Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C42H62O16.5H2O.H3N |
Molecular Weight | 930.039 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N.O.O.O.O.O.[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=YTXJXSKSPIUKIU-TYWIYPESSA-N
InChI=1S/C42H62O16.H3N.5H2O/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;5*1H2/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;;;;;;/m0....../s1
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 |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
|||
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 |
---|---|---|
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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major | |||
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no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0 |
no | |||
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yes | |||
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yes | |||
Page: 1.0 |
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 |
|
[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 |
|
[Licorice-induced pseudoaldosteronism in a patient with a non-functioning adrenal tumor]. | 2001 Sep |
|
[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 |
|
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 |
|
Retinoids inhibit squamous cell carcinoma growth and intercellular communication. | 2002 Apr |
|
Kinetics and mechanism of intercellular ice propagation in a micropatterned tissue construct. | 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 |
|
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 |
|
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 |
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[Effects of glycyrrhetinic acid and IFN-alpha on HSCs collagen metabolism in rat fibrotic liver of varying stages]. | 2002 Feb |
|
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 |
|
Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol. | 2002 Jan |
|
Glycyrrhetinic acid decreases plasma potassium concentrations in patients with anuria. | 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 |
|
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 |
|
Gap junction intercellular communication propagates cell death in cancerous cells. | 2002 Mar 27 |
|
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 |
|
Foetal lung maturation in 11beta-hydroxysteroid dehydrogenase type 1 knockout mice. | 2002 Oct |
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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 |
|
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-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
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:12:48 GMT 2023
by
admin
on
Fri Dec 15 19:12:48 GMT 2023
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Record UNII |
1Z1Y4QY887
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Record Status |
Validated (UNII)
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Record Version |
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91826216
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100000164368
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1371367
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SUB178759
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1Z1Y4QY887
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DTXSID10157438
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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