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.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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
1. Arnt J, Skarsfeldt T. (1998)
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]