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

Details

Stereochemistry ABSOLUTE
Molecular Formula C42H62O16.H3N
Molecular Weight 839.9626
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM GLYCYRRHIZATE

SMILES

N.[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=ILRKKHJEINIICQ-OOFFSTKBSA-N
InChI=1S/C42H62O16.H3N/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/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
Spreading depolarization waves triggered by vagal stimulation in the embryonic chick brain: optical evidence for intercellular communication in the developing central nervous system.
2001
Gap-junctional communication is required for the maturation process of osteoblastic cells in culture.
2001 Apr
Endothelium-dependent vasorelaxation independent of nitric oxide and K(+) release in isolated renal arteries of rats.
2001 Apr
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro.
2001 Apr 27
Do gap junctions couple interstitial cells of Cajal pacing and neurotransmission to gastrointestinal smooth muscle?
2001 Aug
In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice.
2001 Dec 1
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
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
Toward prevention of hepatocellular carcinoma developing in chronic hepatitis C.
2001 Jul
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
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
Potentiation of L-type calcium channels reveals nonsynaptic mechanisms that correlate spontaneous activity in the developing mammalian retina.
2001 Nov 1
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
LAF1, a MYB transcription activator for phytochrome A signaling.
2001 Oct 1
[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
Stimulation of melanogenesis by glycyrrhizin in B16 melanoma cells.
2001 Sep 30
[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
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
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
Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects.
2002 Feb
[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 derivatives inhibit hyperpolarization in endothelial cells of guinea pig and rat arteries.
2002 Jan
Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries.
2002 Jan 25
IL-1beta-induced production of metalloproteinases by synovial cells depends on gap junction conductance.
2002 Jun
[Licorice--not just candy].
2002 Mar 20
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
11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation.
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
Subjects with essential hypertension are more sensitive to the inhibition of 11 beta-HSD by liquorice.
2003 Feb
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
AMMONIUM GLYCYRRHIZATE
EP   II   INCI   USP-RS  
INCI  
Official Name English
NSC-35348
Code English
GLYCYRRHIZIC ACID, MONOAMMONIUM SALT
Common Name English
GLYCYRRHIZIN, AMMONIATED [II]
Common Name English
GLYCYRRHIZIC ACID, AMMONIUM SALT
WHO-DD  
Common Name English
RDX-013 COMPONENT AMMONIUM GLYCYRRHIZATE
Common Name English
MONOAMMONIUM GLYCYRRHIZINATE
JAN  
Common Name English
GLYCYRRHIZIN, AMMONIATED ANHYDROUS
Common Name English
MONOAMMONIUM GLYCYRRHIZINATE [FCC]
Common Name English
GLYCYRRHIZIN, AMMONIATED
II  
Common Name English
RDX013 COMPONENT AMMONIUM GLYCYRRHIZATE
Common Name English
AMMONIUM GLYCYRRHIZATE [II]
Common Name English
AMMONIUM GLYCYRRHIZINATE
Common Name English
GLYCYRRAM
Common Name English
AMMONIUM DIHYDROGEN GLYCYRRHIZINATE
Common Name English
Glycyrrhizic acid, ammonium salt [WHO-DD]
Common Name English
GLYCAMIL
Common Name English
AMMONIUM GLYCYRRHIZATE [USP-RS]
Common Name English
AMMONIUM GLYCYRRHIZATE [INCI]
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-, AMMONIATE
Common Name English
MONOAMMONIUM GLYCYRRHIZATE
Common Name English
AMMONIUM GLYCYRRHIZATE COMPONENT OF RDX013
Common Name English
AMMONIUM GLYCYRRHIZATE COMPONENT OF RDX-013
Common Name English
AMMONIUM GLYCYRRHIZATE [EP MONOGRAPH]
Common Name English
AMMONIATED GLYCYRRHIZIN
Common Name English
AMMONIATED GLYCYRRHIZIN [FCC]
Common Name English
MONOAMMONIUM GLYCYRRHIZINATE [JAN]
Common Name English
NSC-2800
Code English
GLYCYRRHIZINIC ACID, AMMONIUM SALT (1:1)
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-, AMMONIATE
Common Name English
GLYCYRRHIZIN, AMMONIATED [FHFI]
Common Name English
α-D-Glucopyranosiduronic acid, (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-, ammonium salt (1:1)
Common Name English
FEMA NO. 2528
Code English
GLYCYRRHIZIN AMMONIATED
Common Name English
Classification Tree Code System Code
DSLD 3785 (Number of products:2)
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
Code System Code Type Description
NSC
35348
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
FDA UNII
3VRD35U26C
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
CAS
53956-04-0
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
EVMPD
SUB11707MIG
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
EVMPD
SUB50039
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
DAILYMED
3VRD35U26C
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
RXCUI
1311505
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY RxNorm
CAS
53956-04-0
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
RS_ITEM_NUM
1029929
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
CONCEPT Industrial Aid
NSC
2800
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
SMS_ID
100000091521
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
NCI_THESAURUS
C77525
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
EVMPD
SUB11707MIG
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
CAS
53956-04-0
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
PUBCHEM
62074
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
CAS
53956-04-0
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY
ECHA (EC/EINECS)
258-887-7
Created by admin on Fri Dec 15 15:49:57 GMT 2023 , Edited by admin on Fri Dec 15 15:49:57 GMT 2023
PRIMARY