the EP3 receptor.[2] Consequently, enprostil is expected to have a narrower range of actions that may avoid some of the unwanted side-effects and toxicities of prostaglandin E2. A prospective multicenter randomized controlled trial conducted in Japan found combining enprostil with cimetidine was more effective than cimetidine alone in treating gastric ulcer.[3]

See also

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References

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  1. ^ Roszkowski AP, Garay GL, Baker S, Schuler M, Carter H (November 1986). "Gastric antisecretory and antiulcer properties of enprostil, ( /-)-11 alpha, 15 alpha-dihydroxy-16-phenoxy-17,18,19,20-tetranor-9-oxoprosta- 4,5,13(t)-trienoic acid methyl ester". The Journal of Pharmacology and Experimental Therapeutics. 239 (2): 382–389. PMID 3095537.
  2. ^ Moreno JJ (February 2017). "Eicosanoid receptors: Targets for the treatment of disrupted intestinal epithelial homeostasis". European Journal of Pharmacology. 796: 7–19. doi:10.1016/j.ejphar.2016.12.004. PMID 27940058. S2CID 1513449.
  3. ^ Murata H, Kawano S, Tsuji S, Tsujii M, Hori M, Kamada T, et al. (2005). "Combination of enprostil and cimetidine is more effective than cimetidine alone in treating gastric ulcer: prospective multicenter randomized controlled trial". Hepato-Gastroenterology. 52 (66): 1925–1929. PMID 16334808.

Further reading

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  • Toshina K, Hirata I, Maemura K, Sasaki S, Murano M, Nitta M, et al. (December 2000). "Enprostil, a prostaglandin-E(2) analogue, inhibits interleukin-8 production of human colonic epithelial cell lines". Scandinavian Journal of Immunology. 52 (6): 570–575. doi:10.1046/j.1365-3083.2000.00815.x. PMID 11119262.
  • Tari A, Hamada M, Kamiyasu T, Sumii K, Haruma K, Inoue M, et al. (August 1997). "Effect of enprostil on omeprazole-induced hypergastrinemia and inhibition of gastric acid secretion in peptic ulcer patients". Digestive Diseases and Sciences. 42 (8): 1741–1746. doi:10.1023/A:1018825902055. PMID 9286243. S2CID 25069361.
  • Ching CK, Lam SK (October 1995). "A comparison of two prostaglandin analogues (enprostil vs misoprostol) in the treatment of acute duodenal ulcer disease". Journal of Gastroenterology. 30 (5): 607–614. doi:10.1007/BF02367786. PMID 8574332. S2CID 6288648.
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