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=C(Cl)C=C(OCC2=NCCN2)C=C1

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

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-2 114 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2875186	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Minimal brain dysfunction 2 Sources: https://www.google.ch/patents/US4141985	Primary	Phase I 438	Unknown Approved Use Unknown
Schizophrenia 305 Sources: https://www.google.ch/patents/US4141985	Primary	Phase I 438	Unknown Approved Use Unknown
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4979996	Primary	Phase I 438	Unknown Approved Use Unknown
Substance-induced psychosis 2 Sources: https://www.google.ch/patents/US4141985	Primary	Phase I 438	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 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363681067	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363681067	no
CYP2D6 2546	inhibitor 4027 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 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363681067	no

Sourcing

Vendor/Aggregator	ID	URL
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
AOBIOUS INC	AOB5631	http://aobious.com/aobious/search?search_query=AOB5631
Chemspace	CSC009998413	https://chem-space.com/CSC009998413
Compound Cloud	32048
Compound Cloud	32049
eMolecules	232694720	https://orderbb.emolecules.com/search/#?query=232694720
Enamine	BBV-45114500	http://www.enaminestore.com/catalog/BBV-45114500
mcule	MCULE-2449696403	https://mcule.com/MCULE-2449696403/
MuseChem	I013243	https://www.musechem.com/product/I013243.html

PubMed

Title	Date	PubMed
Differential effects of TRH, amphetamine, naloxone, and fenmetozole on ethanol actions: attenuation of the effects of punishment and impairment of aerial righting reflex.	1981	6792942
An evaluation of the selectivity of fenmetozole (DH-524) reversal of ethanol-induced changes in central nervous system function.	1980	6256788
Interactions between alcohol and other drugs on open-field and temperature measurements in gerbils.	1977-05	901059
Alcohol-discrimination in gerbils: interactions with bemegride, DH-524, Amphetamine, and delta9-THC.	1977-05	901060
Alcohol-discrimination in gerbils: interactions with bemegride, DH-524, Amphetamine, and delta9-THC.	1977-05	901060
Methaqualone discrimination in gerbils: interactions with bemegride and imidazoline (DH-524).	1976-12	162743
Some aspects of DH-524 (2(3, 4-dichlorophenoxy) methyl-2-imidazoline) antagonistic-like actions of ethanol intoxication in rats.	1976-05-15	945437
Fenmetazole (DH-524): euphoriant classified by cerebral electrometry.	1975-10	810320
Antagonism of depressant activity of ethanol by DH-524; a comparative study with Bemegride, Doxapram and d-amphetamine.	1975-03	1129305
Selective antagonism of central nervous system depressants by DH-524; a comparative study with bemegride.	1973-10-01	4771574
Clinical trial of imidazoline (DH-524) as an anti-depressant.	1971-06	4996220
Clinical trial of imidazoline (DH-524) as an antidepressant. I. Browsing phase.	1969-07	4979996

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

Name

Type

Language

fenmetozole [INN]

Preferred Name

English

FENMETOZOLE

Official Name

English

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

Systematic Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265