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

Details

Stereochemistry ABSOLUTE
Molecular Formula C42H59O16.2Na
Molecular Weight 865.8878
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge -1

SHOW SMILES / InChI
Structure of DISODIUM GLYCYRRHIZATE

SMILES

[Na+].[Na+].[H][C@@]7(O[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@]1([H])O[C@H]2CC[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=KPQJOKRSYYJJEL-VLQRKCJKSA-K
InChI=1S/C42H62O16.2Na/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-3/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 Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C42H60O16
Molecular Weight 820.9162
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

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
[Simultaneous measurements of electrical coupling and action potential transfer in pairs of ventricular cardiomyocytes].
2001
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
[Rhabdomyolysis and arterial hypertension caused by apparent excess of mineralocorticoids: a case report].
2002 Apr-Jun
UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds.
2002 Aug
The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women.
2002 Aug
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
Blocked gap junctional coupling increases glutamate-induced neurotoxicity in neuron-astrocyte co-cultures.
2002 Feb
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
Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.
2002 Jul
A puzzling cause of hypokalaemia.
2002 Jul 20
Annexin 1 (lipocortin 1) mimics inhibitory effects of glucocorticoids on testosterone secretion and enhances effects of interleukin-1beta.
2002 Jun
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
[Licorice--not just candy].
2002 Mar 20
Gap junction intercellular communication propagates cell death in cancerous cells.
2002 Mar 27
Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora.
2002 May
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
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
[Rhabdomyolysis due to licorice ingestion].
2002 Sep
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
Hepatoprotective effects of 18beta-glycyrrhetinic acid on carbon tetrachloride-induced liver injury: inhibition of cytochrome P450 2E1 expression.
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
Diammonium glycyrrhizinate, a component of traditional Chinese medicine Gan-Cao, prevents murine T-cell-mediated fulminant hepatitis in IL-10- and IL-6-dependent manners.
2007 Oct
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
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 19:51:51 GMT 2023
Edited
by admin
on Fri Dec 15 19:51:51 GMT 2023
Record UNII
L8Q0US0J7V
Record Status Validated (UNII)
Record Version
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Name Type Language
DISODIUM GLYCYRRHIZATE
INCI  
INCI  
Official Name English
Disodium glycyrrhizate [WHO-DD]
Common Name English
DISODIUM GLYCYRRHIZATE [INCI]
Common Name English
Code System Code Type Description
FDA UNII
L8Q0US0J7V
Created by admin on Fri Dec 15 19:51:51 GMT 2023 , Edited by admin on Fri Dec 15 19:51:51 GMT 2023
PRIMARY
RXCUI
1313716
Created by admin on Fri Dec 15 19:51:51 GMT 2023 , Edited by admin on Fri Dec 15 19:51:51 GMT 2023
PRIMARY RxNorm
PUBCHEM
118984432
Created by admin on Fri Dec 15 19:51:51 GMT 2023 , Edited by admin on Fri Dec 15 19:51:51 GMT 2023
PRIMARY
DAILYMED
L8Q0US0J7V
Created by admin on Fri Dec 15 19:51:51 GMT 2023 , Edited by admin on Fri Dec 15 19:51:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID8020670
Created by admin on Fri Dec 15 19:51:51 GMT 2023 , Edited by admin on Fri Dec 15 19:51:51 GMT 2023
PRIMARY
SMS_ID
300000031807
Created by admin on Fri Dec 15 19:51:51 GMT 2023 , Edited by admin on Fri Dec 15 19:51:51 GMT 2023
PRIMARY
CAS
71277-79-7
Created by admin on Fri Dec 15 19:51:51 GMT 2023 , Edited by admin on Fri Dec 15 19:51:51 GMT 2023
PRIMARY