Opipramol

Last updated
Opipramol
Opipramol2.svg
Opipramol 3D structure.png
Clinical data
Trade names Insidon, Pramolan, others
Other namesG-33040; RP-8307 [1]
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances) [2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 94% [3]
Protein binding 91% [3]
Metabolism CYP2D6-mediated [3]
Elimination half-life 6–11 hours [3]
Excretion Urine (70%), feces (10%) [3]
Identifiers
  • 4-[3-(5H-dibenz[b,f]azepin- 5-yl)propyl]-1-piperazinethanol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.687 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H29N3O
Molar mass 363.505 g·mol−1
3D model (JSmol)
  • OCCN1CCN(CC1)CCCN4c2ccccc2\C=C/c3ccccc34
  • 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 Yes check.svgY
  • Key:YNZFUWZUGRBMHL-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Opipramol, sold under the brand name Insidon among others, is an anxiolytic and tricyclic antidepressant that is used throughout Europe. [1] [4] [5] [6] [7] Despite chemically being a tricyclic dibenzazepine (iminostilbene) derivative similar to imipramine, opipramol is not a monoamine reuptake inhibitor like most other tricyclic antidepressants, and instead, uniquely among antidepressants, acts primarily as a SIGMAR1 agonist. [7] It was developed by Schindler and Blattner in 1961. [8]

Contents

Medical uses

Opipramol is typically used in the treatment of generalized anxiety disorder (GAD) and somatoform disorders. [3] [6] Preliminary studies suggest that opipramol shows potential clinical significance in the treatment of severe sleep bruxism. [9]

Contraindications

Pregnancy and lactation

Experimental animal studies did not indicate injurious effects of opipramol on the embryonic development or fertility. Opipramol should only be prescribed during pregnancy, particularly in the first trimester, for compelling indication. It should not be used during lactation and breastfeeding, since it passes into breast milk in small quantities.

Side effects

Frequently (≥1% to <10%) reported adverse reactions with opipramol, especially at the beginning of the treatment, include fatigue, dry mouth, blocked nose, hypotension, and orthostatic dysregulation.

Adverse reactions reported occasionally (≥0.1% to <1%) include dizziness, stupor, micturition disturbances, vigilance, accommodation disturbances, tremor, weight gain, [10] thirst, allergic skin reactions (rash, urticaria), abnormal ejaculation, erectile impotence, constipation, transient increases in liver enzymes, tachycardia, and palpitations. [11] [12] [13] [3]

Rarely (≥0.01% to <0.1%) reported adverse reactions include excitation, headache, paresthesia especially in elderly patients, restlessness, sweating, sleep disturbances, edema, galactorrhea, urine blockage, nausea and vomiting, fever, [14] collapse conditions, stimulation conducting disturbances, intensification of present heart insufficiency, blood profile changes particularly leukopenia, confusion, delirium, stomach complaints, taste disturbance, and paralytic ileus especially with sudden discontinuation of a longer-term high-dose therapy. [3]

Very rarely (<0.01%) reported adverse reactions include seizures, motor disorders (akathisia, dyskinesia, ataxia), polyneuropathy, glaucoma, anxiety, hair loss, agranulocytosis, severe liver dysfunction after long-term treatment, jaundice, and chronic liver damage. [13] [3] [15]

It could also cause headache.

Overdose

Symptoms of intoxication from overdose include drowsiness, insomnia, stupor, agitation, coma, transient confusion, increased anxiety, ataxia, convulsions, oliguria, anuria, tachycardia or bradycardia, arrhythmia, AV block, hypotension, shock, respiratory depression, and, rarely, cardiac arrest.

Since no antidote for tricyclic antidepressant overdose is known, its treatment remains largely supportive. Removal of the drug should be facilitated by vomiting or gastric lavage. Cardiovascular function should be monitored continuously for at least 48 hours. Arrhythmias should be treated on a case-by-case basis with an appropriate pacemaker and correction of metabolic irregularities, particularly electrolyte imbalances. Respiratory failure should be managed by intubation and artificial respiration. Convulsions should be managed with anticonvulsants (typically diazepam), while monitoring for any worsening in CNS depression. Hypotension can be treated by assuming the corresponding recovery position, by increasing plasma volume with saline infusions, or by pressors, such as adrenaline or dobutamine.

