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Details

Stereochemistry ACHIRAL
Molecular Formula C10H8O3.H2O
Molecular Weight 194.184
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYMECROMONE HYDRATE

SMILES

O.CC1=CC(=O)OC2=CC(O)=CC=C12

InChI

InChIKey=HRFJWEHVFMYQSS-UHFFFAOYSA-N
InChI=1S/C10H8O3.H2O/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9;/h2-5,11H,1H3;1H2

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

Molecular Formula H2O
Molecular Weight 18.0153
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
[Effects of 18 alpha-glycyrrhizic acid on rat liver cytochrome P450 isoenzymes and phase II transferase].
2001 May
Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme.
2002 Apr
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
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
Aryl sulfatase from Naja nigricolis venom: characterization and possible contribution in the pathology of snake poisoning.
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
Potent bivalent inhibition of human tryptase-beta by a synthetic inhibitor.
2003 Dec
Verapamil regulates activity and mRNA-expression of human beta-glucuronidase in HepG2 cells.
2003 Dec
Kinetic studies on the hydrolysis of N-acetylated and N-deacetylated derivatives of 4-methylumbelliferyl chitobioside by the family 18 chitinases ChiA and ChiB from Serratia marcescens.
2003 Feb
HNK-1-Reactive oligosaccharide, sulfate-O-3GlcAbeta1-4Xylbeta1-MU, synthesized by cultured human colorectal cancer cells.
2003 Jan
Combined polymorphisms in UDP-glucuronosyltransferases 1A1 and 1A6: implications for patients with Gilbert's syndrome.
2003 Jan
A single site in human beta-hexosaminidase A binds both 6-sulfate-groups on hexosamines and the sialic acid moiety of GM2 ganglioside.
2003 Jan 20
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
Highly sensitive active-site titration of lipase in microscale culture media using fluorescent organophosphorus ester.
2003 Mar 17
Physicochemical and saccharide-binding studies on the galactose-specific seed lectin from Trichosanthes cucumerina.
2003 May 1
Pharmacokinetic analysis of factors determining elimination pathways for sulfate and glucuronide metabolites of xenobiotics II: Studies with isolated perfused rat liver.
2003 Nov
A nonradioactive 96-well plate assay for screening of trans-sialidase activity.
2003 Nov 15
Cloning and expression of alpha-D-glucosidase and N-acetyl-beta-glucosaminidase from the periodontal pathogen, Tannerella forsythensis (Bacteroides forsythus).
2003 Oct
Induction of rat hepatic and intestinal UDP-glucuronosyltransferases by naturally occurring dietary anticarcinogens.
2003 Oct
Inhibition of influenza A virus sialidase activity by sulfatide.
2003 Oct 23
Biochemical and catalytic properties of an endoxylanase purified from the culture filtrate of Sporotrichum thermophile.
2003 Sep 1
Enhanced enzymatic hydrolysis of langostino shell chitin with mixtures of enzymes from bacterial and fungal sources.
2003 Sep 1
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
Development of novel conductometric biosensors based on immobilised whole cell Chlorella vulgaris microalgae.
2004 Apr 15
Pharmacological enhancement of beta-hexosaminidase activity in fibroblasts from adult Tay-Sachs and Sandhoff Patients.
2004 Apr 2
Molecular characterization of membrane type and ganglioside-specific sialidase (Neu3) expressed in E. coli.
2004 Apr 30
Identification of aryl-phospho-beta-D-glucosidases in Bacillus subtilis.
2004 Jan
Evidence that unsaturated fatty acids are potent inhibitors of renal UDP-glucuronosyltransferases (UGT): kinetic studies using human kidney cortical microsomes and recombinant UGT1A9 and UGT2B7.
2004 Jan 1
Structure of the haemagglutinin-neuraminidase from human parainfluenza virus type III.
2004 Jan 30
Risk factors for periodontitis in HIV patients.
2004 Jun
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
Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation.
2004 May 21
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 12:36:54 UTC 2019
Edited
by admin
on Tue Oct 22 12:36:54 UTC 2019
Record UNII
ORG176G874
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYMECROMONE HYDRATE
Common Name English
MENDIAXON MONOHYDRATE
Common Name English
2H-1-BENZOPYRAN-2-ONE, 7-HYDROXY-4-METHYL-, HYDRATE (1:1)
Systematic Name English
4-METHYLUMBELLIFERONE HYDRATE
Common Name English
Code System Code Type Description
CAS
103764-33-6
Created by admin on Tue Oct 22 12:36:54 UTC 2019 , Edited by admin on Tue Oct 22 12:36:54 UTC 2019
PRIMARY
PUBCHEM
60196415
Created by admin on Tue Oct 22 12:36:54 UTC 2019 , Edited by admin on Tue Oct 22 12:36:54 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE