| Identification | Back Directory | [Name]
SERTINDOLE | [CAS]
106516-24-9 | [Synonyms]
S-1991
Zerdol
Serdolect
LU-23-174
Serdoleet
SERTINDOLE
SUBSTANCE 5364890
2-IMidazolidinone, Sertindole
1-[2-[4-[1-(4-Fluorophenyl)-5-chloro-1H-indole-3-yl]piperidino]ethyl]imidazolidine-2-one
1-[2-[4-[5-Chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone
2-IMidazolidinone,1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1-piperidinyl]ethyl]-
1-(2-{4-[5-CHLORO-1-(4-FLUORO-PHENYL)-1H-INDOL-3-YL]-PIPERIDIN-1-YL}-ETHYL)-IMIDAZOLIDIN-2-ONE
1-(4-Fluorophenyl)-5-chloro-3-[1-[2-[(tetrahydro-2-oxo-1H-imidazol)-1-yl]ethyl]piperidin-4-yl]-1H-indole | [Molecular Formula]
C24H26ClFN4O | [MDL Number]
MFCD00867749 | [MOL File]
106516-24-9.mol | [Molecular Weight]
440.94 |
| Chemical Properties | Back Directory | [Melting point ]
95-100°C | [Boiling point ]
592.1±50.0 °C(Predicted) | [density ]
1.36 | [storage temp. ]
2-8°C | [solubility ]
DMSO: >10mg/mL | [form ]
solid | [pka]
14.53±0.20(Predicted) | [color ]
off-white | [Merck ]
14,8466 | [InChI]
InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31) | [InChIKey]
GZKLJWGUPQBVJQ-UHFFFAOYSA-N | [SMILES]
C1(=O)N(CCN2CCC(C3C4=C(N(C5=CC=C(F)C=C5)C=3)C=CC(Cl)=C4)CC2)CCN1 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White to Pale Yellow Solid | [Usage]
Antipsychotic used in the treatment of schizophrenia. | [Usage]
antipsychotic;Dopamine D2/Serotonin 5-HT2 receptor antagonist | [Description]
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 selective for the limbic areas of the brain
and has a high affinity for the serotinin 5-HT2 receptor where it behaves as an
antagonist. It has weak affinity for the α1-adrenergic receptor and no affinity for
dopamine D2 receptors. It is as effective as haloperidol but without the
extrapyramidal symptoms. This may be a consequence of the fact that it expresses
the c-fos protein in a manner different for haloperidol but similar to clozapine. It is
non-sedating, long lasting (several days after a single dose) and has an atypical
mode of action. | [Originator]
Lundbeck (Denmark) | [Uses]
Antipsychotic used in the treatment of schizophrenia. | [Uses]
antipsychotic;Dopamine D2/Serotonin 5-HT2 receptor antagonist | [Definition]
ChEBI: 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. | [Brand name]
SerLect (Abbott). | [Side effects]
Sertindole is an indole-containing compound that behaves as a high-affinity serotonin 5-HT2 receptor antagonist,
with weak affinity for adrenergic α1 receptors and almost no affinity for dopaminergic D2 receptors. It is about as
effective as haloperidol in the treatment of acute and chronic schizophrenia, but with much lower incidence of
extrapyramidal side effects. Sertindole is relatively nonsedating, and its effects are long lasting (several days). | [storage]
Store at -20°C | [References]
[1] B CUSACK E R A Nelson. Binding of antidepressants to human brain receptors: focus on newer generation compounds.[J]. Psychopharmacology, 1994, 114 4: 559-565. DOI: 10.1007/bf02244985
[2] ARNE M?RK J?rn A Louise M Witten. Effect of sertindole on extracellular dopamine, acetylcholine, and glutamate in the medial prefrontal cortex of conscious rats: a comparison with risperidone and exploration of mechanisms involved.[J]. Psychopharmacology, 2009, 206 1: 39-49. DOI: 10.1007/s00213-009-1578-4
[3] AGNIESZKA NIKIFORUK Piotr P. Effects of quetiapine and sertindole on subchronic ketamine-induced deficits in attentional set-shifting in rats.[J]. Psychopharmacology, 2012: 65-74. DOI: 10.1007/s00213-011-2487-x
[4] NAGI IDRIS. Sertindole improves sub-chronic PCP-induced reversal learning and episodic memory deficits in rodents: involvement of 5-HT(6) and 5-HT (2A) receptor mechanisms.[J]. Psychopharmacology, 2010, 208 1: 23-36. DOI: 10.1007/s00213-009-1702-5
[5] MIRJANA CARLI. Sertindole restores attentional performance and suppresses glutamate release induced by the NMDA receptor antagonist CPP.[J]. Psychopharmacology, 2011, 214 3: 625-637. DOI: 10.1007/s00213-010-2066-6 |
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