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lubiprostone

lubiprostone Structure
lubiprostone structure
CAS No.
333963-40-9
Chemical Name:
lubiprostone
Synonyms
Amitiza;UR-021;Spi 0211;Unii-7662kg2R6k;Lubiprostone-d4;Ruby prostaglandin;AMitiza Lubiprostone;Lubiprostone hemiketal;Prostaglin Lubiprostone;Lubiprostone (Ring Closed)
CBNumber:
CB32129504
Molecular Formula:
C20H32F2O5
Molecular Weight:
390.46
MDL Number:
MFCD08444045
MOL File:
333963-40-9.mol
MSDS File:
SDS
Last updated:2026-05-28 01:03:03
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lubiprostone Properties

Boiling point 532.3±50.0 °C(Predicted)
Density 1.175
storage temp. -20°C Freezer
pka 4.77±0.10(Predicted)
InChI InChI=1/C20H32F2O5/c1-2-3-11-19(21,22)20(26)12-10-15-14(16(23)13-17(15)27-20)8-6-4-5-7-9-18(24)25/h14-15,17,26H,2-13H2,1H3,(H,24,25)/t14-,15-,17-,20-/s3
InChIKey WGFOBBZOWHGYQH-JSDKRCIBNA-N
SMILES [C@@]12([H])CC(=O)[C@H](CCCCCCC(O)=O)[C@@]1([H])CC[C@@](C(F)(F)CCCC)(O)O2 |&1:0,5,15,19,r|
FDA UNII 7662KG2R6K

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

lubiprostone price More Price(26)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
ChemScene CS-0009583 Lubiprostone hemiketal 98.00% 333963-40-9 5mg $65 2026-06-04 Buy
ChemScene CS-0009583 Lubiprostone hemiketal 98.00% 333963-40-9 10mg $97 2026-06-04 Buy
ChemScene CS-0009583 Lubiprostone hemiketal 98.00% 333963-40-9 25mg $195 2026-06-04 Buy
ChemScene CS-0009583 Lubiprostone hemiketal 98.00% 333963-40-9 50mg $314 2026-06-04 Buy
ChemScene CS-0009583 Lubiprostone hemiketal 98.00% 333963-40-9 100mg $487 2026-06-04 Buy
Product number Packaging Price Buy
CS-0009583 5mg $65 Buy
CS-0009583 10mg $97 Buy
CS-0009583 25mg $195 Buy
CS-0009583 50mg $314 Buy
CS-0009583 100mg $487 Buy

lubiprostone Chemical Properties, Uses, Production

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.

Originator

Sucampo (US)

Uses

Lubiprostone (Ring Closed) is a bicyclic fatty acid used for the treatment of chronic constipation and constipation associated irritable bowel syndrome (IBS-C).

brand name

Amitiza

General Description

This product is marketed as Amitiza bySucampo Pharmaceuticals, Inc. and Takeda PharmaceuticalsAmerica, Inc. to relieve chronic idiopathic constipation inadults. The recommended oral dosage is 24 μg 2 times a daywith food. Precautions and side effects are similar to thosefor other prostaglandin-derived products.

Synthesis

Synthesis of lupiprostone started with the tetrahydropyran (THP) protected (-)Corey lactone 30. Desilylation of 30 with TBAF in THF gave free carbinol in 82% yield which was oxidized with oxalyl chloride and DMSO to give corresponding crude aldehyde 31. Aldehyde 31 was condensed with dimethyl 3,3,-difluoro-2-oxoheptylphosphonate (32) in the presence of thallium ethoxide to give unsaturated difluoroketone 33 which was hydrogenated with H2 over Pd/C in ethyl acetate and the resulting ketone was subsequently reduced with sodium borohydride in methanol to give lactone 34 in excellent yield. The lactone 34 was reduced to lactol 35 with DIBAL at -78C in toluene and the crude lactol 35 was condensed with 4-carboxybutyl triphenylphosphonium bromide (36) in the presence of t-BuOK in THF to yield compound 37. Crude 37 was reacted with benzyl bromide and DBU in dichloromethane (DCM) to give the benzyl ester in 96% yield. Oxidation of the alcohol with Collins reagent and removal of the THP protecting group under acidic conditions gave corresponding prostaglandin E2 benzyl ester 38. Finally, compound 38 was submitted to simultaneous benzyl ester group cleavage and double bond hydrogenation with H2 over Pd/C in ethyl acetate to give lubiprostone (V) in 94% yield.

