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Compound Detail

CHEMBL715

OLANZAPINE
💊 Approved Drug
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💊 Approved Drug
Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1

Basic Information

ChEMBL ID CHEMBL715
Name OLANZAPINE
Phase Approved
Structure Type MOL
InChI Key KVWDHTXUZHCGIO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Arkolamyl LY-170053 LY170053 Olansek Olanzapina Olanzapine Olanzapine apotex Olanzapine cipla Olanzapine cipla (previously olanzapine neopharma) Olanzapine component of lybalvi Olanzapine component of symbyax Olanzapine glenmark +9 more
55
Targets
297
Activities
4
Assay Types
20
PK Parameters
20
Publications
21
Known Names
20
Indications
3
Mechanisms

Molecular Properties

312.4
MW (Da)
3.44
ALogP
5
HBA
1
HBD
30.9
PSA (Ų)
0.81
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -pine
USAN Year 1992

Extended Properties

Molecular Formula C17H20N4S
MW 312.44
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.99

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 Depressive Disorder, Major Mental Disorders Mental Disorders Psychomotor Agitation Psychotic Disorders Psychotic Disorders Schizophrenia Alcoholism Anorexia Anxiety Borderline Personality Disorder Dementia Depressive Disorder Depressive Disorder, Treatment-Resistant Developmental Disabilities Feeding and Eating Disorders Gambling Genital Neoplasms, Female

