Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Opipramol: Difference between pages

{{Short description|Drug used to treat depressive and anxiety disorders}}

{{cs1 config|name-list-style=vanc}}

{{More citations needed|date=August 2017}}

| verifiedrevid = 462265431

| width = 250px

| image2 = Opipramol 3D structure.png

| width2 = 200px

| tradename = Insidon, Pramolan, others

| pregnancy_category =

| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->

| legal_BR = C1

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>

| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_DE = <!-- Anlage I, II, III or Unscheduled -->

| legal_NZ = <!-- Class A, B, C -->

| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_EU =

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->

| routes_of_administration = [[Oral administration|Oral]]

| bioavailability = 94%<ref name="Mohapatra_2013" />

| protein_bound = 91%<ref name="Mohapatra_2013" />

| metabolism = [[CYP2D6]]-mediated<ref name="Mohapatra_2013" />

| elimination_half-life = 6–11 hours<ref name="Mohapatra_2013" />

| excretion = [[Urine]] (70%), [[feces]] (10%)<ref name="Mohapatra_2013" />

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 315-72-0

| CAS_supplemental = <br />909-39-7 ([[dihydrochloride]])

| UNII_Ref = {{fdacite|correct|FDA}}

| synonyms = G-33040; RP-8307<ref name="Elks2014" />

| SMILES = OCCN1CCN(CC1)CCCN4c2ccccc2\C=C/c3ccccc34

'''Opipramol''', sold under the brand name '''Insidon''' among others, is an [[anxiolytic]] and [[tricyclic antidepressant]] that is used throughout [[Europe]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="pmid11199949">{{cite journal | vauthors = Möller HJ, Volz HP, Reimann IW, Stoll KD | title = Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group | journal = Journal of Clinical Psychopharmacology | volume = 21 | issue = 1 | pages = 59–65 | date = February 2001 | pmid = 11199949 | doi = 10.1097/00004714-200102000-00011 | s2cid = 27014778 }}</ref><ref name="pmid15547785">{{cite journal | vauthors = Müller WE, Siebert B, Holoubek G, Gentsch C | title = Neuropharmacology of the anxiolytic drug opipramol, a sigma site ligand | journal = Pharmacopsychiatry | volume = 37 | issue = Suppl 3 | pages = S189–S197 | date = November 2004 | pmid = 15547785 | doi = 10.1055/s-2004-832677 | s2cid = 260238755 }}</ref> 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, [[Atypical antidepressant|uniquely among antidepressants]], acts primarily as a [[SIGMAR1]] [[agonist]].<ref name="pmid15547785" /> It was developed by Schindler and Blattner in 1961.<ref name="pmid14270525">{{cite journal | vauthors = Grosser HH, Ryan E | title = Drug Treatment of Anxiety: A Controlled Study of Opipramol and Chlordiazepoxide | journal = The British Journal of Psychiatry | volume = 111 | issue = 471 | pages = 134–141 | date = February 1965 | pmid = 14270525 | doi = 10.1192/bjp.111.471.134 | s2cid = 40241272 }}</ref>

==Medical uses==

Opipramol is typically used in the treatment of [[generalized anxiety disorder]] (GAD) and [[somatoform disorder]]s.<ref name="Mohapatra_2013" /><ref name="pmid11199949" /> Preliminary studies suggest that opipramol shows potential clinical significance in the treatment of severe [[Bruxism|sleep bruxism]].<ref>{{cite journal | vauthors = Wieckiewicz M, Martynowicz H, Wieczorek T, Wojakowska A, Sluzalec-Wieckiewicz K, Gac P, Poreba R, Mazur G, Winocur E, Smardz J | display-authors = 6 | title = Consecutive Controlled Case Series on Effectiveness of Opipramol in Severe Sleep Bruxism Management-Preliminary Study on New Therapeutic Path | journal = Brain Sciences | volume = 11 | issue = 2 | pages = 146 | date = January 2021 | pmid = 33499332 | pmc = 7911172 | doi = 10.3390/brainsci11020146 | doi-access = free }}</ref>

==Contraindications==

* In patients with [[hypersensitivity reaction|hypersensitivity]] to opipramol or another component of the formulation

* Acute [[drinking alcohol|alcohol]], [[sedative]], [[analgesic]], and [[antidepressant]] intoxications

* Acute [[urinary retention]]

* Acute [[delirium]]

* Untreated [[glaucoma|narrow-angle glaucoma]]

* [[Benign prostatic hyperplasia]] with residual [[urinary retention]]

* [[Paralytic ileus]]

* Pre-existing higher-grade [[atrioventricular block]]ages or [[supraventricular tachycardia|diffuse supraventricular]] or [[electrical conduction system of the heart|ventricular stimulus]] conduction disturbances

* Combination with [[monoamine oxidase inhibitor]] (MAOI)

===Pregnancy and lactation===

Experimental animal studies did not indicate injurious effects of opipramol on the [[human embryogenesis|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 (medical)|fatigue]], [[dry mouth]], blocked nose, [[hypotension]], and orthostatic dysregulation.

Adverse reactions reported occasionally (≥0.1% to <1%) include [[dizziness]], [[stupor]], [[micturition]] disturbances, [[Vigilance (psychology)|vigilance]], [[accommodation (eye)|accommodation disturbances]], [[tremor]], [[weight gain]],<ref>{{cite journal | vauthors = Carpéné C, Les F, Mercader J, Gomez-Zorita S, Grolleau JL, Boulet N, Fontaine J, Iglesias-Osma MC, Garcia-Barrado MJ | display-authors = 6 | title = Opipramol Inhibits Lipolysis in Human Adipocytes without Altering Glucose Uptake and Differently from Antipsychotic and Antidepressant Drugs with Adverse Effects on Body Weight Control | journal = Pharmaceuticals | volume = 13 | issue = 3 | pages = 41 | date = March 2020 | pmid = 32151075 | pmc = 7151722 | doi = 10.3390/ph13030041 | doi-access = free }}</ref> thirst, allergic skin reactions (rash, urticaria), abnormal [[ejaculation]], [[erectile dysfunction|erectile impotence]], [[constipation]], transient increases in liver enzymes, [[tachycardia]], and [[palpitation]]s.<ref>{{Cite journal | vauthors = Jepson K, Beaumont G |date=March 1973 |title=A Comparative Trial of Opipramol and Chlordiazepoxide in the Treatment of Anxiety |url=https://journals.sagepub.com/doi/abs/10.1177/030006057300100301 |journal=Journal of International Medical Research |volume=1 |issue=3 |pages=145–150 |doi=10.1177/030006057300100301 |s2cid=74130809 |issn=0300-0605}}</ref><ref>{{cite journal | vauthors = Volz HP, Möller HJ, Reimann I, Stoll KD | title = Opipramol for the treatment of somatoform disorders results from a placebo-controlled trial | journal = European Neuropsychopharmacology | volume = 10 | issue = 3 | pages = 211–217 | date = May 2000 | pmid = 10793324 | doi = 10.1016/S0924-977X(00)00074-2 | s2cid = 39368370 }}</ref><ref name=":0">{{cite journal | vauthors = Gahr M, Hiemke C, Connemann BJ | title = [Update Opipramol] | language = de | journal = Fortschritte der Neurologie-Psychiatrie | volume = 85 | issue = 3 | pages = 139–145 | date = March 2017 | pmid = 28320023 | doi = 10.1055/s-0043-100762 }}</ref><ref name="Mohapatra_2013" />

Rarely (≥0.01% to <0.1%) reported adverse reactions include excitation, headache, [[paresthesia]] especially in elderly patients, [[psychomotor agitation|restlessness]], [[sweating]], [[sleep disorder|sleep disturbances]], [[edema]], [[galactorrhea]], urine blockage, [[nausea]] and [[vomiting]], [[fever]],<ref name="renamed_from_333_on_20220402163107">{{cite journal | vauthors = Krysta K, Murawiec S, Warchala A, Zawada K, Cubała WJ, Wiglusz MS, Jakuszkowiak-Wojten K, Krzystanek M, Krupka-Matuszczyk I | display-authors = 6 | title = Modern indications for the use of opipramol | journal = Psychiatria Danubina | volume = 27 | issue = Suppl 1 | pages = S435–S437 | date = September 2015 | pmid = 26417811 | url = https://hrcak.srce.hr/file/384203 | access-date = 2 April 2022 }}</ref> collapse conditions, stimulation conducting disturbances, intensification of present heart insufficiency, blood profile changes particularly [[leukopenia]], [[confusion]], [[delirium]], stomach complaints, taste disturbance, and [[ileus|paralytic ileus]] especially with sudden discontinuation of a longer-term high-dose therapy.<ref name="Mohapatra_2013" />

