Enprostil

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]

Enprostil

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A02BB02 (WHO)
Identifiers
IUPAC name methyl 7-[(1S,2S,3S)-3-hydroxy-2-[(3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
CAS Number	73121-56-9 Y
PubChem CID	5311225
ChemSpider	4470744
UNII	J4IP5Z9DAU
KEGG	D01891 Y
Chemical and physical data
Formula	C23H28O6
Molar mass	400.471 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC(=O)CCC=C=CC[C@@H]1[C@H]([C@@H](CC1=O)O)/C=C/[C@H](COc2ccccc2)O
InChI 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
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