U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H19N5O.2ClH
Molecular Weight 370.277
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPOFEZINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=ZZVWCKAYZSAUKR-UHFFFAOYSA-N
InChI=1S/C16H19N5O.2ClH/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;2*1H

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

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.
Name Type Language
PIPOFEZINE HYDROCHLORIDE
WHO-DD  
Common Name English
2-(4-METHYLPIPERAZINYL)-10-METHYL-3,4-DIAZAPHENOXAZINE DIHYDROCHLORIDE
Systematic Name English
PIPOFEZIN HYDROCHLORIDE
Common Name English
AZAPHEN
Brand Name English
AZAFEN
Brand Name English
5H-PYRIDAZINO(3,4-B)(1,4)BENZOXAZINE, 5-METHYL-3-(4-METHYL-1-PIPERAZINYL)-, HYDROCHLORIDE (1:2)
Systematic Name English
Pipofezine hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
159976
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
CAS
24853-80-3
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
FDA UNII
MFB4TD413U
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID10179554
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
SMS_ID
100000177091
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
CAS
11096-84-7
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
SUPERSEDED
WIKIPEDIA
Azaphen
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY