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

Molecular Formula C42H62O16
Molecular Weight 822.9321
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H3N
Molecular Weight 17.0305
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
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase.
1999 Sep
[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
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
The enhancement of glucose uptake caused by the collapse of gap junction communication is due to an increase in astrocyte proliferation.
2001 Aug
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
Immunoglobulin and cytokine expression in mixed lymphocyte cultures is reduced by disruption of gap junction intercellular communication.
2001 Mar
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
Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo.
2002 Apr
Blocked gap junctional coupling increases glutamate-induced neurotoxicity in neuron-astrocyte co-cultures.
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
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
11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation.
2002 Oct
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
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 15:49:57 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:57 GMT 2023
Record UNII
3VRD35U26C
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
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
Related Record Type Details
SUB_CONCEPT->SUBSTANCE
SUB_CONCEPT->SUBSTANCE
SOLVATE->ANHYDROUS
SUB_CONCEPT->SUBSTANCE
SUB_CONCEPT->SUBSTANCE
SUB_CONCEPT->SUBSTANCE
SUB_CONCEPT->SUBSTANCE
SUB_CONCEPT->SUBSTANCE
PARENT -> CONSTITUENT ALWAYS PRESENT
SOLVATE->ANHYDROUS
SUB_CONCEPT->SUBSTANCE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY