U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C30H46O4
Molecular Weight 470.6838
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOXOLONE

SMILES

[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(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O

InChI

InChIKey=MPDGHEJMBKOTSU-YKLVYJNSSA-N
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H46O4
Molecular Weight 470.6838
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen Volume70B Pages 122-32 Journal 1937

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9UBK2|||Q3LIG1
Gene ID: 10891.0
Gene Symbol: PPARGC1A
Target Organism: Homo sapiens (Human)
Target ID: P24298
Gene ID: 2875.0
Gene Symbol: GPT
Target Organism: Homo sapiens (Human)
779.0 nM [IC50]
257.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Stronger Neo-Minophagen C

Approved Use

Chronic Hepatitis C

Launch Date

1948
Preventing
MASO65D (Xclair®)

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
103.89 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1396.97 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
9.46 h
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

Doses

DosePopulationAdverse events​
1500 mg single, oral
Highest studied dose
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
healthy, 29 years
n = 6
Health Status: healthy
Age Group: 29 years
Sex: M
Population Size: 6
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
major
major
minor
minor
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Therapeutic basis of glycyrrhizin on chronic hepatitis B.
1996 May
Regulation of the action of hydrocortisone in airway epithelial cells by 11beta-hydroxysteroid dehydrogenase.
1999 Sep
Endothelium-dependent vasorelaxation independent of nitric oxide and K(+) release in isolated renal arteries of rats.
2001 Apr
Liquorice-induced rise in blood pressure: a linear dose-response relationship.
2001 Aug
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
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.
2001 Jan 22
Persistence of gap junction communication during myocardial ischemia.
2001 Jun
Allergic contact dermatitis from enoxolone.
2001 Mar
Characterization of bovine angiogenin-1 and lactogenin-like protein as glycyrrhizin-binding proteins and their in vitro phosphorylation by C-kinase.
2001 May
Potentiation of L-type calcium channels reveals nonsynaptic mechanisms that correlate spontaneous activity in the developing mammalian retina.
2001 Nov 1
[Prevention of development of hepatocellular carcinoma from HCV-associated liver cirrhosis by multi-agents therapy including stronger-neo-minophagen C].
2001 Oct
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
Modulation of 11 beta-hydroxysteroid dehydrogenase type 2 activity in Ishikawa cells is associated with changes in cellular proliferation.
2001 Oct 25
An unexpected case of primary pulmonary hypertension of the neonate (PPHN). Potential role of topical administration of enoxolone.
2002
UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds.
2002 Aug
Cell coupling and Cx43 expression in embryonic mouse neural progenitor cells.
2002 Aug 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 Dec
[Effects of glycyrrhetinic acid and IFN-alpha on HSCs collagen metabolism in rat fibrotic liver of varying stages].
2002 Feb
Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.
2002 Jul
[Licorice--not just candy].
2002 Mar 20
Foetal lung maturation in 11beta-hydroxysteroid dehydrogenase type 1 knockout mice.
2002 Oct
Solubilization and stabilization of macular carotenoids by water soluble oligosaccharides and polysaccharides.
2015 Apr 15
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.
100 ml/day of intravenous glycyrrhizin
Route of Administration: Intravenous
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.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:18:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:18:46 GMT 2023
Record UNII
P540XA09DR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENOXOLONE
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
3.BETA.-HYDROXY-11-OXOOLEAN-12-EN-30-OIC ACID
Common Name English
ENOXOLONE [MART.]
Common Name English
ENOXOLONE [MI]
Common Name English
ENOXOLONE [EP MONOGRAPH]
Common Name English
enoxolone [INN]
Common Name English
NSC-35347
Code English
GLYCYRRHETINIC ACID [INCI]
Common Name English
ENOXOLONE [EP IMPURITY]
Common Name English
GLYCYRRHETINIC ACID
INCI   JAN  
INCI  
Official Name English
Enoxolone [WHO-DD]
Common Name English
GLYCYRRHETIC ACID
Common Name English
GLYCYRRHETINIC ACID [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C54678
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
DSLD 3013 (Number of products:1)
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
WHO-VATC QD03AX10
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
WHO-ATC D03AX10
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
Code System Code Type Description
FDA UNII
P540XA09DR
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
CHEBI
30853
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
MESH
D006034
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
NSC
35347
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
MERCK INDEX
m4914
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY Merck Index
INN
1794
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
DAILYMED
P540XA09DR
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
PUBCHEM
10114
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
DRUG BANK
DB13089
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
SMS_ID
100000080236
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
DRUG CENTRAL
3178
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
CAS
471-53-4
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-444-6
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
WIKIPEDIA
GLYCYRRHETINIC ACID
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020669
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
EVMPD
SUB06543MIG
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
NCI_THESAURUS
C526
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
ChEMBL
CHEMBL230006
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY
RXCUI
1311506
Created by admin on Fri Dec 15 15:18:47 GMT 2023 , Edited by admin on Fri Dec 15 15:18:47 GMT 2023
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY