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Merck
CN

C171

Clozapine

solid

Synonym(s):

8-Chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo[b,e][1,4]-diazepine

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About This Item

Empirical Formula (Hill Notation):
C18H19ClN4
CAS Number:
5786-21-0
Molecular Weight:
326.82
UNSPSC Code:
41116107
PubChem Substance ID:
329774905
EC Number:
227-313-7
MDL number:
MFCD00153785

Key Documents

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form

solid

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

color

pale yellow

solubility

ethanol: 11 mg/mL, 0.1 M HCl: 30 mg/mL, DMSO: 4.8 mg/mL

format

neat

SMILES string

CN1CCN(CC1)C2=Nc3cc(Cl)ccc3Nc4ccccc24

InChI

1S/C18H19ClN4/c1-22-8-10-23(11-9-22)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18/h2-7,12,20H,8-11H2,1H3

InChI key

QZUDBNBUXVUHMW-UHFFFAOYSA-N

Gene Information

human ... DRD2(1813), HTR2A(3356)

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Atypical neuroleptic agent which displays greater affinity for the D4 dopamine receptor over D2 or D3 dopamine receptors; displays antipsychotic efficacy against positive and negative symptoms of schizophrenia in patients who do not respond to typical neuroleptics.

Regulatory Information

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Henry F Vischer et al.
Bioorganic & medicinal chemistry, 18(2), 675-688 (2009-12-25)
Human cytomegalovirus (HCMV) is a widespread human pathogen, possessing onco-modulatory properties. Constitutive signaling of the HCMV-encoded chemokine receptor US28 and its ability to bind a broad spectrum of chemokines might facilitate HCMV-associated tumor progression. Novel nonpeptidergic chemotypes were identified as
Stefania Butini et al.
Journal of medicinal chemistry, 52(1), 151-169 (2008-12-17)
Dopamine D(3) antagonism combined with serotonin 5-HT(1A) and 5-HT(2A) receptor occupancy may represent a novel paradigm for developing innovative antipsychotics. The unique pharmacological features of 5i are a high affinity for dopamine D(3), serotonin 5-HT(1A) and 5-HT(2A) receptors, together with
Rogier A Smits et al.
Journal of medicinal chemistry, 49(15), 4512-4516 (2006-07-21)
A series of dibenzodiazepine derivatives was synthesized to probe the binding site of the recently discovered histamine H4 receptor (H4R). Optimization of the lead structure clozapine (2) resulted in (E)-7-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine (7j), a potent H4R agonist (H4R, pKi = 7.6). Pharmacological
Tarek K Rajji et al.
The American journal of psychiatry, 172(6), 579-585 (2015-04-11)
Clozapine's potent antagonism of muscarinic M1 receptors is thought to worsen working memory deficits associated with schizophrenia. In contrast, its major metabolite, N-desmethylclozapine (NDMC), is thought to enhance working memory via its M1 receptor agonist activity. The authors hypothesized that
Enade P Istyastono et al.
Journal of medicinal chemistry, 54(23), 8136-8147 (2011-10-19)
The histamine H(4) receptor (H(4)R) is a G protein-coupled receptor (GPCR) that plays an important role in inflammation. Similar to the homologous histamine H(3) receptor (H(3)R), two acidic residues in the H(4)R binding pocket, D(3.32) and E(5.46), act as essential
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