sertindole   Click here for help

GtoPdb Ligand ID: 98

Synonyms: Serdolect® | Serlect® | sertindol
Approved drug
sertindole is an approved drug
Compound class: Synthetic organic
Comment: Sertindole is an atypical antipsychotic medication, functioning as a dopamine D2 and serotonin 5-HT2 receptor antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 39.99
Molecular weight 440.18
XLogP 4.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc2c(c1)c(cn2c1ccc(cc1)F)C1CCN(CC1)CCN1CCNC1=O
Isomeric SMILES Clc1ccc2c(c1)c(cn2c1ccc(cc1)F)C1CCN(CC1)CCN1CCNC1=O
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)
InChI Key GZKLJWGUPQBVJQ-UHFFFAOYSA-N
References
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Do novel antipsychotics have similar pharmacological characteristics? A review of the evidence.
Neuropsychopharmacology, 18 (2): 63-101. [PMID:9430133]
2. Burstein ES, Ma J, Wong S, Gao Y, Pham E, Knapp AE, Nash NR, Olsson R, Davis RE, Hacksell U et al.. (2005)
Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist.
J. Pharmacol. Exp. Ther., 315 (3): 1278-87. [PMID:16135699]
3. Herrick-Davis K, Grinde E, Teitler M. (2000)
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors.
J. Pharmacol. Exp. Ther., 295 (1): 226-32. [PMID:10991983]
4. Kongsamut S, Kang J, Chen XL, Roehr J, Rampe D. (2002)
A comparison of the receptor binding and HERG channel affinities for a series of antipsychotic drugs.
Eur. J. Pharmacol., 450 (1): 37-41. [PMID:12176106]
5. Kroeze WK, Hufeisen SJ, Popadak BA, Renock SM, Steinberg S, Ernsberger P, Jayathilake K, Meltzer HY, Roth BL. (2003)
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
Neuropsychopharmacology, 28 (3): 519-26. [PMID:12629531]
6. Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verrièle L, Audinot V, Millan MJ. (1998)
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.
Eur. J. Pharmacol., 355 (2-3): 245-56. [PMID:9760039]
7. Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, De Loore K, Leysen JE. (1996)
Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding.
Psychopharmacology (Berl.), 124 (1-2): 57-73. [PMID:8935801]
8. Seeman P. (2001)
Antipsychotic drugs, dopamine receptors, and schizophrenia.
Clinical Neuroscience Research, 1 (1-2): 53-60. DOI: 10.1016/S1566-2772(00)00007-4
9. Seeman P, Corbett R, Van Tol HH. (1997)
Atypical neuroleptics have low affinity for dopamine D2 receptors or are selective for D4 receptors.
Neuropsychopharmacology, 16 (2): 93-110; discussion 111-35. [PMID:9015795]
10. Seeman P, Tallerico T. (1998)
Antipsychotic drugs which elicit little or no parkinsonism bind more loosely than dopamine to brain D2 receptors, yet occupy high levels of these receptors.
Mol. Psychiatry, 3 (2): 123-34. [PMID:9577836]