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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H46O4
Molecular Weight 470.6838
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOXOLONE

SMILES

CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]3(C)[C@@H]2C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(O)=O

InChI

InChIKey=MPDGHEJMBKOTSU-YKLVYJNSSA-N
InChI=1S/C30H46O4/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/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Enoxolone

Glycyrrhizic Acid is specific compound isolated from licorice plants. Ammonium Glycyrrhizate (also known as GLYCYRRHIZIN, AMMONIATED) is a salt, was investigated to be a safe and is used as ingredient in the formulation of makeup, fragrance, hair care, skin care, shaving, personal hygiene and suntan products.

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
846
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha
17
Target ID: Q9UBK2|||Q3LIG1
Gene ID: 10891.0
Gene Symbol: PPARGC1A
Target Organism: Homo sapiens (Human)
Activator
1447
Alanine aminotransferase 1
17
Target ID: P24298
Gene ID: 2875.0
Gene Symbol: GPT
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Palliative
Approved
8583
Stronger Neo-Minophagen C

Approved Use

Chronic Hepatitis C

Launch Date

1948
Preventing
Basic research
MASO65D (Xclair®)

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Palliative
Not Provided
511
Unknown

Approved Use

Unknown
Palliative
Phase I
438
Unknown

Approved Use

Unknown
Palliative
Not Provided
511
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[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
How to close a gap junction channel. Efficacies and potencies of uncoupling agents.
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
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
Evidence of a role for cyclic ADP-ribose in calcium signalling and neurotransmitter release in cultured astrocytes.
2001 Aug
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
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
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
'Pseudo-aldosteronism' induced by intravenous glycyrrhizin treatment of chronic hepatitis C patients.
2001 Jul
Toward prevention of hepatocellular carcinoma developing in chronic hepatitis C.
2001 Jul
The intracellular localization of the mineralocorticoid receptor is regulated by 11beta-hydroxysteroid dehydrogenase type 2.
2001 Jul 27
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
[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
Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo.
2002 Apr
[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
Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave.
2002 Aug
Cell coupling and Cx43 expression in embryonic mouse neural progenitor cells.
2002 Aug 15
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
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
Annexin 1 (lipocortin 1) mimics inhibitory effects of glucocorticoids on testosterone secretion and enhances effects of interleukin-1beta.
2002 Jun
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
Foetal lung maturation in 11beta-hydroxysteroid dehydrogenase type 1 knockout mice.
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
Photoliberating inositol-1,4,5-trisphosphate triggers ATP release that is blocked by the connexin mimetic peptide gap 26.
2003 Jan
Patents

Patents

CN105237609A
16
EP0409005A2
16
EP0472858A2
16
EP2628487A1
16
JP06298668
16
JP2000063254A
16
JP2000143518A
26
JP2000247885A
20
JP2000290199A
28
JP2000512663A
47
JP2001039853A
16
JP2003335651A
17
JP2005220084A
17
JP2007022923A
16
JP2008115109A
16
JP2008222682A
16
JPH0296533A
16
JPH03123465A
16
JPH0315397A
16
JPH03161423A
16
JPH0399023A
26
JPH04207200A
16
JPH0436215A
16
JPH06199648A
16
JPH06279265A
16
JPH07118140A
16
JPH07291857A
16
JPH0748595A
16
JPH09110675A
20
JPH10316555A
16
JPH11139951A
16
JPH11199426A
16
JPS06183145A
16
JPS06251604A
16
JPS06335515A
16
JPS59227812A
20
JPS60260540A
16
JPS61155315A
16
JPS63135351A
16
US20080161377
16
US20110015143
16
US20130143830
16
US20150147357
16
US3164581
16
US5186945
16
US5372744
16
WO2009115455A1
16

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.
Unknown
Route of Administration: Topical
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.
Glycyrrhetinic acid (ENOXOLONE) could inhibit CYP3A4 activity competitively, with a Ki value of 1.57 μM in human liver microsomes.
Name Type Language
ENOXOLONE
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
GLYCYRRHETINIC ACID
INCI   JAN  
INCI  
Preferred Name English
3.BETA.-HYDROXY-11-OXOOLEAN-12-EN-30-OIC ACID
Common Name English
ENOXOLONE [MART.]
Common Name English
ENOXOLONE [MI]
Common Name English
ENOXOLONE [EP MONOGRAPH]
Common Name English
enoxolone [INN]
Common Name English
NSC-35347
Code English
ENOXOLONE [EP IMPURITY]
Common Name English
Enoxolone [WHO-DD]
Common Name English
GLYCYRRHETIC ACID
Common Name English
GLYCYRRHETINIC ACID [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C54678
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
DSLD 3013 (Number of products:1)
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
WHO-VATC QD03AX10
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
WHO-ATC D03AX10
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
Code System Code Type Description
FDA UNII
P540XA09DR
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
CHEBI
30853
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
MESH
D006034
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
NSC
35347
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
MERCK INDEX
m4914
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY Merck Index
INN
1794
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
DAILYMED
P540XA09DR
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
PUBCHEM
10114
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
DRUG BANK
DB13089
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
SMS_ID
100000080236
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
DRUG CENTRAL
3178
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
CAS
471-53-4
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-444-6
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
WIKIPEDIA
GLYCYRRHETINIC ACID
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID9020669
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
EVMPD
SUB06543MIG
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
NCI_THESAURUS
C526
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
ChEMBL
CHEMBL230006
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY
RXCUI
1311506
Created by admin on Mon Mar 31 17:53:41 GMT 2025 , Edited by admin on Mon Mar 31 17:53:41 GMT 2025
PRIMARY RxNorm
ACTIVE MOIETY
Structure of ENOXOLONE
SALT/SOLVATE (PARENT)
Structure of ENOXOLONE ALUMINUM
SALT/SOLVATE (PARENT)
Structure of POTASSIUM GLYCYRRHETINATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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