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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H59O16.K.2H
Molecular Weight 861.0224
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOPOTASSIUM GLYCYRRHIZINATE

SMILES

[H+].[H+].[K+].[H][C@@]7(O[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@]2([H])CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])C(=O)C=C5[C@]6([H])C[C@](C)(CC[C@]6(C)CC[C@@]45C)C([O-])=O)C2(C)C)C([O-])=O)O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C([O-])=O

InChI

InChIKey=YLSUMFQEBHBMQB-OOFFSTKBSA-M
InChI=1S/C42H62O16.K/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);/q;+1/p-1/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;/m0./s1

HIDE SMILES / InChI

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen Volume70B Pages 122-32 Journal 1937

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9UBK2|||Q3LIG1
Gene ID: 10891.0
Gene Symbol: PPARGC1A
Target Organism: Homo sapiens (Human)
Target ID: P24298
Gene ID: 2875.0
Gene Symbol: GPT
Target Organism: Homo sapiens (Human)
779.0 nM [IC50]
257.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Stronger Neo-Minophagen C

Approved Use

Chronic Hepatitis C

Launch Date

1948
Preventing
MASO65D (Xclair®)

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
103.89 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1396.97 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.46 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOXOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
1500 mg single, oral
Highest studied dose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
healthy, 29 years
n = 6
Health Status: healthy
Age Group: 29 years
Sex: M
Population Size: 6
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
major
major
minor
minor
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Therapeutic basis of glycyrrhizin on chronic hepatitis B.
1996 May
Review article: glycyrrhizin as a potential treatment for chronic hepatitis C.
1998 Mar
[The assessment of safety of enoxaparin administration during percutaneous transluminal coronary angioplasty after ticlopidine pretreatment. Application of low molecular weigh heparins in prevention of coronary micro-embolization].
2001
The enhancement of glucose uptake caused by the collapse of gap junction communication is due to an increase in astrocyte proliferation.
2001 Aug
18-beta-Glycyrrhetinic acid (BGA) as an electrical uncoupler for intracellular recordings in confluent monolayer cultures.
2001 Aug
Inhibitory effect of glycyrrhizin on the phosphorylation and DNA-binding abilities of high mobility group proteins 1 and 2 in vitro.
2001 Aug
Antibacterial compounds of licorice against upper airway respiratory tract pathogens.
2001 Jun
Potentiation of L-type calcium channels reveals nonsynaptic mechanisms that correlate spontaneous activity in the developing mammalian retina.
2001 Nov 1
[Prevention of development of hepatocellular carcinoma from HCV-associated liver cirrhosis by multi-agents therapy including stronger-neo-minophagen C].
2001 Oct
Simultaneous determination of glycyrrhizin, glycyrrhetic acid and glycyrrhetic acid mono-glucuronide in Shakuyaku-kanzo-to incubated with rat feces by semi-micro high-performance liquid chromatography.
2001 Oct
Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries.
2001 Oct
Bimodal inhibition of connexin 43 gap junctions decreases ACTH-induced steroidogenesis and increases bovine adrenal cell population growth.
2001 Oct
Modulation of 11 beta-hydroxysteroid dehydrogenase type 2 activity in Ishikawa cells is associated with changes in cellular proliferation.
2001 Oct 25
Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism.
2001 Oct 5
[Licorice-induced pseudoaldosteronism in a patient with a non-functioning adrenal tumor].
2001 Sep
Characterization of secretory type IIA phospholipase A2 (sPLA2-IIA) as a glycyrrhizin (GL)-binding protein and the GL-induced inhibition of the CK-II-mediated stimulation of sPLA2-IIA activity in vitro.
2001 Sep
An unexpected case of primary pulmonary hypertension of the neonate (PPHN). Potential role of topical administration of enoxolone.
2002
Molecular pharmacophore determination of lipid lowering drugs with the receptor mapping method.
2002 Apr
Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo.
2002 Apr
Retinoids inhibit squamous cell carcinoma growth and intercellular communication.
2002 Apr
Kinetics and mechanism of intercellular ice propagation in a micropatterned tissue construct.
2002 Apr
Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave.
2002 Aug
Cell coupling and Cx43 expression in embryonic mouse neural progenitor cells.
2002 Aug 15
Short-term cortisol infusion in the brachial artery, with and without inhibiting 11 beta-hydroxysteroid dehydrogenase, does not alter forearm vascular resistance in normotensive and hypertensive subjects.
2002 Dec
Expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity.
2002 Dec
Inhibitors of gap junctions attenuate myogenic tone in cerebral arteries.
2002 Dec
Smooth muscle membrane potential modulates endothelium-dependent relaxation of rat basilar artery via myo-endothelial gap junctions.
2002 Dec 15
[Effects of glycyrrhetinic acid and IFN-alpha on HSCs collagen metabolism in rat fibrotic liver of varying stages].
2002 Feb
11 Beta-hydroxysteroid dehydrogenase type 1 from human liver: dimerization and enzyme cooperativity support its postulated role as glucocorticoid reductase.
2002 Feb 19
Induction of inducible nitric oxide synthase expression by 18beta-glycyrrhetinic acid in macrophages.
2002 Feb 27
Primary afferent fibers establish dye-coupled connections in the frog central nervous system.
2002 Feb-Mar 1
[Quantitative determinations of glycyrrhizic acid, glycyrrhetinic acid, morphine and sodium benzoate in compound liquorice tablets by capillary zone electrophoresis].
2002 Jan
Influence of honey on the gastrointestinal metabolism and disposition of glycyrrhizin and glycyrrhetic acid in rabbits.
2002 Jan
Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol.
2002 Jan
Glycyrrhetinic acid decreases plasma potassium concentrations in patients with anuria.
2002 Jan
Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.
2002 Jul
IL-1beta-induced production of metalloproteinases by synovial cells depends on gap junction conductance.
2002 Jun
Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora.
2002 May
Foetal lung maturation in 11beta-hydroxysteroid dehydrogenase type 1 knockout mice.
2002 Oct
11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation.
2002 Oct
Modulation of renal calcium handling by 11 beta-hydroxysteroid dehydrogenase type 2.
2002 Oct
Inhibition of 3 alpha/beta,20 beta-hydroxysteroid dehydrogenase by dexamethasone, glycyrrhetinic acid and spironolactone is attenuated by deletion of 12 carboxyl-terminal residues.
2002 Sep
Subjects with essential hypertension are more sensitive to the inhibition of 11 beta-HSD by liquorice.
2003 Feb
Biological activities of synthetic saponins and cardiac glycosides.
2003 Jan
Photoliberating inositol-1,4,5-trisphosphate triggers ATP release that is blocked by the connexin mimetic peptide gap 26.
2003 Jan
Blockade of brain stem gap junctions increases phrenic burst frequency and reduces phrenic burst synchronization in adult rat.
2003 Jan
Final report on the safety assessment of Glycyrrhetinic Acid, Potassium Glycyrrhetinate, Disodium Succinoyl Glycyrrhetinate, Glyceryl Glycyrrhetinate, Glycyrrhetinyl Stearate, Stearyl Glycyrrhetinate, Glycyrrhizic Acid, Ammonium Glycyrrhizate, Dipotassium Glycyrrhizate, Disodium Glycyrrhizate, Trisodium Glycyrrhizate, Methyl Glycyrrhizate, and Potassium Glycyrrhizinate.
2007
Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds.
2008 Jun
Ammonium glycyrrhizinate protects gastric epithelial cells from hydrogen peroxide-induced cell death.
2009 Mar
Ammonium glycyrrhizinate-loaded niosomes as a potential nanotherapeutic system for anti-inflammatory activity in murine models.
2014
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Disodium Glycyrrhizate was not carcinogenic in mice in a drinking water study at exposure levels up to 12.2 mg/kg day(-1) for 96 weeks.
100 ml/day of intravenous glycyrrhizin
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: The suppressor cell activity of T6S cells was clearly counteracted by glycyrrhizin mononuclear cells (GR-MNC) in vitro in a mixed lymphocyte-tumor cell reaction. The type of cells responsible for anti-suppressor cells in GR-MNC was shown to be a CD4+ CD28+ TCR alpha/beta + Vicia villosa lectin-adherent T cell. These results suggest that GR may reverse the increased susceptibility of thermally injured mice to herpes simplex virus type 1 (HSV) infection through the induction of CD4+ contrasuppressor T cells.
Unknown
Name Type Language
MONOPOTASSIUM GLYCYRRHIZINATE
Common Name English
MONOPOTASSIUM GLYCYRRHIZATE
Common Name English
.ALPHA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-, POTASSIUM SALT (1:1), (3.BETA.)-
Systematic Name English
18.BETA.-GLYCYRRHIZIC ACID MONOPOTASSIUM SALT
Common Name English
Glycyrrhizinate potassium [WHO-DD]
Common Name English
.ALPHA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-, MONOPOTASSIUM SALT
Common Name English
Code System Code Type Description
CAS
42294-03-1
Created by admin on Sat Dec 16 08:31:38 GMT 2023 , Edited by admin on Sat Dec 16 08:31:38 GMT 2023
PRIMARY
PUBCHEM
23685726
Created by admin on Sat Dec 16 08:31:38 GMT 2023 , Edited by admin on Sat Dec 16 08:31:38 GMT 2023
PRIMARY
FDA UNII
T8XVV1JDN8
Created by admin on Sat Dec 16 08:31:38 GMT 2023 , Edited by admin on Sat Dec 16 08:31:38 GMT 2023
PRIMARY
CAS
68039-19-0
Created by admin on Sat Dec 16 08:31:38 GMT 2023 , Edited by admin on Sat Dec 16 08:31:38 GMT 2023
NON-SPECIFIC STOICHIOMETRY
CAS
11052-18-9
Created by admin on Sat Dec 16 08:31:38 GMT 2023 , Edited by admin on Sat Dec 16 08:31:38 GMT 2023
SUPERSEDED
ECHA (EC/EINECS)
268-237-4
Created by admin on Sat Dec 16 08:31:38 GMT 2023 , Edited by admin on Sat Dec 16 08:31:38 GMT 2023
PRIMARY
CAS
79165-04-1
Created by admin on Sat Dec 16 08:31:38 GMT 2023 , Edited by admin on Sat Dec 16 08:31:38 GMT 2023
SUPERSEDED