{{short description|Chemical compound}} {{Drugbox | Watchedfields = changed | verifiedrevid = 447573683 | IUPAC_name = methyl 7-[(1''S'',2''S'',3''S'')-3-hydroxy-2-[(3''R'')-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate | image = Enprostil.svg | image_class = skin-invert-image | width = 240
<!--Clinical data--> | tradename = | Drugs.com = {{drugs.com|international|enprostil}} | pregnancy_category = | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | metabolism = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 73121-56-9 | ATC_prefix = A02 | ATC_suffix = BB02 | PubChem = 5311225 | ChemSpiderID = 4470744 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = J4IP5Z9DAU | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01891
<!--Chemical data--> | C=23 | H=28 | O=6 | smiles = COC(=O)CCC=C=CC[C@@H]1[C@H]([C@@H](CC1=O)O)/C=C/[C@H](COc2ccccc2)O | StdInChI = 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 | StdInChIKey = PTOJVMZPWPAXER-VFJVYMGBSA-N }} '''Enprostil''' is a synthetic prostaglandin designed to resemble dinoprostone. Enprostil was found to be a highly potent inhibitor of gastric HCl secretion.<ref>{{cite journal | vauthors = Roszkowski AP, Garay GL, Baker S, Schuler M, Carter H | title = 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 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 239 | issue = 2 | pages = 382–389 | date = November 1986 | pmid = 3095537 }}</ref> 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.<ref name="pmid27940058">{{cite journal | vauthors = Moreno JJ | title = Eicosanoid receptors: Targets for the treatment of disrupted intestinal epithelial homeostasis | journal = European Journal of Pharmacology | volume = 796 | pages = 7–19 | date = February 2017 | pmid = 27940058 | doi = 10.1016/j.ejphar.2016.12.004 | s2cid = 1513449 }}</ref> 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.<ref name="pmid16334808">{{cite journal | vauthors = Murata H, Kawano S, Tsuji S, Tsujii M, Hori M, Kamada T, Matsuzawa Y, Katsu K, Inoue K, Kobayashi K, Mitsufuji S, Bamba T, Kawasaki H, Kajiyama G, Umegaki E, Inoue M, Saito I | display-authors = 6 | title = Combination of enprostil and cimetidine is more effective than cimetidine alone in treating gastric ulcer: prospective multicenter randomized controlled trial | journal = Hepato-Gastroenterology | volume = 52 | issue = 66 | pages = 1925–1929 | year = 2005 | pmid = 16334808 }}</ref>
== See also == *Prostaglandin receptors *EP3 and peptic ulcer
== References == {{reflist}}
== Further reading == {{refbegin}} * {{cite journal | vauthors = Toshina K, Hirata I, Maemura K, Sasaki S, Murano M, Nitta M, Yamauchi H, Nishikawa T, Hamamoto N, Katsu K | display-authors = 6 | title = Enprostil, a prostaglandin-E(2) analogue, inhibits interleukin-8 production of human colonic epithelial cell lines | journal = Scandinavian Journal of Immunology | volume = 52 | issue = 6 | pages = 570–575 | date = December 2000 | pmid = 11119262 | doi = 10.1046/j.1365-3083.2000.00815.x }} * {{cite journal | vauthors = Tari A, Hamada M, Kamiyasu T, Sumii K, Haruma K, Inoue M, Kishimoto S, Kajiyama G, Walsh JH | display-authors = 6 | title = Effect of enprostil on omeprazole-induced hypergastrinemia and inhibition of gastric acid secretion in peptic ulcer patients | journal = Digestive Diseases and Sciences | volume = 42 | issue = 8 | pages = 1741–1746 | date = August 1997 | pmid = 9286243 | doi = 10.1023/A:1018825902055 | s2cid = 25069361 }} * {{cite journal | vauthors = Ching CK, Lam SK | title = A comparison of two prostaglandin analogues (enprostil vs misoprostol) in the treatment of acute duodenal ulcer disease | journal = Journal of Gastroenterology | volume = 30 | issue = 5 | pages = 607–614 | date = October 1995 | pmid = 8574332 | doi = 10.1007/BF02367786 | s2cid = 6288648 }} {{refend}}
{{Drugs for peptic ulcer and GORD}} {{Prostaglandins}} {{Prostanoidergics}}
Category:Prostaglandins Category:Phenol ethers Category:Methyl esters Category:Drugs developed by Hoffmann-La Roche
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