Carbenoxolone disodium
Synonym(s):3β-Hydroxy-11-oxoolean-12-en-30-oic acid 3-hemisuccinate
- CAS NO.:7421-40-1
- Empirical Formula: C34H48Na2O7
- Molecular Weight: 614.72
- MDL number: MFCD03840711
- EINECS: 231-044-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-15 19:19:13
What is Carbenoxolone disodium?
Chemical properties
White Solid
Originator
Biogastrone,Winthrop,UK,1963
The Uses of Carbenoxolone disodium
beta-adrenergic agonist, growth stimulant
The Uses of Carbenoxolone disodium
Anti-inflammatory glucocorticoid related to Enoxolone. Antiulcerative
The Uses of Carbenoxolone disodium
Carbenoxolone 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.
Definition
ChEBI: Carbenoxolone sodium is a triterpenoid.
What are the applications of Application
Carbenoxolone disodium is an inhibitor of 11 β-hydroxysteroid dehydrogenase (11β-HSD)
Manufacturing Process
23.5 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 Function
Antiinflammatory (gastric)
General Description
Carbenoxolone disodium is a water soluble disodium salt of glycyrrhetinic acid hemisuccinate. It acts as an efficient promoter for the nasal absorption of insulin.
Biological Activity
Glucocorticoid that inhibits 11 β -hydroxysteroid dehydrogenase (11-HSD) and blocks gap juntion communication.
storage
Store at +4°C
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.
Properties of Carbenoxolone disodium
Melting point: | >275°C (dec.) |
storage temp. | 2-8°C |
solubility | Methanol (Slightly), Water (Slightly) |
form | Solid |
pka | pKa1 4.18; pKa2 5.52(at 25℃) |
color | White to Off-White |
Water Solubility | Soluble in water to 100 mM. |
Stability: | Hygroscopic |
CAS DataBase Reference | 7421-40-1(CAS DataBase Reference) |
Safety information for Carbenoxolone disodium
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Carbenoxolone disodium
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