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
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
| 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 |
DescriptionSources: http://medind.nic.in/daa/t13/i2/daat13i2p409.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25722522
Sources: http://medind.nic.in/daa/t13/i2/daat13i2p409.pdf
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.
Originator
Sources: http://medind.nic.in/daa/t13/i2/daat13i2p409.pdf
Curator's Comment: 1961
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11199949 |
|||
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25722522 |
|||
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25722522 |
|||
Target ID: CHEMBL2095200 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25722522 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642963/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642963/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
170 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642963/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642963/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642963/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12642963/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9% |
OPIPRAMOL plasma | Homo sapiens |
Doses
| Dose | Population | Adverse 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%) Sources: Menstruation abnormal (1%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| Title | Date | PubMed |
|---|---|---|
| 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
Sample Use Guides
In Vivo Use Guide
Sources: http://medind.nic.in/daa/t13/i2/daat13i2p409.pdf
50 mg in morning; 50 mg in the afternoon and 100 mg in the evening
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:49:04 GMT 2025
by
admin
on
Mon Mar 31 17:49:04 GMT 2025
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| Record UNII |
D23ZXO613C
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C28197
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NCI_THESAURUS |
C265
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WHO-VATC |
QN06AA05
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WHO-ATC |
N06AA05
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C90612
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SUB09450MIG
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D23ZXO613C
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CHEMBL370753
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100000091965
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206-254-0
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7674
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9417
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DB12930
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169867
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DTXSID3023394
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1838
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OPIPRAMOL
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1993
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315-72-0
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D009888
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m8218
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |