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 is one of three, orally-active prostaglandins (see rnisoprostol and rosaprostol) for the treatment of gastric and duodenal ulcers. An allenic PGE2 derivative, enprostil is both antisecretory (acid, gastrin) and cytoprotective.

Originator

Syntex (USA)

Uses

Different sources of media describe the Uses of 73121-56-9 differently. You can refer to the following data:
1. Enprostil is a synthetic analogue of prostaglandin E2 and was found to be effective in the treatment of patients with duodenal or gastric ulcers.
2. Antisecretory; antiulcerative.

Brand name

Gardrin (Syntex).

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

• 149862-37-3 (R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne 
• 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 
• 117253-98-2 (3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone 
• 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 

Relevant articles and documents

Synthesis of prostaglandins III: Efficient and practical synthesis of antisecretory prostaglandin enprostil

An efficient and practical 8-step synthesis of enprostil (1) starting from the lactone 2 has been developed. The propargylic acetate 5 was prepared from the lactol 3 by the reaction with ethynylmagnesium bromide followed by acetylation. Propargylic acetate 5 was converted into enprostil (1) via the introduction of an allene moity by reaction with a Grignard reagent in the presence of a CuI · P(OEt)3 complex.

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.