73121-56-9

Basic information

• Product Name: ENPROSTIL
• Synonyms: ENPROSTIL;4,5-heptadienoicacid,7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocycl;gardrin;methylester,(1-alpha,2-beta(1e,3r*),3-alpha)-opentyl);Enprotil;4,5-Heptadienoic acid, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxocyclopentyl]-, methyl ester, rel-;Camleed;Fundyl
• CAS NO: 73121-56-9
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.46
• Mol File: 73121-56-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: <46 °C
• Boiling Point: 552.9°C at 760 mmHg
• Flash Point: 185.7°C
• Appearance: /
• Density: 1.201g/cm³
• Vapor Pressure: 4.64E-13mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 13.46±0.20(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: ENPROSTIL(CAS DataBase Reference)
• NIST Chemistry Reference: ENPROSTIL(73121-56-9)
• EPA Substance Registry System: ENPROSTIL(73121-56-9)

Safety Data

• Hazardous Substances Data: 73121-56-9(Hazardous Substances Data)

Usage

Description

Enprostil, a synthetic analogue of prostaglandin E2, is an orally-active compound designed for the treatment of gastric and duodenal ulcers. It exhibits antisecretory properties by reducing the secretion of acid and gastrin, and also provides cytoprotection. Enprostil is one of the three prostaglandins, along with rnisoprostol and rosaprostol, that are used for this purpose. It is available under the brand name Gardrin by Syntex.

Uses

Used in Pharmaceutical Industry:
ENPROSTIL is used as an antisecretory and antiulcerative agent for the treatment of patients with duodenal or gastric ulcers. It helps in reducing the secretion of acid and gastrin, which are the primary factors contributing to the development and persistence of ulcers. Additionally, its cytoprotective properties aid in the healing and protection of the stomach lining.
ENPROSTIL is used as a therapeutic agent for promoting healing and reducing the risk of complications in patients with gastric and duodenal ulcers. Its effectiveness in treating these conditions is attributed to its ability to modulate the secretion of acid and gastrin, as well as providing cytoprotection to the stomach lining.

Originator

Syntex (USA)

Hazard

Moderately toxic by ingestion.

InChI:InChI=1/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

Upstream product

• 157543-66-3 (-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester 
• 286840-20-8 1-<5α-hydroxy-2β-<(E)-4-phenoxy-3α-tetrahydropyran-2-yloxy-1-butenyl>-3α-tetrahydropyran-2-yloxycyclopent-1α-yl>but-3-yn-2-ol 
• 54347-99-8 (3aR,4R,5R,6aS)-Hexahydro-4-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-2-one 
• 286840-19-5 (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 
• 149862-37-3 (R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne 
• 117253-98-2 (3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone 

Relevant articles and documents

Synthesis of a Key Intermediate for Preparation of 4,5-Didehydro Prostaglandins containing an Allenyl Side-chain Group via Two-component Coupling Process. Synthesis of Enprostil

Enone 8, a key intermediate in the preparation of 4,5-didehydro prostaglandins via a two component coupling process, is prepared efficiently from readily available enone 6; the synthesis of enprostil, an antiulcer agent developed by Syntex, using enone 8 is also described.

Synthesis of the four stereoisomers of enprostil

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(dl)-16-Phenoxy- and 16-substituted phenoxy-9-keto prostatrienoic acid derivatives and processes for the production thereof

Novel 16-phenoxy and 16-(o, m or p)-substituted phenoxy derivatives of (dl)-9-keto-11α,15α-dihydroxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid, the pharmaceutically acceptable, non-toxic lower alkyl esters and salts thereof and processes for the production of such compounds. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretion; and as agents for the control of asthmatic attack, because of their bronchodilating activity.