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Carbenoxolone disodium

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CAS:7421-40-1
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Carbenoxolone disodium Basic information
Product Name:Carbenoxolone disodium
Synonyms:(3BETA-HYDROXY-11-OXOOLEAN-12-EN-30-OIC ACID 3-HEMISUCCINATE) DISODIUM SALT;CARBENOXOLONE DISODIUM SALT;CARBENOXOLONE SODIUM;18-beta-glycyrrhetinicacidhydrogensuccinate,disodiumsalt;20-beta)-3-bet;3-beta-hydroxy-11-oxoolean-12-en-30-oicacidhydrogensuccinate,disodiumsal;3-o-(beta-carboxypropionyl)-11-oxo-18-beta-olean-12-en-30-oicacid,disodium;disodiumglycyrrhetinylsuccina
CAS:7421-40-1
MF:C34H48Na2O7
MW:614.72
EINECS:231-044-0
Product Categories:OPTAFLEXX;Heterocycles;Miscellaneous;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
Mol File:7421-40-1.mol
Carbenoxolone disodium Structure
Carbenoxolone disodium Chemical Properties
Melting point >275°C (dec.)
storage temp. 2-8°C
solubility Methanol (Slightly), Water (Slightly)
pkapKa1 4.18; pKa2 5.52(at 25℃)
form Solid
color White to Off-White
Water Solubility Soluble in water to 100 mM.
Stability:Hygroscopic
CAS DataBase Reference7421-40-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36
Safety Statements 26-36
WGK Germany 3
RTECS RK0250000
ToxicityLD50 in male mice (mg/kg): 198 i.v.; 120 i.p.; in male rats (mg/kg): 3200 orally (Robson, Sullivan)
MSDS Information
ProviderLanguage
SigmaAldrich English
Carbenoxolone disodium Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorBiogastrone,Winthrop,UK,1963
UsesAnti-inflammatory glucocorticoid related to Enoxolone. Antiulcerative
Usesbeta-adrenergic agonist, growth stimulant
UsesCarbenoxolone is anti-inflammatory. It is often used as a gap junction inhibitor in neuroscience research. Carbenoxolone is also an inhibitor of the steroid dehydrogenase enzymes 11 β-hydroxysteroid dehydrogenase (human) and 3α, 20 β-hydroxysteroid dehydrogenase (bacterial). It is used for the treatment of digestive tract ulcers, especially in the stomach. Used in the treatment of peptic, mainly gastric, ulcers. It is often used as a gap junction inhibitor in neuroscience research.
Manufacturing Process23.5 g of glycyrrhetinic acid were dissolved in 50 cc of dry pyridine. A solution of 6.0 g of succinic anhydride in 30 cc of dry pyridine was added, followed by 30 cc of dry triethylamine and then, for washing purposes, 5 cc of dry pyridine. The solution was heated on a boiling water bath for ten hours and then poured into excess of dilute hydrochloric acid and ice. The fine gray precipitate formed was filtered off, washed with water, dissolved in chloroform, and the solution repeatedly extracted with dilute hydrochloric acid and later with water. It was dried over sodium sulfate and evaporated to dryness. Crystallization from methanol, using charcoal to effect decolorization, gave the hydrogen succinate as cream-colored crystals, MP 291° to 294°C, with previous softening.
One molecular proportion of glycyrrhetinic acid hydrogen succinate was ground with a dilute (5%) aqueous solution containing two molecular proportions of sodium hydroxide. The solution was filtered and evaporated in vacuum over concentrated sulfuric acid. The sodium salt is then obtained as a creamy white water-soluble solid. Glycyrrhetinic acid is obtainable from licorice root.
Therapeutic FunctionAntiinflammatory (gastric)
General DescriptionCarbenoxolone disodium is a water soluble disodium salt of glycyrrhetinic acid hemisuccinate. It acts as an efficient promoter for the nasal absorption of insulin.
Biological ActivityGlucocorticoid that inhibits 11 β -hydroxysteroid dehydrogenase (11-HSD) and blocks gap juntion communication.
references[1]. jellinck ph, monder c, mcewen bs, et al. differential inhibition of 11 beta-hydroxysteroid dehydrogenase by carbenoxolone in rat brain regions and peripheral tissues. j steroid biochem mol biol, 1993, 46(2): 209-213.
[2]. sagar gd, larson dm. carbenoxolone inhibits junctional trasnfer and upregulates connexin43 expression by a protein kinase a-dependent pathway. j cell biochem, 2006, 98(6): 1543-1551.
Carbenoxolone disodium Preparation Products And Raw materials
Raw materials18β-Glycyrrhetinic Acid-->Succinic anhydride
Tag:Carbenoxolone disodium(7421-40-1) Related Product Information
Sodium benzoate Sodium carbonate Carbenoxolone 18β-Glycyrrhetinic Acid 4-cyclohexyl-4-methylpentan-2-one Sodium chlorate SODIUM MYRISTATE 18alpha-Glycyrrhetinic acid 3-Methyl-5-ethyl-2-cyclohexen-1-one 4-n-Heptylcyclohexanecarboxylicacid 4-n-Decylcyclohexanecarboxylicacid 3,3-DIMETHYLCYCLOHEXYLIDENEACETALDEHYDE Sodium cyclohexanecarboxylate CIS-9-HEXADECENYL ACETATE 12-METHOXYDODECANOIC ACID 2,2-DIMETHYL-7-OCTENOIC ACID CARBENOXOLON SODIUM LAURIC ACID SODIUM SALT