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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
New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity.
2001 Apr
Determination of UDP-glucuronosyltransferase UGT1A6 activity in human and rat liver microsomes by HPLC with UV detection.
2001 Apr
Molecular cloning and expression of an alpha-mannosidase gene in Mycobacterium tuberculosis.
2001 Jan
A convenient fluorometric method for the detection of extracellular N-acetylglucosaminidase production by filamentous fungi.
2001 Jan
Translocon pores in the endoplasmic reticulum are permeable to a neutral, polar molecule.
2001 Jun 22
Improved method for the fluorimetric detection of beta-D-galactosidase in water.
2001 Mar
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
[Ground and first singlet excited dissociation constants of 4-methylumbelliferone: application for indirect spectrofluorimetry of nitriles and nitrosamines].
2001 Sep
Rapid enzymatic detection of Escherichia coli contamination in polluted river water.
2001 Sep
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
A beta-glucosidase/xylosidase from the phytopathogenic oomycete, Phytophthora infestans.
2002 Apr
Expression of active human beta-glucuronidase in Sf9 cells infected with recombinant baculovirus.
2002 Aug 16
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
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
Pharmacokinetic analysis of factors determining elimination pathways for sulfate and glucuronide metabolites of drugs. I: studies by in vivo constant infusion.
2002 May
A colorimetric and fluorometric microplate assay for the detection of microcystin-LR in drinking water without preconcentration.
2002 Nov
A 45-kDa midgut glycoprotein from Anopheles albimanus mosquito mediates the killing of trypanosomes.
2002 Sep
[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
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
Combined polymorphisms in UDP-glucuronosyltransferases 1A1 and 1A6: implications for patients with Gilbert's syndrome.
2003 Jan
Microtiter plate cellular assay for human steroid sulfatase with fluorescence readout.
2003 Jul 15
Development of fluorescence-based selective assays for serine/threonine and tyrosine phosphatases.
2003 Jun
Highly sensitive active-site titration of lipase in microscale culture media using fluorescent organophosphorus ester.
2003 Mar 17
Solid-phase peptide synthesis by ion-paired alpha-chymotrypsin in nonaqueous media.
2003 Mar 30
Physicochemical and saccharide-binding studies on the galactose-specific seed lectin from Trichosanthes cucumerina.
2003 May 1
Enhanced enzymatic hydrolysis of langostino shell chitin with mixtures of enzymes from bacterial and fungal sources.
2003 Sep 1
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
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
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 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
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY