HYMECROMONE

Details

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

SHOW SMILES / InChI

Structure Search

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

Description
Sources: https://www.sopharma.com/hymecromon.php
Curator's Comment: description was created based on several sources, including 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

Condition	Modality	Targets	Highest Phase	Product
Biliary duct dyskinesia 3 Sources: https://www.sopharma.com/hymecromon.php	Primary		Approved 8429	Unknown Approved Use Unknown
Chronic cholecystitis 3 Sources: https://www.sopharma.com/hymecromon.php	Primary		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Sensitization and crossreaction of simple coumarins].	2001 Jan	11201168
[Effects of 18 alpha-glycyrrhizic acid on rat liver cytochrome P450 isoenzymes and phase II transferase].	2001 May	12584850
A fluorimetric enzyme assay for the diagnosis of MPS II (Hunter disease).	2001 Nov	11768586
[Dysfunction of the Oddi's sphincter].	2001 Sep	11787376
Protection against damaged DNA in the single cell by polyphenols.	2002 Dec	12561251
Aryl sulfatase from Naja nigricolis venom: characterization and possible contribution in the pathology of snake poisoning.	2003	12616648
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	12527415
Cloning and characterization of two alpha-glucosidases from Bifidobacterium adolescentis DSM20083.	2003 Mar	12658515
Highly sensitive active-site titration of lipase in microscale culture media using fluorescent organophosphorus ester.	2003 Mar 17	12633686
Solid-phase peptide synthesis by ion-paired alpha-chymotrypsin in nonaqueous media.	2003 Mar 30	12557314
Mechanism of the hydrolysis of 4-methylumbelliferyl-beta-D-glucoside by germinating and outgrowing spores of Bacillus species.	2004	15139916
DNA damage in healthy term neonate.	2004 Apr	15113635
Molecular characterization of membrane type and ganglioside-specific sialidase (Neu3) expressed in E. coli.	2004 Apr 30	15179041
Risk factors for periodontitis in HIV patients.	2004 Jun	15102043
Expression of chitinase-encoding genes in Bacillus thuringiensis and toxicity of engineered B. thuringiensis subsp. aizawai toward Lymantria dispar larvae.	2004 Mar	15057461
Stability of the complexes of some lanthanides with coumarin derivatives. I. Cerium(III)-4-methyl-7-hydroxycoumarin.	2004 Mar	15050043
Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation.	2004 May 21	15136802
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	15178567

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.

Name

Type

Language

HYMECROMONE

Official Name

English

HYMECROMONE [MART.]

Common Name

English

HYMECROMONE [JAN]

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

7-Hydroxy-4-methylcoumarin

Systematic Name

English

HYMECROMONE [USAN]

Common Name

English

CANTABILINE

Brand Name

English

Hymecromone [WHO-DD]

Common 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