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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
Sigma nonopioid intracellular receptor 1 mutations cause frontotemporal lobar degeneration-motor neuron disease.
2010-11
Tricyclic antidepressants and headaches: systematic review and meta-analysis.
2010-10-20
Nutritional and herbal supplements for anxiety and anxiety-related disorders: systematic review.
2010-10-07
In vitro studies of DNA damage caused by tricyclic antidepressants: a role of peroxidase in the side effects of the drugs.
2010-09-20
Opipramol dipicrate.
2010-07-10
Determination of the chemical structure of potential organic impurities occurring in the drug substance opipramol.
2010-04
Binding of imipramine, dosulepin, and opipramol to liposomes for overdose treatment.
2009-10
Magnitude of potentially inappropriate prescribing in Germany among older patients with generalized anxiety disorder.
2009-07-27
Gastroprotective and antioxidant effects of opipramol on indomethacin-induced ulcers in rats.
2009-07
The sigma-1 antagonist BMY-14802 inhibits L-DOPA-induced abnormal involuntary movements by a WAY-100635-sensitive mechanism.
2009-07
Opipramol as nighttime medication.
2009-05
sigma-1 receptor modulation of acid-sensing ion channel a (ASIC1a) and ASIC1a-induced Ca2+ influx in rat cortical neurons.
2008-11
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.
2008-10
Frequency of different anti-depressants associated with suicides and drug deaths.
2008-03
Generalised anxiety disorder.
2007-11-20
[Pathologic worry].
2007-11-15
[Generalized anxiety disorder (GAD)--diagnosis and therapy].
2007-11
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.
2006-10-20
A retrospective analysis of antidepressant poisonings in the emergency department: 11-year experience.
2006-10
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006-06
Induction of a mixed depressive episode during rTMS treatment in a patient with refractory major depression.
2006
Anti-proliferative activity of haloperidol in B16 mouse and human SK-MEL-28 melanoma cell lines.
2005-10
Combined pH/organic solvent gradient HPLC in analysis of forensic material.
2005-04-29
2,2'-Bipyridine as a new and sensitive spectrophotometric reagent for the determination of nanoamounts of certain dibenzazepine class of tricyclic antidepressant drugs.
2005-01
Clinical trials with sigma ligands.
2004-11
Neuropharmacology of the anxiolytic drug opipramol, a sigma site ligand.
2004-11
[Somatoform disorders--what must the general practitioner know?].
2004-08-19
Urine sample preparation of tricyclic antidepressants by means of a supported liquid membrane technique for high-performance liquid chromatographic analysis.
2004-03-05
Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry.
2003-12
Specific modulation of sigma binding sites by the anxiolytic drug opipramol.
2003-10
Kava-Kava extract LI 150 is as effective as Opipramol and Buspirone in Generalised Anxiety Disorder--an 8-week randomized, double-blind multi-centre clinical trial in 129 out-patients.
2003
Bioavailability of opipramol from a film-coated tablet, a sugar-coated tablet and an aqueous solution in healthy volunteers.
2003
The treatment of generalised anxiety disorder. A systematic review.
2002-12
Simultaneous determination of seven tricyclic antidepressant drugs in human plasma by direct-injection HPLC-APCI-MS-MS with an ion trap detector.
2002-08
Effects of opipramol as an evening anaesthesiologic premedication.
2002
Determination of opipramol in human plasma by high-performance liquid chromatography with photometric detection using a cyanopropyl column.
2001-04-05
Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group.
2001-02
Some central effects of opipramol given repeatedly.
1990-09-01
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
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ACTIVE MOIETY