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Compound Detail

CHEMBL708

ZIPRASIDONE
💊 Approved Drug
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💊 Approved Drug
O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1

Basic Information

ChEMBL ID CHEMBL708
Name ZIPRASIDONE
Phase Approved
Structure Type MOL
InChI Key MVWVFYHBGMAFLY-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

CP-88059 Zipradon Ziprasidona Ziprasidone
28
Targets
97
Activities
2
Assay Types
18
PK Parameters
20
Publications
4
Known Names
15
Indications

Molecular Properties

412.9
MW (Da)
3.81
ALogP
5
HBA
1
HBD
48.5
PSA (Ų)
0.71
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -sidone
USAN Year 1994

Extended Properties

Molecular Formula C21H21ClN4OS
MW 412.95
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -1.57

Indications

Psychotic Disorders Psychotic Disorders Anxiety Bipolar Disorder Dementia Depressive Disorder Schizophrenia Autistic Disorder Borderline Personality Disorder Depressive Disorder, Major Mood Disorders Phobia, Social Cardiovascular Diseases Opioid-Related Disorders Substance-Related Disorders

ATC Classification

N05AE04
ziprasidone
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

Ki 84 meas. best 10.1
IC50 13 meas. best 9.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 10.1 9.4556 0.1 9
Dopamine D2 receptor and Serotonin 2a receptor (D2 and 5HT2a)
CHEMBL2111406
Ki 9.38 9.38 0.4 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 9.38 9.38 0.4 1
5-hydroxytryptamine receptor 2A
CHEMBL322
Ki 9.38 9.38 0.4 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 9.3 9.3 0.5 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 9.26 8.5671 0.6 7
D(2) dopamine receptor
CHEMBL217
Ki 9.1 8.5421 0.8 14
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 8.8 8.386 1.6 5
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.8 8.8 1.6 1
Adrenergic receptor alpha-1
CHEMBL2094251
Ki 8.72 8.14 1.9 4
D(2) dopamine receptor
CHEMBL339
Ki 8.32 8.32 4.8 2
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 8.3 8.2733 5.0 3
D(2) dopamine receptor
CHEMBL217
IC50 8.3 8.3 5.0 1
Histamine H1 receptor
CHEMBL231
Ki 8.28 7.404 5.3 5
Alpha-1A adrenergic receptor
CHEMBL229
Ki 8.22 8.22 6.0 1
D(3) dopamine receptor
CHEMBL234
Ki 8.2 8.12 6.3 5
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 8.1 8.0133 7.9 3
D(1A) dopamine receptor
CHEMBL2056
Ki 8.02 7.13 9.5 3
Adrenergic receptor alpha-1
CHEMBL2094251
IC50 7.96 7.96 11.0 1
Histamine H1 receptor
CHEMBL3943
Ki 7.8 7.8 15.8 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.7 7.288 20.0 5
D(4) dopamine receptor
CHEMBL219
Ki 7.5 7.405 32.0 4
Transporter
CHEMBL6184
Ki 7.32 7.32 48.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 7.28 7.11 53.0 3
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.92 6.875 120.2 8
Histamine H1 receptor
CHEMBL4701
IC50 6.82 6.82 150.0 1
Adrenergic receptor alpha-2
CHEMBL2095158
Ki 6.41 6.41 390.0 2
Serotonin 3 (5-HT3) receptor
CHEMBL2094132
Ki 6.4 6.4 398.1 1
Adrenergic receptor alpha-2
CHEMBL2093864
Ki 6.3 6.3 501.2 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.29 5.29 5100.0 1
Aspartate aminotransferase, cytoplasmic
CHEMBL2189139
IC50 5.27 5.27 5390.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 5.1 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Homo sapiens
CL 5.1 mL.min-1.kg-1 Homo sapiens
CL 5.1 mL.min-1.kg-1 Homo sapiens
CL 29.0 mL.min-1.g-1 Homo sapiens
CL 118.0 mL.min-1.g-1 Homo sapiens
CL 15.0 mL.min-1.g-1 Homo sapiens
CL 23.0 mL.min-1.g-1 Homo sapiens
CL 28.0 mL.min-1.g-1 Homo sapiens
CL 89.0 mL.min-1.g-1 Homo sapiens
CL 1.8 mL.min-1.g-1 Homo sapiens
CL 15.0 mL.min-1.g-1 Homo sapiens
CL 28.0 mL.min-1.g-1 Homo sapiens
F 60.0 % Homo sapiens
Fu 0.0012 - Homo sapiens
Fu 0.0012 - Homo sapiens
MRT 3.3 hr Homo sapiens
T1/2 3.1 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.08 nM 10.1 Displacement of [3H]ketanserin from human 5HT2A receptor expressed in Swiss 3T3 ... 18160289
5-hydroxytryptamine receptor 2A Ki = 0.25 nM 9.6 Binding affinity for human 5-hydroxytryptamine 2A receptor 11170639
5-hydroxytryptamine receptor 2A Ki = 0.28 nM 9.55 Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1... -
5-hydroxytryptamine receptor 2A Ki = 0.28 nM 9.55 Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1... -
5-hydroxytryptamine receptor 2A Ki = 0.3 nM 9.52 Binding affinity towards human serotonin 5-hydroxytryptamine 2A receptor 14998318
5-hydroxytryptamine receptor 2A Ki = 0.39 nM 9.41 Binding affinity to human cloned 5HT2A receptor 18595716
5-hydroxytryptamine receptor 2A Ki = 0.4 nM 9.4 Binding affinity to 5HT2A receptor (unknown origin) by radioligand binding assay 23919353
Dopamine D2 receptor and Serotonin 2a receptor (D2 and 5HT2a) Ki = 0.42 nM 9.38 Relative binding affinity for D2 receptor and 5-hydroxytryptamine 2A receptor, r... 8568801
5-hydroxytryptamine receptor 2A IC50 = 0.42 nM 9.38 Inhibitory concentration against 5-hydroxytryptamine 2 receptor 16220969
5-hydroxytryptamine receptor 2A Ki = 0.4169 nM 9.38 Displacement of [3H]-ketanserin from rat brain 5-hydroxytryptamine 2A receptor 8568801
Alpha-1A adrenergic receptor Ki = 0.5 nM 9.3 Displacement of [3H]prazosin from rat adrenergic alpha1A receptor expressed in f... 18160289
5-hydroxytryptamine receptor 2C Ki = 0.55 nM 9.26 Binding affinity towards human 5-hydroxytryptamine 2C receptor 11170639
5-hydroxytryptamine receptor 2A Ki = 0.631 nM 9.2 Displacement of [3H]ketanserin from human 5HT2A receptor expressed in CHO cells 17880057
5-hydroxytryptamine receptor 2C Ki = 0.72 nM 9.14 Binding affinity to human cloned 5HT2C receptor 18595716
D(2) dopamine receptor Ki = 0.8 nM 9.1 Displacement of [3H]-raclopride from human D2LR expressed in HEK293 cell membran... 29407591
D(2) dopamine receptor Ki = 0.8511 nM 9.07 Displacement of [3H]-methylspiperone from human D2 long receptor expressed in HE... 31229883
D(2) dopamine receptor Ki = 0.9 nM 9.05 Displacement of [3H]-methylspiperone from human D2 long receptor expressed in HE... 31229883
D(2) dopamine receptor Ki = 0.9 nM 9.05 Displacement of [3H] raclopride from human recombinant D2L receptor expressed in... 30904783
5-hydroxytryptamine receptor 2C Ki = 1.259 nM 8.9 Displacement of [3H]mesulergine from 5HT2C receptor expressed in CHO cells 17880057
5-hydroxytryptamine receptor 2C Ki = 1.3 nM 8.89 Binding affinity to 5HT2C receptor (unknown origin) by radioligand binding assay 23919353

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 71
- 10.5281/zenodo.13943903 ADMET 60
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23444387 10.1124/dmd.113.051177 ADMET 10
29407591 10.1016/j.ejmech.2018.01.002 Rattus norvegicus 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 5
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 5
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 5
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 5
8568801 10.1021/jm950625l Rattus norvegicus 5
22834877 10.1021/jm3004976 Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
23043306 10.1021/jm300975f Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3

Data from ChEMBL 36 via Core Engine