PIPOFEZINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H19N5O
Molecular Weight	297.355
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC1)C2=NN=C3OC4=CC=CC=C4N(C)C3=C2

InChI

InChIKey=SDYYIRPAZHJOLM-UHFFFAOYSA-N

InChI=1S/C16H19N5O/c1-19-7-9-21(10-8-19)15-11-13-16(18-17-15)22-14-6-4-3-5-12(14)20(13)2/h3-6,11H,7-10H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C16H19N5O
Molecular Weight	297.355
Charge	0
Count

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

Description
Sources: http://en.remedy-info.com/azafen.html | http://drdoping.com/blog/azaphen-pipofezine-tablets-instructions-for-use-dosage-side-effects-reviews/

Pipofezine (Azafen or Azaphen) is a tricyclic antidepressant (TCA) approved in Russia for the treatment of depression. It was introduced in the late 1960s and is still used today. Pipofezine has been shown to act as a potent inhibitor of the reuptake of serotonin. In addition to its antidepressant action, pipofezine has sedative effects as well, suggesting antihistamine activity. Other properties such as anticholinergic or antiadrenergic actions are less clear but are likely. The main advantage of Azafen compared with other tricyclic antidepressants is that this drug has a low toxic effect on the body, including the heart, and it does not block cholinergic receptors and does not change the activity of monoamine oxidase. The maximum concentration in the blood is reached after 1-2 hours after taking the drug. Absorbed in the gastrointestinal tract, metabolism occurs in the liver, and is excreted by Azaphene kidneys.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
serotonin uptake 20 Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7198493	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: http://en.remedy-info.com/azafen.html http://drdoping.com/blog/azaphen-pipofezine-tablets-instructions-for-use-dosage-side-effects-reviews/	Primary		Approved 8583	Azaphen Approved Use Treatment of depression

C_max

Value	Dose	Co-administered	Analyte	Population
24.5 ng/mL DRUG LABEL https://www.stada.ru/upload/iblock/d24/Azafen_tabletki_25mg_instrukciya_010221.pdf	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		PIPOFEZINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.stada.ru/upload/iblock/d24/Azafen_tabletki_25mg_instrukciya_010221.pdf	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		PIPOFEZINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP19A1 429 CYP1A2 2153	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 5.0	inconclusive [IC50 4.7724 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 18.0	no [IC50 26.6032 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 101.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 101.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 96.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 86.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 103.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 103.0	inconclusive

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/159977#section=BioAssay-Results Page: 37.0

PubMed

Title	Date	PubMed
[Atypical antidepressants: effect on synaptosomal uptake of serotonin and GABA].	1981-11	7198493

Patents

Sample Use Guides

In Vivo Use Guide

The initial dose for adults is 25–50 mg in 2 divided doses (morning and afternoon). With good endurance gradually increase the dose to 150–200 mg/day (3–4 hours, last admission at bedtime), in some cases - up to 400 mg/day. The optimal daily dose - 150–200 mg, the maximum daily dose - 400–500 mg. When the desired effect of switching to maintenance dose - 25–75 mg/day. The course of treatment - up to 1 year (at least 1–1.5 months). After establishing the optimal daily dose using tablets Azaphen 25 mg, administered Azafen MB (modified-release tablets) 150 mg of 1 times (morning) or 2 times (morning and evening) based on efficacy and tolerance.

Route of Administration: Oral

In Vitro Use Guide

Inkasan and azaphen were the most potent inhibitors of the 3H-serotonin uptake (65-70% inhibition at a concentration of 50 u M. Azaphen and chlorimipramine were the only ones to inhibit the uptake of 3H-GABA at a concentration of 50 uM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:21:11 GMT 2025` Edited by `admin` on `Wed Apr 02 08:21:11 GMT 2025`
Record UNII	P8T739L1FA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5H-PYRIDAZINO(3,4-B)(1,4)BENZOXAZINE, 5-METHYL-3-(4-METHYL-1-PIPERAZINYL)-

Preferred Name

English

PIPOFEZINE

Official Name

English

pipofezine [INN]

Common Name

English

5-METHYL-3-(4-METHYL-1-PIPERAZINYL)-5H-PYRIDAZINO(3,4-B)(1,4)BENZOXAZINE

Systematic Name

English

Pipofezine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265