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Details

Stereochemistry ACHIRAL
Molecular Formula C10H8O3
Molecular Weight 176.1687
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYMECROMONE

SMILES

CC1=CC(=O)OC2=C1C=CC(O)=C2

InChI

InChIKey=HSHNITRMYYLLCV-UHFFFAOYSA-N
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3

HIDE SMILES / InChI

Molecular Formula C10H8O3
Molecular Weight 176.1687
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Hymecromone (4-methylumbelliferone) is already approved drug in Europe and Asia where it is used to treat biliary spasm. It is used as choleretic and antispasmodic drugs and as a standard for the fluorometric determination of enzyme activity. The concomitant administration of Hymecromone with products, containing metoclopramide, leads to mutual decrease of their action. Due to a danger of diarrhea with subsequent hypokalemia, Hymecromone should be applied with caution to patients on cardiac glycosides therapy (in these cases the sensitivity to them is increased). Hymecromone can be administered simultaneously with otherspasmolytics and analgesics. Very rare allergic reactions, itching, erythema, rashes; diarrhea which normally disappears by reduction of dose or discontinuance of therapy.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
PubMed

PubMed

TitleDatePubMed
Hymecromone in the treatment of motor disorders of the bile ducts: a multicenter, double-blind, placebo-controlled clinical study.
2001
Effects of ATP on regulation of galactosyltransferase-I activity responsible for synthesis of the linkage region between the core protein and glycosaminoglycan chains of proteoglycans.
2001
Isolation and characterization of the UGT2B28 cDNA encoding a novel human steroid conjugating UDP-glucuronosyltransferase.
2001 Apr 3
Leishmania donovani: expression and characterization of Escherichia coli-expressed recombinant chitinase LdCHT1.
2001 Dec
Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation.
2001 Dec
Molecular cloning and expression of an alpha-mannosidase gene in Mycobacterium tuberculosis.
2001 Jan
Improved method for the fluorimetric detection of beta-D-galactosidase in water.
2001 Mar
High beta-galactosidase and ganglioside GM1 levels in the human parotid gland.
2001 Nov
[Ground and first singlet excited dissociation constants of 4-methylumbelliferone: application for indirect spectrofluorimetry of nitriles and nitrosamines].
2001 Sep
[Dysfunction of the Oddi's sphincter].
2001 Sep
New metal complexes of 4-methyl-7-hydroxycoumarin sodium salt and their pharmacological activity.
2001 Sep
Effect of CuCl2, NaCl and EDTA on the enzyme alpha-L-iduronidase in the plasma of normal individuals and heterozygotes for MPS I.
2002 Apr
Expression of active human beta-glucuronidase in Sf9 cells infected with recombinant baculovirus.
2002 Aug 16
Protection against damaged DNA in the single cell by polyphenols.
2002 Dec
Utilization of fluorogenic assay for rapid detection of Escherichia coli in acidic fruit juice.
2002 Dec
Optimisation of an enzymatic method for beta-galactosidase.
2002 Dec
Hydrolysis of 4-methylumbelliferyl-beta-D-glucuronide in differing sample fractions of river waters and its implication for the detection of fecal pollution.
2002 Feb
UDP-glucuronosyltransferase activity, expression and cellular localization in human placenta at term.
2002 Feb 1
Influence of t-butylhydroquinone and beta-naphthoflavone on formation and transport of 4-methylumbelliferone glucuronide in Caco-2/TC-7 cell monolayers.
2002 Jan 15
A fully human anti-Ep-CAM scFv-beta-glucuronidase fusion protein for selective chemotherapy with a glucuronide prodrug.
2002 Mar 4
Tissue-specific regulation of canine intestinal and hepatic phenol and morphine UDP-glucuronosyltransferases by beta-naphthoflavone in comparison with humans.
2002 May 1
The importance of cysteine 126 in the human liver UDP-glucuronosyltransferase UGT1A6.
2002 May 20
Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9.
2002 Nov
Inhibition of hyaluronan synthesis in Streptococcus equi FM100 by 4-methylumbelliferone.
2002 Oct
Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption.
2002 Oct
[Effect of vegetotropic pharmacologic preparations of the motor-evacuatory function of the gallbladder in patients with chronic biliary tract pathology].
2003
Polar organic solvent added to an aqueous solution changes hydrolytic property of lipase.
2003 Aug
[A case of successful use of odeston in the diagnostics and treatment of biliary dysfunctional disorders].
2003 Dec
Inhibition of rat liver sulfotransferases SULT1A1 and SULT2A1 and glucuronosyltransferase by dietary flavonoids.
2003 Dec
Verapamil regulates activity and mRNA-expression of human beta-glucuronidase in HepG2 cells.
2003 Dec
HNK-1-Reactive oligosaccharide, sulfate-O-3GlcAbeta1-4Xylbeta1-MU, synthesized by cultured human colorectal cancer cells.
2003 Jan
Microtiter plate cellular assay for human steroid sulfatase with fluorescence readout.
2003 Jul 15
Glucuronidation of 4-methylumbelliferone and 4-hydroxybiphenyl and in vitro induction of UDP-glucuronosyltransferase 2B12-mRNA in precision-cut rat liver slices.
2003 Jun
Detection and characterization of a novel extracellular fungal enzyme that catalyzes the specific and hydrolytic cleavage of lignin guaiacylglycerol beta-aryl ether linkages.
2003 Jun
Cloning and characterization of two alpha-glucosidases from Bifidobacterium adolescentis DSM20083.
2003 Mar
Solid-phase peptide synthesis by ion-paired alpha-chymotrypsin in nonaqueous media.
2003 Mar 30
A nonradioactive 96-well plate assay for screening of trans-sialidase activity.
2003 Nov 15
Induction of rat hepatic and intestinal UDP-glucuronosyltransferases by naturally occurring dietary anticarcinogens.
2003 Oct
Structural requirements of hydroxylated coumarins for in vitro anti-Helicobacter pylori activity.
2003 Sep-Oct
Mechanism of the hydrolysis of 4-methylumbelliferyl-beta-D-glucoside by germinating and outgrowing spores of Bacillus species.
2004
DNA damage in healthy term neonate.
2004 Apr
Human udp-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents, and inhibition by diclofenac and probenecid.
2004 Apr
Susceptibility of human influenza viruses from Australasia and South East Asia to the neuraminidase inhibitors zanamivir and oseltamivir.
2004 Apr
Molecular characterization of membrane type and ganglioside-specific sialidase (Neu3) expressed in E. coli.
2004 Apr 30
Structure of the haemagglutinin-neuraminidase from human parainfluenza virus type III.
2004 Jan 30
Expression of chitinase-encoding genes in Bacillus thuringiensis and toxicity of engineered B. thuringiensis subsp. aizawai toward Lymantria dispar larvae.
2004 Mar
Stability of the complexes of some lanthanides with coumarin derivatives. I. Cerium(III)-4-methyl-7-hydroxycoumarin.
2004 Mar
Synthesis and biological activity of substituted 2,4,6-s-triazines.
2004 Mar
Effects of dietary anticarcinogens and nonsteroidal anti-inflammatory drugs on rat gastrointestinal UDP-glucuronosyltransferases.
2004 Mar-Apr
A novel efflux-recapture process underlies the mechanism of high-density lipoprotein cholesteryl ester-selective uptake mediated by the low-density lipoprotein receptor-related protein.
2004 Sep
Patents

Sample Use Guides

In Vivo Use Guide
1 tablet 3 times daily during basic meals. The tablets are administered unchewed with a liquid.
Route of Administration: Oral
In Vitro Use Guide
4-Methylumbelliferone (4-MU/HYMECROMONE) inhibits hyaluronan synthesis and retards cancer spreading in experimental animals through mechanisms not fully understood. These mechanisms were studied in A2058 melanoma cells, MCF-7 and MDA-MB-361 breast, SKOV-3 ovarian and UT-SCC118 squamous carcinoma cells by analysing hyaluronan synthesis, UDP-glucuronic acid (UDP-GlcUA) content, and hyaluronan synthase (HAS) mRNA levels. The maximal inhibition in hyaluronan synthesis ranged 22-80% in the cell lines tested. Active glucuronidation of 4-MU produced large quantities of 4-MU-glucuronide, depleting the cellular UDP-GlcUA pool. The maximal reduction varied between 38 and 95%. 4-MU also downregulated HAS mRNA levels: HAS3 was 84-60% lower in MDA-MB-361, A2058 and SKOV-3 cells.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:28:31 UTC 2019
Edited
by admin
on Tue Oct 22 00:28:31 UTC 2019
Record UNII
3T5NG4Q468
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYMECROMONE
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
HYMECROMONE [MART.]
Common Name English
4-METHYLUMBELLIFERONE
Common Name English
LM-94
Code English
HYMECROMONE [MI]
Common Name English
HYMECROMONE [EP]
Common Name English
NSC-9408
Code English
2H-1-BENZOPYRAN-2-ONE, 7-HYDROXY-4-METHYL-
Systematic Name English
HYMECROMONE [WHO-DD]
Common Name English
7-HYDROXY-4-METHYLCOUMARIN
Systematic Name English
HYMECROMONE [USAN]
Common Name English
CANTABILINE
Brand Name English
HYMECROMONE [INN]
Common Name English
NSC-19026
Code English
Classification Tree Code System Code
WHO-VATC QA05AX02
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
WHO-ATC A05AX02
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
Code System Code Type Description
EVMPD
SUB08089MIG
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
MESH
C489431
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
ChEMBL
CHEMBL12208
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
CAS
90-33-5
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
MERCK INDEX
M6164
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
201-986-7
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
WIKIPEDIA
HYMECROMONE
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
RXCUI
5556
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY RxNorm
INN
1891
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
MESH
D006923
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
PUBCHEM
5280567
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
EPA CompTox
90-33-5
Created by admin on Tue Oct 22 00:28:31 UTC 2019 , Edited by admin on Tue Oct 22 00:28:31 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY