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Identification
- Summary
Mesoridazine is a phenothiazine antipsychotic used to treat schizophrenia, organic brain disorders, alcoholism, and psychoneuroses.
- Generic Name
- Mesoridazine
- DrugBank Accession Number
- DB00933
- Background
A phenothiazine antipsychotic with effects similar to chlorpromazine.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Mesoridazine (DB00933)
- Weight
- Average: 386.574
Monoisotopic: 386.148654844 - Chemical Formula
- C21H26N2OS2
- Synonyms
- 10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulfinyl phenothiazine
- 10-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazine
- 2-Methanesulfinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazine
- Mesoridazina
- Mesoridazine
- Mesoridazinum
- Thioridazine 2-sulfoxide
- Thioridazine thiomethyl sulfoxide
- Thioridazine-2-sulfoxide
- External IDs
- NC-123
- TPS-23
Pharmacology
- Indication
Used in the treatment of schizophrenia, organic brain disorders, alcoholism and psychoneuroses.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Mesoridazine, the besylate salt of a metabolite of thioridazine, is a phenothiazine tranquilizer. Pharmacological studies in laboratory animals have established that mesoridazine has a spectrum of pharmacodynamic actions typical of a major tranquilizer. In common with other tranquilizers it inhibits spontaneous motor activity in mice, prolongs thiopental and hexobarbital sleeping time in mice and produces spindles and block of arousal reaction in the EEG of rabbits. It is effective in blocking spinal reflexes in the cut and antagonizes d-amphetamine excitation and toxicity in grouped mice. It shows a moderate adrenergic blocking activity in vitro and in vivo and antagonizes 5-hydroxytryptamine in vivo. Intravenously administered, it lowers the blood pressure of anesthetized dogs. It has a weak antiacetylcholine effect in vitro.
- Mechanism of action
Based upon animal studies, mesoridazine, as with other phenothiazines, acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. In addition, the phenothiazines exhibit at least part of their activities through depression of hypothalamic centers. Neurochemically, the phenothiazines are thought to exert their effects by a central adrenergic blocking action.
Target Actions Organism AD(2) dopamine receptor antagonistHumans A5-hydroxytryptamine receptor 2A antagonistHumans - Absorption
Well absorbed from the gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
4%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
24 to 48 hours
- Clearance
Not Available
- Adverse Effects
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Oral LD50 is 560 ± 62.5 mg/kg and 644 ± 48 mg/kg in mouse and rat, respectively. Symptoms of overdose may include emesis, muscle tremors, decreased food intake and death associated with aspiration of oral-gastric contents into the respiratory system.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Mesoridazine is combined with 1,2-Benzodiazepine. Abatacept The metabolism of Mesoridazine can be increased when combined with Abatacept. Abiraterone The metabolism of Mesoridazine can be decreased when combined with Abiraterone. Acebutolol The serum concentration of Acebutolol can be increased when it is combined with Mesoridazine. Acenocoumarol The risk or severity of adverse effects can be increased when Mesoridazine is combined with Acenocoumarol. - Food Interactions
- Take with food. Food reduces irritation.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Mesoridazine besylate T4G2I958J2 32672-69-8 CRJHBCPQHRVYBS-UHFFFAOYSA-N Mesoridazine mesilate Not Available Not Available Not applicable - International/Other Brands
- Lidanar / Lidanil
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Serentil Tablet, film coated 100 mg/1 Oral Physicians Total Care, Inc. 1994-05-18 2011-06-30 US 
Serentil Tablet, film coated 10 mg/1 Oral Boehringer Ingelheim 2001-01-24 2003-06-19 US Serentil Tablet, film coated 100 mg/1 Oral Boehringer Ingelheim 2001-01-24 2004-01-23 US Serentil Tablet, film coated 50 mg/1 Oral Boehringer Ingelheim 2001-01-24 2002-05-20 US Serentil Solution, concentrate 25 mg/1mL Oral Boehringer Ingelheim 2003-06-19 2004-01-23 US
Categories
- ATC Codes
- N05AC03 — Mesoridazine
- Drug Categories
- Antidepressive Agents
- Antipsychotic Agents
- Antipsychotic Agents (First Generation [Typical])
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Heterocyclic Compounds, Fused-Ring
- Moderate Risk QTc-Prolonging Agents
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- Phenothiazines
- Phenothiazines With Piperidine Structure
- Psycholeptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Sulfur Compounds
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazines
- Sub Class
- Phenothiazines
- Direct Parent
- Phenothiazines
- Alternative Parents
- Alkyldiarylamines / Diarylthioethers / Piperidines / Benzenoids / 1,4-thiazines / Trialkylamines / Sulfoxides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds show 2 more
- Substituents
- Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- phenothiazines, tertiary amino compound, sulfoxide (CHEBI:6780)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5XE4NWM740
