Lubiprostone

Base Information

• Chemical Name: Lubiprostone
• CAS No.: 333963-40-9
• Deprecated CAS: 946081-34-1
• Molecular Formula: C20H32F2O5
• Molecular Weight: 390.468
• European Community (EC) Number: 603-977-7
• UNII: 7662KG2R6K
• DSSTox Substance ID: DTXSID80861338
• Nikkaji Number: J2.581.749D
• Wikipedia: Lubiprostone
• Wikidata: Q6695342
• NCI Thesaurus Code: C66040
• RXCUI: 623033
• Pharos Ligand ID: B41CCY15MQ8S
• Metabolomics Workbench ID: 145771
• ChEMBL ID: CHEMBL1201134
• Mol file: 333963-40-9.mol

Synonyms:0211, RU;0211, SPI;Amitiza;lubiprostone;Prostan-1-oic acid, 16,16-difluoro-11-hydroxy-9,15-dioxo-, (11alpha)-;RU 0211;RU-0211;RU0211;SPI 0211;SPI-0211;SPI0211

Chemical Property of Lubiprostone

Chemical Property:

• Vapor Pressure: 1.49E-13mmHg at 25°C
• Refractive Index: 1.486
• Boiling Point: 532.3 °C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 275.7 °C
• PSA: 83.83000
• Density: 1.175 g/cm³
• LogP: 4.30990
• Storage Temp.: -20°C Freezer
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 390.22178044
• Heavy Atom Count: 27
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

7-((2R,4AR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: CCCCC(C1(CCC2C(O1)CC(=O)C2CCCCCCC(=O)O)O)(F)F
• Isomeric SMILES: CCCCC([C@]1(CC[C@H]2[C@H](O1)CC(=O)[C@@H]2CCCCCCC(=O)O)O)(F)F
• Recent ClinicalTrials: Amitiza in Constipation Associated With PD (Parkinson's Disease)
• Recent EU Clinical Trials: A Multicentre, Long-term Safety, Efficacy and Pharmacokinetics Study of Lubiprostone in Paediatric Subjects Aged ≥6 to <18 years with Functional Constipation
• Recent NIPH Clinical Trials: Switch Study
• Description: Chronic constipation is an affliction affecting 4–5 million Americans alone. When no specific cause is identified, it is classified as idiopathic. Dietary and lifestyle modifications are the first-line conventional approaches followed by the administration of laxatives. Unfortunately, chronic idiopathic constipation is frequently refractory to traditional therapy; thus, the need for novel agents exists. Lubiprostone is a bicyclic fatty acid with a novel mechanism of action. Without affecting sodium and potassium ion concentrations, lubiprostone activates intestinal chloride ion channels, thereby, increasing intestinal water secretion and intestinal fluid chloride ion concentration. In basolateral membranepermeabilized T84 gastrointestinal epithelial cells under chloride gradient conditions, lubiprostone concentration-dependently increased short-circuit current with an EC50 of approximately 20 nM.
• Uses: Lubiprostone (Ring Closed) is a bicyclic fatty acid used for the treatment of chronic constipation and constipation associated irritable bowel syndrome (IBS-C).

Technology Process of Lubiprostone

There total 90 articles about Lubiprostone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(Z)-7-(1R,2R,3R)-[2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(benzyl-2-oxy)-cyclopentyl]-5-heptenoic acid benzyl ester → lubiprostone (333963-40-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 45 ℃; for 6h; under 6080.41 Torr; Temperature; Pressure;

Reference yield: 92.0%

7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (876068-08-5) → lubiprostone (333963-40-9)

Guidance literature:

With phosphoric acid; In water; acetonitrile; at 0 - 5 ℃; for 2h;

Reference yield: 91.0%

(7-((1R,2R,3R)-3-(tert-butyldimethylsilyloxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid) (1372609-16-9) → lubiprostone (333963-40-9)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; at 0 ℃; for 3h;

upstream raw materials:

benzyl 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)octahydro-2-hydroxy-6-oxocyclopenta[b]pyran-5-yl]heptanoate

(Z)-7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]heptanoic acid-5-enbenzyl ester

[(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde]

13,14-dihydro-15-keto-16,16-difluoro-Prostaglandin E₁

Downstream raw materials:

7-((2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl)heptanoate guanidinium

N₁-ethyl-7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxoperhydrocyclopenta[b]pyran-5-yl]heptanamide

Refernces

• 1、 -. "Process for the preparation of Lubiprostone and intermediates thereof". . . Retrieved 2019/11/11.
• 2、 -. "Method for synthesizing 1R,2R,3R-substituted cyclopentanone compound". Paragraph 0076; 0084-0086. . Retrieved 2018/09/28.