Clomipramine
Vue d'ensemble
Description
La clomipramine est un antidépresseur tricyclique principalement utilisé pour traiter le trouble obsessionnel compulsif. Il est également efficace pour traiter d’autres affections telles que la dépression majeure, le trouble panique et la douleur chronique. La this compound a été découverte en 1964 par le fabricant suisse de médicaments Ciba-Geigy et est vendue sous le nom de marque Anafranil, entre autres .
Mécanisme D'action
La clomipramine agit en inhibant la recapture de la sérotonine et de la norépinéphrine dans le système nerveux central. Cela entraîne une augmentation des concentrations de ces neurotransmetteurs dans la fente synaptique, conduisant à une neurotransmission accrue. Le composé bloque également les récepteurs de l’histamine-H1, les récepteurs α1-adrénergiques et les récepteurs muscariniques, contribuant à ses effets sédatifs, hypotensifs et anticholinergiques .
Composés similaires :
Imipramine : Un autre antidépresseur tricyclique utilisé pour des indications similaires.
Amitriptyline : Connu pour ses propriétés sédatives et utilisé dans le traitement de la dépression et de la douleur chronique.
Nortriptyline : Un antidépresseur tricyclique amine secondaire avec un profil d’effets secondaires différent.
Unicité de la this compound : La this compound est unique en raison de sa forte inhibition de la recapture de la sérotonine par rapport aux autres antidépresseurs tricycliques. Cela le rend particulièrement efficace pour traiter le trouble obsessionnel compulsif. De plus, son métabolite, la déméthylthis compound, inhibe préférentiellement la recapture de la norépinéphrine, offrant un double mécanisme d’action .
Applications De Recherche Scientifique
Clomipramine has a wide range of scientific research applications:
Chemistry: Used as a model compound in the study of tricyclic antidepressants.
Biology: Investigated for its effects on neurotransmitter systems and neuronal autophagy.
Industry: Utilized in the development of diagnostic tools and eco-friendly sensors.
Méthodes De Préparation
Voies synthétiques et conditions réactionnelles : La clomipramine est synthétisée par un processus en plusieurs étapes à partir de l’iminodibenzyle. Les principales étapes sont :
Chloration : L’iminodibenzyle est chloré pour former du 3-chloroiminodibenzyle.
Réduction : Le produit chloré est réduit en 3-chloro-10,11-dihydro-5H-dibenzo[b,f]azépine.
Alkylation : La dernière étape consiste en une alkylation avec du chlorure de 3-diméthylaminopropyle pour obtenir la this compound.
Méthodes de production industrielle : La production industrielle de this compound suit généralement la même voie synthétique, mais à plus grande échelle. Le processus implique un contrôle strict des conditions réactionnelles afin d’assurer une grande pureté et un rendement élevé. Le produit final est souvent converti en sa forme de sel chlorhydrate pour sa stabilité et sa facilité de formulation .
Analyse Des Réactions Chimiques
Types de réactions : La clomipramine subit plusieurs types de réactions chimiques, notamment :
Oxydation : La this compound peut être oxydée pour former son dérivé N-oxyde.
Réduction : Le composé peut être réduit en son métabolite déméthylé, la déméthylthis compound.
Substitution : Des réactions d’halogénation et d’alkylation peuvent modifier la molécule de this compound.
Réactifs et conditions courants :
Oxydation : Le peroxyde d’hydrogène ou les peracides sont couramment utilisés.
Réduction : L’hydrure de lithium et d’aluminium ou le borohydrure de sodium sont des agents réducteurs typiques.
Substitution : Des agents d’halogénation comme le chlore ou le brome, et des agents d’alkylation comme les halogénures d’alkyle.
Principaux produits formés :
Déméthylthis compound : Formée par réduction.
Dérivé N-oxyde : Formé par oxydation.
4. Applications de la recherche scientifique
La this compound a une large gamme d’applications de recherche scientifique :
Chimie : Utilisé comme composé modèle dans l’étude des antidépresseurs tricycliques.
Biologie : Enquête sur ses effets sur les systèmes de neurotransmetteurs et l’autophagie neuronale.
Industrie : Utilisé dans le développement d’outils de diagnostic et de capteurs écologiques.
Comparaison Avec Des Composés Similaires
Imipramine: Another tricyclic antidepressant used for similar indications.
Amitriptyline: Known for its sedative properties and used in the treatment of depression and chronic pain.
Nortriptyline: A secondary amine tricyclic antidepressant with a different side effect profile.
Uniqueness of Clomipramine: this compound is unique due to its strong inhibition of serotonin reuptake compared to other tricyclic antidepressants. This makes it particularly effective in treating obsessive-compulsive disorder. Additionally, its metabolite, desmethylthis compound, preferentially inhibits norepinephrine reuptake, providing a dual mechanism of action .
Propriétés
IUPAC Name |
3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C19H23ClN2/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
GDLIGKIOYRNHDA-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CN(C)CCCN1C2=CC=CC=C2CCC3=C1C=C(C=C3)Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C19H23ClN2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
17321-77-6 (mono-hydrochloride) |
Source
|
| Record name | Clomipramine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000303491 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID6022844 |
Source
|
| Record name | Clomipramine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID6022844 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
314.9 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Clomipramine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015372 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Boiling Point |
160-170 °C at 3.00E-01 mm Hg, 160-170 °C at 0.3 mm Hg |
Source
|
| Record name | Clomipramine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01242 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Clomipramine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7746 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Solubility |
1.44e-02 g/L |
Source
|
| Record name | Clomipramine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01242 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Clomipramine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015372 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
Clomipramine is a strong, but not completely selective serotonin reuptake inhibitor (SRI), as the active main metabolite desmethyclomipramine acts preferably as an inhibitor of noradrenaline reuptake. α1-receptor blockage and β-down-regulation have been noted and most likely play a role in the short term effects of clomipramine. A blockade of sodium-channels and NDMA-receptors might, as with other tricyclics, account for its effect in chronic pain, in particular the neuropathic type., The pharmacology of clomipramine is complex and in many ways resembles that of other antidepressants, particularly those agents (eg, selective serotonin-reuptake inhibitors, trazodone) that predominantly potentiate the pharmacologic effects of serotonin (5-HT). Although clomipramine's principal pharmacologic effect in vitro is the selective inhibition of serotonin reuptake, in vivo the drug's pharmacologic activity is not so selective because of the action of its demethylated metabolite, desmethylclomipramine, as an inhibitor of norepinephrine reuptake. As a result of this and other effects, clomipramine also shares the pharmacologic profile of other tricyclic antidepressants., The precise mechanism of action that is responsible for the efficacy of clomipramine in the treatment of obsessive-compulsive disorder is unclear. However, because of its pronounced potency in blocking serotonin reuptake at the presynaptic neuronal membrane and its efficacy in the treatment of obsessive-compulsive disorder, a serotonin hypothesis has been developed to explain the pathogenesis of the condition. The hypothesis postulates that a dysregulation of serotonin is responsible for obsessive-compulsive disorder and that clomipramine is effective because it corrects this imbalance., Clomipramine and its principal metabolite, desmethylclomipramine, have been shown to block the reuptake of serotonin and norepinephrine, respectively, at the presynaptic neuronal membrane. The effects of serotonin and norepinephrine may thus be potentiated. However, it has been suggested that postsynaptic receptor modification is mainly responsible for the antidepressant action observed during long-term administration of antidepressant agents. During long-term therapy with most antidepressants (eg, tricyclic antidepressants, monoamine oxidase [MAO] inhibitors), these adaptive changes generally consist of subsensitivity of the noradrenergic adenylate cyclase system in association with a decrease in the number of beta-adrenergic receptors; such effects on noradrenergic receptor function commonly are referred to as "down-regulation." In addition, some antidepressants reportedly decrease the number of 5-HT binding sites following chronic administration., Clomipramine's principal metabolite, desmethylclomipramine, is an inhibitor of norepinephrine reuptake. Clomipramine decreases the concentration of 3-methoxy-4-hydroxyphenylglycol (MHPG), a metabolite of norepinephrine, in CSF in patients with obsessive-compulsive disorder. Patients with depressive affective (mood) disorders (e.g., major depressive episode) also exhibit decreases in concentrations of 5-HIAA and MHPG in CSF during treatment with clomipramine. The decrease in the concentration of 5-HIAA in CSF was correlated with inhibition of the in vitro uptake of 3H-serotonin in plasma. The change in concentration of MHPG in CSF during clomipramine therapy was correlated with amelioration of depression., For more Mechanism of Action (Complete) data for Clomipramine (10 total), please visit the HSDB record page. |
Source
|
| Record name | Clomipramine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01242 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Clomipramine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7746 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Impurities |
N-[3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-t-yl)propyl]-N,N',N'-trimethylpropane-1,3-diamine, 3-(3-chloro-5H-dibenzo[b,f]azepin-5-yl]-N,N-dimethylpropan-1-amine, 3-(3,7-dichloro-10,11-dihydro-5H-dibenzol[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine, 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine, For more Impurities (Complete) data for Clomipramine (11 total), please visit the HSDB record page. |
Source
|
| Record name | Clomipramine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7746 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
CAS No. |
303-49-1 |
Source
|
| Record name | Clomipramine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=303-49-1 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Clomipramine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000303491 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Clomipramine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01242 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | clomipramine | |
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| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=169865 | |
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| Record name | Clomipramine | |
| Source | EPA DSSTox | |
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| Record name | Clomipramine | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.005.587 | |
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| Record name | CLOMIPRAMINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/NUV44L116D | |
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| Record name | Clomipramine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7746 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Clomipramine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015372 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
191.5-192, 189.5 °C |
Source
|
| Record name | Clomipramine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01242 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Clomipramine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015372 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
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Veuillez noter que tous les articles et informations sur les produits présentés sur BenchChem sont destinés uniquement à des fins informatives. Les produits disponibles à l'achat sur BenchChem sont spécifiquement conçus pour des études in vitro, qui sont réalisées en dehors des organismes vivants. Les études in vitro, dérivées du terme latin "in verre", impliquent des expériences réalisées dans des environnements de laboratoire contrôlés à l'aide de cellules ou de tissus. Il est important de noter que ces produits ne sont pas classés comme médicaments et n'ont pas reçu l'approbation de la FDA pour la prévention, le traitement ou la guérison de toute condition médicale, affection ou maladie. Nous devons souligner que toute forme d'introduction corporelle de ces produits chez les humains ou les animaux est strictement interdite par la loi. Il est essentiel de respecter ces directives pour assurer la conformité aux normes légales et éthiques en matière de recherche et d'expérimentation.
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