Glycyrrhizic acid

Glycyrrhizic acid

Clinical data
Trade names	Epigen, Glycyron
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, intravenous
ATC code	A05BA08 (WHO)
Legal status
Legal status	Generally regarded as safe
Pharmacokinetic data
Metabolism	Hepatic and by intestinal bacteria
Biological half-life	6.2-10.2 hours
Excretion	Faeces, urine (0.31-0.67%)
Identifiers
IUPAC name (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
CAS Number	1405-86-3 (α-D-Glucopyranosiduronic acid), 103000-77-7 (β-D-Glucopyranosiduronic acid)
PubChem (CID)	128229
ChemSpider	14263 Y
UNII	6FO62043WK
ChEBI	CHEBI:15939 Y
ChEMBL	CHEMBL441687 Y
E number	E958 (glazing agents, ...)
ECHA InfoCard	100.014.350
Chemical and physical data
Formula	C42H62O16
Molar mass	822.93 g/mol
3D model (Jmol)	Interactive image
Solubility in water	1-10 mg/mL (20 °C)
SMILES O=C(O)[C@H]7O[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]6O[C@@H]2C(C)(C)[C@@H]3CC[C@@]1(C)[C@]5(C(=C/C(=O)[C@@H]1[C@@]3(C)CC2)\[C@@H]4C[C@](C(=O)O)(C)CC[C@]4(C)CC5)C)C(=O)O)[C@H](O)[C@@H](O)[C@@H]7O
InChI InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1 Y Key:LPLVUJXQOOQHMX-QWBHMCJMSA-N Y

Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally it is a saponin and has been used as an emulsifier and gel-forming agent in foodstuff and cosmetics. Its aglycone is enoxolone and it has therefore been used as a prodrug for that compound, for example it is used in Japan to prevent liver carcinogenesis in patients with chronic hepatitis C.

Glycyrrhizin inhibits liver cell injury and is given intravenously for the treatment of chronic viral hepatitis and cirrhosis in Japan. It has also proven itself effective in the treatment of autoimmune hepatitis in one clinical trial.

The most widely reported side effects of glycyrrhizin use are fluid retention. These effects are related to the inhibition of cortisol metabolism within the kidney, and the subsequent stimulation of the mineralocorticoid receptors. Other side effects include:

It inhibits the enzyme 11beta-hydroxysteroid dehydrogenase, which likely contributes to its anti-inflammatory and mineralocorticoid activity. It has a broad-spectrum of antiviral activity in vitro against:

After oral ingestion, glycyrrhizin is first hydrolysed to 18β-glycyrrhetinic acid by intestinal bacteria. After complete absorption from the gut, β-glycyrrhetinic acid is metabolised to 3β-monoglucuronyl-18β-glycyrrhetinic acid in the liver. This metabolite then circulates in the bloodstream. Consequently its oral bioavailability is poor. The main part is eliminated by bile and only a minor part (0.31–0.67%) by urine. After oral ingestion of 600 mg of glycyrrhizin the metabolite appeared in urine after 1.5 to 14 hours. Maximal concentrations (0.49 to 2.69 mg/l) were achieved after 1.5 to 39 hours and metabolite can be detected in the urine after 2 to 4 days.