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Compound Detail

CHEMBL12713

SERTINDOLE
💊 Approved Drug
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💊 Approved Drug
O=C1NCCN1CCN1CCC(c2cn(-c3ccc(F)cc3)c3ccc(Cl)cc23)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL12713
Name SERTINDOLE
Phase Approved
Structure Type MOL
InChI Key GZKLJWGUPQBVJQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

LU 23-174 LU-23-174 Serdolect Serlect Sertindol Sertindole Zerdol
29
Targets
76
Activities
2
Assay Types
3
PK Parameters
20
Publications
7
Known Names
6
Indications
3
Mechanisms

Molecular Properties

440.9
MW (Da)
4.63
ALogP
3
HBA
1
HBD
40.5
PSA (Ų)
0.63
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Withdrawn
Chirality Achiral

Routes of Administration

Oral

Flags

Withdrawn
USAN Year 1992

Extended Properties

Molecular Formula C24H26ClFN4O
MW 440.95
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.44

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine D2 receptor antagonist ANTAGONIST D(2) dopamine receptor ✓ ✓
Adrenergic receptor alpha-1 antagonist ANTAGONIST Adrenergic receptor alpha-1 ✓ ✓
Serotonin 2 receptors; 5-HT2a & 5-HT2c antagonist ANTAGONIST Serotonin 2 receptors; 5-HT2a & 5-HT2c ✓ ✓

Indications

Psychotic Disorders Anxiety Cognitive Dysfunction Dementia Depressive Disorder Schizophrenia

ATC Classification

N05AE03
sertindole
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Withdrawn
cardiotoxicity
Arrhythmias and Sudden Cardiac Death (Arrhythmias and Sudden)
Country: Germany; European Union; Ireland; United Kingdom; Italy; Netherlands; Bulgaria   Year: 1998
Withdrawn
cardiotoxicity
Arrhythmias and Sudden Cardiac Death (Arrhythmias and Sudden)
Country: Germany; European Union; Ireland; United Kingdom; Italy; Netherlands; Bulgaria   Year: 1998
Withdrawn
General Warning
serious adverse reactions
Country: Germany; European Union; Ireland; United Kingdom; Italy; Netherlands; Bulgaria   Year: 1998

Activity Summary

IC50 41 meas. best 9.41
Ki 35 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 9.7 9.1967 0.2 3
5-hydroxytryptamine receptor 2A
CHEMBL322
 Ki 9.7 9.7 0.2 1
Alpha-1B adrenergic receptor
CHEMBL3122
 Ki 9.48 9.48 0.3 3
Alpha-1A adrenergic receptor
CHEMBL4892
 Ki 9.43 9.43 0.4 3
D(2) dopamine receptor
CHEMBL217
 Ki 9.42 9.0625 0.4 4
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 IC50 9.41 9.3875 0.4 4
5-hydroxytryptamine receptor 2A
CHEMBL322
 IC50 9.41 9.41 0.4 1
D(2) dopamine receptor
CHEMBL339
 Ki 9.35 9.35 0.5 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 Ki 9.29 9.29 0.5 1
Histamine H1 receptor
CHEMBL231
 Ki 9.29 7.765 0.5 2
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 9.22 9.145 0.6 2
Alpha-1D adrenergic receptor
CHEMBL326
 Ki 9.18 9.18 0.7 3
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 8.85 8.85 1.4 1
Adrenergic receptor alpha-1
CHEMBL2094251
 Ki 8.74 8.74 1.8 1
D(3) dopamine receptor
CHEMBL234
 Ki 8.59 8.34 2.6 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 8.57 8.025 2.7 14
Alpha-1A adrenergic receptor
CHEMBL319
 IC50 8.47 8.47 3.4 2
Adrenergic receptor alpha-1
CHEMBL1907610
 IC50 8.47 8.47 3.4 1
D(2) dopamine receptor
CHEMBL339
 IC50 8.39 8.39 4.1 5
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 8.3 8.3 5.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 7.96 7.82 11.0 2
D(1A) dopamine receptor
CHEMBL265
 Ki 7.92 7.92 12.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.48 7.48 33.0 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
 Ki 7.25 7.25 56.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 6.68 6.68 210.0 1
Unchecked
CHEMBL612545
 IC50 5.85 5.54 1425.2 8
Adrenergic receptor alpha-2
CHEMBL2095158
 Ki 5.78 5.78 1680.0 1
Potassium voltage-gated channel subfamily A member 5
CHEMBL4306
 IC50 5.7 5.7 2000.0 1
Sodium channel alpha subunit
CHEMBL2331043
 IC50 5.64 5.64 2300.0 1
Voltage-gated L-type calcium channel
CHEMBL2095229
 IC50 5.2 5.125 6300.0 2
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.19 5.19 6500.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.08 4.08 82700.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 75.0 % Homo sapiens
T1/2 53.0 hr Rattus norvegicus
Vd 20.0 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.2 nM 9.7 Displacement of [3H]ketanserin (0.5 nM) from rat cerebral cortex 5-hydroxytrypta... 12519065
5-hydroxytryptamine receptor 2C Ki = 0.2 nM 9.7 Displacement of [3H]prozosin from human cloned 5HT2C receptor expressed in CHO c... 20857909
Alpha-1B adrenergic receptor Ki = 0.33 nM 9.48 Displacement of [3H]prazosin (0.5 nM) from hamster Alpha-1B adrenergic receptor ... 12519065
Alpha-1B adrenergic receptor Ki = 0.33 nM 9.48 Displacement of [3H]prozosin from hamster cloned alpha-1b receptor 20857909
Alpha-1B adrenergic receptor Ki = 0.33 nM 9.48 Displacement of [3H]prazosine from hamster alpha1B adrenoceptor expressed in Rat... 23218776
Alpha-1A adrenergic receptor Ki = 0.37 nM 9.43 Displacement of [3H]prazosin (0.3 nM) from bovine Alpha-1A adrenergic receptor e... 12519065
Alpha-1A adrenergic receptor Ki = 0.37 nM 9.43 Displacement of [3H]prozosin from bovine cloned Alpha-1A receptor expressed in B... 20857909
Alpha-1A adrenergic receptor Ki = 0.37 nM 9.43 Displacement of [3H]prazosine from bovine alpha1A adrenoceptor expressed in BHK ... 23218776
D(2) dopamine receptor Ki = 0.38 nM 9.42 Binding affinity to dopamine D2 receptor (unknown origin) assessed as inhibition... 38516587
Serotonin 2 (5-HT2) receptor IC50 = 0.39 nM 9.41 Displacement of [3H]ketanserin from 5-hydroxytryptamine 2 receptor from rat cort... 1336053
Serotonin 2 (5-HT2) receptor IC50 = 0.39 nM 9.41 Binding affinity at serotonin 5-hydroxytryptamine 2 receptor by [3H]ketanserin d... 8151622
5-hydroxytryptamine receptor 2A IC50 = 0.39 nM 9.41 Binding affinity to serotonin 5-hydroxytryptamine 2A receptors using a radioliga... 8809161
Serotonin 2 (5-HT2) receptor IC50 = 0.39 nM 9.41 Displacement of [3H]ketanserin from 5-hydroxytryptamine 2 receptor in rat cortic... 1336054
D(2) dopamine receptor Ki = 0.45 nM 9.35 Displacement of [3H]spiperone from human dopamine D2 receptor expressed in CHO c... 23218776
D(2) dopamine receptor Ki = 0.45 nM 9.35 Displacement of [3H]prozosin from human cloned dopamine D2 receptor expressed in... 20857909
D(2) dopamine receptor Ki = 0.45 nM 9.35 Displacement of [3H]spiperone (0.5 nM) from rat corpus striatum dopamine D2 rece... 12519065
Serotonin 2 (5-HT2) receptor IC50 = 0.48 nM 9.32 Inhibition of [3H]ketanserin binding to rat 5-hydroxytryptamine 2 receptors. 1348090
Histamine H1 receptor Ki = 0.51 nM 9.29 Displacement of [3H]prozosin from human cloned histamine H1 receptor expressed i... 20857909
5-hydroxytryptamine receptor 2C Ki = 0.51 nM 9.29 Displacement of [3H]mesulergine (0.5 nM) from rat 5-hydroxytryptamine 2C recepto... 12519065
5-hydroxytryptamine receptor 2A Ki = 0.6 nM 9.22 Binding affinity towards Serotonin 5-hydroxytryptamine 2A receptor 12747773

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
1336054 10.1021/jm00104a007 Rattus norvegicus 4
1336053 10.1021/jm00104a006 Rattus norvegicus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
8809161 10.1021/jm960159f Rattus norvegicus 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
1348090 10.1021/jm00084a014 D(2) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
38516587 10.1039/d3md00677h ADMET 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Voltage-dependent L-type calcium channel subunit alpha-1C 2
19534531 10.1021/jm900002x Voltage-gated inwardly rectifying potassium channel KCNH2 2
1348090 10.1021/jm00084a014 Rattus norvegicus 2
11356099 10.1021/jm000484+ Voltage-gated inwardly rectifying potassium channel KCNH2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
1336053 10.1021/jm00104a006 Mus musculus 2

Data from ChEMBL 36 via Core Engine