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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=C(C=CC=C3)C=CC4=C2C=CC=C4)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

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
PubMed

PubMed

TitleDatePubMed
Some central effects of opipramol given repeatedly.
1990 Sep-Oct
Determination of opipramol in human plasma by high-performance liquid chromatography with photometric detection using a cyanopropyl column.
2001 Apr 5
Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group.
2001 Feb
The treatment of generalised anxiety disorder. A systematic review.
2002 Dec
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
Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry.
2003 Dec
Specific modulation of sigma binding sites by the anxiolytic drug opipramol.
2003 Oct
[Somatoform disorders--what must the general practitioner know?].
2004 Aug 19
Urine sample preparation of tricyclic antidepressants by means of a supported liquid membrane technique for high-performance liquid chromatographic analysis.
2004 Mar 5
Clinical trials with sigma ligands.
2004 Nov
Neuropharmacology of the anxiolytic drug opipramol, a sigma site ligand.
2004 Nov
Combined pH/organic solvent gradient HPLC in analysis of forensic material.
2005 Apr 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 Jan
Anti-proliferative activity of haloperidol in B16 mouse and human SK-MEL-28 melanoma cell lines.
2005 Oct
Induction of a mixed depressive episode during rTMS treatment in a patient with refractory major depression.
2006
[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 Jun
A retrospective analysis of antidepressant poisonings in the emergency department: 11-year experience.
2006 Oct
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.
2006 Oct 20
[Generalized anxiety disorder (GAD)--diagnosis and therapy].
2007 Nov
[Pathologic worry].
2007 Nov 15
Generalised anxiety disorder.
2007 Nov 20
Frequency of different anti-depressants associated with suicides and drug deaths.
2008 Mar
sigma-1 receptor modulation of acid-sensing ion channel a (ASIC1a) and ASIC1a-induced Ca2+ influx in rat cortical neurons.
2008 Nov
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.
2008 Oct
Gastroprotective and antioxidant effects of opipramol on indomethacin-induced ulcers in rats.
2009 Jul
The sigma-1 antagonist BMY-14802 inhibits L-DOPA-induced abnormal involuntary movements by a WAY-100635-sensitive mechanism.
2009 Jul
Magnitude of potentially inappropriate prescribing in Germany among older patients with generalized anxiety disorder.
2009 Jul 27
Opipramol as nighttime medication.
2009 May
Binding of imipramine, dosulepin, and opipramol to liposomes for overdose treatment.
2009 Oct
Determination of the chemical structure of potential organic impurities occurring in the drug substance opipramol.
2010 Apr
Opipramol dipicrate.
2010 Jul 10
Sigma nonopioid intracellular receptor 1 mutations cause frontotemporal lobar degeneration-motor neuron disease.
2010 Nov
Tricyclic antidepressants and headaches: systematic review and meta-analysis.
2010 Oct 20
Nutritional and herbal supplements for anxiety and anxiety-related disorders: systematic review.
2010 Oct 7
In vitro studies of DNA damage caused by tricyclic antidepressants: a role of peroxidase in the side effects of the drugs.
2010 Sep 20
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
Name Type Language
OPIPRAMOL
INN   MI   WHO-DD  
INN  
Official Name English
OPIPRAMOL DURA
Brand 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 Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
NCI_THESAURUS C265
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
WHO-VATC QN06AA05
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
WHO-ATC N06AA05
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C90612
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
EVMPD
SUB09450MIG
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
FDA UNII
D23ZXO613C
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL370753
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
SMS_ID
100000091965
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-254-0
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
RXCUI
7674
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY RxNorm
PUBCHEM
9417
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
DRUG BANK
DB12930
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
NSC
169867
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID3023394
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
INN
1838
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
WIKIPEDIA
OPIPRAMOL
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
DRUG CENTRAL
1993
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
CAS
315-72-0
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
MESH
D009888
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY
MERCK INDEX
m8218
Created by admin on Fri Dec 15 15:10:38 UTC 2023 , Edited by admin on Fri Dec 15 15:10:38 UTC 2023
PRIMARY Merck Index