Carbenoxolone

Title: Carbenoxolone
CAS Registry Number: 5697-56-3
CAS Name: (3b,20b)-3-(3-Carboxy-1-oxopropoxy)-11-oxoolean-12-en-29-oic acid
Additional Names: 3b-hydroxy-11-oxoolean-12-en-30-oic acid hydrogen succinate; 3-O-(b-carboxypropionyl)-11-oxo-18b-olean-12-en-30-oic acid; 18b-glycyrrhetic acid hydrogen succinate; carbenoxalone
Molecular Formula: C34H50O7
Molecular Weight: 570.76
Percent Composition: C 71.55%, H 8.83%, O 19.62%
Literature References: Anti-inflammatory glucocorticoid related to enoxolone, q.v. Prepn: Gottfried, Baxendale, GB 843133; US 3070623 (1960, 1961 to Biorex). Monograph: Carbenoxolone Sodium, J. M. Robson, F. M. Sullivan, Eds. (Butterworths, London, 1969) 263 pp. Symposium on clinical efficacy: Scand. J. Gastroenterol. 15, Suppl. 65, 1-121 (1980). Effect on gastric prostaglandin levels in humans: J. Rask-Madsen et al., Eur. J. Clin. Invest. 13, 351 (1983); P. Minuz et al., Pharmacol. Res. Commun. 16, 875 (1984). Comprehensive description: S. Pindado et al., Anal. Profiles Drug Subs. Excip. 24, 1-43 (1996).
Properties: Cream-colored crystals, mp 291-294°. [a]D20 +128° (chloroform).
Melting point: mp 291-294°
Optical Rotation: [a]D20 +128° (chloroform)
Derivative Type: Disodium salt
CAS Registry Number: 7421-40-1
Trademarks: Bioplex (Thames); Bioral (SKB); Neogel (Hexal); Sanodin; Ulcus-Tablinen (Sanorania)
Molecular Formula: C34H48Na2O7
Molecular Weight: 614.72
Percent Composition: C 66.43%, H 7.87%, Na 7.48%, O 18.22%
Properties: Creamy-white solid. Freely sol in water. Insol in chloroform, ether. pKa1 4.18; pKa2 5.52. uv max (water): 260 nm (Ecm1% 172). LD50 in male mice (mg/kg): 198 i.v.; 120 i.p.; in male rats (mg/kg): 3200 orally (Robson, Sullivan).
pKa: pKa1 4.18; pKa2 5.52
Absorption maximum: uv max (water): 260 nm (Ecm1% 172)
Toxicity data: LD50 in male mice (mg/kg): 198 i.v.; 120 i.p.; in male rats (mg/kg): 3200 orally (Robson, Sullivan)
Therap-Cat: Antiulcerative.
Keywords: Antiulcerative; Cytoprotectant (Gastric).
Carbetapentane Carbetocin Carbic Anhydride Carbimazole Carbinoxamine

Carbenoxolone
Carbenoxolone.png
Systematic (IUPAC) name
(3β)-3-[(3-carboxypropanoyl)oxy]-11-oxoolean-12-en-30-oic acid
OR
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-(3-carboxypropanoyloxy)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 5697-56-3 N
ATC code A02BX01
PubChem CID 636403
DrugBank DB02329
ChemSpider 552190 YesY
UNII MM6384NG73 YesY
ChEMBL CHEMBL499915 YesY
Chemical data
Formula C34H50O7 
Mol. mass 570.765 g/mol
 N (what is this?)  (verify)

Carbenoxolone, a synthetic derivative of glycyrrhetinic acid, is a licensed drug (in the UK) for oesophageal ulceration and inflammation. Other uses include treatment of oral and perioral lesions.

Carbenoxolone (aka Carbenoxolone, CBX) is also used as a blocker of the enzyme 11β-hydroxysteroid dehydrogenase (11β-HSD), of pannexon membrane channels (comprising 6 subunits of pannexin) and the related innexon channels (consisting of invertebrate innexins), and at higher concentrations, as a blocker of connexon channels ("hemichannels" made up of 6 connexin subunits each) and of gap junctions (2 connexons joined together). Animal and in vitro studies suggest that this blockade can increase insulin sensitivity.[citation needed]