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Compound Detail

CHEMBL2218896

NABILONE
💊 Approved Drug
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💊 Approved Drug
CCCCCCC(C)(C)c1cc(O)c2c(c1)OC(C)(C)C1CCC(=O)CC21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2218896
Name NABILONE
Phase Approved
Structure Type MOL
InChI Key GECBBEABIDMGGL-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Cesamet CPD 109514 CPD-109514 Nabilona Nabilone
4
Targets
13
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names
13
Indications
1
Mechanisms

Molecular Properties

372.6
MW (Da)
6.26
ALogP
3
HBA
1
HBD
46.5
PSA (Ų)
0.60
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem nab-
USAN Year 1976

Extended Properties

Molecular Formula C24H36O3
MW 372.55
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness 1.72

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cannabinoid CB1 receptor agonist AGONIST Cannabinoid receptor 1 ✓ ✓

Indications

Nausea Neoplasms Postoperative Nausea and Vomiting Postoperative Nausea and Vomiting Diabetic Neuropathies Parkinson Disease Fibromyalgia Marijuana Abuse Muscle Spasticity Neuralgia Obesity Suicidal Ideation Obsessive-Compulsive Disorder

ATC Classification

A04AD11
nabilone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIEMETICS AND ANTINAUSEANTS

Activity Summary

Ki 10 meas. best 8.74
EC50 3 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL5373
 Ki 8.74 8.74 1.8 1
Cannabinoid receptor 2
CHEMBL253
 Ki 8.73 8.3525 1.8 4
Cannabinoid receptor 1
CHEMBL218
 Ki 8.66 8.5025 2.2 4
Cannabinoid receptor 1
CHEMBL3571
 Ki 8.66 8.66 2.2 1
Cannabinoid receptor 1
CHEMBL218
 EC50 8.4 8.4 4.0 2
Cannabinoid receptor 2
CHEMBL253
 EC50 7.8 7.8 15.8 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 Ki = 1.8 nM 8.74 Displacement of [3H]CP55940 from mouse spleen CB2 receptor 20925434
Cannabinoid receptor 2 Ki = 1.84 nM 8.73 Binding affinity against human Cannabinoid receptor 2 by using radioligand ([3H]... -
Cannabinoid receptor 2 Ki = 1.84 nM 8.73 Binding affinity to human CB2 receptor 23865723
Cannabinoid receptor 1 Ki = 2.19 nM 8.66 Binding affinity against human cannabinoid receptor by using radioligand ([3H]CP... -
Cannabinoid receptor 1 Ki = 2.2 nM 8.66 Displacement of [3H]CP55940 from rat brain CB1 receptor 20925434
Cannabinoid receptor 1 Ki = 2.19 nM 8.66 Binding affinity to human CB1 receptor 23865723
Cannabinoid receptor 1 EC50 = 3.981 nM 8.4 Agonist activity at human recombinant CB1 receptor expressed in CHO cells assess... 20688519
Cannabinoid receptor 1 EC50 = 3.981 nM 8.4 Agonist activity at human CB1 receptor expressed in CHO cells assessed as stimul... 21885167
Cannabinoid receptor 1 Ki = 3.981 nM 8.4 Displacement of [3H]-CP55940 from human CB1 receptor expressed in CHO cells by l... 21885167
Cannabinoid receptor 1 Ki = 5.1 nM 8.29 Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in CH... 20688519
Cannabinoid receptor 2 Ki = 6.31 nM 8.2 Displacement of [3H]-CP55940 from human CB2 receptor expressed in CHO cells by l... 21885167
Cannabinoid receptor 2 EC50 = 15.85 nM 7.8 Agonist activity at human CB2 receptor expressed in CHO cells assessed as increa... 21885167
Cannabinoid receptor 2 Ki = 17.6 nM 7.75 Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in CH... 20688519

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
21885167 10.1016/j.ejmech.2011.08.021 No relevant target 4
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
21885167 10.1016/j.ejmech.2011.08.021 Cannabinoid receptor 1 2
- 10.6019/CHEMBL4651402 Vero C1008 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
21885167 10.1016/j.ejmech.2011.08.021 Cannabinoid receptor 2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 2
20688519 10.1016/j.bmcl.2010.07.056 Cannabinoid receptor 1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2

Data from ChEMBL 36 via Core Engine