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Compound Detail

CHEMBL831

LOXAPINE
💊 Approved Drug
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💊 Approved Drug
CN1CCN(C2=Nc3ccccc3Oc3ccc(Cl)cc32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL831
Name LOXAPINE
Phase Approved
Structure Type MOL
InChI Key XJGVXQDUIWGIRW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Adasuve CL 62,362 CL-62362 Loxapina Loxapine SUM 3170 SUM-3170
15
Targets
21
Activities
3
Assay Types
1
PK Parameters
20
Publications
7
Known Names
13
Indications
3
Mechanisms

Molecular Properties

327.8
MW (Da)
3.77
ALogP
4
HBA
0
HBD
28.1
PSA (Ų)
0.74
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -pine
USAN Year 1969

Extended Properties

Molecular Formula C18H18ClN3O
MW 327.81
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.75

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin 2a (5-HT2a) receptor antagonist ANTAGONIST 5-hydroxytryptamine receptor 2A ✓ ✓
Serotonin 2c (5-HT2c) receptor antagonist ANTAGONIST 5-hydroxytryptamine receptor 2C ✓ ✓
D2-like dopamine receptor antagonist ANTAGONIST D2-like dopamine receptor ✓ ✓

Indications

Bipolar Disorder Bipolar Disorder Mental Disorders Psychomotor Agitation Psychotic Disorders Schizophrenia Anxiety Delirium Migraine Disorders Neuralgia Asthma Pulmonary Disease, Chronic Obstructive Tobacco Use Disorder

ATC Classification

N05AH01
loxapine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning
respiratory toxicity
Country: United States

Activity Summary

Ki 10 meas. best 8.62
IC50 9 meas. best 8.22
EC50 2 meas. best 6.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 8.62 8.62 2.4 1
D(4) dopamine receptor
CHEMBL219
 Ki 8.31 8.2233 4.9 3
5-hydroxytryptamine receptor 2A
CHEMBL322
 IC50 8.22 8.22 6.0 1
D(4) dopamine receptor
CHEMBL219
 IC50 7.85 7.85 14.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
 Ki 7.82 7.82 15.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
 IC50 7.75 7.75 18.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 7.68 7.68 21.0 2
D(2) dopamine receptor
CHEMBL339
 Ki 7.68 7.68 21.0 1
D(3) dopamine receptor
CHEMBL234
 IC50 7.66 7.66 22.0 1
5-hydroxytryptamine receptor 7
CHEMBL3223
 Ki 7.37 7.37 43.0 1
D(2) dopamine receptor
CHEMBL217
 IC50 7.27 7.27 54.0 1
Histamine H4 receptor
CHEMBL3759
 EC50 6.66 6.66 218.8 1
Histamine H1 receptor
CHEMBL4701
 IC50 6.0 6.0 1000.0 1
5-hydroxytryptamine receptor 2C
CHEMBL324
 IC50 6.0 6.0 1000.0 1
Histamine H4 receptor
CHEMBL3759
 Ki 5.34 5.34 4570.9 1
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 5.26 5.26 5500.0 1
Salmonella typhimurium
CHEMBL351
 EC50 5.24 5.24 5770.0 1
Potassium channel subfamily K member 2
CHEMBL2321615
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.011 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 2.42 nM 8.62 Displacement of [3H]ketanserin from human recombinant 5HT2A receptor expressed i... 22268448
D(4) dopamine receptor Ki = 4.9 nM 8.31 Affinity was evaluated by inhibition of [3H]-spiperone binding to COS cells tran... 8064797
D(4) dopamine receptor Ki = 4.9 nM 8.31 Ability to inhibit the binding of [3H]spiperone to the Dopamine receptor D4 in C... 7861418
5-hydroxytryptamine receptor 2A IC50 = 6.0 nM 8.22 Binding affinity towards 5-hydroxytryptamine 2A receptor from rat frontal cortex... 10377229
D(4) dopamine receptor Ki = 9.0 nM 8.05 Displacement of [3H]-YM09151-2 from human cloned dopamine D4 receptor expressed ... 22268448
D(4) dopamine receptor IC50 = 14.0 nM 7.85 Compound was tested in vitro for its binding affinity towards human Dopamine rec... 10377229
5-hydroxytryptamine receptor 6 Ki = 15.0 nM 7.82 Binding affinity towards human 5-hydroxytryptamine 6 receptor 12825922
Adrenergic receptor alpha-1 IC50 = 18.0 nM 7.75 In vitro binding affinity towards Alpha-1 adrenergic receptor by the displacemen... 10377229
D(2) dopamine receptor Ki = 21.0 nM 7.68 Ability to inhibit the binding of [3H]spiperone to the Dopamine receptor D2L in ... 7861418
D(2) dopamine receptor Ki = 21.0 nM 7.68 In vitro binding affinity towards Dopamine receptor D2 in rat tissue homogenate ... 14695828
D(2) dopamine receptor Ki = 21.0 nM 7.68 Affinity was evaluated by inhibition of [3H]spiperone binding to COS cells trans... 8064797
D(3) dopamine receptor IC50 = 22.0 nM 7.66 Binding affinity towards human Dopamine receptor D3 10377229
5-hydroxytryptamine receptor 7 Ki = 43.0 nM 7.37 Binding affinity towards rat 5-hydroxytryptamine 7 receptor 12825922
D(2) dopamine receptor IC50 = 54.0 nM 7.27 Compound was tested in vitro for its binding affinity towards human Dopamine rec... 10377229
Histamine H4 receptor EC50 = 218.78 nM 6.66 Activity at human histamine H4 receptor transfected in SK-N-MC cells by cAMP ass... 16854056
Histamine H1 receptor IC50 = 1000.0 nM 6.0 Binding affinity towards histamine H1 receptor from rat brain membranes using [3... 10377229
5-hydroxytryptamine receptor 2C IC50 = 1000.0 nM 6.0 Compound was tested in vitro for its binding affinity towards 5-hydroxytryptamin... 10377229
Histamine H4 receptor Ki = 4570.88 nM 5.34 Displacement of [3H]histamine from human histamine H4 receptor transfected in SK... 16854056
Muscarinic acetylcholine receptor M1 IC50 = 5500.0 nM 5.26 Inhibition of binding of 1.0 nM [3H]pirenzepine to cloned human Muscarinic acety... 10377229
Salmonella typhimurium EC50 = 5770.0 nM 5.24 Antibacterial activity against Salmonella typhimurium ATCC14028 infected in mous... 38283231

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 70
- 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
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
19256501 10.1021/jm801441s No relevant target 4
16854056 10.1021/jm051008s Histamine H4 receptor 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 3

Data from ChEMBL 36 via Core Engine