Compound: carbenoxolone
SMILES: O=C1C=C2[C@](CC[C@@]3([C@H]2C[C@](C(=O)O)(C)CC3)C)(C)[C@]4([C@H]1[C@@]5([C@H](C([C@@H](OC(=O)CCC(=O)O)CC5)(C)C)CC4)C)C
InChIKey: OBZHEBDUNPOCJG-WBXJDKIVSA-N
Synonyms: carbenoxolone, 5697-56-3, Carbenoxolona, Carbenoxolonum, MM6384NG73, DTXSID4022733, (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-(4-hydroxy-4-oxobutanoyl)oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid, Olean-12-en-29-oic acid, 3-(3-carboxy-1-oxopropoxy)-11-oxo-, (3beta,20beta)-, (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-(3-carboxypropanoyloxy)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid, (3beta,20beta)-3-(3-Carboxy-1-oxopropoxy)-11-oxoolean-12-en-29-oic acid, 18alpha Carbenoxolone, Carbeneoxolone, Carbenoxalone, Glycyrrhetinic acid hydrogen succinate, RefChem:123513, DTXCID702733, A02BX01, 18alpha Glycyrrhetinic Acid 3beta O Hemisuccinate, 18alpha-Glycyrrhetinic Acid 3beta-O-Hemisuccinate, 3beta-O-Hemisuccinate, 18alpha-Glycyrrhetinic Acid, Acid 3beta-O-Hemisuccinate, 18alpha-Glycyrrhetinic, 227-174-2, Carbenoxolone (INN), CARBENOXOLONE [INN], (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-((3-carboxypropanoyl)oxy)-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, Carbenoxolone [INN:BAN], Carbenoxolonum [INN-Latin], Carbenoxolona [INN-Spanish], UNII-MM6384NG73, Olean-12-en-29-oic acid, 3-(3-carboxy-1-oxopropoxy)-11-oxo-, (3.beta.,20.beta.)-, EINECS 227-174-2, Prestwick0_000837, Prestwick1_000837, Prestwick2_000837, Prestwick3_000837, CARBENOXOLONE [MI], SCHEMBL76013, BSPBio_000793, SPBio_002714, CARBENOXOLONE [WHO-DD], BPBio1_000873, CHEMBL499915, GTPL4151, orb1299555, 3beta-Hydroxy-11-oxoolean-12-en-30-saeure hydogensuccinat, 3beta-(3-Carboxypropionyloxy)-11-oxo-olean-12-en-30-saeure, GLXC-21343, 3-beta-(3-Carboxypropionyloxy)-11-oxo-olean-12-en-30-oic acid, HY-B1588, BDBM50247012, AKOS015951361, AKOS016036240, DB02329, FC140637, MS-33212, CS-0013487, 3beta-O-Succinyl-18-beta-glycyrrhetinic acid, D07615, Q752861, BRD-K12765235-304-03-8, 3.beta.-Hydroxy-11-oxoolean-12-en-30-oic acid 3-hemisuccinate, 3beta-[(3-Carboxypropanoyl)oxy]-11-oxoolean-12-en-30-oic acid, (3beta)-3-[(3-carboxypropanoyl)oxy]-11-oxoolean-12-en-30-oic acid, 3.BETA.-HYDROXY-11-OXOOLEAN-12-EN-30-OIC ACID HYDROGEN SUCCINATE, Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-, hydrogen succinate, (3beta,5beta,10alpha,14beta)-3-[(3-carboxypropanoyl)oxy]-11-oxoolean-12-en-29-oic acid, CBX, OLEAN-12-EN-29-OIC ACID, 3-(3-CARBOXY-1-OXOPROPOXY)-11-OXO, (3.BETA.,20.BETA.)-
Theoretical properties:
molecular_formula: C34H50O7
molecular_weight: 570.8 g/mol
exact_mass: 570.35565393 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 6
heavy_atom_count: 41
topological_polar_surface_area: 118 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: CARBENOXOLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Carbenoxolone (CBX) is a glycyrrhetinic acid derivative with a steroid-like structure, similar to substances found in the root of the licorice plant. Carbenoxolone is used for the treatment of peptic, esophageal and oral ulceration and inflammation. Electrolyte imbalance is a serious side effect of carbenoxolone when used systemically.
Carbenoxolone reversibly inhibits the conversion of inactive cortisone to cortisol by blocking 11β-hydroxysteroid dehydrogenase (11β-HSD). 11β-HSD also reversibly catalyzes the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol.
Carbenoxolone is a modestly potent, reasonably effective, water-soluble blocker of gap junctions.
Carbenoxolone has also been used in topical creams such as Carbosan gel, marketed for treatment of lip sores and mouth ulcers.