AMMONIUM GLYCYRRHIZINATE TRIHYDRATE

US Previously Marketed

First marketed in 1921

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

Structure of AMMONIUM GLYCYRRHIZINATE TRIHYDRATE

Structure Search

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

HIDE SMILES / InChI

Description
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
reactive oxygen species metabolic process 68 Target ID: GO:0072593 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19144869	Modulator 828
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha 17 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	Activator 1430
Alanine aminotransferase 1 17 Target ID: P24298 Gene ID: 2875.0 Gene Symbol: GPT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10574137	Inhibitor 8297
11-beta-hydroxysteroid dehydrogenase 1 21 Target ID: CHEMBL2391 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429	Inhibitor 8297	779.0 nM [IC50]
11-beta-hydroxysteroid dehydrogenase 2 18 Target ID: CHEMBL2908 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19429429	Inhibitor 8297	257.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7439375	Primary	Basic research	Unknown Approved Use Unknown
Erythema 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15935505 https://www.ncbi.nlm.nih.gov/pubmed/17252206	Primary	Phase I 428	Unknown Approved Use Unknown
Cardiomyopathy 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25298583	Primary	Preclinical	Unknown Approved Use Unknown
Autoimmune hepatitis 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21681505	Primary	Phase I 428	Unknown Approved Use Unknown
Chronic hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10574137 https://www.ncbi.nlm.nih.gov/pubmed/9570253 http://www.eisai.com/news/news200744.html	Palliative	Approved 8429	Stronger Neo-Minophagen C Approved Use Chronic Hepatitis C Launch Date 1948
Unknown 2578
Radiodermatitis 16 Sources: https://www.ons.org/intervention/maso65d-xclair%C2%AE	Preventing	Basic research	MASO65D (Xclair®) Approved Use Unknown
Ovarian cancer 157 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25364659	Primary	Basic research	Unknown Approved Use Unknown
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27376261	Primary	Basic research	Unknown Approved Use Unknown
Hepatitis B 57 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8783808	Palliative	Not Provided 504	Unknown Approved Use Unknown
Autoimmune hepatitis 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21681505	Palliative	Phase I 428	Unknown Approved Use Unknown
Chronic hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9570253	Palliative	Not Provided 504	Unknown Approved Use Unknown

C_max

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

T_1/2

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

Doses

Dose	Population	Adverse events
1500 mg single, oral Highest studied dose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8126129	healthy, 29 years n = 6 Health Status: healthy Age Group: 29 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8126129	Sources: https://pubmed.ncbi.nlm.nih.gov/8126129

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 MRP1 106 UGT1A3 84	CYP2C19 991 CYP1A2 1054 CYP2E1 667 P-gp 1537 MRP1 107 UGT1A1 418 UGT1A3 422 UGT2B4 249 UGT2B7 389 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 291 UGT2B15 203 UGT2B17 213

Drug as perpetrator

Target	Modality	Activity
MRP1 172	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/	likely
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/	likely
UGT1A3 93	inhibitor 3277 Sources: https://static-content.springer.com/esm/art%3A10.1038%2Fsrep09627/MediaObjects/41598_2015_BFsrep09627_MOESM1_ESM.pdf Page: 8.0	yes [IC50 6.12 uM]

Drug as victim

Target	Modality	Activity
MRP1 107	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0	likely
CYP3A4 1737	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	major
UGT1A3 422	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	major
CYP2C19 991	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	minor
CYP2C9 1037	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	minor
CYP1A2 1054	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	no
CYP2D6 1217	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	no
CYP2E1 667	substrate 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.2012.01516.x Page: 1.0	no
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18204840/ Page: 6.0	no
UGT1A10 291	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A4 347	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A6 307	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A7 236	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A8 283	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A9 380	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT2B15 203	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT2B17 213	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	no
UGT1A1 418	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	yes
UGT2B4 249	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	yes
UGT2B7 389	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/dmpk/24/6/24_6_523/_pdf/-char/en Page: 1.0	yes

Sourcing

Vendor/Aggregator	ID	URL
AEchem Scientific Corp., USA	AE1-006547	http://www.aechemsc.com/info_products/AE1-006547.php
Achemtek	0104-020457	http://www.achemtek.com/471-53-4
Acorn PharmaTech	ACN-036282	http://www.acornpharmatech.com/
Acros Organics	AC120150050	https://www.fishersci.com/shop/products/18-glycyrrhetinic-acid-98-acros-organics/AC120150050
Acros Organics	AC120150250	https://www.fishersci.com/shop/products/18-glycyrrhetinic-acid-98-acros-organics/AC120150250
Aurora Fine Chemicals LLC	A13.139.522	http://online.aurorafinechemicals.com/info?ID=A13.139.522
AvaChem Scientific	1106	http://www.avachem.com/productSearch.asp?1106
Avantor Inc	101179-654	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101179-654
Avantor Inc	200015-658	https://us.vwr.com/store/product/18599070/18-beta-glycyrrhetinic-acid-98
Avantor Inc	700006-634	https://us.vwr.com/store/product/21572407/glycyrrhetic-acid-98
Avantor Inc	700006-636	https://us.vwr.com/store/product/21572407/glycyrrhetic-acid-98
BioSynth	Q-201057	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/Q-201057.html
Boerchem	BC201656	http://www.boerchem.com/?product_33783.html
Chem Scene	CS-W020624	http://www.chemscene.com/471-53-4.html
ChemFaces	CFN99152	http://www.chemfaces.com/natural/Glycyrrhetinic-acid-CFN99152.html
ChemMol	30100980	http://www.chemmol.com/chemmol/30100980.html
ChemMol	30114287	http://www.chemmol.com/chemmol/30114287.html
ChemMol	44000914	http://www.chemmol.com/chemmol/44000914.html
ChemMol	99088065	http://www.chemmol.com/chemmol/99088065.html
Chemspace	CSSB00020617985	https://chem-space.com/CSSB00020617985
China MainChem Co., Ltd	471-53-4	https://www.mainchem.com/product/china-enoxolone-cas-471-53-4-glycyrrhetinic-acid-supplier/
DC Chemicals	DCG-032	http://www.dcchemicals.com//product_show-18_beta_Glycyrrhetintic_Acid.html
Glentham Life Sciences	GP8041	http://www.glentham.com/products/product/GP8041/
Hairui	HR135798	http://www.hairuichem.com/en/product/471-53-4.html
Herbest Bio-Tech	HH231694	http://www.bjherbest.com/analytical-standard/saponins/18-beta-glycyrrhetinic-acid-471-53-4.html
LGC Standards	DRE-A13167700AL-100	https://www.lgcstandards.com/US/en/p/DRE-A13167700AL-100
LGC Standards	DRE-C13167700	https://www.lgcstandards.com/US/en/p/DRE-C13167700
LGC Standards	MM3399.00	https://www.lgcstandards.com/US/en/p/MM3399.00
Lab Network	LN00839314	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00839314
MedChem Express	HY-N0180	https://www.medchemexpress.com/18_beta_-Glycyrrhetinic_acid.html
MuseChem	R048750	https://www.musechem.com/product/R048750.html
OChem	3435	http://www.ocheminc.com/index.php?act=psearch&pid=471G534
Oakwood	103973	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=194966&ExtHyperLink=1
R&D Chemicals	43	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=7860
Sigma-Aldrich	G10105_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/g10105?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	50510_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/50510?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E0180500_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/e0180500?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S527188	http://www.smolecule.com/products/s527188
TCI (Tokyo Chemical Industry)	G0149	http://www.tcichemicals.com/eshop/en/us/commodity/G0149/index.html
THE BioTek	bt-267335	https://www.thebiotek.com/product/inhibitors/bt-267335
VladaChem	VL277837-1G	https://www.vladachem.com/product.php?products=471-53-4
Yuhao Chemical	JZ1453	http://www.chemyuhao.com/471-53-4.html
abcr GmbH	AB136427	http://www.abcr.com/shop/en/AB136427
eNovation Chemicals	D676398	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676398
eNovation Chemicals	D765568	https://www.enovationchem.com/ProductDetails.asp?ProductID=D765568
mcule	MCULE-4676598997	https://mcule.com/MCULE-4676598997/

PubMed

Title	Date	PubMed
[Anti-inflammatory activity of glycyrrhizic acid derivatives].	1980 Jul-Aug	7439375
Tumorigenicity study of disodium glycyrrhizinate administered orally to mice.	1985 Nov	4076931
Therapeutic basis of glycyrrhizin on chronic hepatitis B.	1996 May	8783808
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase.	1999 Sep	10460758
How to close a gap junction channel. Efficacies and potencies of uncoupling agents.	2001	11218664
Endothelium-dependent vasorelaxation independent of nitric oxide and K(+) release in isolated renal arteries of rats.	2001 Apr	11264250
Do gap junctions couple interstitial cells of Cajal pacing and neurotransmission to gastrointestinal smooth muscle?	2001 Aug	11576389
Inhibitory effect of glycyrrhizin on the phosphorylation and DNA-binding abilities of high mobility group proteins 1 and 2 in vitro.	2001 Aug	11510483
Magnolol from Magnolia officinalis inhibits 11beta-hydroxysteroid dehydrogenase without increases of corticosterone and thymocyte apoptosis in mice.	2001 Feb	11270719
Glycyrrhetinic acid induced apoptosis in murine splenocytes.	2001 Jan	11201246
Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder.	2001 Jan 15	11208975
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	11384873
Toward prevention of hepatocellular carcinoma developing in chronic hepatitis C.	2001 Jul	11446875
Immunoglobulin and cytokine expression in mixed lymphocyte cultures is reduced by disruption of gap junction intercellular communication.	2001 Mar	11259395
Allergic contact dermatitis from enoxolone.	2001 Mar	11218003
K+ currents underlying the action of endothelium-derived hyperpolarizing factor in guinea-pig, rat and human blood vessels.	2001 Mar 1	11230509
[Prevention of development of hepatocellular carcinoma from HCV-associated liver cirrhosis by multi-agents therapy including stronger-neo-minophagen C].	2001 Oct	11762054
Effect of pH on metabolism of glycyrrhizin, glycyrrhetic acid and glycyrrhetic acid monoglucuronide by collected human intestinal flora.	2001 Oct	11642312
Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries.	2001 Oct	11606334
Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism.	2001 Oct 5	11681629
An unexpected case of primary pulmonary hypertension of the neonate (PPHN). Potential role of topical administration of enoxolone.	2002	12442611
[Rhabdomyolysis and arterial hypertension caused by apparent excess of mineralocorticoids: a case report].	2002 Apr-Jun	12150047
Effect of glycyrrhetinic acid on 11 beta-hydroxysteroid dehydrogenase activity in normotensive and hypertensive subjects.	2002 Feb	11834140
Primary afferent fibers establish dye-coupled connections in the frog central nervous system.	2002 Feb-Mar 1	11922980
[Quantitative determinations of glycyrrhizic acid, glycyrrhetinic acid, morphine and sodium benzoate in compound liquorice tablets by capillary zone electrophoresis].	2002 Jan	12541626
Influence of honey on the gastrointestinal metabolism and disposition of glycyrrhizin and glycyrrhetic acid in rabbits.	2002 Jan	11824564
Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries.	2002 Jan 25	11798159
Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.	2002 Jul	12060103
Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese medicine, by human intestinal flora.	2002 May	12033492
[Rhabdomyolysis due to licorice ingestion].	2002 Sep	12355986
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	12230123
Biological activities of synthetic saponins and cardiac glycosides.	2003 Jan	12557254
18α-Glycyrrhetinic acid lethality for neuroblastoma cells via de-regulating the Beclin-1/Bcl-2 complex and inducing apoptosis.	2016 Oct 1	27520483

Patents

Sample Use Guides

In Vivo Use Guide

100 ml/day of intravenous glycyrrhizin

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

AMMONIUM GLYCYRRHIZINATE TRIHYDRATE

Common Name

English

.ALPHA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,20.BETA.)-20-CARBOXY-11-OXO-30-NOROLEAN-12-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANURONOSYL-, MONOAMMONIUM SALT, TRIHYDRATE

Systematic Name

English

GLYCYRRHIZIC ACID AMMONIUM SALT TRIHYDRATE

Common Name

English

Code System Code Type Description

DRUG BANK

DBSALT002692