Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 4C42H59O16.9Mg |
Molecular Weight | 3498.378 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 76 / 76 |
E/Z Centers | 0 |
Charge | 6 |
SHOW SMILES / InChI
SMILES
[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[Mg++].[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.[H][C@@]%14(O[C@@H]8[C@@H](O)[C@H](O)[C@H](O[C@]8([H])O[C@H]9CC[C@@]%10(C)[C@@]([H])(CC[C@]%11(C)[C@]%10([H])C(=O)C=C%12[C@]%13([H])C[C@](C)(CC[C@]%13(C)CC[C@@]%11%12C)C([O-])=O)C9(C)C)C([O-])=O)O[C@@H]([C@@H](O)[C@H](O)[C@H]%14O)C([O-])=O.[H][C@@]%21(O[C@@H]%15[C@@H](O)[C@H](O)[C@H](O[C@]%15([H])O[C@H]%16CC[C@@]%17(C)[C@@]([H])(CC[C@]%18(C)[C@]%17([H])C(=O)C=C%19[C@]%20([H])C[C@](C)(CC[C@]%20(C)CC[C@@]%18%19C)C([O-])=O)C%16(C)C)C([O-])=O)O[C@@H]([C@@H](O)[C@H](O)[C@H]%21O)C([O-])=O.[H][C@@]%28(O[C@@H]%22[C@@H](O)[C@H](O)[C@H](O[C@]%22([H])O[C@H]%23CC[C@@]%24(C)[C@@]([H])(CC[C@]%25(C)[C@]%24([H])C(=O)C=C%26[C@]%27([H])C[C@](C)(CC[C@]%27(C)CC[C@@]%25%26C)C([O-])=O)C%23(C)C)C([O-])=O)O[C@@H]([C@@H](O)[C@H](O)[C@H]%28O)C([O-])=O
InChI
InChIKey=JJEHQPDDSCFWJY-UTVHMKFVSA-B
InChI=1S/4C42H62O16.9Mg/c4*1-37(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;;;;;;;;;/h4*16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54);;;;;;;;;/q;;;;9*+2/p-12/t4*19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;;;;;;;;;/m0000........./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9570253 | https://www.ncbi.nlm.nih.gov/pubmed/8783808https://www.ncbi.nlm.nih.gov/pubmed/24493924 | https://www.ncbi.nlm.nih.gov/pubmed/19144869 | https://www.ncbi.nlm.nih.gov/pubmed/17613133 | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/cfrsearch.cfm?fr=184.1408http://www.etatpur.co.uk/index.php/enoxolone-sheethttps://www.ncbi.nlm.nih.gov/pubmed/27376261https://www.ncbi.nlm.nih.gov/pubmed/17613133https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2015.3971/pdf | http://www.cosmeticsinfo.org/ingredient/disodium-glycyrrhizate | http://www.google.com.pg/patents/WO2009115455A1https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://www.cosmeticsinfo.org/ingredient/potassium-glycyrrhetinateCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19429429 | https://www.ncbi.nlm.nih.gov/pubmed/27520483
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9570253 | https://www.ncbi.nlm.nih.gov/pubmed/8783808https://www.ncbi.nlm.nih.gov/pubmed/24493924 | https://www.ncbi.nlm.nih.gov/pubmed/19144869 | https://www.ncbi.nlm.nih.gov/pubmed/17613133 | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/cfrsearch.cfm?fr=184.1408http://www.etatpur.co.uk/index.php/enoxolone-sheethttps://www.ncbi.nlm.nih.gov/pubmed/27376261https://www.ncbi.nlm.nih.gov/pubmed/17613133https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2015.3971/pdf | http://www.cosmeticsinfo.org/ingredient/disodium-glycyrrhizate | http://www.google.com.pg/patents/WO2009115455A1https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://www.cosmeticsinfo.org/ingredient/potassium-glycyrrhetinate
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19429429 | https://www.ncbi.nlm.nih.gov/pubmed/27520483
Potassium Glycyrrhetinate (CAS no. 85985-61-1) is the
potassium salt of Glycyrrhetinic Acid. Potassium Glycyrrhetinate
is also known as Olean-12-En-29-Oic Acid, 3-Hydroxy-1,
1-Oxo-, Monopotassium Salt. Potassium Glycyrrhetinate functions as a flavoring agent and skin-conditioning agent—miscellaneous in cosmetic products.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0072593 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19144869 |
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Target ID: Q9UBK2|||Q3LIG1 Gene ID: 10891.0 Gene Symbol: PPARGC1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24675225 |
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Target ID: P24298 Gene ID: 2875.0 Gene Symbol: GPT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10574137 |
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Target ID: CHEMBL2391 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429 |
779.0 nM [IC50] | ||
Target ID: CHEMBL2908 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429 |
257.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Palliative | Stronger Neo-Minophagen C Approved UseChronic Hepatitis C Launch Date1948 |
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Preventing | MASO65D (Xclair®) Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
103.89 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1396.97 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.46 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18452416 |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
likely | ||||
yes [IC50 6.12 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0 |
likely | |||
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Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0 |
no | |||
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yes | |||
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yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice. | 2001 Dec 1 |
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Enzyme-linked immunosorbent assay for glycyrrhizin using anti-glycyrrhizin monoclonal antibody and an eastern blotting technique for glucuronides of glycyrrhetic acid. | 2001 Dec 15 |
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Effects of glycyrrhetinic acid on collagen metabolism of hepatic stellate cells at different stages of liver fibrosis in rats. | 2001 Feb |
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[Prevention of development of hepatocellular carcinoma from HCV-associated liver cirrhosis by multi-agents therapy including stronger-neo-minophagen C]. | 2001 Oct |
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Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism. | 2001 Oct 5 |
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[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 |
|
The isolated rat spinal cord as an in vitro model to study the pharmacologic control of myoclonic-like activity. | 2002 |
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Molecular pharmacophore determination of lipid lowering drugs with the receptor mapping method. | 2002 Apr |
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Retinoids inhibit squamous cell carcinoma growth and intercellular communication. | 2002 Apr |
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Kinetics and mechanism of intercellular ice propagation in a micropatterned tissue construct. | 2002 Apr |
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[Rhabdomyolysis and arterial hypertension caused by apparent excess of mineralocorticoids: a case report]. | 2002 Apr-Jun |
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The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women. | 2002 Aug |
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Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave. | 2002 Aug |
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Cell coupling and Cx43 expression in embryonic mouse neural progenitor cells. | 2002 Aug 15 |
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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 |
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Expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity. | 2002 Dec |
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Inhibitors of gap junctions attenuate myogenic tone in cerebral arteries. | 2002 Dec |
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[Effects of glycyrrhetinic acid and IFN-alpha on HSCs collagen metabolism in rat fibrotic liver of varying stages]. | 2002 Feb |
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Blocked gap junctional coupling increases glutamate-induced neurotoxicity in neuron-astrocyte co-cultures. | 2002 Feb |
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Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects. | 2002 Feb |
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11 Beta-hydroxysteroid dehydrogenase type 1 from human liver: dimerization and enzyme cooperativity support its postulated role as glucocorticoid reductase. | 2002 Feb 19 |
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Induction of inducible nitric oxide synthase expression by 18beta-glycyrrhetinic acid in macrophages. | 2002 Feb 27 |
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Primary afferent fibers establish dye-coupled connections in the frog central nervous system. | 2002 Feb-Mar 1 |
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[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 |
|
Glycyrrhetinic acid decreases plasma potassium concentrations in patients with anuria. | 2002 Jan |
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Glycyrrhetinic derivatives inhibit hyperpolarization in endothelial cells of guinea pig and rat arteries. | 2002 Jan |
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Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries. | 2002 Jan 25 |
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Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries. | 2002 Jul |
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A puzzling cause of hypokalaemia. | 2002 Jul 20 |
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Annexin 1 (lipocortin 1) mimics inhibitory effects of glucocorticoids on testosterone secretion and enhances effects of interleukin-1beta. | 2002 Jun |
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IL-1beta-induced production of metalloproteinases by synovial cells depends on gap junction conductance. | 2002 Jun |
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[Effects of glycyrrhetic acid on transmitter secretion]. | 2002 Mar |
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Gap junction intercellular communication propagates cell death in cancerous cells. | 2002 Mar 27 |
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Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora. | 2002 May |
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[Rhabdomyolysis due to licorice ingestion]. | 2002 Sep |
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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 |
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Subjects with essential hypertension are more sensitive to the inhibition of 11 beta-HSD by liquorice. | 2003 Feb |
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Biological activities of synthetic saponins and cardiac glycosides. | 2003 Jan |
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Photoliberating inositol-1,4,5-trisphosphate triggers ATP release that is blocked by the connexin mimetic peptide gap 26. | 2003 Jan |
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Blockade of brain stem gap junctions increases phrenic burst frequency and reduces phrenic burst synchronization in adult rat. | 2003 Jan |
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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 |
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Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds. | 2008 Jun |
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Ammonium glycyrrhizinate protects gastric epithelial cells from hydrogen peroxide-induced cell death. | 2009 Mar |
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Ammonium glycyrrhizinate-loaded niosomes as a potential nanotherapeutic system for anti-inflammatory activity in murine models. | 2014 |
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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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21681505
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7721345
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
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Systematic Name | English |
Code System | Code | Type | Description | ||
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444046-50-8
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PRIMARY | |||
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691410-17-0
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NON-SPECIFIC STOICHIOMETRY | |||
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154584823
Created by
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4U2UBI61D7
Created by
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD