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

Details

Stereochemistry ABSOLUTE
Molecular Formula C42H62O16
Molecular Weight 822.9321
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCYRRHIZIN

SMILES

[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=LPLVUJXQOOQHMX-QWBHMCJMSA-N
InChI=1S/C42H62O16/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)/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

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
[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
In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice.
2001 Dec 1
Enzyme-linked immunosorbent assay for glycyrrhizin using anti-glycyrrhizin monoclonal antibody and an eastern blotting technique for glucuronides of glycyrrhetic acid.
2001 Dec 15
Effects of glycyrrhetinic acid on collagen metabolism of hepatic stellate cells at different stages of liver fibrosis in rats.
2001 Feb
[Prevention of development of hepatocellular carcinoma from HCV-associated liver cirrhosis by multi-agents therapy including stronger-neo-minophagen C].
2001 Oct
Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism.
2001 Oct 5
Stimulation of melanogenesis by glycyrrhizin in B16 melanoma cells.
2001 Sep 30
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
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
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
11 Beta-hydroxysteroid dehydrogenase type 1 from human liver: dimerization and enzyme cooperativity support its postulated role as glucocorticoid reductase.
2002 Feb 19
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
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
Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.
2002 Jul
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
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
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 16:00:04 GMT 2023
Edited
by admin
on Fri Dec 15 16:00:04 GMT 2023
Record UNII
6FO62043WK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLYCYRRHIZIN
HSDB   II   JAN  
Common Name English
Glycyrrhizic acid [WHO-DD]
Common Name English
GLYCYRRHIZIC ACID (GLYCYRRHIZIN) (CONSTITUENT OF LICORICE) [DSC]
Common Name English
GLYCYRRHIZIC ACID [USP-RS]
Common Name English
GLYCYRRHIZIN [JAN]
Common Name English
GLYCYRRHIZIC ACID [MART.]
Common Name English
GLYCYRRHIZIC ACID [MI]
Common Name English
GLYCYRRHIZIC ACID
INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
GLYCYRRHIZIN [II]
Common Name English
GLYCYRRHIZINIC ACID
Common Name English
GLYCYRRHIZIC ACID [INCI]
Common Name English
GLYCYRRHIZATE
Common Name English
POTENLINI
Common Name English
GLYCYRRHIZINATE
Common Name English
NSC-167409
Code English
18.BETA.-GLYCYRRHIZIC ACID
Common Name English
.BETA.-GLYCYRRHIZIN
Common Name English
(3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-.ALPHA.-D-GLUCOPYRANOSIDURONIC ACID
Common Name English
NSC-234419
Code English
GLYCYRRHIZIN [HSDB]
Common Name English
GLYCYRON
Common Name English
Classification Tree Code System Code
DSLD 3011 (Number of products:14)
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
WHO-ATC A05BA08
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
WHO-VATC QA05BA08
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
Code System Code Type Description
SMS_ID
100000078200
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
RXCUI
26143
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY RxNorm
EU FOOD ADDITIVES
GLYCYRRHIZIN
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
RXCUI
1370586
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
ALTERNATIVE
EVMPD
SUB14004MIG
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
DAILYMED
6FO62043WK
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
ECHA (EC/EINECS)
215-785-7
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
FDA UNII
6FO62043WK
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID8047006
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
NSC
167409
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
RXCUI
1359426
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
ALTERNATIVE
CHEBI
29807
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
WIKIPEDIA
GLYCYRRHIZIN
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
HSDB
496
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
DRUG CENTRAL
1325
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
RS_ITEM_NUM
1295888
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
CAS
1405-86-3
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
DRUG BANK
DB13751
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
ChEMBL
CHEMBL441687
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
NSC
234419
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
MERCK INDEX
m5811
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C1117
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
PUBCHEM
14982
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
MESH
D019695
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
CHEBI
15939
Created by admin on Fri Dec 15 16:00:04 GMT 2023 , Edited by admin on Fri Dec 15 16:00:04 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
2.49% of dry weight of contents.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
DERIVATIVE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
3.27% of dry weight of contents.
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
The compound did not show significant cytotoxicity against uninfected MDCK cells at 100 uM, but showed inhibitory activity against the H1N1 virus at 100 uM. The compound was also evaluated for anti-HIV activity.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY