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Mesoridazine

HCID 4078
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
5588-33-0
Standard-SMILES
CN1CCCCC1CCN1c2ccccc2Sc2ccc(S(C)=O)cc21
InChIKey
SLVMESMUVMCQIY-UHFFFAOYSA-N
Summenformel
C21H26N2OS2
Durchschnittliche Molmasse
386,6 g/mol
Monoisotopische Masse
386,1486558

Überblick

Mesoridazine is a phenothiazine substituted at position 2 (para to the S atom) by a methylsulfinyl group, and on the nitrogen by a 2-(1-methylpiperidin-2-yl)ethyl group. It has a role as a dopaminergic antagonist and a first generation antipsychotic. It is a sulfoxide, a member of phenothiazines and a tertiary amino compound.

Namen und Bezeichner

Bevorzugter Name
Mesoridazine
IUPAC
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine
Englischer Name
mesoridazine
Summenformel
C21H26N2OS2
Molmasse
386.57

Namen und Synonyme

mesoridazine5588-33-0LidanarThioridazine-2-sulfoxideTPS-23MesoridazinaThioridazine thiomethyl sulfoxideTps23NC-123MesoridazinumDTXSID3023265Thioridazien thiomethyl sulfoxide
Weitere Namen anzeigen
TPS 23NSC 186066Mesoridazine free baseThioridazine EP Impurity Bmesoridazine ISO 9001:2015 REACHThioridazine EP Impurity B-d3 (Mesoridazine-d3)10-[2-(1-methyl-2-piperidyl)ethyl]-2-methylsulfinyl-phenothiazine
10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulfinyl phenothiazineNSC-1860665XE4NWM74010-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine10H-Phenothiazine, 10-(2-(1-methyl-2-piperidinyl)ethyl)-2-(methylsulfinyl)-CHEBI:6780DTXCID50326510-(2(1-Methyl-2-piperidyl)ethyl)-2-(methylsulfinyl)phenothiazine

Datenbank-Bezeichner

CAS
5588-33-0
PubChem CID
4078
DTXSID
DTXSID3023265

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,5
Polarare Oberfläche (TPSA)
68,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
26
Formalladung
0
Komplexität
502

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

3.9

4.27

Color/FormOily product
Solubility · 2 Einträge

WHITE TO PALE YELLOW CRYSTALLINE POWDER; FAINT ODOR; DECOMP @ ABOUT 178 °C; 1 G SOL IN 20 ML WATER, ABOUT 30 ML ALC, IN 8 ML CHLOROFORM, ABOUT 6.6 ML METHANOL /BESYLATE/

7.67e-02 g/L

Human Drugs · 2 Einträge

Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents; Phenothiazines

Pharmaceuticals

DecompositionWhen heated to decomposition it emits very toxic fumes of sulfoxides and nitroxides.
Melting PointCrystals from ethyl acetate; MP: 115-120 °C /tartrate/
Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN SOLN OF PH 4.0-6.5; SOLN ARE LIGHT-SENSITIVE /BESYLATE/
Dissociation Constants · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Gefahrenhinweise

FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Interactions · 5 Einträge

CHLORPROMAZINE & OTHER ANTIPSYCHOTIC DRUGS...MAY BLOCK ANTIHYPERTENSIVE EFFECTS OF GUANETHIDINE. /CHLORPROMAZINE/

INTERACTIONS BETWEEN CHLORPROMAZINE & AMPHETAMINE, ALTHOUGH NOT DOCUMENTED, MAY APPLY TO OTHER PHENOTHIAZINE DERIV. /PHENOTHIAZINES/

PRETREATMENT WITH 3 MG/KG OF MESORIDAZINE-HCL ORALLY WAS MORE EFFECTIVE THAN THIORIDAZINE-HCL (6 MG/KG) IN DECR D-AMPHETAMINE SULFATE INDUCED BEHAVIOR IN DOGS.

Additive QT interval prolongation may increase the risk of ventricular tachycardia when /probucol is used with phenothiazines/. /Phenothiazines/

For more Interactions (Complete) data for MESORIDAZINE (31 total), please visit the HSDB record page.

Exposure RoutesOral; Intramuscular injection. Well absorbed from the gastrointestinal tract.
Milk Concentrations · 1 Eintrag

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

N - Nervous system

QN - Nervous system

Protein Binding4%
Pharmacodynamics · 1 Eintrag

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 · 2 Einträge

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.

...MECHANISM OF ACTION OF ANTIPSYCHOTIC DRUGS WITH RESPECT TO THERAPEUTIC EFFICACY & SIDE EFFECTS MAY RELATE TO INHIBITION OF DOPAMINE ACTIVATION OF ADENYLATE CYCLASE. /PHENOTHIAZINES/

Biological Half-Life24 to 48 hours
Metabolism/Metabolites · 3 Einträge

THIORIDAZINE-2-SULFOXIDE PROBABLY YIELDS THIORIDAZINE-2,5-DISULFOXIDE IN RAT: ZEHNDER, K ET AL, BIOCHEM PHARMAC, 11, 535 (1962). /FROM TABLE/

Thioridazine 2-sulfoxide is a known human metabolite of Thioridazine.

Half Life: 24 to 48 hours

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Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL1088
ChEBI
CHEBI:6780
UNII
5XE4NWM740
Nikkaji
J8.016K

9.61

9.5

Other Experimental PropertiesINJECTION HAS PH OF 4.0-5.0 /BESYLATE/

Physikochemische Eigenschaften

Schmelzpunkt
128 · 128-131 °C
Siedepunkt
570.5 · 570.5±50.0 °C(Predicted)
Dichte
1.1234 · 1.1234 (rough estimate)
Brechungsindex
1.595 · 1.5950 (estimate)
Löslichkeit
Acetonitrile: slightly soluble; DMSO: slightly, heated; Methanol: slightly soluble
Aggregatzustand
Sticky Solid
pka
9.84 · 9.84±0.10(Predicted)
Farbe
Pale Yellow to Orange
Stabilität
Hygroscopic

PHENOTHIAZINES CROSS PLACENTAL BARRIER & MAY APPEAR IN MILK OF NURSING MOTHERS...PHENOTHIAZINES &...METABOLITES...EXCRETED IN URINE, BILE, & FECES. CERTAIN METABOLITES &...FREE DRUGS...DETECTED IN URINE UP TO 6 MO AFTER THERAPY...DISCONTINUED /HUMAN, ORAL, IM/

Toxicity Summary · 1 Eintrag

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.

Signs and SymptomsSymptoms of overdose may include emesis, muscle tremors, decreased food intake and death associated with aspiration of oral-gastric contents into the respiratory system.
Human Toxicity Excerpts · 2 Einträge

Sudden and unexpected deaths have occurred in patients receiving phenothiazines, especially during long-term administration of the drugs. In some patients, sudden death appeared to result from asphyxia (secondary to failure of the cough reflex) or cardiac arrest. /Phenothiazines/

In general, overdosage of phenothiazines may be expected to produce effects that are extensions of common adverse effects; severe extrapyramidal reactions, hypotension, and sedation have been the principal effects reported. CNS depression progressing to coma with areflexia may occur; patients with early or mild intoxication may experience restlessness, confusion, and excitement. Other reported effects associated with acute phenothiazine overdosage have included tachycardia, ECG changes and cardiac arrhythmias, hypothermia, miosis, tremor, muscle twitching, spasm or rigidity, seizures, muscular hypotonia, ileus, dry mouth, difficulty in swallowing or breathing, cyanosis, and respiratory and/or vasomotor collapse, possibly with sudden apnea. /Phenothiazines/

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 5 Einträge

...THIORIDAZINE SULFOXIDE.../WAS FOUND/ TO HAVE RELATIVELY SLIGHT EFFECT ON RETINAL ENZYMES IN VIVO & NO EVIDENT TOXIC EFFECT ON RETINA IN CATS...

LD50 Rat oral 664 mg/kg

LD50 Mouse oral 560 mg/kg

LD50 Mouse iv 26 mg/kg

LD50 Rabbit oral 7800 mg/kg

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataOral LD<sub>50</sub> is 560 &plusmn; 62.5 mg/kg and 644 &plusmn; 48 mg/kg in mouse and rat, respectively.
Non-Human Toxicity Values · 3 Einträge

LD50 MICE INTRAVENOUS 33 MG/KG /BESYLATE/

LD50 MICE SUBCUTANEOUS 611 MG/KG /BESYLATE/

LD50 MICE ORAL 346 MG/KG /BESYLATE/

Regulatorische Informationen

FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Sicherheitsdaten

Giftige Stoffe Daten
5588-33-0(Hazardous Substances Data)
FDA Pharmacological Classification · 5 Einträge

5XE4NWM740

MESORIDAZINE

Established Pharmacologic Class [EPC] - Phenothiazine

Chemical Structure [CS] - Phenothiazines

Mesoridazine is a Phenothiazine.

MeSH Pharmacological Classification · 2 Einträge

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Absorption, Distribution and Excretion · 5 Einträge

Well absorbed from the gastrointestinal tract.

TOTAL URINARY & FECAL EXCRETION BY MONKEYS (10 DAY PERIOD) OF THIORIDAZINE WAS 64-76% & 83-92% FOR MESORIDAZINE (FECAL EXCRETION 2-4 TIMES GREATER). GREATER EXCRETION OF LATTER MAY BE DUE TO LESSER OVERALL TISSUE ADSORPTION OR LESS EXTENSIVE ENTERO-HEPATIC CYCLING.

WELL ABSORBED FROM GI TRACT. ONSET & DURATION OF ACTION & METABOLIC FATE... NOT...PRECISELY DETERMINED /HUMAN, ORAL, IM/. IN ANIMAL STUDIES, APPROX 2/3 OF DOSE...EXCRETED IN FECES VIA BILE & 1/3 OF DOSE...EXCRETED IN URINE. /BESYLATE/

PHENOTHIAZINES CROSS PLACENTAL BARRIER & MAY APPEAR IN MILK OF NURSING MOTHERS...PHENOTHIAZINES &...METABOLITES...EXCRETED IN URINE, BILE, & FECES. CERTAIN METABOLITES &...FREE DRUGS...DETECTED IN URINE UP TO 6 MO AFTER THERAPY...DISCONTINUED /HUMAN, ORAL, IM/

PHENOTHIAZINES...ABSORBED WELL FROM GI TRACT & FROM PARENTERAL SITES. GENERALLY...CLEARED FROM PLASMA WITHIN APPROX 3 HR...DISTRIBUTED TO MOST BODY TISSUES...HIGH CONCN OF UNCHANGED DRUG...IN BRAIN...METABOLITES PREDOMINATE IN LUNG, LIVER, KIDNEYS...SPLEEN /HUMAN, ORAL, IM/

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 2 Einträge

Antipsychotic

Used in the treatment of schizophrenia, organic brain disorders, alcoholism and psychoneuroses.

Methods of ManufacturingRenz et al, US patent 3,084,161 (1963 to Sandoz).
Formulations/PreparationsBenzenesulfonate, mesoridazine besylate, NC-123, Lidanar, Lidanil, Serentil. /Besylate/
Use ClassificationPharmaceuticals

Anwendungen

VerwendenMesoridazine is an antipsychotic.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

EssigsäureanhydridWasserstoffperoxidNatriumhydroxidKaliumcarbonat

Anbieter22 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: A phenothiazine substituted at position 2 (para to the S atom) by a methylsulfinyl group, and on the nitrogen by a 2-(1-methylpiperidin-2-yl)ethyl group.