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++].C[C@]12CC[C@@](C)(C[C@H]1C3=CC(=O)[C@@H]4[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@@H]5CC[C@@]4(C)[C@]3(C)CC2)C([O-])=O.C[C@]89CC[C@@](C)(C[C@H]8C%10=CC(=O)[C@@H]%11[C@@]%12(C)CC[C@H](O[C@H]%13O[C@@H]([C@@H](O)[C@H](O)[C@H]%13O[C@@H]%14O[C@@H]([C@@H](O)[C@H](O)[C@H]%14O)C([O-])=O)C([O-])=O)C(C)(C)[C@@H]%12CC[C@@]%11(C)[C@]%10(C)CC9)C([O-])=O.C[C@]%15%16CC[C@@](C)(C[C@H]%15C%17=CC(=O)[C@@H]%18[C@@]%19(C)CC[C@H](O[C@H]%20O[C@@H]([C@@H](O)[C@H](O)[C@H]%20O[C@@H]%21O[C@@H]([C@@H](O)[C@H](O)[C@H]%21O)C([O-])=O)C([O-])=O)C(C)(C)[C@@H]%19CC[C@@]%18(C)[C@]%17(C)CC%16)C([O-])=O.C[C@]%22%23CC[C@@](C)(C[C@H]%22C%24=CC(=O)[C@@H]%25[C@@]%26(C)CC[C@H](O[C@H]%27O[C@@H]([C@@H](O)[C@H](O)[C@H]%27O[C@@H]%28O[C@@H]([C@@H](O)[C@H](O)[C@H]%28O)C([O-])=O)C([O-])=O)C(C)(C)[C@@H]%26CC[C@@]%25(C)[C@]%24(C)CC%23)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
| Molecular Formula | Mg |
| Molecular Weight | 24.305 |
| Charge | 2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C42H59O16 |
| Molecular Weight | 819.9083 |
| Charge | -3 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.etatpur.co.uk/index.php/enoxolone-sheethttps://www.ncbi.nlm.nih.gov/pubmed/9570253 | https://www.ncbi.nlm.nih.gov/pubmed/8783808https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://www.cosmeticsinfo.org/ingredient/potassium-glycyrrhetinatehttps://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/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=184.1408https://www.ncbi.nlm.nih.gov/pubmed/17613133Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Enoxolone
Sources: http://www.etatpur.co.uk/index.php/enoxolone-sheethttps://www.ncbi.nlm.nih.gov/pubmed/9570253 | https://www.ncbi.nlm.nih.gov/pubmed/8783808https://www.ncbi.nlm.nih.gov/pubmed/17613133 | http://www.cosmeticsinfo.org/ingredient/potassium-glycyrrhetinatehttps://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/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=184.1408https://www.ncbi.nlm.nih.gov/pubmed/17613133
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0072593 |
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Target ID: Q9UBK2|||Q3LIG1 Gene ID: 10891.0 Gene Symbol: PPARGC1A Target Organism: Homo sapiens (Human) |
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Target ID: P24298 Gene ID: 2875.0 Gene Symbol: GPT Target Organism: Homo sapiens (Human) |
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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| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Subjects with essential hypertension are more sensitive to the inhibition of 11 beta-HSD by liquorice. | 2003-02 |
|
| Biological activities of synthetic saponins and cardiac glycosides. | 2003-01 |
|
| Photoliberating inositol-1,4,5-trisphosphate triggers ATP release that is blocked by the connexin mimetic peptide gap 26. | 2003-01 |
|
| Blockade of brain stem gap junctions increases phrenic burst frequency and reduces phrenic burst synchronization in adult rat. | 2003-01 |
|
| Smooth muscle membrane potential modulates endothelium-dependent relaxation of rat basilar artery via myo-endothelial gap junctions. | 2002-12-15 |
|
| 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. | 2002-12 |
|
| Expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity. | 2002-12 |
|
| Inhibitors of gap junctions attenuate myogenic tone in cerebral arteries. | 2002-12 |
|
| Acute intrarenal administration of cortisol has no effect on renal blood flow in hypertensive individuals. | 2002-11 |
|
| Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication. | 2002-11 |
|
| Foetal lung maturation in 11beta-hydroxysteroid dehydrogenase type 1 knockout mice. | 2002-10 |
|
| 11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation. | 2002-10 |
|
| Modulation of renal calcium handling by 11 beta-hydroxysteroid dehydrogenase type 2. | 2002-10 |
|
| [Rhabdomyolysis due to licorice ingestion]. | 2002-09 |
|
| Inhibition of 3 alpha/beta,20 beta-hydroxysteroid dehydrogenase by dexamethasone, glycyrrhetinic acid and spironolactone is attenuated by deletion of 12 carboxyl-terminal residues. | 2002-09 |
|
| Hepatoprotective effects of 18beta-glycyrrhetinic acid on carbon tetrachloride-induced liver injury: inhibition of cytochrome P450 2E1 expression. | 2002-09 |
|
| Cell coupling and Cx43 expression in embryonic mouse neural progenitor cells. | 2002-08-15 |
|
| [Rhabdomyolysis and arterial hypertension caused by apparent excess of mineralocorticoids: a case report]. | 2002-08-02 |
|
| UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds. | 2002-08 |
|
| The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women. | 2002-08 |
|
| Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave. | 2002-08 |
|
| A puzzling cause of hypokalaemia. | 2002-07-20 |
|
| Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries. | 2002-07 |
|
| Annexin 1 (lipocortin 1) mimics inhibitory effects of glucocorticoids on testosterone secretion and enhances effects of interleukin-1beta. | 2002-06 |
|
| IL-1beta-induced production of metalloproteinases by synovial cells depends on gap junction conductance. | 2002-06 |
|
| Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora. | 2002-05 |
|
| Endothelin 1 type a receptor antagonism prevents vascular dysfunction and hypertension induced by 11beta-hydroxysteroid dehydrogenase inhibition: role of nitric oxide. | 2002-04-30 |
|
| Molecular pharmacophore determination of lipid lowering drugs with the receptor mapping method. | 2002-04 |
|
| Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo. | 2002-04 |
|
| Retinoids inhibit squamous cell carcinoma growth and intercellular communication. | 2002-04 |
|
| Kinetics and mechanism of intercellular ice propagation in a micropatterned tissue construct. | 2002-04 |
|
| Primary afferent fibers establish dye-coupled connections in the frog central nervous system. | 2002-03-30 |
|
| Gap junction intercellular communication propagates cell death in cancerous cells. | 2002-03-27 |
|
| [Licorice--not just candy]. | 2002-03-20 |
|
| [Effects of glycyrrhetic acid on transmitter secretion]. | 2002-03 |
|
| Induction of inducible nitric oxide synthase expression by 18beta-glycyrrhetinic acid in macrophages. | 2002-02-27 |
|
| 11 Beta-hydroxysteroid dehydrogenase type 1 from human liver: dimerization and enzyme cooperativity support its postulated role as glucocorticoid reductase. | 2002-02-19 |
|
| [Effects of glycyrrhetinic acid and IFN-alpha on HSCs collagen metabolism in rat fibrotic liver of varying stages]. | 2002-02 |
|
| Blocked gap junctional coupling increases glutamate-induced neurotoxicity in neuron-astrocyte co-cultures. | 2002-02 |
|
| Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects. | 2002-02 |
|
| Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries. | 2002-01-25 |
|
| [Quantitative determinations of glycyrrhizic acid, glycyrrhetinic acid, morphine and sodium benzoate in compound liquorice tablets by capillary zone electrophoresis]. | 2002-01 |
|
| Influence of honey on the gastrointestinal metabolism and disposition of glycyrrhizin and glycyrrhetic acid in rabbits. | 2002-01 |
|
| Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol. | 2002-01 |
|
| 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 |
|
| Enzyme-linked immunosorbent assay for glycyrrhizin using anti-glycyrrhizin monoclonal antibody and an eastern blotting technique for glucuronides of glycyrrhetic acid. | 2001-12-15 |
|
| Effects of glycyrrhetinic acid on collagen metabolism of hepatic stellate cells at different stages of liver fibrosis in rats. | 2001-02 |
|
| [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 |
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.
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.
| Substance Class |
Chemical
Created
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admin
on
Edited
Wed Apr 02 07:59:47 GMT 2025
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| Record UNII |
4U2UBI61D7
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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