ATC Classification

N05AH03
olanzapine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

Ki 252 meas. best 9.52
IC50 41 meas. best 8.3
EC50 2 meas. best 8.0
Kd 2 meas. best 10.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Kd 10.06 10.06 0.1 1
Histamine H1 receptor
CHEMBL4701
Ki 9.52 8.945 0.3 2
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 9.38 8.4572 0.4 25
Histamine H1 receptor
CHEMBL231
Ki 8.92 8.471 1.2 10
D(2) dopamine receptor
CHEMBL217
Ki 8.68 7.7207 2.1 30
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 8.68 8.0025 2.1 4
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 8.55 8.1092 2.8 12
5-hydroxytryptamine receptor 2A
CHEMBL322
Ki 8.4 8.3914 4.0 7
Unchecked
CHEMBL612545
Ki 8.39 7.355 4.1 4
Dopamine receptor D2 and D3
CHEMBL2111342
Ki 8.32 7.685 4.8 2
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 8.3 8.1176 5.0 21
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 8.3 7.875 5.0 4
Histamine H1 receptor
CHEMBL3943
Ki 8.2 8.2 6.3 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.2 7.8533 6.3 3
D(2) dopamine receptor
CHEMBL339
Ki 8.15 7.4436 7.0 14
Adrenergic receptor alpha-1
CHEMBL2094251
Ki 8.14 7.75 7.3 5
Mus musculus
CHEMBL375
EC50 8.0 8.0 10.0 1
D(2) dopamine receptor
CHEMBL217
IC50 8.0 7.465 10.0 2
Serotonin 2 (5-HT2) receptor
CHEMBL2095200
Ki 8.0 8.0 10.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 8.0 7.2233 10.0 9
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 8.0 7.77 10.0 2
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
Ki 7.92 7.91 12.0 2
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 7.9 7.1867 12.6 3
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 7.89 7.89 13.0 1
Histamine H1 receptor
CHEMBL231
IC50 7.89 7.89 13.0 1
Histamine H1 receptor
CHEMBL4701
IC50 7.89 7.89 13.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 7.84 7.58 14.6 4
D(4) dopamine receptor
CHEMBL219
Ki 7.72 7.4888 19.0 8
D(3) dopamine receptor
CHEMBL234
Ki 7.7 7.3633 19.9 12
D(1A) dopamine receptor
CHEMBL265
Ki 7.7 7.1867 20.0 9
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.68 7.415 21.0 2
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.68 7.42 21.0 2
Muscarinic acetylcholine receptor M1
CHEMBL276
Ki 7.66 7.66 22.0 2
Alpha-1A adrenergic receptor
CHEMBL319
Ki 7.6 7.59 25.1 2
Muscarinic acetylcholine receptor
CHEMBL2094109
Ki 7.58 7.375 26.0 2
Alpha-1B adrenergic receptor
CHEMBL315
IC50 7.43 7.43 37.0 1
D(3) dopamine receptor
CHEMBL3138
Ki 7.41 7.345 38.9 6
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 7.4 7.4 40.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.35 7.35 45.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
IC50 7.33 7.33 47.0 1
D(4) dopamine receptor
CHEMBL3361
Ki 7.3 7.3 50.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 7.24 7.24 57.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 7.22 6.8133 60.0 3
Alpha-1A adrenergic receptor
CHEMBL319
IC50 7.19 7.19 65.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 7.14 7.14 72.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.11 7.0667 77.0 3
D(3) dopamine receptor
CHEMBL234
IC50 7.11 7.11 78.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 7.1 6.592 79.4 5
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 7.08 7.04 83.0 2
D(1B) dopamine receptor
CHEMBL1850
Ki 7.05 7.025 90.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 184.7 - Rattus norvegicus
AUC 157.7 - Rattus norvegicus
AUC 113.1 - Rattus norvegicus
AUC 220.8 - Rattus norvegicus
AUC 20.73 - Rattus norvegicus
AUC 143.7 - Rattus norvegicus
AUC 2.8 - Rattus norvegicus
AUC 1825.0 - Rattus norvegicus
AUC 128.4 - Rattus norvegicus
AUC 288.8 - Chlorocebus sabaeus
CL 0.000113 mL.min-1.g-1 Homo sapiens
CL 6e-06 mL.min-1.g-1 Homo sapiens
CL 0.119 uL/min Homo sapiens
CL(app) 25.0 L/hr Homo sapiens
Excretion 7.0 % Homo sapiens
F 79.0 % Homo sapiens
Fu 0.034 - Rattus norvegicus
T1/2 30.0 hr Homo sapiens
Tmax 6.0 hr Homo sapiens
Vd 1000.0 L Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Kd = 0.087 nM 10.06 Binding affinity to human histamine H1 receptor 21062081
Histamine H1 receptor Ki = 0.3 nM 9.52 Half-maximal inhibition of [3H]7-OH-DPAT binding to Histamine H1 receptor in rat... 11784139
5-hydroxytryptamine receptor 2A Ki = 0.42 nM 9.38 Binding affinity to human 5HT2A receptor 32976928
Histamine H1 receptor Ki = 1.2 nM 8.92 Inhibition of [3H]pyrilamine binding to human Histamine H1 receptor 15771415
5-hydroxytryptamine receptor 2A Ki = 1.433 nM 8.84 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Histamine H1 receptor Ki = 1.473 nM 8.83 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
5-hydroxytryptamine receptor 2A Ki = 1.585 nM 8.8 Displacement of [3H]ketanserin from human 5HT2A receptor expressed in CHO cells 17880057
5-hydroxytryptamine receptor 2A Ki = 1.905 nM 8.72 Displacement of [3H]-ketanserin from human human 5-HT2A receptor transfected in ... 34436892
5-hydroxytryptamine receptor 2A Ki = 1.9 nM 8.72 Binding affinity for human 5-hydroxytryptamine 2A receptor 11170639
5-hydroxytryptamine receptor 2A Ki = 1.9 nM 8.72 Binding affinity towards human serotonin 5-hydroxytryptamine 2A receptor 14998318
Histamine H1 receptor Ki = 2.0 nM 8.7 Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1... -
Histamine H1 receptor Ki = 2.0 nM 8.7 Inhibition of histamine H1 receptor (unknown origin) 24559051
Muscarinic acetylcholine receptor M1 Ki = 2.1 nM 8.68 Binding affinity towards human M1 receptor. 11170639
D(2) dopamine receptor Ki = 2.1 nM 8.68 Binding affinity towards human D2 dopamine receptor. 11170639
5-hydroxytryptamine receptor 2A Ki = 2.3 nM 8.64 Inhibition of [125I]R91150 binding to human 5-hydroxytryptamine 2A receptor 15771415
5-hydroxytryptamine receptor 2A Ki = 2.5 nM 8.6 Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1... -
5-hydroxytryptamine receptor 2A Ki = 2.5 nM 8.6 Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1... -
5-hydroxytryptamine receptor 2A Ki = 2.5 nM 8.6 Displacement of [125]DOI from human recombinant full length 5HT2A receptor expre... 24559051
5-hydroxytryptamine receptor 2C Ki = 2.8 nM 8.55 Binding affinity towards human 5-hydroxytryptamine 2C receptor 11170639
Histamine H1 receptor Ki = 2.8 nM 8.55 Binding affinity to human cloned histamine H1 receptor 18595716

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 461
- 10.5281/zenodo.13943903 ADMET 80
31158845 10.1038/s41586-019-1291-3 ADMET 59
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15771414 10.1021/jm049629t Rattus norvegicus 10
29407591 10.1016/j.ejmech.2018.01.002 Rattus norvegicus 10
11784139 10.1021/jm010982y Rattus norvegicus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
14695828 10.1021/jm0309811 Rattus norvegicus 8
9748351 10.1021/jm9706832 Rattus norvegicus 7
32976928 10.1016/j.bmcl.2020.127563 Unchecked 6
11784139 10.1021/jm010982y Mus musculus 6
15771415 10.1021/jm049632c Rattus norvegicus 5
34436892 10.1021/acs.jmedchem.1c00497 Rattus norvegicus 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 4
24631727 10.1016/j.ejmech.2014.02.058 D(2) dopamine receptor 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
20155917 10.1021/jm901689v D(2) dopamine receptor 4

Data from ChEMBL 36 via Core Engine