Enoxolone

Title: Enoxolone
CAS Registry Number: 471-53-4
CAS Name: (3b,20b)-3-Hydroxy-11-oxoolean-12-en-29-oic acid
Additional Names: 3b-hydroxy-11-oxoolean-12-en-30-oic acid; glycyrrhetic acid; 18b-glycyrrhetinic acid; uralenic acid
Trademarks: Arthrodont (Veyron-Froment); Biosone (Berk); P.O. 12 (Biothžax)
Molecular Formula: C30H46O4
Molecular Weight: 470.68
Percent Composition: C 76.55%, H 9.85%, O 13.60%
Literature References: From glycyrrhizic acid, q.v. Structure: Ruzicka et al., Helv. Chim. Acta 26, 2143, 2278 (1943). Stereochemistry: Beaton, Spring, J. Chem. Soc. 1955, 3126. Prepn from shredded licorice root: Mer, Am. Perfum. Aromat. 74(6), 39 (1959). Manuf: GB 833184 (1960 to Carlo Erba). Identity with uralenic acid: Belous et al., Zh. Obshch. Khim. 35, 401 (1965). Metabolism: Parke et al., J. Pharm. Pharmacol. 15, 500 (1963). Mechanism of action: Helbing, Berntsen, Pharm. Weekbl. 100, 1438 (1965).
Properties: Needles from alcohol + petr ether, mp 296°. [a]D21 +86° (alc); [a]D20 +145.5° (dioxane); [a]D20 +163° (chloroform). Freely sol in chloroform, dioxane. Soluble in alcohol, pyridine, acetic acid. Practically insol in petr ether.
Melting point: mp 296°
Optical Rotation: [a]D21 +86° (alc); [a]D20 +145.5° (dioxane); [a]D20 +163° (chloroform)
Derivative Type: 18a-Hydrogen Form
Properties: Platelets from dil alcohol, mp 335°. [a]D20 +140° (alcohol); [a]D +98° (c = 0.1 in chloroform). Sol in alcohol, dioxane, chloroform.
Melting point: mp 335°
Optical Rotation: [a]D20 +140° (alcohol); [a]D +98° (c = 0.1 in chloroform)
Therap-Cat: Anti-inflammatory (topical).
Keywords: Glucocorticoid.
Enprostil Enrofloxacin Ensulizole Enterogastrone Enterolactone

Enoxolone
Glycyrrhetinic acid structure.svg
Systematic (IUPAC) name
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-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
Trade names Arthrodont, PruClair
AHFS/Drugs.com International Drug Names
Legal status -only (US)
Routes Oral, topical
Identifiers
CAS number 471-53-4
ATC code D03AX10
PubChem CID 10114
ChemSpider 9710
ChEBI CHEBI:30853
ChEMBL CHEMBL230006
Chemical data
Formula C30H46O4 
Mol. mass 470.6838

Enoxolone (INN, BAN), glycyrrhetinic acid or glycyrrhetic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice. It is used in flavoring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties.[1] It has some additional pharmacological properties including antiviral, antifungal, antiprotozoal, and antibacterial activities.[2][3][4][5]