U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C42H59O16.2K.H
Molecular Weight 899.1128
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCYRRHIZINATE DIPOTASSIUM

SMILES

[H+].[K+].[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=BIVBRWYINDPWKA-VLQRKCJKSA-L
InChI=1S/C42H62O16.2K/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;2*+1/p-2/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;;/m0../s1

HIDE SMILES / InChI

Molecular Formula C42H59O16
Molecular Weight 819.9083
Charge -3
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula K
Molecular Weight 39.0983
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H
Molecular Weight 1.0079
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[Simultaneous measurements of electrical coupling and action potential transfer in pairs of ventricular cardiomyocytes].
2001
[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
How to close a gap junction channel. Efficacies and potencies of uncoupling agents.
2001
Gap-junctional communication is required for the maturation process of osteoblastic cells in culture.
2001 Apr
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Do gap junctions couple interstitial cells of Cajal pacing and neurotransmission to gastrointestinal smooth muscle?
2001 Aug
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
Enzyme-linked immunosorbent assay for glycyrrhizin using anti-glycyrrhizin monoclonal antibody and an eastern blotting technique for glucuronides of glycyrrhetic acid.
2001 Dec 15
Effects of glycyrrhetinic acid on collagen metabolism of hepatic stellate cells at different stages of liver fibrosis in rats.
2001 Feb
A gap-junction-mediated signal, rather than an external paracrine factor, predominates during meiotic induction in isolated mouse oocytes.
2001 Feb
[Experimental study of anti-inflammatory and wound healing properties of 1% ointments of 18-dehydroglycyrrhetic acid sodium salt].
2001 Jul-Aug
Antibacterial compounds of licorice against upper airway respiratory tract pathogens.
2001 Jun
Immunoglobulin and cytokine expression in mixed lymphocyte cultures is reduced by disruption of gap junction intercellular communication.
2001 Mar
Potentiation of L-type calcium channels reveals nonsynaptic mechanisms that correlate spontaneous activity in the developing mammalian retina.
2001 Nov 1
An endothelium-derived hyperpolarizing factor-like factor moderates myogenic constriction of mesenteric resistance arteries in the absence of endothelial nitric oxide synthase-derived nitric oxide.
2001 Oct
LAF1, a MYB transcription activator for phytochrome A signaling.
2001 Oct 1
[Immunoenzyme test-system for detection of glycyrrhizic acid].
2001 Sep-Oct
An unexpected case of primary pulmonary hypertension of the neonate (PPHN). Potential role of topical administration of enoxolone.
2002
The isolated rat spinal cord as an in vitro model to study the pharmacologic control of myoclonic-like activity.
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
Endothelin 1 type a receptor antagonism prevents vascular dysfunction and hypertension induced by 11beta-hydroxysteroid dehydrogenase inhibition: role of nitric oxide.
2002 Apr 30
Expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity.
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
Blocked gap junctional coupling increases glutamate-induced neurotoxicity in neuron-astrocyte co-cultures.
2002 Feb
Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects.
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
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
Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries.
2002 Jan 25
A puzzling cause of hypokalaemia.
2002 Jul 20
IL-1beta-induced production of metalloproteinases by synovial cells depends on gap junction conductance.
2002 Jun
[Effects of glycyrrhetic acid on transmitter secretion].
2002 Mar
Gap junction intercellular communication propagates cell death in cancerous cells.
2002 Mar 27
Acute intrarenal administration of cortisol has no effect on renal blood flow in hypertensive individuals.
2002 Nov
Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication.
2002 Nov
11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation.
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
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
Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds.
2008 Jun
Ammonium glycyrrhizinate-loaded niosomes as a potential nanotherapeutic system for anti-inflammatory activity in murine models.
2014
Study of an Acid-Free Technique for the Preparation of Glycyrrhetinic Acid from Ammonium Glycyrrhizinate in Subcritical Water.
2015 Nov
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:59 GMT 2023
Edited
by admin
on Fri Dec 15 16:13:59 GMT 2023
Record UNII
CA2Y0FE3FX
Record Status Validated (UNII)
Record Version
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Name Type Language
GLYCYRRHIZINATE DIPOTASSIUM
Common Name English
DIPOTASSIUM GLYCYRRHIZATE [INCI]
Common Name English
DIPOTASSIUM GLYCYRRHIZINATE [JAN]
Common Name English
Dipotassium Glycyrrhizate [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-, POTASSIUM SALT (1:2)
Common Name English
DIPOTASSIUM GLYCYRRHIZATE
INCI   MART.   WHO-DD  
INCI  
Official Name English
DIPOTASSIUM GLYCYRRHIZINATE
JAN  
Common Name English
GLYCYRRHIZIC ACID DIPOTASSIUM
Common Name English
DIPOTASSIUM (3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL-2-O-.BETA.-D-GLUCOPYRANURONOSYL-.ALPHA.-D-GLUCOPYRANOSIDURONATE
Common Name English
DIPOTASSIUM GLYCYRRHIZATE [MART.]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
272-296-1
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
DRUG BANK
DBSALT002693
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
CAS
68039-19-0
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
NON-SPECIFIC STOICHIOMETRY
NCI_THESAURUS
C80931
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
DAILYMED
CA2Y0FE3FX
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
PUBCHEM
656852
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL441687
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
SMS_ID
100000085835
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID501015077
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
FDA UNII
CA2Y0FE3FX
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
CONCEPT Industrial Aid
RXCUI
1367264
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY RxNorm
CAS
68797-35-3
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
EVMPD
SUB22293
Created by admin on Fri Dec 15 16:13:59 GMT 2023 , Edited by admin on Fri Dec 15 16:13:59 GMT 2023
PRIMARY
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ACTIVE MOIETY