METRALINDOLE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H17N3O
Molecular Weight	255.315
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2N3CCN(C)C4=NCCC(C2=C1)=C34

InChI

InChIKey=GVXBHSBKKJRBMS-UHFFFAOYSA-N

InChI=1S/C15H17N3O/c1-17-7-8-18-13-4-3-10(19-2)9-12(13)11-5-6-16-15(17)14(11)18/h3-4,9H,5-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C15H17N3O
Molecular Weight	255.315
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1884793 | https://link.springer.com/article/10.1007/BF00781063 | https://www.ncbi.nlm.nih.gov/pubmed/4043371

Metralindole (Inkazan) is a reversible inhibitor of monoamine oxidase A (RIMA) which was used in Russia as an antidepressant. Inkasan (3-methyl-8-methoxy-3H, 1,2,5,6- tetrahydropyrazine /1.2.3-ab/-beta-carboline hydrochloride) has pharmacological properties characteristic of antidepressants. The clinical antidepressant effect of inkasan is combined with stimulating action. The drug is primarily indicated for patients in whom adynamic (anergic) disturbances are predominant in the clinical picture of depression.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase A 52 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1884793	Inhibitor 8504
Monoamine oxidase A 52 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1884793	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: http://provizor-online.ru/2013/03/inkazan_Incazanum https://www.ncbi.nlm.nih.gov/pubmed/2728714 https://www.ncbi.nlm.nih.gov/pubmed/4043371	Primary		Approved 8583	Inkazan Approved Use Treatment of depression. The drug is primarily indicated for patients in whom adynamic (anergic) disturbances are predominant in the clinical picture of depression.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inducer 440	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP1A2 2153	P-gp 2052	CYP2C19 329

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 5.0	inconclusive [IC50 16.1957 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 8.0	no [IC50 38.9018 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 43.0	no
CYP2C19 2141	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 99.0	no
CYP2C9 2497	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 93.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 88.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 4.0	yes [IC50 15.4871 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 87 \| 89	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/68713#section=Biological-Test-Results Page: 2.0

PubMed

Title	Date	PubMed
Maintenance treatment is not necessary after Helicobacter pylori eradication and healing of bleeding peptic ulcer: a 5-year prospective, randomized, controlled study.	2003-09-22	14504114
[The comparative influence of pyrazidol, inkazan and other antidepressant monoamine oxidase inhibitors on the pressor effect of tyramine].	1991-03-01	1884793
Cellular and humoral IgA responses after single and multiple local injections of antigen.	1983-04-15	6682716

Patents

Sample Use Guides

In Vivo Use Guide

Cats: Electroencephalographic investigations conducted by L. F. Roshchina showed that in cats inkazan in doses of 10-40 mg/kg (intravenously) caused increased cortical and subcortical activity and intensified the reaction of cortex to photo- and photon stimulation. The electrophysiological response of inkazan persists for 3-4 h. In doses of 5-50 mg/kg administered intraperitoneally, the preparation slows conditioned reflexes of avoidance in rats.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:26:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:26:04 GMT 2025`
Record UNII	2QW3FL6OPA
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

METRALINDOLE [MI]

Preferred Name

English

METRALINDOLE

Official Name

English

metralindole [INN]

Common Name

English

2,4,5,6-TETRAHYDRO-9-METHOXY-4-METHYL-1H-3,4,6A-TRIAZAFLUORANTHENE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265