Structure via PubChem · Public domain (PubChem)
enprostil
Sign in to saveEnprostil is a synthetic prostaglandin designed to resemble dinoprostone. Enprostil was found to be a highly potent inhibitor of gastric HCl secretion. 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. 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 mult
Chemical data
- Formula
- C23H28O6
- Molecular weight
- 400.5 g/mol
- IUPAC name
- methyl 7-[(1S,2S,3S)-3-hydroxy-2-[(E,3S)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
- SMILES
- COC(=O)CCC=C=CC[C@H]1[C@@H]([C@H](CC1=O)O)/C=C/[C@@H](COC2=CC=CC=C2)O
- InChIKey
- PTOJVMZPWPAXER-FPXSIRDUSA-N
- XLogP
- 1.3
- Polar surface area
- 93.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- Peptic ulcer, gastroesophageal reflux disease
via ChEMBL · EBI
Research
193 papers- Enprostil. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the treatment of peptic ulcer disease.Drugs · 1987
- Gastric ulcer healing: a comparison of enprostil versus ranitidine.Journal of clinical gastroenterology · 1991
- Enprostil, a prostaglandin-E(2) analogue, inhibits interleukin-8 production of human colonic epithelial cell lines.Scandinavian journal of immunology · 2000
- Enprostil reduces the increase of gastric corpus mucosal mass induced by the hydrogen-potassium-stimulated adenosine triphosphatase inhibitor BY 831-78 in the rat.Gastroenterology · 1989
- Enprostil, a synthetic prostaglandin E2 analogue, inhibits meal-stimulated gastric acid secretion and gastrin release in patients with duodenal ulcer.The American journal of medicine · 1986
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 400.18858861599995
Show 4 more facts
- chemical formula
- C₂₃H₂₈O₆
- Commons category
- Enprostil
- isomeric SMILES
- COC(=O)CCC=C=CC[C@@H]1C(=O)C[C@H](O)[C@H]1/C=C/[C@H](O)COc1ccccc1
- canonical SMILES
- COC(=O)CCC=C=CCC1C(=O)CC(O)C1C=CC(O)COc1ccccc1
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- Further reading
Enprostil is a synthetic prostaglandin designed to resemble dinoprostone. Enprostil was found to be a highly potent inhibitor of gastric HCl secretion. 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. 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.
== See also == Prostaglandin receptors EP3 and peptic ulcer
Excerpted from Wikipedia’s “enprostil” article, available under the CC BY-SA 4.0 licence.