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

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
Hymecromone in the treatment of motor disorders of the bile ducts: a multicenter, double-blind, placebo-controlled clinical study.
2001
Leishmania donovani: expression and characterization of Escherichia coli-expressed recombinant chitinase LdCHT1.
2001 Dec
Deglucuronidation of a flavonoid, luteolin monoglucuronide, during inflammation.
2001 Dec
A fluorimetric enzyme assay for the diagnosis of MPS II (Hunter disease).
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
Development of an enzyme assay for rapid assessment of Escherichia coli in seawaters.
2002
A beta-glucosidase/xylosidase from the phytopathogenic oomycete, Phytophthora infestans.
2002 Apr
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
A sulfated proteoglycan is necessary for storage of exocrine secretory proteins in the rat parotid gland.
2002 Aug
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
UDP-glucuronosyltransferase activity, expression and cellular localization in human placenta at term.
2002 Feb 1
Persistence and degradation of coumaphos in model cattle dipping vats.
2002 Jan
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
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
4-Methylumbelliferone induces the expression of membrane type 1-matrix metalloproteinase in cultured human skin fibroblasts.
2002 Nov 15
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
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
[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
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
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
Development of fluorescence-based selective assays for serine/threonine and tyrosine phosphatases.
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
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
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
Mechanism of the hydrolysis of 4-methylumbelliferyl-beta-D-glucoside by germinating and outgrowing spores of Bacillus species.
2004
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
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 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