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Sertindole

Sertindole structure

CAS No:
106516-24-9
Formula:
C24H26ClFN4O
Chemical Name:
Sertindole
Synonyms:
2-Imidazolidinone,1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1-piperidinyl]ethyl]-;1-[2-[4-[5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone;Sertindole;Lu 23-174;Serdolect;Zerdol;Serlect;1-[2-[4-[5-Chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one
Categories:
Active Pharmaceutical Ingredients > Nervous System Drugs

Description

Off-White to Pale Yellow SolidChEBI: A phenylindole that is 1H-indole which is substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-o oimidazolidin-1-yl)ethyl group.Serdolect was launched in the UK for acute and chronic schizophrenia and schizoaffective psychoses. It is synthetically available in three steps from 5chloro-l- (4-fluorophenyl)-l H-indole. Sertindole is

Solid

Sertindole is a phenylindole that is 1H-indole which is substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-oxoimidazolidin-1-yl)ethyl group. It has a role as a serotonergic antagonist, an alpha-adrenergic antagonist, a H1-receptor antagonist and a second generation antipsychotic. It is a phenylindole, an organofluorine compound, an organochlorine compound, a heteroarylpiperidine and an imidazolidinone.|Sertindole, a neuroleptic, is one of the newer antipsychotic medications available. Serdolect is developed by the Danish pharmaceutical company H. Lundbeck. It is a phenylindole derivative used in the treatment of schizophrenia. It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects. It has once again been approved and should soon be available on the French and Australian market.

Sertindole Basic Attributes

Molecular Weight：

440.94

Exact Mass：

440.94

UNII：

GVV4Z879SP

DSSTox ID：

DTXSID6048967

ATC Code：

N - Nervous system

Characteristics

PSA：

40.5

XLogP3：

5.26

Appearance：

Solid

Density：

1.36

Melting Point：

95-100°C

Boiling Point：

592.1±50.0 °C(Predicted)

Flash Point：

311.9±30.1 °C

Refractive Index：

1.671

Water Solubility：

DMSO: >10mg/mL

Storage Conditions：

2-8°C

Vapor Pressure：

5.44E-14mmHg at 25°C

Collision Cross Section：

215.9 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

RTECS Number：

NJ0621100

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335-H413

GHS Classification：

|Warning|H315 (95.12%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Used in the treatment of schizophrenia.

Pharmacology：

Sertindole is an atypical antipsychotic at least as effective as haloperidol and risperidone in the treatment of neuroleptic-responsive schizophrenia. Sertindole improves negative symptoms, and is also effective for the treatment of neuroleptic-resistant schizophrenia. Sertindole is generally well tolerated and is associated with a low rate of extrapyramidal symptoms (EPS).

MeSH：

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. (See all compounds classified as Antipsychotic Agents.)

Absorption：

Orally available.

Metabolism/Metabolites：

Hepatic. Sertindole is metabolized by cytochrome P450 isoenzymes CYP 2D6 and CYP 3A4.|Sertindole has known human metabolites that include 1-[2-[4-[5-Chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-4-hydroxyimidazolidin-2-one and 5-Chloro-1-(4-fluorophenyl)-3-(piperidin-4-yl)-1H-indole.

Biological Half-Life：

3 days

Mechanism of Action：

Sertindole is an antipsychotic drug with affinity for dopamine D2, serotonin 5-HT2A and 5-HT2C, and alpha1-adrenoreceptors. Preclinical studies suggest that sertindole acts preferentially on limbic and cortical dopaminergic neurons and clinical trials have confirmed that sertindole is effective at a low dopamine D2 occupancy level.

MeSH Entry Terms：

1-(2-(4-(5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone

Sertindole Use and Manufacturing

Antipsychotic used in the treatment of schizophrenia.

Computed Properties

Molecular Weight:440.9
XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:440.1779173
Monoisotopic Mass:440.1779173
Topological Polar Surface Area:40.5
Heavy Atom Count:31
Complexity:623
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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SERTINDOLE

CAS No.: 106516-24-9

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Sertindole CAS 106516-24-9

CAS No.: 106516-24-9

Grade: Pharmaceutical Grade

Content: 99%

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