Prométhazine
Vue d'ensemble
Description
La Prométhazine est un antihistaminique de première génération appartenant à la classe des phénothiazines. Elle est largement utilisée pour ses propriétés sédatives, antiémétiques et antiallergiques. La this compound est généralement prescrite pour traiter les allergies, le mal des transports, les nausées et les vomissements. Elle a été synthétisée pour la première fois dans les années 1940 par des scientifiques des laboratoires Rhône-Poulenc et a été approuvée pour un usage médical aux États-Unis en 1951 .
Mécanisme D'action
Target of Action
Promethazine, a first-generation antihistamine, primarily targets histamine H1 receptors and muscarinic acetylcholine receptors . It also weakly antagonizes dopamine receptors . These receptors play crucial roles in allergic reactions, pain, sedation, nausea, and vomiting .
Mode of Action
Promethazine acts as an antagonist at its target receptors. It blocks the action of histamine at H1 receptors, which can alleviate allergic reactions and induce sedation . It also blocks muscarinic acetylcholine receptors, contributing to its sedative effects . The weak antagonism at dopamine receptors may contribute to its antiemetic (anti-vomiting) effects .
Biochemical Pathways
Promethazine’s antagonism of histamine H1 and muscarinic acetylcholine receptors disrupts several biochemical pathways. For instance, blocking H1 receptors can inhibit the effects of histamine, reducing allergic reactions . Antagonizing muscarinic receptors can affect the activity of adenylate cyclase, potentially influencing various cellular processes .
Pharmacokinetics
Promethazine is well absorbed from the gastrointestinal tract and parenteral sites . Its oral bioavailability is only 25% due to first-pass metabolism . It is predominantly metabolized to promethazine sulfoxide, with minor metabolism to desmethylpromethazine and a hydroxy metabolite . Hydroxylation of promethazine is predominantly mediated by CYP2D6 .
Result of Action
The antagonism of histamine H1 and muscarinic acetylcholine receptors by promethazine results in a variety of molecular and cellular effects. These include the reduction of allergic reactions, the induction of sedation, and the prevention of nausea and vomiting . At the cellular level, promethazine can inhibit adenylate cyclase, leading to changes in intracellular levels of cyclic AMP .
Action Environment
Environmental factors can influence the action, efficacy, and stability of promethazine. For instance, the formulation of promethazine can affect its bioavailability and therapeutic effects . Additionally, individual factors such as the patient’s metabolic rate and the presence of other medications can also influence the drug’s action .
Applications De Recherche Scientifique
Promethazine has a wide range of scientific research applications. In medicine, it is used as an antihistamine, sedative, and antiemetic. It has been studied for its neuroprotective effects, particularly in reducing ischemia-mediated injury by inhibiting mitochondrial dysfunction . Promethazine has also been explored as a potential imaging probe for Alzheimer’s disease due to its ability to bind to amyloid-beta plaques .
In chemistry, promethazine is used in various analytical techniques, such as sequential injection analysis for the determination of phenothiazines in pharmaceutical formulations . Additionally, it has applications in the development of potentiometric sensors for drug analysis .
Analyse Biochimique
Biochemical Properties
Promethazine acts mainly as a strong H1 receptor antagonist (antihistamine) . Additionally, it has high anticholinergic properties, since it blocks acetylcholine responses through the mediation of muscarinic receptors . The binding affinity to human serum albumin (HSA) of Promethazine and its primary metabolites [N-desmethyl promethazine (DMPMZ) and promethazine sulphoxide (PMZSO)] was investigated by high-performance affinity chromatography (HPAC) though zonal approach .
Cellular Effects
Promethazine easily penetrates the blood-brain barrier and is associated with adverse effects such as moderate/intense sedation . An overdose of Promethazine can lead to anticholinergic toxidrome, where signs and symptoms such as dry mouth, difficulty swallowing, mydriasis with blurred vision, and photophobia can be seen .
Molecular Mechanism
Promethazine and its metabolites exhibited a notable binding affinity for HSA (% b values higher than 80%) . Molecular docking studies corroborated the experimental results, reinforcing the insights gained from the empirical data .
Temporal Effects in Laboratory Settings
Promethazine alone in either formulation is rapidly absorbed after oral administration with peak concentrations after 2–3 h . Clinical effects are seen within 20 min and its effects last 4–6 h .
Dosage Effects in Animal Models
The main feature of Promethazine toxicity is delirium, the probability of which can be predicted from the dose ingested . The administration of charcoal and the presence of co-ingestants appears to reduce the probability of delirium in a predictable manner .
Metabolic Pathways
Promethazine is rapidly metabolized into its main metabolites: promethazine sulphoxide (PMZSO) and N-desmonomethyl promethazine (DMPMZ) .
Transport and Distribution
Promethazine and its metabolites bind to both sites of HSA, but mainly in site II . The in silico data also suggested that competition between Promethazine and its metabolites can occur in both sites of HSA .
Subcellular Localization
Given its ability to cross the blood-brain barrier , it can be inferred that Promethazine may localize in various compartments within the cell.
Méthodes De Préparation
La Prométhazine peut être synthétisée par plusieurs méthodes. Une voie de synthèse courante implique la réaction de la diéthylamine avec l'époxypropane pour obtenir du 1-diéthylamino-2-propanol. Cet intermédiaire est ensuite mis à réagir avec le chlorure de thionyle et le toluène pour produire du 1-diéthylamino-2-chloropropane. Enfin, le 1-diéthylamino-2-chloropropane est mis à réagir avec la phénothiazine pour produire de la this compound brute, qui est purifiée et salifiée avec de l'acide chlorhydrique pour obtenir le chlorhydrate de this compound .
Les méthodes de production industrielle font souvent appel à des processus de cristallisation et de salification pour obtenir une pureté et un rendement élevés. Par exemple, la base de this compound peut être préparée puis convertie en chlorhydrate de this compound par cristallisation utilisant du gaz chlorhydrique sec .
Analyse Des Réactions Chimiques
La Prométhazine subit diverses réactions chimiques, notamment l'oxydation, la réduction et la substitution. Une réaction notable est son oxydation par le cérium (IV) en milieu acide, qui conduit à la formation d'un produit coloré détectable par spectrométrie . Une autre réaction implique le couplage oxydatif de la this compound avec l'aniline, qui suit un modèle cinétique du premier ordre et produit un produit stable .
Les réactifs couramment utilisés dans ces réactions comprennent les ions cérium (IV), l'aniline et les ions hydrogène. Les principaux produits formés à partir de ces réactions dépendent des conditions et des réactifs spécifiques utilisés.
Applications de la recherche scientifique
La this compound a un large éventail d'applications de recherche scientifique. En médecine, elle est utilisée comme antihistaminique, sédatif et antiémétique. Elle a été étudiée pour ses effets neuroprotecteurs, en particulier pour réduire les lésions induites par l'ischémie en inhibant le dysfonctionnement mitochondrial . La this compound a également été explorée comme une sonde d'imagerie potentielle pour la maladie d'Alzheimer en raison de sa capacité à se lier aux plaques bêta-amyloïdes .
En chimie, la this compound est utilisée dans diverses techniques analytiques, telles que l'analyse par injection séquentielle pour la détermination des phénothiazines dans les formulations pharmaceutiques . De plus, elle a des applications dans le développement de capteurs potentiométriques pour l'analyse des médicaments .
Mécanisme d'action
La this compound exerce ses effets en antagonisant plusieurs récepteurs, notamment les récepteurs H1 de l'histamine, les récepteurs dopaminergiques mésolimbiques post-synaptiques, les récepteurs alpha-adrénergiques, muscariniques et NMDA . Son action antihistaminique est principalement responsable du traitement des réactions allergiques, tandis que l'antagonisme des récepteurs muscariniques et NMDA contribue à ses effets sédatifs et antiémétiques .
Comparaison Avec Des Composés Similaires
La Prométhazine est souvent comparée à d'autres antihistaminiques et antiémétiques. Des composés similaires comprennent la chlorpromazine, la lévomépromazine et la métoclopramide. Bien que la chlorpromazine et la lévomépromazine soient également des dérivés de la phénothiazine, elles sont principalement utilisées comme antipsychotiques . La métoclopramide, en revanche, est utilisée pour les troubles gastro-intestinaux et a un mécanisme d'action différent .
La particularité de la this compound réside dans sa large gamme d'applications, allant du traitement des allergies et du mal des transports à son utilisation potentielle dans les études de neuroprotection et d'imagerie. Sa capacité à interagir avec plusieurs types de récepteurs la distingue également des autres composés similaires.
Propriétés
IUPAC Name |
N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
PWWVAXIEGOYWEE-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C17H20N2S |
Source
|
| Record name | PROMETHAZINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20956 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID7023518 |
Source
|
| Record name | Promethazine | |
| Source | EPA DSSTox | |
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Molecular Weight |
284.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Crystals. Melting point 60 °C. Used as an antihistamine., Solid |
Source
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| Record name | PROMETHAZINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20956 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Promethazine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015202 | |
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Boiling Point |
374 to 379 °F at 3 mmHg (NTP, 1992), 190-192 °C at 3.00E+00 mm Hg, BP: 190-192 °C at 3 mm Hg, BP: 191 °C at 0.5 mm Hg |
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| Record name | Promethazine | |
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Solubility |
Very soluble in dilute hydrogen chloride, In water, 1.56X10-2 g/L (15.6 mg/L) at 24 °C, 2.45e-02 g/L |
Source
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| Record name | Promethazine | |
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| Record name | Promethazine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015202 | |
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Mechanism of Action |
Promethazine is a an antagonist of histamine H1, post-synaptic mesolimbic dopamine, alpha adrenergic, muscarinic, and NMDA receptors. The antihistamine action is used to treat allergic reactions. Antagonism of muscarinic and NMDA receptors contribute to its use as a sleep aid, as well as for anxiety and tension. Antagonism of histamine H1, muscarinic, and dopamine receptors in the medullary vomiting center make promethazine useful in the treatment of nausea and vomiting., Promethazine is a phenothiazine derivative with potent sedative properties. Although the drug can produce either CNS stimulation or CNS depression, CNS depression manifested by sedation is more common with therapeutic doses of promethazine. The precise mechanism of the CNS effects of the drug is not known., Although it has been reported that the drug has slight antitussive activity, this may result from its anticholinergic and CNS depressant effects. In therapeutic doses, promethazine appears to have no substantial effect on the cardiovascular system. Although rapid IV administration of promethazine may produce a transient fall in blood pressure, blood pressure usually is maintained or slightly elevated when the drug is given slowly., Promethazine hydrochloride is a phenothiazine derivative which possesses antihistaminic, sedative, antimotion-sickness, antiemetic, and anticholinergic effects. Promethazine is a competitive H1 receptor antagonist, but does not block the release of histamine. Structural differences from the neuroleptic phenothiazines result in its relative lack (1/10 that of chlorpromazine) of dopamine antagonist properties., The development of phenothiazine derivatives as psychopharmacologic agents resulted from the observation that certain phenothiazine antihistaminic compounds produced sedation. In an attempt to enhance the sedative effects of these drugs, promethazine and chlorpromazine were synthesized. Chlorpromazine is the pharmacologic prototype of the phenothiazines. The pharmacology of phenothiazines is complex, and because of their actions on the central and autonomic nervous systems, the drugs affect many different sites in the body. Although the actions of the various phenothiazines are generally similar, these drugs differ both quantitatively and qualitatively in the extent to which they produce specific pharmacologic effects. /Phenothiazine General Statement/, For more Mechanism of Action (Complete) data for Promethazine (18 total), please visit the HSDB record page. |
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| Record name | Promethazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01069 | |
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| Record name | Promethazine | |
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Color/Form |
Crystals, White to faint yellow crystalline powder | |
CAS No. |
60-87-7, 38878-40-9 |
Source
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| Record name | PROMETHAZINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20956 | |
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| Record name | 10H-Phenothiazine-10-ethanamine, N,N,α-trimethyl-, radical ion(1+) | |
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Melting Point |
140 °F (NTP, 1992), 60 °C, Crystals from ethylene dichloride. Freely soluble in water. Soluble in alcohol, chlorform, practically insoluble in acetone, ether, ethyl acetate; MP: 230-232 °C with some decomp. Max absorption (water): 249, 297 nm (epsilon 28770, 3400). pH of 10% aqueous solution 5.3 /Promethazine hydrochloride/ |
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| Record name | PROMETHAZINE | |
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| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015202 | |
| 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. | |
Synthesis routes and methods
Procedure details
Retrosynthesis Analysis
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Feasible Synthetic Routes
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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.
![[(2R)-3,6-dioxopiperazin-2-yl]methyl (2R,4R)-2-benzyl-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-(methylamino)propanoyl]-methylamino]-5-(4-hydroxyphenyl)-3-oxo-4-[[(E)-3-[2-[(E)-pent-2-enyl]phenyl]prop-2-enoyl]amino]pentanoate](/img/structure/B1679557.png)
