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Compound Detail

CHEMBL1201

THIOTHIXENE
💊 Approved Drug
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💊 Approved Drug
CN1CCN(CC/C=C2/c3ccccc3Sc3ccc(S(=O)(=O)N(C)C)cc32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201
Name THIOTHIXENE
Phase Approved
Structure Type MOL
InChI Key GFBKORZTTCHDGY-UWVJOHFNSA-N
Therapeutic ✓ Yes

Known Names

(z)-thiothixene Cis-thiothixene CP-12252-1 Navane NSC-108165 Orbinamon P-4657 B P-4657B Thiothixene Thiothixene cis-isomer Tiotixene Tiotixeno
1
Targets
1
Activities
1
Assay Types
0
PK Parameters
20
Publications
12
Known Names
2
Indications
2
Mechanisms

Molecular Properties

443.6
MW (Da)
3.47
ALogP
5
HBA
0
HBD
43.9
PSA (Ų)
0.60
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1967
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1965

Extended Properties

Molecular Formula C23H29N3O2S2
MW 443.64
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness -1.31

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine D2 receptor antagonist ANTAGONIST D(2) dopamine receptor ✓ ✓
Serotonin 2a (5-HT2a) receptor antagonist ANTAGONIST 5-hydroxytryptamine receptor 2A ✓ ✓

Indications

Psychotic Disorders Schizophrenia

ATC Classification

N05AF04
tiotixene
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 1 meas. best 4.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bile salt export pump
CHEMBL6020
 IC50 4.52 4.52 30400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bile salt export pump IC50 = 30400.0 nM 4.52 Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21... 22961681

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 83
- 10.5281/zenodo.13943903 ADMET 60
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
6104732 10.1021/jm00180a011 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Histamine H2 receptor 2
628000 10.1021/jm00201a004 Rattus norvegicus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2

Data from ChEMBL 36 via Core Engine