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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
15 ng/mL
50 mg single, oral
OPIPRAMOL plasma
Homo sapiens
28 ng/mL
100 mg single, oral
OPIPRAMOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
170 ng × h/mL
50 mg single, oral
OPIPRAMOL plasma
Homo sapiens
320 ng × h/mL
100 mg single, oral
OPIPRAMOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
50 mg single, oral
OPIPRAMOL plasma
Homo sapiens
11 h
100 mg single, oral
OPIPRAMOL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
9%
OPIPRAMOL plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Record UNII
D23ZXO613C
Record Status Validated (UNII)
Record Version