quetiapine   Click here for help

GtoPdb Ligand ID: 50

Synonyms: Seroquel® | ZM-204636
Approved drug
quetiapine is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Quetiapine displays affinity for numerous receptors from the dopamine, serotonin and adrenergic families, in addition to the histamine H1 receptor. The anti-psychotic properties of the drug are believed to result from its antagonism of dopamine D2 and 5-HT2A receptors.
Marketed formulations may contain quetiapine fumarate (PubChem CID 5281025) or quetiapine hemifumarate (PubChem CID 73013330).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 73.6
Molecular weight 383.17
XLogP 2.95
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCCOCCN1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2
Isomeric SMILES OCCOCCN1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2
InChI InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2
InChI Key URKOMYMAXPYINW-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. Jensen NH, Rodriguiz RM, Caron MG, Wetsel WC, Rothman RB, Roth BL. (2008)
N-desalkylquetiapine, a potent norepinephrine reuptake inhibitor and partial 5-HT1A agonist, as a putative mediator of quetiapine's antidepressant activity.
Neuropsychopharmacology, 33 (10): 2303-12. [PMID:18059438]
3. 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]
4. 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]
5. 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]
6. 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]