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Mesoridazine

HCID 4078
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
5588-33-0
Standard SMILES
CN1CCCCC1CCN1c2ccccc2Sc2ccc(S(C)=O)cc21
InChIKey
SLVMESMUVMCQIY-UHFFFAOYSA-N
Molecular formula
C21H26N2OS2
Average molar mass
386.6 g/mol
Monoisotopic mass
386.1486558

Overview

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.

Names & identifiers

Preferred name
Mesoridazine
IUPAC
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine
English name
mesoridazine
Molecular formula
C21H26N2OS2
Molecular weight
386.57

Names & synonyms

mesoridazine5588-33-0LidanarThioridazine-2-sulfoxideTPS-23MesoridazinaThioridazine thiomethyl sulfoxideTps23NC-123MesoridazinumDTXSID3023265Thioridazien thiomethyl sulfoxide
Show more names
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

Database identifiers

CAS
5588-33-0
PubChem CID
4078
DTXSID
DTXSID3023265

Properties

Computed structural properties

XLogP
4.5
Topological polar surface area
68.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
26
Formal charge
0
Complexity
502

Experimental & physicochemical properties

LogP · 2 items

3.9

4.27

Color/FormOily product
Solubility · 2 items

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 items

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 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

FDA Requirements · 1 item

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).

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Interactions · 5 items

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 item

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/

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Protein Binding4%
Pharmacodynamics · 1 item

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 items

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 items

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

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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/

Physicochemical properties

Melting point
128 · 128-131 °C
Boiling point
570.5 · 570.5±50.0 °C(Predicted)
Density
1.1234 · 1.1234 (rough estimate)
refractive index
1.595 · 1.5950 (estimate)
solubility
Acetonitrile: slightly soluble; DMSO: slightly, heated; Methanol: slightly soluble
form
Sticky Solid
pka
9.84 · 9.84±0.10(Predicted)
color
Pale Yellow to Orange
Stability
Hygroscopic
FDA UNII
5 XE4NWM740 · 5XE4NWM740
Symbol(GHS)
2 · GHS02,GHS07
Signal word
Danger
Hazard statements
225 · H225-H302+H312+H332-H319
Precautionary statements
210 · P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P321-P330-P362+P364-P337+P313-P370+P378-P403+P235-P501
Hazardous Substances Data
5588 · 5588-33-0(Hazardous Substances Data)
Toxicity Summary · 1 item

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 items

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 items

...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 items

LD50 MICE INTRAVENOUS 33 MG/KG /BESYLATE/

LD50 MICE SUBCUTANEOUS 611 MG/KG /BESYLATE/

LD50 MICE ORAL 346 MG/KG /BESYLATE/

Regulatory information

FDA Requirements · 1 item

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).

Safety data

Signal word
Danger
Symbol(GHS)
GHS02,GHS07
Hazard statements
H225-H302+H312+H332-H319
Precautionary statements
P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P321-P330-P362+P364-P337+P313-P370+P378-P403+P235-P501
Hazardous Substances Data
5588-33-0(Hazardous Substances Data)
FDA Pharmacological Classification · 5 items

5XE4NWM740

MESORIDAZINE

Established Pharmacologic Class [EPC] - Phenothiazine

Chemical Structure [CS] - Phenothiazines

Mesoridazine is a Phenothiazine.

MeSH Pharmacological Classification · 2 items

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 items

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

Uses & manufacturing

Uses · 2 items

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

Applications

UsesMesoridazine (Thioridazine EP Impurity B) is an antipsychotic.

UsesMesoridazine is an antipsychotic.

Upstream & downstream products

Upstream raw materials

Acetic anhydrideHydrogen peroxideSodium hydroxidePotassium carbonate

Suppliers22 total

北京华美互利生物化工010-56205725 · [email protected]
陕西缔都新材料有限公司81124267 17392282731 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
孟成科技(上海)有限公司400-820-6829 · [email protected]
InvivoChem中国13549236410 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
河南誉康卓宁进出口有限公司13393721940 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
TLC梯尔希(南京)药物研发有限公司18012923235 18012923235 · [email protected]
ChemeGen 中国18818260767 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
InvivoChem+1-708-310-1919 +1-13798911105 · [email protected]

Additional notes

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.