Enprostil

Title: Enprostil
CAS Registry Number: 73121-56-9
CAS Name: rel-7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxocyclopentyl]-4,5-heptadienoic acid methyl ester
Additional Names: (dl)-9-keto-11a,15a-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester
Manufacturers' Codes: RS-84135
Trademarks: Camleed (Tanabe Seiyaku); Gardrin(e) (Syntex)
Molecular Formula: C23H28O6
Molecular Weight: 400.46
Percent Composition: C 68.98%, H 7.05%, O 23.97%
Literature References: Prostaglandin E2 derivative with antisecretory activity. Prepn: A. R. Van Horn et al., US 4178457 (1979 to Syntex). Pharmacokinetics: D. R. Stanski et al., Clin. Pharmacol. Ther. 31, 273 (1982). Cytoprotective effect against aspirin-induced gastromucosal injury in humans: M. M. Cohen et al., Gastroenterology 88, 382 (1985). Clinical comparison with cimetidine of antisecretory and antigastrin activity in duodenal ulcer: V. Mahachai et al., ibid. 89, 555 (1985); of efficacy in ulcer healing: L. Carling et al., Scand. J. Gastroenterol. 22, 325 (1987). Series of articles on pharmacology, clinical efficacy and safety: Am. J. Med. 81, Suppl. 2A, 1-88 (1986).
Properties: White to off-white waxy solid. Softens at 30°, liquid at 46°. Very slightly sol in water. Sol in alcohol, propylene glycol, propylene carbonate. uv max (methanol): 220, 265, 271, 277 nm (log e 4.01, 3.14, 3.24, 3.16).
Absorption maximum: uv max (methanol): 220, 265, 271, 277 nm (log e 4.01, 3.14, 3.24, 3.16)
Therap-Cat: Antiulcerative.
Keywords: Antiulcerative; Prostaglandin/Prostaglandin Analog.
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Enprostil
Enprostil.svg
Systematic (IUPAC) name
methyl 7-[(1S,2S,3S)-3-hydroxy-2-[(3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 73121-56-9 YesY
ATC code A02BB02
PubChem CID 51744
UNII J4IP5Z9DAU YesY
KEGG D01891 YesY
Chemical data
Formula C23H28O6 
Mol. mass 400.46 g/mol
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Enprostil is a synthetic prostaglandin designed to resemble dinoprostone. Enprostil was found to be a highly potent inhibitor of gastric HCl secretion.[1]