Very rarely (<0.01%) reported adverse reactions include [[seizures]], [[motor disorder]]s ([[akathisia]], [[dyskinesia]], [[ataxia]]), [[polyneuropathy]], [[glaucoma]], [[anxiety]], [[hair loss]], [[agranulocytosis]], severe liver dysfunction after long-term treatment, [[jaundice]], and chronic liver damage.<ref name=":0" /><ref name="Mohapatra_2013" /><ref>{{cite journal | vauthors = Braun JS, Geiger R, Wehner H, Schäffer S, Berger M | title = Hepatitis caused by antidepressive therapy with maprotiline and opipramol | journal = Pharmacopsychiatry | volume = 31 | issue = 4 | pages = 152–155 | date = July 1998 | pmid = 9754852 | doi = 10.1055/s-2007-979319 | s2cid = 260242120 }}</ref>

It could also cause headache.

==Overdose==

{{Main|Tricyclic antidepressant 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. [[Arrhythmia]]s 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 [[anticonvulsant]]s (typically [[diazepam]]), while monitoring for any worsening in [[Central nervous system depression|CNS depression]]. Hypotension can be treated by assuming the corresponding [[recovery position]], by increasing plasma volume with saline infusions, or by [[Antihypotensive agent|pressors]], such as [[adrenaline]] or [[dobutamine]].

== Interactions ==

Opipramol can be co-prescribed with other psychiatric drugs, such as antidepressants, [[anxiolytic]]s and [[antipsychotic]]s, 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 blocker]]s, [[antiarrhythmic agent|antiarrhythmic]]s (of [[Antiarrhythmic agent#Class I agents|class 1c]]) and other drugs for [[microsome|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 [[anticonvulsant]]s, on the other hand, can reduce the plasma concentration of opipramol and thereby weaken its therapeutic effect.<ref name="Mohapatra_2013" />

==Pharmacology==

===Pharmacodynamics===

{{See also|Pharmacology of antidepressants|Tricyclic antidepressant#Binding profiles}}

{| class="wikitable floatright"

|+ Opipramol<ref name="PDSP">{{cite web | title = PDSP K_i Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth | vauthors = Roth BL, Driscol J | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 14 August 2017 | url = https://kidbdev.med.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=opipramol&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query}}</ref>

|-

! Site !! K_i (nM) !! Species !! Ref

|-

| '''[[Sigma-1 receptor|σ₁]]''' || '''0.2–50''' || Rodent || <ref name="pmid8755605">{{cite journal | vauthors = Hanner M, Moebius FF, Flandorfer A, Knaus HG, Striessnig J, Kempner E, Glossmann H | title = Purification, molecular cloning, and expression of the mammalian sigma1-binding site | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 93 | issue = 15 | pages = 8072–8077 | date = July 1996 | pmid = 8755605 | pmc = 38877 | doi = 10.1073/pnas.93.15.8072 | doi-access = free | bibcode = 1996PNAS...93.8072H }}</ref><ref name="pmid2477524">{{cite journal | vauthors = Klein M, Musacchio JM | title = High affinity dextromethorphan binding sites in guinea pig brain. Effect of sigma ligands and other agents | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 251 | issue = 1 | pages = 207–215 | date = October 1989 | pmid = 2477524 }}</ref><ref name="pmid1963476">{{cite journal | vauthors = Rao TS, Cler JA, Mick SJ, Dilworth VM, Contreras PC, Iyengar S, Wood PL | title = Neurochemical characterization of dopaminergic effects of opipramol, a potent sigma receptor ligand, in vivo | journal = Neuropharmacology | volume = 29 | issue = 12 | pages = 1191–1197 | date = December 1990 | pmid = 1963476 | doi = 10.1016/0028-3908(90)90044-r | s2cid = 23110359 }}</ref>

|-

| '''[[Sigma-2 receptor|σ₂]]''' || '''110''' || {{abbr|ND|No data}} || <ref name="pmid2568580">{{cite journal | vauthors = Sills MA, Loo PS | title = Tricyclic antidepressants and dextromethorphan bind with higher affinity to the phencyclidine receptor in the absence of magnesium and L-glutamate | journal = Molecular Pharmacology | volume = 36 | issue = 1 | pages = 160–165 | date = July 1989 | pmid = 2568580 }}</ref>

|-

| {{abbrlink|SERT|Serotonin transporter}} || ≥2,200 || Rat/? || <ref name="pmid6128769">{{cite journal | vauthors = Hyttel J | title = Citalopram--pharmacological profile of a specific serotonin uptake inhibitor with antidepressant activity | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 6 | issue = 3 | pages = 277–295 | year = 1982 | pmid = 6128769 | doi = 10.1016/s0278-5846(82)80179-6 | s2cid = 36424574 }}</ref><ref name="BoultonBaker1988">{{cite book| vauthors = Boulton AA, Baker GB, Coutts TR |title=Analysis of Psychiatric Drugs|volume=10|year=1988|isbn=978-0-89603-121-0|doi=10.1385/0896031217|page=336}}</ref><ref name="pmid14523629">{{cite journal | vauthors = Holoubek G, Müller WE | title = Specific modulation of sigma binding sites by the anxiolytic drug opipramol | journal = Journal of Neural Transmission | volume = 110 | issue = 10 | pages = 1169–1179 | date = October 2003 | pmid = 14523629 | doi = 10.1007/s00702-003-0019-5 | s2cid = 5832198 }}</ref>

|-

| {{abbrlink|NET|Norepinephrine transporter}} || ≥700 || Rat/? || <ref name="pmid6128769" /><ref name="BoultonBaker1988" /><ref name="pmid14523629" />

|-

| {{abbrlink|DAT|Dopamine transporter}} || ≥3,000 || Rat/? || <ref name="pmid6128769" /><ref name="BoultonBaker1988" /><ref name="pmid14523629" />

|-

| [[5-HT1A receptor|5-HT_1A]] || >10,000 || ? || <ref name="pmid14523629" />

|-

| '''[[5-HT2A receptor|5-HT_2A]]''' || '''120''' || ? || <ref name="pmid14523629" />

|-

| [[5-HT2C receptor|5-HT_2C]] || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}

|-

| '''[[Alpha-1 adrenergic receptor|α₁]]''' || '''200''' || ? || <ref name="pmid14523629" />

|-

| [[Alpha-2 adrenergic receptor|α₂]] || 6,100 || ? || <ref name="pmid14523629" />

|-

| [[Dopamine D1 receptor|D₁]] || 900 || Rat || <ref name="pmid1963476" />

|-

| '''[[Dopamine D2 receptor|D₂]]''' || '''120–300''' || Rat || <ref name="pmid14523629" /><ref name="pmid1963476" />

|-

| '''[[Histamine H1 receptor|H₁]]''' || '''6.03''' || Human || <ref name="pmid22033803">{{cite journal | vauthors = Appl H, Holzammer T, Dove S, Haen E, Strasser A, Seifert R | title = Interactions of recombinant human histamine H₁R, H₂R, H₃R, and H₄R receptors with 34 antidepressants and antipsychotics | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 385 | issue = 2 | pages = 145–170 | date = February 2012 | pmid = 22033803 | doi = 10.1007/s00210-011-0704-0 | s2cid = 14274150 }}</ref>

|-

| [[Histamine H2 receptor|H₂]] || 4,470 || Human || <ref name="pmid22033803" />

|-

| [[Histamine H3 receptor|H₃]] || 61,700 || Human || <ref name="pmid22033803" />

|-

| [[Histamine H4 receptor|H₄]] || >100,000 || Human || <ref name="pmid22033803" />

|-

| {{abbrlink|mACh|Muscarinic acetylcholine receptor}} || 3,300 || ? || <ref name="pmid14523629" />

|-

| [[NMDA receptor|NMDA/{{abbr|PCP|Phencyclidine site}}]] || >30,000 || Rat || <ref name="pmid1963476" />

|- class="sortbottom"

| colspan="4" style="width: 1px;" | Values are K_i (nM). The smaller the value, the more strongly the drug binds to the site.

|}

Opipramol acts as a high [[affinity (pharmacology)|affinity]] [[sigma receptor]] [[agonist]], primarily of the [[sigma-1 receptor|σ₁]] subtype, but also of the [[sigma-2 receptor|σ₂]] subtype with lower affinity.<ref name="pmid11199949" /><ref name="Mohapatra_2013">{{cite journal|vauthors=Mohapatra S, Rath NM, Agrawal A, Verma J|title=Opipramol: A Novel Drug|journal=Delhi Psychiatry Journal|date=October 2013|volume=16|issue=2|pages=409–411|url=http://medind.nic.in/daa/t13/i2/daat13i2p409.pdf|access-date=2014-03-25|archive-date=2020-07-11|archive-url=https://web.archive.org/web/20200711034539/http://medind.nic.in/daa/t13/i2/daat13i2p409.pdf|url-status=dead}}</ref> In one study of σ₁ receptor [[ligand (biochemistry)|ligand]]s that also included [[haloperidol]], [[pentazocine]], [[(+)-3-PPP]], [[ditolylguanidine]], [[dextromethorphan]], [[SKF-10,047]] ((±)-alazocine), [[ifenprodil]], [[progesterone]], and others, opipramol showed the highest affinity (K_i = 0.2–0.3) for the [[guinea pig]] σ₁ receptor of all the tested ligands except haloperidol, which it was approximately [[equipotent]] with.<ref name="pmid8755605" /> The sigma receptor agonism of opipramol is thought to be responsible for its therapeutic benefits against anxiety and depression.<ref name="pmid15547785" /><ref name="Mohapatra_2013" />

Unlike other TCAs, opipramol does not [[reuptake inhibitor|inhibit]] the [[reuptake]] of [[serotonin]] or [[norepinephrine]].<ref name="Mohapatra_2013" /> However, it does act as a high affinity [[receptor antagonist|antagonist]] of the [[histamine]] [[H1 receptor|H₁ receptor]]<ref name="pmid22033803" /> and is a low to moderate affinity antagonist of the [[dopamine]] [[D2 receptor|D₂]], [[serotonin]] [[5-HT2 receptor|5-HT₂]], and [[alpha-1 adrenergic receptor|α₁-adrenergic receptor]]s.<ref name="Mohapatra_2013" /><ref name="pmid14523629" /> H₁ receptor antagonism accounts for its [[antihistamine]] effects and associated [[sedative]] side effects.<ref name="pmid11199949" /><ref name="Mohapatra_2013" /> In contrast to other TCAs, opipramol has very low affinity for the [[muscarinic acetylcholine receptor]]s and virtually no [[anticholinergic]] effects.<ref name="pmid14523629" /><ref name="BotanaLoza2012">{{cite book| vauthors = Botana LM, Loza M |title=Therapeutic Targets: Modulation, Inhibition, and Activation|url=https://books.google.com/books?id=3XJ8PXFCXq4C&pg=PA251|date=20 April 2012|publisher=John Wiley & Sons|isbn=978-1-118-18552-0|pages=251–}}</ref>

Sigma receptors are a set of [[protein]]s located in the [[endoplasmic reticulum]].<ref name="Mohapatra_2013" /> σ₁ receptors play key role in potentiating intracellular calcium mobilization thereby acting as sensor or modulator of calcium signaling.<ref name="Mohapatra_2013" /> 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.<ref name="Mohapatra_2013" /> Opipramol is said to have a biphasic action, with prompt initial improvement of tension, anxiety, and insomnia followed by improved mood later.<ref name="Mohapatra_2013" /> Hence, it is an anxiolytic with an antidepressant component.<ref name="Mohapatra_2013" /> After sub-chronic treatment with opipramol, σ₂ receptors are significantly [[downregulated]] but σ₁ receptors are not.<ref name="Mohapatra_2013" />

===Pharmacokinetics===

Opipramol is rapidly and completely [[absorption (pharmacokinetics)|absorbed]] by the [[gastrointestinal tract]].<ref name="Mohapatra_2013" /> The [[bioavailability]] of opipramol amounts to 94%.<ref name="Mohapatra_2013" /> After single [[oral administration]] of 50&nbsp;mg, the [[Cmax (pharmacology)|peak plasma concentration]] of the drug is reached after 3.3&nbsp;hours and amounts to 15.6&nbsp;ng/mL.<ref name="Mohapatra_2013" /> After single oral administration of 100&nbsp;mg the maximum plasma concentration is reached after 3&nbsp;hours and amounts to 33.2&nbsp;ng/mL.<ref name="Mohapatra_2013" /> Therapeutic concentrations of opipramol range from 140 to 550&nbsp;nmol/L.<ref name="pmid14708881">{{cite journal | vauthors = Gutteck U, Rentsch KM | title = Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry | journal = Clinical Chemistry and Laboratory Medicine | volume = 41 | issue = 12 | pages = 1571–1579 | date = December 2003 | pmid = 14708881 | doi = 10.1515/CCLM.2003.240 | s2cid = 24448788 }}</ref> The [[plasma protein binding]] amounts to approximately 91% and the [[volume of distribution]] is approximately 10&nbsp;L/kg.<ref name="Mohapatra_2013" /> Opipramol is partially [[metabolism|metabolized]] in the [[liver]] to deshydroxyethylopipramol.<ref name="Mohapatra_2013" /> Metabolism occurs through the [[CYP2D6]] [[isoenzyme]].<ref name="Mohapatra_2013" /> Its [[terminal half-life]] in plasma is 6–11 hours.<ref name="Mohapatra_2013" /> About 70% is [[elimination (pharmacology)|eliminated]] in [[urine]] with 10% unaltered.<ref name="Mohapatra_2013" /> The remaining portion is eliminated through [[feces]].<ref name="Mohapatra_2013"/>

==History==

Opipramol was developed by [[Geigy]].<ref name="pmid19557250">{{cite journal | vauthors = Andersen J, Kristensen AS, Bang-Andersen B, Strømgaard K | title = Recent advances in the understanding of the interaction of antidepressant drugs with serotonin and norepinephrine transporters | journal = Chemical Communications | issue = 25 | pages = 3677–3692 | date = July 2009 | pmid = 19557250 | doi = 10.1039/b903035m }}</ref> It first appeared in the literature in 1952 and was patented in 1961.<ref name="pmid19557250" /> The drug was first introduced for use in medicine in 1961.<ref name="pmid19557250" /> Opipramol was one of the first TCAs to be introduced, with [[imipramine]] marketed in the 1950s and [[amitriptyline]] marketed in 1961.<ref name="pmid19557250" />

==Society and culture==

{{Multiple image

| direction = horizontal

| total_width = 450

| caption_align =

| header =

| footer = Opipramol as Insidon and Pramolan 50&nbsp;mg tablets.

| image1 = Insidon opipramol.jpg

| width1 = 300

| height1 = 239

| alt1 =

| caption1 =

| image2 = Pramolan PL photo.jpg

| width2 = 300

| height2 = 200

| alt2 =

| caption2 =

}}

===Generic names===

''Opipramol'' is the [[English language|English]], [[German language|German]], [[French language|French]], and [[Spanish language|Spanish]] [[generic term|generic name]] of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|DCF|Dénomination Commune Française}}, while ''opipramol hydrochloride'' is its {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BANM|British Approved Name}}, and {{abbrlink|JAN|Japanese Accepted Name}}.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA904|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=904–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA760|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=760–761}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA209|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=209–}}</ref><ref name="Drugs.com">{{Cite web | url=https://www.drugs.com/international/opipramol.html |title = Opipramol}}</ref> Its generic name in [[Italian language|Italian]] and its {{abbrlink|DCIT|Denominazione Comune Italiana}} is ''opipramolo'' and in [[Latin language|Latin]] is ''opipramolum''.<ref name="IndexNominum2000" /><ref name="Drugs.com" />

===Brand names===

Opipramol is marketed under the brand names Deprenil, Dinsidon, Ensidon, Insidon, Insomin, Inzeton, Nisidana, Opipram, Opramol, Oprimol, Pramolan, and Sympramol among others.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" />

== References ==

{{Reflist|2}}

{{Anxiolytics}}

{{Antidepressants}}

{{Navboxes

| title = [[Pharmacodynamics]]

| titlestyle = background:#ccccff

| list1 =

{{Adrenergic receptor modulators}}

{{Dopamine receptor modulators}}

{{Histamine receptor modulators}}

{{Serotonin receptor modulators}}

{{Sigma receptor modulators}}

}}

{{Tricyclics}}

[[Category:Primary alcohols]]

[[Category:Alpha-1 blockers]]

[[Category:Antihistamines]]

[[Category:Anxiolytics]]

[[Category:D2 antagonists]]

[[Category:Dibenzazepines]]

[[Category:H1 receptor antagonists]]

[[Category:Piperazines]]

[[Category:Sedatives]]

[[Category:Serotonin receptor antagonists]]

[[Category:Sigma agonists]]

[[Category:Tricyclic antidepressants]]

[[Category:Ethanolamines]]