- CAS number
- 5588-33-0
- InChI Key
- SLVMESMUVMCQIY-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
- IUPAC Name
- 2-methanesulfinyl-10-[2-(1-methylpiperidin-2-yl)ethyl]-10H-phenothiazine
- SMILES
- CN1CCCCC1CCN1C2=C(SC3=C1C=C(C=C3)S(C)=O)C=CC=C2
References
- Synthesis Reference
- US3084161
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015068
- KEGG Drug
- D02671
- KEGG Compound
- C07143
- PubChem Compound
- 4078
- PubChem Substance
- 46506724
- ChemSpider
- 3936
- BindingDB
- 50131440
- 6779
- ChEBI
- 6780
- ChEMBL
- CHEMBL1088
- Therapeutic Targets Database
- DAP000252
- PharmGKB
- PA450386
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Mesoridazine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Bipolar Disorder (BD) / Psychosis / Schizoaffective Disorders / Schizophrenia / Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Novartis pharmaceuticals corp
- Packagers
- Novartis AG
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Injection, suspension Intramuscular 25 mg/1mL Solution, concentrate Oral 25 mg/1mL Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet Oral 10 mg / tab Tablet Oral 25 mg / tab Tablet Oral 50 mg / tab - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 3.9 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0767 mg/mL ALOGPS logP 3.83 ALOGPS logP 3.57 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 15.86 Chemaxon pKa (Strongest Basic) 8.19 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 23.55 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 115.13 m3·mol-1 Chemaxon Polarizability 43.83 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9322 Blood Brain Barrier + 0.9863 Caco-2 permeable + 0.5609 P-glycoprotein substrate Substrate 0.7284 P-glycoprotein inhibitor I Inhibitor 0.8978 P-glycoprotein inhibitor II Inhibitor 0.5334 Renal organic cation transporter Inhibitor 0.7467 CYP450 2C9 substrate Non-substrate 0.7962 CYP450 2D6 substrate Non-substrate 0.5465 CYP450 3A4 substrate Substrate 0.5561 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5635 Ames test Non AMES toxic 0.6982 Carcinogenicity Non-carcinogens 0.8829 Biodegradation Not ready biodegradable 0.9954 Rat acute toxicity 2.7465 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7565 hERG inhibition (predictor II) Inhibitor 0.762
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 203.9741622 predictedDarkChem Lite v0.1.0 [M-H]- 180.84587 predictedDeepCCS 1.0 (2019) [M-H]- 203.9741622 predictedDarkChem Lite v0.1.0 [M-H]- 180.84587 predictedDeepCCS 1.0 (2019) [M+H]+ 203.7335622 predictedDarkChem Lite v0.1.0 [M+H]+ 183.20386 predictedDeepCCS 1.0 (2019) [M+H]+ 203.7335622 predictedDarkChem Lite v0.1.0 [M+H]+ 183.20386 predictedDeepCCS 1.0 (2019) [M+Na]+ 203.7788622 predictedDarkChem Lite v0.1.0 [M+Na]+ 189.29701 predictedDeepCCS 1.0 (2019) [M+Na]+ 203.7788622 predictedDarkChem Lite v0.1.0 [M+Na]+ 189.29701 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- dopamine binding
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Burstein ES, Ma J, Wong S, Gao Y, Pham E, Knapp AE, Nash NR, Olsson R, Davis RE, Hacksell U, Weiner DM, Brann MR: Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist. J Pharmacol Exp Ther. 2005 Dec;315(3):1278-87. Epub 2005 Aug 31. [Article]
- Choi S, Haggart D, Toll L, Cuny GD: Synthesis, receptor binding and functional studies of mesoridazine stereoisomers. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4379-82. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895, PubMed:21645528, PubMed:22300836, PubMed:35084960, PubMed:38552625). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538, PubMed:35084960). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:28129538, PubMed:35084960). HTR2A is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:28129538, PubMed:35084960). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538, PubMed:35084960). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity)
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Choi S, Haggart D, Toll L, Cuny GD: Synthesis, receptor binding and functional studies of mesoridazine stereoisomers. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4379-82. [Article]
- Rauser L, Savage JE, Meltzer HY, Roth BL: Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor. J Pharmacol Exp Ther. 2001 Oct;299(1):83-9. [Article]
- Herrick-Davis K, Grinde E, Teitler M: Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors. J Pharmacol Exp Ther. 2000 Oct;295(1):226-32. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Berecz R, de la Rubia A, Dorado P, Fernandez-Salguero P, Dahl ML, LLerena A: Thioridazine steady-state plasma concentrations are influenced by tobacco smoking and CYP2D6, but not by the CYP2C9 genotype. Eur J Clin Pharmacol. 2003 May;59(1):45-50. doi: 10.1007/s00228-003-0576-4. Epub 2003 Mar 28. [Article]
- Llerena A, Berecz R, de la Rubia A, Norberto MJ, Benitez J: Use of the mesoridazine/thioridazine ratio as a marker for CYP2D6 enzyme activity. Ther Drug Monit. 2000 Aug;22(4):397-401. doi: 10.1097/00007691-200008000-00006. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 03, 2024 07:19