Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C42H62O16 |
Molecular Weight | 822.9321 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[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
InChI
InChIKey=LPLVUJXQOOQHMX-QWBHMCJMSA-N
InChI=1S/C42H62O16/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)/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 |
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Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 | |||
Page: 1.0 |
major | |||
Page: 1.0 |
major | |||
Page: 1.0 |
minor | |||
Page: 1.0 |
minor | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
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 |
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[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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Stimulation of melanogenesis by glycyrrhizin in B16 melanoma cells. | 2001 Sep 30 |
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An unexpected case of primary pulmonary hypertension of the neonate (PPHN). Potential role of topical administration of enoxolone. | 2002 |
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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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Glycyrrhizic acid suppresses type 2 11 beta-hydroxysteroid dehydrogenase expression in vivo. | 2002 Apr |
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Endothelin 1 type a receptor antagonism prevents vascular dysfunction and hypertension induced by 11beta-hydroxysteroid dehydrogenase inhibition: role of nitric oxide. | 2002 Apr 30 |
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[Rhabdomyolysis and arterial hypertension caused by apparent excess of mineralocorticoids: a case report]. | 2002 Apr-Jun |
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UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds. | 2002 Aug |
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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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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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Smooth muscle membrane potential modulates endothelium-dependent relaxation of rat basilar artery via myo-endothelial gap junctions. | 2002 Dec 15 |
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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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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 |
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Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol. | 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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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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[Licorice--not just candy]. | 2002 Mar 20 |
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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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Acute intrarenal administration of cortisol has no effect on renal blood flow in hypertensive individuals. | 2002 Nov |
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Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication. | 2002 Nov |
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11beta-hydroxysteroid dehydrogenase type 1: a new regulator of fetal lung maturation. | 2002 Oct |
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Modulation of renal calcium handling by 11 beta-hydroxysteroid dehydrogenase type 2. | 2002 Oct |
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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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Hepatoprotective effects of 18beta-glycyrrhetinic acid on carbon tetrachloride-induced liver injury: inhibition of cytochrome P450 2E1 expression. | 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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Final report on the safety assessment of Glycyrrhetinic Acid, Potassium Glycyrrhetinate, Disodium Succinoyl Glycyrrhetinate, Glyceryl Glycyrrhetinate, Glycyrrhetinyl Stearate, Stearyl Glycyrrhetinate, Glycyrrhizic Acid, Ammonium Glycyrrhizate, Dipotassium Glycyrrhizate, Disodium Glycyrrhizate, Trisodium Glycyrrhizate, Methyl Glycyrrhizate, and Potassium Glycyrrhizinate. | 2007 |
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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
Substance Class |
Chemical
Created
by
admin
on
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Fri Dec 15 16:00:04 GMT 2023
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on
Fri Dec 15 16:00:04 GMT 2023
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Record UNII |
6FO62043WK
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DSLD |
3011 (Number of products:14)
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WHO-ATC |
A05BA08
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WHO-VATC |
QA05BA08
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Code System | Code | Type | Description | ||
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100000078200
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26143
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PRIMARY | RxNorm | ||
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GLYCYRRHIZIN
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1370586
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SUB14004MIG
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6FO62043WK
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215-785-7
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6FO62043WK
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DTXSID8047006
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167409
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1359426
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29807
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GLYCYRRHIZIN
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496
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1325
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1295888
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1405-86-3
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DB13751
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CHEMBL441687
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234419
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m5811
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C1117
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14982
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D019695
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15939
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
2.49% of dry weight of contents.
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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DERIVATIVE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
3.27% of dry weight of contents.
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The compound did not show significant cytotoxicity against uninfected MDCK cells at 100 uM, but showed inhibitory activity against the H1N1 virus at 100 uM. The compound was also evaluated for anti-HIV activity.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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