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Enprostil

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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 syntheticprostaglandin designed to resembledinoprostone. Enprostil was found to be a highly potent inhibitor of gastric HCl secretion.[1] It is an analog ofprostaglandin E2 but unlike this prostaglandin, which binds to and activates all four cellularreceptors viz.,EP1,EP2,EP3, andEP4 receptors, enprostil is a more selectivereceptor 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

[edit]

References

[edit]
  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

[edit]
  • 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.
H2 antagonists ("-tidine")
Prostaglandins (E)/
analogues ("-prost-")
Proton-pump inhibitors
("-prazole")
Potassium-competitive
acid blockers ("-prazan")
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Combinations
Precursor
Prostanoids
Prostaglandins (PG)
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(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
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FP (F2α)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
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PGD2STooltip Prostaglandin D synthase
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