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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H59O16.2H.3H2O.H4N
Molecular Weight 894.0084
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM GLYCYRRHIZINATE TRIHYDRATE

SMILES

[H+].[H+].[NH4+].O.O.O.[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=RSPXVECNDMCBGQ-YMYWBCTMSA-N
InChI=1S/C42H62O16.H3N.3H2O/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);1H3;3*1H2/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 H
Molecular Weight 1.0079
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H4N
Molecular Weight 18.0385
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
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
[Anti-inflammatory activity of glycyrrhizic acid derivatives].
1980 Jul-Aug
Tumorigenicity study of disodium glycyrrhizinate administered orally to mice.
1985 Nov
Therapeutic basis of glycyrrhizin on chronic hepatitis B.
1996 May
Review article: glycyrrhizin as a potential treatment for chronic hepatitis C.
1998 Mar
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase.
1999 Sep
[Simultaneous measurements of electrical coupling and action potential transfer in pairs of ventricular cardiomyocytes].
2001
How to close a gap junction channel. Efficacies and potencies of uncoupling agents.
2001
Spreading depolarization waves triggered by vagal stimulation in the embryonic chick brain: optical evidence for intercellular communication in the developing central nervous system.
2001
Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro.
2001 Apr 27
18-beta-Glycyrrhetinic acid (BGA) as an electrical uncoupler for intracellular recordings in confluent monolayer cultures.
2001 Aug
Glycyrrhetinic acid induced apoptosis in murine splenocytes.
2001 Jan
Blockade of chloride channels reveals relaxations of rat small mesenteric arteries to raised potassium.
2001 Jan
A population physiologically based pharmacokinetic/pharmacodynamic model for the inhibition of 11-beta-hydroxysteroid dehydrogenase activity by glycyrrhetic acid.
2001 Jan 1
Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder.
2001 Jan 15
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.
2001 Jan 22
Expression of the 11beta-hydroxysteroid dehydrogenase type II enzyme in breast tumors and modulation of activity and cell growth in PMC42 cells.
2001 Jan-Mar
'Pseudo-aldosteronism' induced by intravenous glycyrrhizin treatment of chronic hepatitis C patients.
2001 Jul
Toward prevention of hepatocellular carcinoma developing in chronic hepatitis C.
2001 Jul
Immunoglobulin and cytokine expression in mixed lymphocyte cultures is reduced by disruption of gap junction intercellular communication.
2001 Mar
Allergic contact dermatitis from enoxolone.
2001 Mar
K+ currents underlying the action of endothelium-derived hyperpolarizing factor in guinea-pig, rat and human blood vessels.
2001 Mar 1
The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling.
2001 May
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
Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism.
2001 Oct 5
Molecular pharmacophore determination of lipid lowering drugs with the receptor mapping method.
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
Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave.
2002 Aug
Expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity.
2002 Dec
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
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
Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora.
2002 May
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
[Rhabdomyolysis due to licorice ingestion].
2002 Sep
Hepatoprotective effects of 18beta-glycyrrhetinic acid on carbon tetrachloride-induced liver injury: inhibition of cytochrome P450 2E1 expression.
2002 Sep
Solubilization and stabilization of macular carotenoids by water soluble oligosaccharides and polysaccharides.
2015 Apr 15
18α-Glycyrrhetinic acid lethality for neuroblastoma cells via de-regulating the Beclin-1/Bcl-2 complex and inducing apoptosis.
2016 Oct 1
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 Sat Dec 16 09:33:02 GMT 2023
Edited
by admin
on Sat Dec 16 09:33:02 GMT 2023
Record UNII
78NEL3149I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMMONIUM GLYCYRRHIZINATE TRIHYDRATE
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-, MONOAMMONIUM SALT, TRIHYDRATE
Systematic Name English
GLYCYRRHIZIC ACID AMMONIUM SALT TRIHYDRATE
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT002692
Created by admin on Sat Dec 16 09:33:03 GMT 2023 , Edited by admin on Sat Dec 16 09:33:03 GMT 2023
PRIMARY
PUBCHEM
2724236
Created by admin on Sat Dec 16 09:33:03 GMT 2023 , Edited by admin on Sat Dec 16 09:33:03 GMT 2023
PRIMARY
FDA UNII
78NEL3149I
Created by admin on Sat Dec 16 09:33:03 GMT 2023 , Edited by admin on Sat Dec 16 09:33:03 GMT 2023
PRIMARY
CAS
911217-00-0
Created by admin on Sat Dec 16 09:33:03 GMT 2023 , Edited by admin on Sat Dec 16 09:33:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID5047243
Created by admin on Sat Dec 16 09:33:03 GMT 2023 , Edited by admin on Sat Dec 16 09:33:03 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY