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Details

Stereochemistry ACHIRAL
Molecular Formula C10H8O3
Molecular Weight 176.1691
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYMECROMONE

SMILES

Cc1cc(=O)oc2cc(ccc12)O

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 176.1691
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: http://www.ncbi.nlm.nih.gov/pubmed/25852691

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
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
Cloning and characterization of a bacterial cell-bound type B carboxylesterase from Bacillus sp. BP-7.
2001 Apr
Excited-state dipole moments of some hydroxycoumarin dyes using an efficient solvatochromic method based on the solvent polarity parameter, EN(T).
2001 Jan
[Sensitization and crossreaction of simple coumarins].
2001 Jan
Thermodynamic analysis of saccharide binding to snake gourd (Trichosanthes anguina) seed lectin. Fluorescence and absorption spectroscopic studies.
2001 Jan
A convenient fluorometric method for the detection of extracellular N-acetylglucosaminidase production by filamentous fungi.
2001 Jan
Extracellular enzyme activities during slow sand filtration in a water recharge plant.
2001 Jul
Presteady-state kinetics of Bacillus 1,3-1,4-beta-glucanase: binding and hydrolysis of a 4-methylumbelliferyl trisaccharide substrate.
2001 Jul 1
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
Characterization of autoantibodies against uridine-diphosphate glucuronosyltransferase in patients with inflammatory liver diseases.
2001 May
New metal complexes of 4-methyl-7-hydroxycoumarin sodium salt and their pharmacological activity.
2001 Sep
Rapid enzymatic detection of Escherichia coli contamination in polluted river water.
2001 Sep
An alternative approach for enumeration of Escherichia coli in foods.
2001 Sep 1
Development of an enzyme assay for rapid assessment of Escherichia coli in seawaters.
2002
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
Utilization of fluorogenic assay for rapid detection of Escherichia coli in acidic fruit juice.
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
4-Methylumbelliferone induces the expression of membrane type 1-matrix metalloproteinase in cultured human skin fibroblasts.
2002 Nov 15
Effects of bergamottin on human and monkey drug-metabolizing enzymes in primary cultured hepatocytes.
2002 Sep
A 45-kDa midgut glycoprotein from Anopheles albimanus mosquito mediates the killing of trypanosomes.
2002 Sep
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
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
Development of fluorescence-based selective assays for serine/threonine and tyrosine phosphatases.
2003 Jun
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
Molecular characterization of membrane type and ganglioside-specific sialidase (Neu3) expressed in E. coli.
2004 Apr 30
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 Fri Jun 25 21:12:22 UTC 2021
Edited
by admin
on Fri Jun 25 21:12:22 UTC 2021
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
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
HYMECROMONE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 735220
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
WHO-VATC QA05AX02
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
FDA ORPHAN DRUG 732620
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
WHO-ATC A05AX02
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
FDA ORPHAN DRUG 733820
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
Code System Code Type Description
EVMPD
SUB08089MIG
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
MESH
C489431
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL12208
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
CAS
90-33-5
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
DRUG CENTRAL
1401
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
MERCK INDEX
M6164
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB07118
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-986-7
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
WIKIPEDIA
HYMECROMONE
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
RXCUI
5556
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY RxNorm
FDA UNII
3T5NG4Q468
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
INN
1891
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
NCI_THESAURUS
C166696
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
MESH
D006923
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
PUBCHEM
5280567
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
EPA CompTox
90-33-5
Created by admin on Fri Jun 25 21:12:22 UTC 2021 , Edited by admin on Fri Jun 25 21:12:22 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY