lubiprostone
- Product Name
- lubiprostone
- CAS No.
- 333963-40-9
- Chemical Name
- lubiprostone
- Synonyms
- UR-021;Amitiza;Spi 0211;Lubiprostone;Unii-7662kg2R6k;Lubiprostone-d4;Ruby prostaglandin;AMitiza Lubiprostone;Lubiprostone hemiketal;Prostaglin Lubiprostone
- CBNumber
- CB32129504
- Molecular Formula
- C20H32F2O5
- Formula Weight
- 390.46
- MOL File
- 333963-40-9.mol
lubiprostone Property
- Boiling point:
- 532.3±50.0 °C(Predicted)
- Density
- 1.175
- storage temp.
- -20°C Freezer
- pka
- 4.77±0.10(Predicted)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- API0005783
- Product name
- LUBIPROSTONE-D4
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $496.11
- Updated
- 2021/12/16
- Product number
- 333963409
- Product name
- 7-((2R,4AR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoicacid
- Packaging
- 250mg
- Price
- $888.8
- Updated
- 2021/12/16
- Product number
- CM182388
- Product name
- 7-((2R,4AR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoicacid
- Purity
- 95%+
- Packaging
- 1g
- Price
- $1889
- Updated
- 2021/12/16
- Product number
- 333963409
- Product name
- 7-((2R,4AR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoicacid
- Packaging
- 1g
- Price
- $1979.6
- Updated
- 2021/12/16
- Product number
- CD11142139
- Product name
- 7-((2R,4AR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoicacid
- Purity
- 97%
- Packaging
- 1g
- Price
- $2020
- Updated
- 2021/12/16
lubiprostone Chemical Properties,Usage,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 -78??C 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.
lubiprostone Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from lubiprostone manufacturers
- Product
- Lubiprostone 333963-40-9
- Price
- US $180.00-100.00/G/Bag
- Min. Order
- 1G/Bag
- Purity
- 99% up
- Supply Ability
- 2 tons
- Release date
- 2024-01-03
- Product
- lubiprostone 333963-40-9
- Price
- US $1.00/ASSAYS
- Min. Order
- 1ASSAYS
- Purity
- 85.0-99.8%
- Supply Ability
- 20tons
- Release date
- 2020-01-08