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

Details

Stereochemistry ABSOLUTE
Molecular Formula C42H62O16.5H2O.H3N
Molecular Weight 930.039
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM GLYCYRRHIZATE PENTAHYDRATE

SMILES

N.O.O.O.O.O.[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]3(C)C2=CC(=O)[C@]4([H])[C@@]5(C)CC[C@H](O[C@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C(O)=O)C(O)=O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O

InChI

InChIKey=YTXJXSKSPIUKIU-TYWIYPESSA-N
InChI=1S/C42H62O16.H3N.5H2O/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;5*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

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
[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
Spreading depolarization waves triggered by vagal stimulation in the embryonic chick brain: optical evidence for intercellular communication in the developing central nervous system.
2001
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Dual mechanism of intercellular communication in HOBIT osteoblastic cells: a role for gap-junctional hemichannels.
2001 Aug
Liquorice-induced rise in blood pressure: a linear dose-response relationship.
2001 Aug
A gap-junction-mediated signal, rather than an external paracrine factor, predominates during meiotic induction in isolated mouse oocytes.
2001 Feb
Glycyrrhetinic acid induced apoptosis in murine splenocytes.
2001 Jan
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.
2001 Jan 22
'Pseudo-aldosteronism' induced by intravenous glycyrrhizin treatment of chronic hepatitis C patients.
2001 Jul
Determination of 14 chemical constituents in the traditional Chinese medicinal preparation Huangqin-Tang by high performance liquid chromatography.
2001 Jun
Persistence of gap junction communication during myocardial ischemia.
2001 Jun
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
Characterization of bovine angiogenin-1 and lactogenin-like protein as glycyrrhizin-binding proteins and their in vitro phosphorylation by C-kinase.
2001 May
[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
Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism.
2001 Oct 5
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
Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo.
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
Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave.
2002 Aug
[Effects of glycyrrhetinic acid and IFN-alpha on HSCs collagen metabolism in rat fibrotic liver of varying stages].
2002 Feb
Induction of inducible nitric oxide synthase expression by 18beta-glycyrrhetinic acid in macrophages.
2002 Feb 27
[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
A puzzling cause of hypokalaemia.
2002 Jul 20
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
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
Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds.
2008 Jun
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
AMMONIUM GLYCYRRHIZATE PENTAHYDRATE
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, PENTAHYDRATE
Common Name English
GLYCYRRHIZIN, AMMONIATED PENTAHYDRATE
Common Name English
Code System Code Type Description
CAS
132215-36-2
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
PUBCHEM
91826216
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
SMS_ID
100000164368
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
RXCUI
1371367
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY RxNorm
EVMPD
SUB178759
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
FDA UNII
1Z1Y4QY887
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID10157438
Created by admin on Fri Dec 15 19:12:48 GMT 2023 , Edited by admin on Fri Dec 15 19:12:48 GMT 2023
PRIMARY