FENMETOZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H10Cl2N2O
Molecular Weight	245.105
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(OCC2=NCCN2)C=C1Cl

InChI

InChIKey=FVHAONUKSUFJKN-UHFFFAOYSA-N

InChI=1S/C10H10Cl2N2O/c11-8-2-1-7(5-9(8)12)15-6-10-13-3-4-14-10/h1-2,5H,3-4,6H2,(H,13,14)

HIDE SMILES / InChI

Molecular Formula	C10H10Cl2N2O
Molecular Weight	245.105
Charge	0
Count

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

Description
Sources: https://www.google.ch/patents/US4141985
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6256788

Fenmetozole is an alpha-2 adrenergic receptor antagonist which was developed for the treatment of schizophrenic and/or depressed patients, however never reached the market. It was also shown that the drug may reduce symptoms of minimal brain dysfunction in children and antagonize the effect of barbiturates and ethanol.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2875186	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Minimal brain dysfunction 2 Sources: https://www.google.ch/patents/US4141985	Primary	Phase I 428	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://www.google.ch/patents/US4141985	Primary	Phase I 428	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4979996	Primary	Phase I 428	Unknown Approved Use Unknown
Substance-induced psychosis 2 Sources: https://www.google.ch/patents/US4141985	Primary	Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
500 mg 1 times / day multiple, oral Dose: 500 mg, 1 times / day Route: oral Route: multiple Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1095283	unknown Health Status: unknown Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1095283	Sources: https://pubmed.ncbi.nlm.nih.gov/1095283

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363681067	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363681067	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=363681067	yes [IC50 8.4866 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363681067	no

Sourcing

Vendor/Aggregator	ID	URL
AOBIOUS INC	AOB5631	http://aobious.com/aobious/search?search_query=AOB5631
AbovChem LLC	HY-U00402	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-U00402
Alfa Chemistry	ACM41473090	http://www.alfa-chemistry.com/search.aspx?q=ACM41473090
Chemspace	CSC009998413	https://chem-space.com/CSC009998413
Compound Cloud	32048
Compound Cloud	32049
Enamine	BBV-45114500	http://www.enaminestore.com/catalog/BBV-45114500
MuseChem	I013243	https://www.musechem.com/product/I013243.html
eMolecules	232694720	https://orderbb.emolecules.com/search/#?query=232694720
mcule	MCULE-2449696403	https://mcule.com/MCULE-2449696403/

PubMed

Title	Date	PubMed
Clinical trial of imidazoline (DH-524) as an antidepressant. I. Browsing phase.	1969 Jul	4979996
Clinical trial of imidazoline (DH-524) as an anti-depressant.	1971 Jun	4996220
Selective antagonism of central nervous system depressants by DH-524; a comparative study with bemegride.	1973 Oct 1	4771574
Antagonism of depressant activity of ethanol by DH-524; a comparative study with Bemegride, Doxapram and d-amphetamine.	1975 Mar	1129305
Fenmetazole (DH-524): euphoriant classified by cerebral electrometry.	1975 Oct	810320
Methaqualone discrimination in gerbils: interactions with bemegride and imidazoline (DH-524).	1976 Dec	162743
Some aspects of DH-524 (2(3, 4-dichlorophenoxy) methyl-2-imidazoline) antagonistic-like actions of ethanol intoxication in rats.	1976 May 15	945437
Interactions between alcohol and other drugs on open-field and temperature measurements in gerbils.	1977 May	901059
Alcohol-discrimination in gerbils: interactions with bemegride, DH-524, Amphetamine, and delta9-THC.	1977 May	901060
Alcohol-discrimination in gerbils: interactions with bemegride, DH-524, Amphetamine, and delta9-THC.	1977 May	901060
An evaluation of the selectivity of fenmetozole (DH-524) reversal of ethanol-induced changes in central nervous system function.	1980	6256788
Differential effects of TRH, amphetamine, naloxone, and fenmetozole on ethanol actions: attenuation of the effects of punishment and impairment of aerial righting reflex.	1981 Summer	6792942

Patents

Sample Use Guides

In Vivo Use Guide

Administer 250 to 450 milligrams of fenmetozole hydrochloride per day for 3-4 weeks (schizophrenic and/or depressed patients) or orally at a daily dosage rate of about 3 mg/kg/day using three divided dosages (in children with Minimal Brain Dysfunction).

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:15:10 GMT 2023` Edited by `admin` on `Fri Dec 15 16:15:10 GMT 2023`
Record UNII	C15WFN6GMO
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FENMETOZOLE

Official Name

English

2((3,4-DICHLOROPHENOXY)METHYL)-2-IMIDAZOLINE

Systematic Name

English

fenmetozole [INN]

Common Name

English

1H-IMIDAZOLE, 2-((3,4-DICHLOROPHENOXY)METHYL)-4,5-DIHYDRO-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265