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Details

Stereochemistry ACHIRAL
Molecular Formula C23H29N3O
Molecular Weight 363.4959
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OPIPRAMOL

SMILES

OCCN1CCN(CCCN2C3=CC=CC=C3C=CC4=CC=CC=C24)CC1

InChI

InChIKey=YNZFUWZUGRBMHL-UHFFFAOYSA-N
InChI=1S/C23H29N3O/c27-19-18-25-16-14-24(15-17-25)12-5-13-26-22-8-3-1-6-20(22)10-11-21-7-2-4-9-23(21)26/h1-4,6-11,27H,5,12-19H2

HIDE SMILES / InChI

Molecular Formula C23H29N3O
Molecular Weight 363.4959
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25722522

Opipramol (Insidon, Pramolan, Ensidon, Oprimol) is an antidepressant and anxiolytic used in Germany and other European countries. Although it is a member of the tricyclic antidepressants, opipramol's primary mechanism of action is much different in comparison, it doesn’t represent a tricyclic antidepressant drug as it does not inhibit the neuronal uptake of norepinephrine and/or serotonin. Opipramol also acts as a low to moderate affinity antagonist for the D2, 5-HT2, H1, H2, and muscarinic acetylcholine receptors. H1 and H2 receptor antagonism account for its antihistamine effects, and muscarinic acetylcholine receptor antagonism is responsible for its anticholinergic properties. Opipramol was developed by Schindler and Blattner in 1961. Opipramol is typically used in the treatment of generalized anxiety disorder (GAD) and somatoform disorders. Its anxiolysis becomes prominent after only one to two weeks of chronic administration. Upon first commencing treatment, opipramol is rather sedating in nature due to its antihistamine properties, but this effect becomes less prominent with time. The therapy with Opipramol indicates an additional therapy with neuroleptics, hypnotics and tranquilizers (e.g. Barbiturates, Benzodiazepines). Therefore, it should be noted that some specific reactions, particularly CNS depressant effects could be intensified and an intensification of common side effects may occur. If necessary the dosage may be reduced. Co-administration with alcohol can cause stupor. MAO Inhibitors should be discontinued at least 14 days before the treatment with Opipramol. Concomitant use of Opipramol with β-blockers, antiarrhythmics (of class 1c), as well as drugs from tricyclic antidepressant group and preparations which influence the microsomal enzyme system, can lead to change in plasma concentration of these drugs. Co-administration of neuroleptics (example- haloperidol, risperidone) can increase the plasma concentration.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OPIPRAMOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
28 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OPIPRAMOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
170 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OPIPRAMOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
320 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OPIPRAMOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OPIPRAMOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OPIPRAMOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Exanthema, Menstruation abnormal...
AEs leading to
discontinuation/dose reduction:
Exanthema (2%)
Menstruation abnormal (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Menstruation abnormal 1%
Disc. AE
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Exanthema 2%
Disc. AE
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
A retrospective analysis of antidepressant poisonings in the emergency department: 11-year experience.
2006 Oct
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.
2008 Oct
Patents

Patents

Sample Use Guides

50 mg in morning; 50 mg in the afternoon and 100 mg in the evening
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:04 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:04 GMT 2025
Record UNII
D23ZXO613C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OPIPRAMOL DURA
Preferred Name English
OPIPRAMOL
INN   MI   WHO-DD  
INN  
Official Name English
1-PIPERAZINEETHANOL, 4-(3-(5H-DIBENZ(B,F)AZEPIN-5-YL)PROPYL)-
Systematic Name English
Opipramol [WHO-DD]
Common Name English
OPIPRAMOL [MI]
Common Name English
4-(3-(5H-DIBENZ(B,F)AZEPIN-5-YL)PROPYL)-1-PIPERAZINEETHANOL
Systematic Name English
NSC-169867
Code English
opipramol [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
NCI_THESAURUS C265
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
WHO-VATC QN06AA05
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
WHO-ATC N06AA05
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C90612
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
EVMPD
SUB09450MIG
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
FDA UNII
D23ZXO613C
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
ChEMBL
CHEMBL370753
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
SMS_ID
100000091965
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-254-0
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
RXCUI
7674
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY RxNorm
PUBCHEM
9417
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
DRUG BANK
DB12930
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
NSC
169867
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID3023394
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
INN
1838
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
WIKIPEDIA
OPIPRAMOL
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
DRUG CENTRAL
1993
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
CAS
315-72-0
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
MESH
D009888
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY
MERCK INDEX
m8218
Created by admin on Mon Mar 31 17:49:04 GMT 2025 , Edited by admin on Mon Mar 31 17:49:04 GMT 2025
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY