METHYLCHROMONE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H8O2
Molecular Weight	160.1693
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=COC2=C(C=CC=C2)C1=O

InChI

InChIKey=ABJKIHHNDMEBNA-UHFFFAOYSA-N

InChI=1S/C10H8O2/c1-7-6-12-9-5-3-2-4-8(9)10(7)11/h2-6H,1H3

HIDE SMILES / InChI

Molecular Formula	C10H8O2
Molecular Weight	160.1693
Charge	0
Count

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

Description
Sources: DOI: 10.1080/00397919808005928 | Charlier, R. (2012) Antianginal Drugs, page 160, retrieved from: https://books.google.ru/books?id=iFnsCAAAQBAJ | https://www.ncbi.nlm.nih.gov/pubmed/13177494 | (2011) Progress in Medicinal Chemistry, v. 9, page 105, retrieved from: https://books.google.ru/books?id=8gKyiG4m9SkC | https://www.ncbi.nlm.nih.gov/pubmed/3992155 | https://www.ncbi.nlm.nih.gov/pubmed/13332753

Methylchromone (3-methylchromone) is the first synthetic chromone to be used clinically. It has both antispasmodic and coronary vasodilator actions. It was recommended for the treatment of angina pectoris but it doesn’t produce any remarkable improvements and its clinical use has been discontinued. Osteomalacia case caused by the ingestion of 3-methylchromone was reported. 3-methylchromone was used in ureteral lithiasis and gravels. 3-methylchromone stated to have better vitamin K activity.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Angina pectoris 110 Sources: Charlier, R. (2012) Antianginal Drugs, page 160, retrieved from: https://books.google.ru/books?id=iFnsCAAAQBAJ	Primary		Approved 8583	Cromonalgina Approved Use Unknown Launch Date 1960
Ureteral lithiasis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13332753	Palliative		Not Provided 511	Cromonalgina Approved Use Unknown Launch Date 1960

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 CYP2C19 2057 OATP1B3 961 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/66569#section=BioAssay-Results Page: 3.0	inconclusive [IC50 9.7717 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/66569#section=BioAssay-Results Page: 81.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/66569#section=BioAssay-Results Page: 76.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/66569#section=BioAssay-Results Page: 77.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/66569#section=BioAssay-Results Page: 3.0	yes [IC50 15.4871 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMDUyMTUifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMDUyMTUifX0=	yes [Inhibition 10 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/66569#section=BioAssay-Results Page: 81.0

PubMed

Title	Date	PubMed
3-Methyl-4H-chromen-4-one.	2010-06-05	21587807
[Osteomalacia disclosing de Toni-Debré-Fanconi syndrome caused by the ingestion of 3-methylchromone].	1985-01	3992155
[Characteristic reactions and the determination of 3-methylchromone].	1961-01	13720650
[Clinical experimentation with a new synthetic coronary dialator: 3-methylchromone].	1960-05-09	13839356
[Pharmacological actions of some derivatives of 3-methylchromone. Preliminary communication].	1960-02	14434933
[Clinical experimentation with 3-methylchromone (chromethyl) in some urological forms].	1959-11-01	13826157
[The preparation for surgery of patients with choledochal lithiasis; combined use of 3-methylchromone and theophylline].	1959-08-15	14441761
[Effect of 3-methylchromone on the central nervous system].	1958	13597923
[Effect of 3-methylchromone on deficient coronary flow].	1958	13603400
[Prevention & treatment of anginose attacks of coronary origin with 3-methylchromone].	1957-08	13501524
[3-Methylchromone in ureteral lithiasis and gravels].	1955-12	13332753
[Trial use of 3-methyl-chromone as a fundamental treatment of angina pectoris].	1954-06-02	13177494

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:18:28 GMT 2025` Edited by `admin` on `Wed Apr 02 08:18:28 GMT 2025`
Record UNII	KJ0091KAAH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-76095

Preferred Name

English

METHYLCHROMONE

Official Name

English

TRICROMYL [MI]

Common Name

English

METHYLCHROMONE [MART.]

Common Name

English

3-METHYL-4(H)-CHROMEN-4-ONE

Common Name

English

methylchromone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29698