Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C42H59O16.2H.3H2O.H4N |
Molecular Weight | 894.0084 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].[H+].[NH4+].O.O.O.[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=RSPXVECNDMCBGQ-YMYWBCTMSA-N
InChI=1S/C42H62O16.H3N.3H2O/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;3*1H2/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;;;;/m0..../s1
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 |
Molecular Formula | H |
Molecular Weight | 1.0079 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H4N |
Molecular Weight | 18.0385 |
Charge | 1 |
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 |
|||
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 |
|||
Target ID: P24298 Gene ID: 2875.0 Gene Symbol: GPT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10574137 |
|||
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 |
|||
Preventing | MASO65D (Xclair®) Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Palliative | Unknown Approved UseUnknown |
|||
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 | |||
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 | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[Anti-inflammatory activity of glycyrrhizic acid derivatives]. | 1980 Jul-Aug |
|
Tumorigenicity study of disodium glycyrrhizinate administered orally to mice. | 1985 Nov |
|
Therapeutic basis of glycyrrhizin on chronic hepatitis B. | 1996 May |
|
Review article: glycyrrhizin as a potential treatment for chronic hepatitis C. | 1998 Mar |
|
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase. | 1999 Sep |
|
[Simultaneous measurements of electrical coupling and action potential transfer in pairs of ventricular cardiomyocytes]. | 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 |
|
Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro. | 2001 Apr 27 |
|
18-beta-Glycyrrhetinic acid (BGA) as an electrical uncoupler for intracellular recordings in confluent monolayer cultures. | 2001 Aug |
|
Glycyrrhetinic acid induced apoptosis in murine splenocytes. | 2001 Jan |
|
Blockade of chloride channels reveals relaxations of rat small mesenteric arteries to raised potassium. | 2001 Jan |
|
A population physiologically based pharmacokinetic/pharmacodynamic model for the inhibition of 11-beta-hydroxysteroid dehydrogenase activity by glycyrrhetic acid. | 2001 Jan 1 |
|
Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder. | 2001 Jan 15 |
|
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5. | 2001 Jan 22 |
|
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 |
|
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 |
|
An endothelium-derived hyperpolarizing factor-like factor moderates myogenic constriction of mesenteric resistance arteries in the absence of endothelial nitric oxide synthase-derived nitric oxide. | 2001 Oct |
|
LAF1, a MYB transcription activator for phytochrome A signaling. | 2001 Oct 1 |
|
Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism. | 2001 Oct 5 |
|
Molecular pharmacophore determination of lipid lowering drugs with the receptor mapping method. | 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 |
|
Coordination of mesangial cell contraction by gap junction--mediated intercellular Ca(2+) wave. | 2002 Aug |
|
Expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue is not increased in human obesity. | 2002 Dec |
|
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 |
|
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 |
|
[Effects of glycyrrhetic acid on transmitter secretion]. | 2002 Mar |
|
Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora. | 2002 May |
|
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 |
|
[Rhabdomyolysis due to licorice ingestion]. | 2002 Sep |
|
Hepatoprotective effects of 18beta-glycyrrhetinic acid on carbon tetrachloride-induced liver injury: inhibition of cytochrome P450 2E1 expression. | 2002 Sep |
|
Solubilization and stabilization of macular carotenoids by water soluble oligosaccharides and polysaccharides. | 2015 Apr 15 |
|
18α-Glycyrrhetinic acid lethality for neuroblastoma cells via de-regulating the Beclin-1/Bcl-2 complex and inducing apoptosis. | 2016 Oct 1 |
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
Sat Dec 16 09:33:02 GMT 2023
by
admin
on
Sat Dec 16 09:33:02 GMT 2023
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Record UNII |
78NEL3149I
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Record Status |
Validated (UNII)
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Record Version |
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-
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DBSALT002692
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2724236
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78NEL3149I
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911217-00-0
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DTXSID5047243
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Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |