Sertindole
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Grundinformationen
- CAS
106516-24-9- Standard-SMILES
O=C1NCCN1CCN1CCC(c2cn(-c3ccc(F)cc3)c3ccc(Cl)cc23)CC1- InChIKey
GZKLJWGUPQBVJQ-UHFFFAOYSA-N- Summenformel
- C24H26ClFN4O
- Durchschnittliche Molmasse
- 440,9 g/mol
- Monoisotopische Masse
- 440,17791735
Überblick
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 an alpha-adrenergic antagonist, a H1-receptor antagonist, a serotonergic antagonist and a second generation antipsychotic. It is an organochlorine compound, an organofluorine compound, a phenylindole, a heteroarylpiperidine and an imidazolidinone.
Namen und Bezeichner
- Bevorzugter Name
- Sertindole
- IUPAC
- 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one
Namen und Synonyme
SERTINDOLE106516-24-9SerLectSerdolectSertindolSertindolumLu 23-174zerdolLu-23-1741-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-oneDTXSID60489671-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one
Weitere Namen anzeigen
GVV4Z879SP1-(2-(4-(5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl)piperidin-1-yl)ethyl)imidazolidin-2-oneCHEBI:9122DTXCID30288931-(2-(4-(5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone1-[2-[4-[5-chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-one1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone1-(2-(4-(5-chloro-1-(4-fluorophenyl)-indol-3-yl)-1-piperidyl)ethyl)imidazolidin-2-one
Datenbank-Bezeichner
- CAS
106516-24-9- PubChem CID
- 60149
- DTXSID
DTXSID6048967- ChEMBL
CHEMBL12713- ChEBI
CHEBI:9122- UNII
- GVV4Z879SP
- EC Number
- 634-595-9
- Nikkaji
- J380.356B
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 4,1
- Polarare Oberfläche (TPSA)
- 40,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 31
- Formalladung
- 0
- Komplexität
- 623
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antipsychotics
Pharmaceuticals -> Nervous system -> Antipsychotics
Solubility9.63e-03 g/L
Physical DescriptionSolid
Collision Cross Section215.9 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (95.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (95.2%)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
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).
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.
Biological Half-Life3 days
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.
MeSH Pharmacological Classification
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.
Absorption, Distribution and ExcretionOrally available.
Zugehörige Reaktionen
6
Notizen zur Verbindung
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