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

Details

Stereochemistry ABSOLUTE
Molecular Formula C30H44O4.2K
Molecular Weight 546.8646
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOXOLONE DIPOTASSIUM

SMILES

[K+].[K+].[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(C)(C)[C@]5([H])CC[C@@]34C)C([O-])=O

InChI

InChIKey=ZLSFWAPBBIIMKI-KVINTPOGSA-M
InChI=1S/C30H45O4.2K/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6;;/h16,19,21-23H,8-15,17H2,1-7H3,(H,33,34);;/q-1;2*+1/p-1/t19-,21-,22-,23+,26+,27-,28-,29+,30+;;/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
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase.
1999 Sep
How to close a gap junction channel. Efficacies and potencies of uncoupling agents.
2001
Endothelium-dependent vasorelaxation independent of nitric oxide and K(+) release in isolated renal arteries of rats.
2001 Apr
Do gap junctions couple interstitial cells of Cajal pacing and neurotransmission to gastrointestinal smooth muscle?
2001 Aug
Inhibitory effect of glycyrrhizin on the phosphorylation and DNA-binding abilities of high mobility group proteins 1 and 2 in vitro.
2001 Aug
Enzyme-linked immunosorbent assay for glycyrrhizin using anti-glycyrrhizin monoclonal antibody and an eastern blotting technique for glucuronides of glycyrrhetic acid.
2001 Dec 15
Magnolol from Magnolia officinalis inhibits 11beta-hydroxysteroid dehydrogenase without increases of corticosterone and thymocyte apoptosis in mice.
2001 Feb
Glycyrrhetinic acid induced apoptosis in murine splenocytes.
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
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
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
[Prevention of development of hepatocellular carcinoma from HCV-associated liver cirrhosis by multi-agents therapy including stronger-neo-minophagen C].
2001 Oct
Effect of pH on metabolism of glycyrrhizin, glycyrrhetic acid and glycyrrhetic acid monoglucuronide by collected human intestinal flora.
2001 Oct
Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries.
2001 Oct
Modulation of 11 beta-hydroxysteroid dehydrogenase type 2 activity in Ishikawa cells is associated with changes in cellular proliferation.
2001 Oct 25
Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism.
2001 Oct 5
[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
Kinetics and mechanism of intercellular ice propagation in a micropatterned tissue construct.
2002 Apr
[Rhabdomyolysis and arterial hypertension caused by apparent excess of mineralocorticoids: a case report].
2002 Apr-Jun
The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women.
2002 Aug
Inhibitors of gap junctions attenuate myogenic tone in cerebral arteries.
2002 Dec
Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects.
2002 Feb
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
Influence of honey on the gastrointestinal metabolism and disposition of glycyrrhizin and glycyrrhetic acid in rabbits.
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
Gap junction intercellular communication propagates cell death in cancerous cells.
2002 Mar 27
Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora.
2002 May
[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
Biological activities of synthetic saponins and cardiac glycosides.
2003 Jan
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
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
Name Type Language
ENOXOLONE DIPOTASSIUM
Common Name English
Enoxolone potassium [WHO-DD]
Common Name English
OLEAN-12-EN-29-OIC ACID, 3-HYDROXY-11-OXO-, DIPOTASSIUM SALT, (3.BETA.,20.BETA.)-
Common Name English
ENOXOLONE DIPOTASSIUM SALT
Common Name English
DIPOTASSIUM GLYCYRRHETINATE
Common Name English
GLYCYRRHETINIC ACID DIPOTASSIUM SALT
Common Name English
OLEAN-12-EN-29-OIC ACID, 3-HYDROXY-11-OXO-, POTASSIUM SALT (1:2)
Systematic Name English
Code System Code Type Description
CAS
23327-65-3
Created by admin on Sat Dec 16 08:29:54 GMT 2023 , Edited by admin on Sat Dec 16 08:29:54 GMT 2023
PRIMARY
PUBCHEM
9850441
Created by admin on Sat Dec 16 08:29:54 GMT 2023 , Edited by admin on Sat Dec 16 08:29:54 GMT 2023
PRIMARY
DAILYMED
ZJI2YIM6Z9
Created by admin on Sat Dec 16 08:29:54 GMT 2023 , Edited by admin on Sat Dec 16 08:29:54 GMT 2023
PRIMARY
RXCUI
2043284
Created by admin on Sat Dec 16 08:29:54 GMT 2023 , Edited by admin on Sat Dec 16 08:29:54 GMT 2023
PRIMARY
FDA UNII
ZJI2YIM6Z9
Created by admin on Sat Dec 16 08:29:54 GMT 2023 , Edited by admin on Sat Dec 16 08:29:54 GMT 2023
PRIMARY