clozapine   Click here for help

GtoPdb Ligand ID: 38

Synonyms: Clorazil® | HF-1854
Approved drug
clozapine is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: Note that PubChem CID 2818 has different double bond structure on the central heptane ring which results in a different InChIKey. Our structure is an exact match for the chemical structure in the INN record for this compound.

The major active metabolite of clozapine is N-desmethylclozapine.
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View more information in the IUPHAR Pharmacology Education Project: clozapine

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 30.87
Molecular weight 326.13
XLogP 3.86
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN1CCN(CC1)C1=Nc2cc(Cl)ccc2Nc2c1cccc2
Isomeric SMILES CN1CCN(CC1)C1=Nc2cc(Cl)ccc2Nc2c1cccc2
InChI 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
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
H1 receptor Hs Antagonist Antagonist 8.8 – 9.6 pKi - 5,16,31
pKi 8.8 – 9.6 [5,16,31]
5-HT2A receptor Rn Antagonist Inverse agonist 8.9 pKi - 6
pKi 8.9 [6]
5-HT2B receptor Hs Antagonist Antagonist 8.0 – 8.8 pKi - 11,23,42
pKi 8.0 – 8.8 [11,23,42]
5-HT2A receptor Primary target of this compound Hs Antagonist Inverse agonist 7.6 – 9.0 pKi - 11,16,23,31,41
pKi 7.6 – 9.0 [11,16,23,31,41]
α1B-adrenoceptor Hs Antagonist Antagonist 8.2 pKi - 43
pKi 8.2 [43]
α1A-adrenoceptor Hs Antagonist Antagonist 8.1 pKi - 43
pKi 8.1 [43]
5-HT2C receptor Hs Antagonist Inverse agonist 7.4 – 8.7 pKi - 7,10-11,16,23,41
pKi 7.4 – 8.7 [7,10-11,16,23,41]
5-HT6 receptor Hs Antagonist Inverse agonist 7.8 – 8.1 pKi - 1,4,13,27
pKi 7.8 – 8.1 [1,4,13,27]
5-HT6 receptor Rn Antagonist Inverse agonist 7.5 – 8.4 pKi - 2-4,14,23-24,29
pKi 7.5 – 8.4 [2-4,14,23-24,29]
5-HT7 receptor Rn Antagonist Inverse agonist 7.2 – 8.2 pKi - 14,29-30,33
pKi 7.2 – 8.2 [14,29-30,33]
α1D-adrenoceptor Hs Antagonist Antagonist 7.7 pKi - 43
pKi 7.7 [43]
5-HT7 receptor Hs Antagonist Inverse agonist 7.2 – 7.8 pKi - 15,27,40
pKi 7.2 – 7.8 [15,27,40]
D4 receptor Hs Antagonist Antagonist 7.5 pKi - 17
pKi 7.5 [17]
5-HT7 receptor Mm Antagonist Inverse agonist 7.4 pKi - 26
pKi 7.4 [26]
5-HT1F receptor Hs Agonist Full agonist 6.9 pKi - 31
pKi 6.9 [31]
D1 receptor Hs Antagonist Antagonist 6.9 pKi - 37
pKi 6.9 [37]
5-HT1A receptor Hs Agonist Full agonist 6.8 – 6.9 pKi - 23,25,31
pKi 6.8 – 6.9 [23,25,31]
D5 receptor Hs Antagonist Antagonist 6.6 pKi - 37
pKi 6.6 [37]
H4 receptor Hs Antagonist Antagonist 6.2 – 6.7 pKi - 18-20,44
pKi 6.2 – 6.7 [18-20,44]
5-HT1D receptor Hs Agonist Full agonist 6.4 pKi - 31
pKi 6.4 [31]
5-ht1e receptor Hs Agonist Full agonist 6.4 pKi - 31
pKi 6.4 [31]
D2 receptor Primary target of this compound Hs Antagonist Antagonist 5.8 – 6.9 pKi - 8,22,32,34,39
pKi 5.8 – 6.9 [8,22,32,34,39]
5-HT5A receptor Hs Antagonist Antagonist 6.0 – 6.5 pKi - 9,28
pKi 6.0 – 6.5 [9,28]
5-HT1B receptor Hs Agonist Full agonist 6.2 pKi - 31
pKi 6.2 [31]
D2 receptor Rn Antagonist Antagonist 6.2 pKi - 35
pKi 6.2 [35]
H3 receptor Rn Antagonist Antagonist 5.8 pKi - 21
pKi 5.8 [21]
D3 receptor Hs Antagonist Antagonist 5.2 – 6.3 pKi - 8,34
pKi 5.2 – 6.3 [8,34]
D3 receptor Rn Antagonist Antagonist 5.7 pKi - 35
pKi 5.7 [35]
H4 receptor Rn Antagonist Antagonist 5.7 pKi - 20
pKi 5.7 [20]
H4 receptor Mm Antagonist Antagonist 5.5 pKi - 20
pKi 5.5 [20]
5-HT5A receptor Mm Antagonist Antagonist 5.3 pKi - 9
pKi 5.3 [9]
M1 receptor Hs Allosteric modulator Positive 7.9 pIC50 - 38
pIC50 7.9 [38]
M1 receptor Rn Allosteric modulator Positive 7.7 pIC50 - 36
pIC50 7.7 [36]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kir3.2 Mm Gating inhibitor Antagonist 3.8 pEC50 - 12
pEC50 3.8 [12]
Voltage: -70.0 mV