ziprasidone   Click here for help

GtoPdb Ligand ID: 59

Synonyms: CP-88059 | CP-88059-27 | CP-880591 | CP-8805927 | Geodon®
Approved drug PDB Ligand
ziprasidone is an approved drug (FDA (2001))
Compound class: Synthetic organic
Comment: Ziprasidone is a monoaminergic antagonist with affinity for a range of receptors including dopamine receptors, alpha 1 and 2 adrenoceptors, the histamine H1 receptor, and serotonin 5-HT receptors. Marketed formulations may contain ziprasidone hydrochloride (PubChem CID 219099).
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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 4
Topological polar surface area 76.71
Molecular weight 412.11
XLogP 3.89
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)c1nsc2c1cccc2
Isomeric SMILES O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)c1nsc2c1cccc2
InChI InChI=1S/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)
InChI Key MVWVFYHBGMAFLY-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2A receptor Primary target of this compound Hs Antagonist Antagonist 8.8 – 9.5 pKi - 4-5,8-9
pKi 8.8 – 9.5 [4-5,8-9]
5-HT1D receptor Hs Agonist Full agonist 9.0 pKi - 8
pKi 9.0 [8]
D2 receptor Primary target of this compound Hs Antagonist Antagonist 8.6 pKi - 2
pKi 8.6 (Ki 2.8x10-9 M) [2]
5-HT2C receptor Primary target of this compound Hs Antagonist Inverse agonist 7.9 – 9.0 pKi - 3,5,9
pKi 7.9 – 9.0 [3,5,9]
5-HT1A receptor Hs Agonist Partial agonist 7.9 – 8.9 pKi - 6,8
pKi 7.9 – 8.9 [6,8]
5-HT7 receptor Hs Antagonist Inverse agonist 8.4 pKi - 7
pKi 8.4 [7]
5-HT1B receptor Hs Agonist Full agonist 8.3 pKi - 8
pKi 8.3 [8]
H1 receptor Hs Antagonist Antagonist 7.4 – 7.8 pKi - 5,8
pKi 7.4 – 7.8 [5,8]
5-ht1e receptor Hs Agonist Full agonist 6.4 pKi - 8
pKi 6.4 [8]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
NET Rn Inhibitor Inhibition 7.3 pKi - 1
pKi 7.3 (Ki 4.8x10-8 M) [1]
SERT Hs Inhibitor Inhibition 7.3 pKi -
pKi 7.3 (Ki 5.3x10-8 M)