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

Details

Stereochemistry ACHIRAL
Molecular Formula C16H19N5O
Molecular Weight 297.3556
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPOFEZINE

SMILES

CN1CCN(CC1)c2cc3c(nn2)Oc4ccccc4N3C

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
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
[Atypical antidepressants: effect on synaptosomal uptake of serotonin and GABA].
1981 Nov
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
INN   WHO-DD  
INN  
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
5H-PYRIDAZINO(3,4-B)(1,4)BENZOXAZINE, 5-METHYL-3-(4-METHYL-1-PIPERAZINYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
Code System Code Type Description
CAS
24886-52-0
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY
EVMPD
SUB09877MIG
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL1886755
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY
FDA UNII
P8T739L1FA
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY
EPA CompTox
24886-52-0
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY
PUBCHEM
159977
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY
INN
4414
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY
NCI_THESAURUS
C66403
Created by admin on Sat Jun 26 03:34:23 UTC 2021 , Edited by admin on Sat Jun 26 03:34:23 UTC 2021
PRIMARY