Synthesis_333963-40-9

lubiprostone Preparation Products And Raw materials

Raw materials

Preparation Products

lubiprostone Suppliers

Global Suppliers ( 200)
Supplier Tel Email Country ProdList Advantage
Shanghai finete Pharmaceutical Co., Ltd. 021-021-00000000 18221039705 finetechpharm@126.com China 216 58
Nanjing Vcare PharmaTech Co., Ltd 025-58741518 13327700685 sales@vcarepharmatech.com China 483 58
Huigen Biotech (Shanghai) Co., Ltd. 13761582449; 13761582449 qingqing_claire@126.com China 193 58
Hubei Lingyan Biotechnology Co., Ltd 027-59304846 13297025796 2331003879@qq.com China 56 58
shang hai langyang 15900804645 1139985181@qq.com China 9 58
Shanghai Boyle Chemical Co., Ltd. sales@boylechem.com China 2915 55
Chemvon Biotechnology Co., Ltd 021-50790412 info@chemvon.com China 371 57
Chembest Research Laboratories Limited 021-20908456 sales@BioChemBest.com China 5996 61
Nanjing Chemlin Chemical Co., Ltd 025-83697070 13770331960 info@chemlin.com.cn China 16305 64
Shanghai Hanhong Scientific Co.,Ltd. 021-54306202 13764082696 info@hanhongsci.com China 42917 64
Supplier Advantage
Shanghai finete Pharmaceutical Co., Ltd. 58
Nanjing Vcare PharmaTech Co., Ltd 58
Huigen Biotech (Shanghai) Co., Ltd. 58
Hubei Lingyan Biotechnology Co., Ltd 58
shang hai langyang 58
Shanghai Boyle Chemical Co., Ltd. 55
Chemvon Biotechnology Co., Ltd 57
Chembest Research Laboratories Limited 61
Nanjing Chemlin Chemical Co., Ltd 64
Shanghai Hanhong Scientific Co.,Ltd. 64

Related articles

View Latest Price from lubiprostone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Lubiprostone pictures 2026-09-14 Lubiprostone
333963-40-9
 1g More Than 99% 100kg/Month BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Lubiprostone pictures 2026-08-17 Lubiprostone
333963-40-9
 1G/Bag 99% up 2 tons Sinoway Industrial co., ltd.
lubiprostone pictures 2026-06-30 lubiprostone
333963-40-9
 1kg 98% 1000kg Shaanxi Dideu New Materials Co. Ltd
  • Lubiprostone pictures
  • Lubiprostone
    333963-40-9
  • $0.00
  • More Than 99%
  • BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
  • lubiprostone pictures
  • lubiprostone
    333963-40-9
  • $0.00
  • 98%
  • Shaanxi Dideu New Materials Co. Ltd

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(2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-heptanoic acid Prostan-1-oic acid, 11,15-epoxy-16,16-difluoro-15-hydroxy-9-oxo-, (11alpha,15R)- Spi 0211 Unii-7662kg2R6k (2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-h 7-((1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl)heptanoic acid AMitiza Lubiprostone 7-((2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoic acid UR-021 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-yl]heptanoic acid Lubiprostone (Mixture of Tautomeric Isomers) Lubiprostone-d4 Lubiprostone (Ring Closed) Ruby prostaglandin 7-((2R,4aR,5R,7aS)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoic acid Lubiprostone hemiketal Prostan-1-oic acid, 11,15-epoxy-16,16-difluoro-15-hydroxy-9-oxo-, (11α,15R)- (-)-7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6- oxooctahydrocyclopenta[b]pyran-5-yl]heptanoic acid Prostaglin Lubiprostone 7-((1R,2S)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopent-3-en-1-yl)heptanoic acid Amitiza 333963-40-9 33963-40-9 API