Interactions

Opipramol can be co-prescribed with other psychiatric drugs, such as antidepressants, anxiolytics and antipsychotics, in which case it can interact with them. Most problematic interactions are generally additive or synergistic, such that, when drugs are combined, their effects intensify, which usually manifests as an increase in side effects, but can also be dangerous, depending on the drugs involved.

While opipramol is not a monoamine reuptake inhibitor, any irreversible MAOIs should still be discontinued at least 14 days before treatment. Opipramol can compete with other TCAs, beta blockers, antiarrhythmics (of class 1c) and other drugs for microsomal enzymes, which can lead to slower metabolism and higher plasma concentrations of these drugs. Co-administration of antipsychotics (e.g., haloperidol, risperidone) can increase the plasma concentration of opipramol. Barbiturates and anticonvulsants, on the other hand, can reduce the plasma concentration of opipramol and thereby weaken its therapeutic effect. [3]

Pharmacology

Pharmacodynamics

Opipramol [16]
SiteKi (nM)SpeciesRef
σ1 0.2–50Rodent [17] [18] [19]
σ2 110ND [20]
SERT Tooltip Serotonin transporter≥2,200Rat/? [21] [22] [23]
NET Tooltip Norepinephrine transporter≥700Rat/? [21] [22] [23]
DAT Tooltip Dopamine transporter≥3,000Rat/? [21] [22] [23]
5-HT1A >10,000 ? [23]
5-HT2A 120 ? [23]
5-HT2C NDNDND
α1 200 ? [23]
α2 6,100 ? [23]
D1 900Rat [19]
D2 120–300Rat [23] [19]
H1 6.03Human [24]
H2 4,470Human [24]
H3 61,700Human [24]
H4 >100,000Human [24]
mACh Tooltip Muscarinic acetylcholine receptor3,300 ? [23]
NMDA/PCP >30,000Rat [19]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Opipramol acts as a high affinity sigma receptor agonist, primarily of the σ1 subtype, but also of the σ2 subtype with lower affinity. [6] [3] In one study of σ1 receptor ligands that also included haloperidol, pentazocine, (+)-3-PPP, ditolylguanidine, dextromethorphan, SKF-10,047 ((±)-alazocine), ifenprodil, progesterone, and others, opipramol showed the highest affinity (Ki = 0.2–0.3) for the guinea pig σ1 receptor of all the tested ligands except haloperidol, which it was approximately equipotent with. [17] The sigma receptor agonism of opipramol is thought to be responsible for its therapeutic benefits against anxiety and depression. [7] [3]

Unlike other TCAs, opipramol does not inhibit the reuptake of serotonin or norepinephrine. [3] However, it does act as a high affinity antagonist of the histamine H1 receptor [24] and is a low to moderate affinity antagonist of the dopamine D2, serotonin 5-HT2, and α1-adrenergic receptors. [3] [23] H1 receptor antagonism accounts for its antihistamine effects and associated sedative side effects. [6] [3] In contrast to other TCAs, opipramol has very low affinity for the muscarinic acetylcholine receptors and virtually no anticholinergic effects. [23] [25]

Sigma receptors are a set of proteins located in the endoplasmic reticulum. [3] σ1 receptors play key role in potentiating intracellular calcium mobilization thereby acting as sensor or modulator of calcium signaling. [3] Occupancy of σ1 receptors by agonists causes translocation of the receptor from endoplasmic reticulum to peripheral areas (membranes) where the σ1 receptors cause neurotransmitter release. [3] Opipramol is said to have a biphasic action, with prompt initial improvement of tension, anxiety, and insomnia followed by improved mood later. [3] Hence, it is an anxiolytic with an antidepressant component. [3] After sub-chronic treatment with opipramol, σ2 receptors are significantly downregulated but σ1 receptors are not. [3]

Pharmacokinetics

Opipramol is rapidly and completely absorbed by the gastrointestinal tract. [3] The bioavailability of opipramol amounts to 94%. [3] After single oral administration of 50 mg, the peak plasma concentration of the drug is reached after 3.3 hours and amounts to 15.6 ng/mL. [3] After single oral administration of 100 mg the maximum plasma concentration is reached after 3 hours and amounts to 33.2 ng/mL. [3] Therapeutic concentrations of opipramol range from 140 to 550 nmol/L. [26] The plasma protein binding amounts to approximately 91% and the volume of distribution is approximately 10 L/kg. [3] Opipramol is partially metabolized in the liver to deshydroxyethylopipramol. [3] Metabolism occurs through the CYP2D6 isoenzyme. [3] Its terminal half-life in plasma is 6–11 hours. [3] About 70% is eliminated in urine with 10% unaltered. [3] The remaining portion is eliminated through feces. [3]

History

Opipramol was developed by Geigy. [27] It first appeared in the literature in 1952 and was patented in 1961. [27] The drug was first introduced for use in medicine in 1961. [27] Opipramol was one of the first TCAs to be introduced, with imipramine marketed in the 1950s and amitriptyline marketed in 1961. [27]

Society and culture

Insidon opipramol.jpg
Pramolan PL photo.jpg
Opipramol as Insidon and Pramolan 50 mg tablets.

Generic names

Opipramol is the English, German, French, and Spanish generic name of the drug and its INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name, and DCF Tooltip Dénomination Commune Française, while opipramol hydrochloride is its USAN Tooltip United States Adopted Name, BANM Tooltip British Approved Name, and JAN Tooltip Japanese Accepted Name. [1] [4] [28] [5] Its generic name in Italian and its DCIT Tooltip Denominazione Comune Italiana is opipramolo and in Latin is opipramolum. [4] [5]

Brand names

Opipramol is marketed under the brand names Deprenil, Dinsidon, Ensidon, Insidon, Insomin, Inzeton, Nisidana, Opipram, Opramol, Oprimol, Pramolan, and Sympramol among others. [1] [4] [5]

Related Research Articles

An anxiolytic is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxiety disorders and their related psychological and physical symptoms.

<span class="mw-page-title-main">Tricyclic antidepressant</span> Class of medications

Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants. TCAs were discovered in the early 1950s and were marketed later in the decade. They are named after their chemical structure, which contains three rings of atoms. Tetracyclic antidepressants (TeCAs), which contain four rings of atoms, are a closely related group of antidepressant compounds.

<span class="mw-page-title-main">Tetracyclic antidepressant</span> Class of pharmaceutical drugs

Tetracyclic antidepressants (TeCAs) are a class of antidepressants that were first introduced in the 1970s. They are named after their tetracyclic chemical structure, containing four rings of atoms, and are closely related to the tricyclic antidepressants (TCAs), which contain three rings of atoms.

<span class="mw-page-title-main">Serotonin–norepinephrine reuptake inhibitor</span> Class of antidepressant medication

Serotonin–norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant medications used to treat major depressive disorder (MDD), anxiety disorders, social phobia, chronic neuropathic pain, fibromyalgia syndrome (FMS), and menopausal symptoms. Off-label uses include treatments for attention-deficit hyperactivity disorder (ADHD), obsessive–compulsive disorder (OCD), and migraine prevention. SNRIs are monoamine reuptake inhibitors; specifically, they inhibit the reuptake of serotonin and norepinephrine. These neurotransmitters are thought to play an important role in mood regulation. SNRIs can be contrasted with the selective serotonin reuptake inhibitors (SSRIs) and norepinephrine reuptake inhibitors (NRIs), which act upon single neurotransmitters.

<span class="mw-page-title-main">Azapirone</span> Drug class of psycotropic drugs

Azapirones are a class of drugs used as anxiolytics, antidepressants, and antipsychotics. They are commonly used as add-ons to other antidepressants, such as selective serotonin reuptake inhibitors (SSRIs).

<span class="mw-page-title-main">Amoxapine</span> Tricyclic antidepressant medication

Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylated metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1980, approximately 10 to 20 years after most of the other TCAs were introduced in the United States.

<span class="mw-page-title-main">Imipramine</span> Antidepressant

Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. Imipramine is taken by mouth.

<span class="mw-page-title-main">Desipramine</span> Antidepressant

Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used in the treatment of depression. It acts as a relatively selective norepinephrine reuptake inhibitor, though it does also have other activities such as weak serotonin reuptake inhibitory, α1-blocking, antihistamine, and anticholinergic effects. The drug is not considered a first-line treatment for depression since the introduction of selective serotonin reuptake inhibitor (SSRI) antidepressants, which have fewer side effects and are safer in overdose.

<span class="mw-page-title-main">Nortriptyline</span> Antidepressant medication

Nortriptyline, sold under the brand name Pamelor, among others, is a medication used to treat depression. This medicine is also sometimes used for neuropathic pain, attention deficit hyperactivity disorder (ADHD), smoking cessation and anxiety. As with many antidepressants, its use for young people with depression and other psychiatric disorders may be limited due to increased suicidality in the 18–24 population initiating treatment. Nortriptyline is a less preferred treatment for ADHD and stopping smoking. It is taken by mouth.

<span class="mw-page-title-main">Doxepin</span> Medication to treat depressive disorder, anxiety disorders, chronic hives, and trouble sleeping

Doxepin is a medication belonging to the tricyclic antidepressant (TCA) class of drugs used to treat major depressive disorder, anxiety disorders, chronic hives, and insomnia. For hives it is a less preferred alternative to antihistamines. It has a mild to moderate benefit for sleeping problems. It is used as a cream for itchiness due to atopic dermatitis or lichen simplex chronicus.

<span class="mw-page-title-main">Trimipramine</span> Antidepressant

Trimipramine, sold under the brand name Surmontil among others, is a tricyclic antidepressant (TCA) which is used to treat depression. It has also been used for its sedative, anxiolytic, and weak antipsychotic effects in the treatment of insomnia, anxiety disorders, and psychosis, respectively. The drug is described as an atypical or "second-generation" TCA because, unlike other TCAs, it seems to be a fairly weak monoamine reuptake inhibitor. Similarly to other TCAs, however, trimipramine does have antihistamine, antiserotonergic, antiadrenergic, antidopaminergic, and anticholinergic activities.

<span class="mw-page-title-main">Tianeptine</span> Atypical antidepressant

Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.

<span class="mw-page-title-main">Dosulepin</span> Antidepressant

Dosulepin, also known as dothiepin and sold under the brand name Prothiaden among others, is a tricyclic antidepressant (TCA) which is used in the treatment of depression. Dosulepin was once the most frequently prescribed antidepressant in the United Kingdom, but it is no longer widely used due to its relatively high toxicity in overdose without therapeutic advantages over other TCAs. It acts as a serotonin–norepinephrine reuptake inhibitor (SNRI) and also has other activities including antihistamine, antiadrenergic, antiserotonergic, anticholinergic, and sodium channel-blocking effects.

<span class="mw-page-title-main">Dibenzepin</span> Chemical compound

Dibenzepin, sold under the brand name Noveril among others, is a tricyclic antidepressant (TCA) used widely throughout Europe for the treatment of depression. It has similar efficacy and effects relative to other TCAs like imipramine but with fewer side effects.

<span class="mw-page-title-main">Mianserin</span> Antidepressant

Mianserin, sold under the brand name Tolvon among others, is an atypical antidepressant that is used primarily in the treatment of depression in Europe and elsewhere in the world. It is a tetracyclic antidepressant (TeCA). Mianserin is closely related to mirtazapine, both chemically and in terms of its actions and effects, although there are significant differences between the two drugs.

<span class="mw-page-title-main">Lofepramine</span> Chemical compound

Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression. The TCAs are so named as they share the common property of having three rings in their chemical structure. Like most TCAs lofepramine is believed to work in relieving depression by increasing concentrations of the neurotransmitters norepinephrine and serotonin in the synapse, by inhibiting their reuptake. It is usually considered a third-generation TCA, as unlike the first- and second-generation TCAs it is relatively safe in overdose and has milder and less frequent side effects.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

<span class="mw-page-title-main">Quinupramine</span> Tricyclic antidepressant

Quinupramine is a tricyclic antidepressant (TCA) used in Europe for the treatment of depression.

<span class="mw-page-title-main">Metapramine</span> Chemical compound

Metapramine is a tricyclic antidepressant (TCA) developed by Rhone Poulenc that was introduced for the treatment of depression in France in 1984. In addition to its efficacy against affective disorders, it also has analgesic properties, and may be useful in the treatment of pain.

Selective serotonin reuptake inhibitors, or serotonin-specific re-uptake inhibitor (SSRIs), are a class of chemical compounds that have contributed to the major advances as antidepressants where they have revolutionised the treatment of depression and other psychiatric disorders. The SSRIs are therapeutically useful in the treatment of panic disorder (PD), posttraumatic stress disorder (PTSD), social anxiety disorder, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), and anorexia. There is also clinical evidence of SSRIs efficiency in the treatment of the negative symptoms of schizophrenia and their ability to prevent cardiovascular diseases.

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