Compound Detail

CHEMBL465

DRONABINOL

💊 Approved Drug

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💊 Approved Drug

CCCCCc1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(C)=C[C@@H]21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL465
Name	DRONABINOL
Phase	Approved
Structure Type	MOL
InChI Key	CYQFCXCEBYINGO-IAGOWNOFSA-N
Therapeutic	✓ Yes

Known Names

.delta.-9-tetrahydrocannabinol .delta.1-thc .delta.9-tetrahydrocannabinol .delta.9-thc ABBOTT 40566 ABBOTT-40566 Delta-9-tetrahydrocannabinol Delta-9-thc Dronabinol Dronabinol component of ad-313 Dronabinol component of ad313 Dronabinol component of sci-110 +10 more

Targets

122

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

314.5

MW (Da)

5.74

ALogP

HBA

HBD

29.5

PSA (Å²)

0.57

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1985
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-nab-
USAN Year	1984

Extended Properties

Molecular Formula	C21H30O2
MW	314.47
Aromatic Rings	1
Heavy Atoms	23
NP-Likeness	2.31

Mechanism of Action

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

Indications

Anorexia Nausea Nausea Nausea Neoplasms Vomiting Anorexia Nervosa Osteoarthritis, Knee Alcohol Drinking Amyotrophic Lateral Sclerosis Anemia, Sickle Cell Arthritis, Psoriatic Arthritis, Rheumatoid Child Development Disorders, Pervasive Chronic Pain Dementia HIV Infections Irritable Bowel Syndrome Marijuana Abuse Migraine with Aura

ATC Classification

A04AD10

dronabinol

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: ANTIEMETICS AND ANTINAUSEANTS

Activity Summary

Ki 71 meas. best 8.54

EC50 27 meas. best 8.85

IC50 24 meas. best 8.55

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cannabinoid receptor 2 CHEMBL253	EC50	8.85	7.998	1.4	5
Cannabinoid receptor 1 CHEMBL218	IC50	8.55	8.55	2.8	1
Cannabinoid receptor 1 CHEMBL218	Ki	8.54	7.6576	2.9	21
Cannabinoid receptor 2 CHEMBL253	Ki	8.48	7.4564	3.3	25
Mus musculus CHEMBL375	IC50	8.4	8.4	4.0	2
Cannabinoid receptor 1 CHEMBL3571	IC50	8.24	8.24	5.8	1
Cannabinoid receptor CHEMBL2111385	IC50	8.24	7.45	5.8	2
Cannabinoid receptor 1 CHEMBL218	EC50	8.17	7.398	6.7	5
Cannabinoid receptor 2 CHEMBL5373	EC50	8.14	8.14	7.3	1
Cannabinoid receptor 2 CHEMBL5373	Ki	8.04	7.5625	9.2	4
Cannabinoid receptor 2 CHEMBL253	IC50	8.02	8.02	9.5	1
D(3) dopamine receptor CHEMBL234	EC50	7.99	7.99	10.2	1
Cannabinoid receptor 1 CHEMBL3571	EC50	7.96	7.33	11.0	2
Cannabinoid receptor 1 CHEMBL3037	Ki	7.82	7.5367	15.3	3
Unchecked CHEMBL612545	Ki	7.7	6.61	20.0	3
Cannabinoid receptor 1 CHEMBL3571	Ki	7.44	7.3473	36.0	11
G-protein coupled receptor 183 CHEMBL3259470	EC50	7.42	7.42	38.0	1
Cannabinoid receptor CHEMBL2096981	Ki	7.39	7.39	41.0	1
Cannabinoid receptor CHEMBL2111385	Ki	7.34	7.215	46.0	2
Cannabinoid receptor 1 CHEMBL3037	EC50	7.11	7.11	77.0	1
Transient receptor potential cation channel subfamily M member 8 CHEMBL1075319	IC50	6.8	6.8	160.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	EC50	6.64	6.64	230.0	1
Autotaxin CHEMBL3691	EC50	6.34	6.34	460.0	1
Plasmodium falciparum CHEMBL364	IC50	6.14	6.12	720.0	2
N-arachidonyl glycine receptor CHEMBL2384898	EC50	6.02	5.5425	960.0	4
Glycine receptor subunit alpha-1 CHEMBL5845	EC50	5.89	5.89	1300.0	1
Unchecked CHEMBL612545	IC50	5.57	5.57	2700.0	1
MDA-MB-231 CHEMBL400	IC50	5.3	5.3	5000.0	1
Hemozoin CHEMBL613898	IC50	4.95	4.95	11300.0	1
Lysophosphatidylserine lipase ABHD12 CHEMBL5516	IC50	4.94	4.94	11600.0	1
Nuclear receptor subfamily 1 group I member 2 CHEMBL3401	EC50	4.9	4.7667	12600.0	3
G-protein coupled receptor 55 CHEMBL1075322	EC50	4.85	4.85	14200.0	1
L-lactate dehydrogenase A chain CHEMBL4835	Ki	4.85	4.85	14000.0	1
G-protein coupled receptor 55 CHEMBL1075322	IC50	4.85	4.85	14200.0	1
HCT-116 CHEMBL394	IC50	4.38	4.38	42000.0	1
Fatty-acid amide hydrolase 1 CHEMBL2243	IC50	4.36	4.36	43600.0	1
A549 CHEMBL392	IC50	4.35	4.35	45000.0	1
Monoacylglycerol lipase ABHD6 CHEMBL2189127	IC50	4.32	4.32	48200.0	1
SH-SY5Y CHEMBL614910	IC50	4.3	4.3	50000.0	1
MCF7 CHEMBL387	IC50	4.24	4.24	57000.0	1
HepG2 CHEMBL395	IC50	4.23	4.23	59000.0	1
OVCAR CHEMBL614212	IC50	4.2	4.2	63000.0	1
PC-3 CHEMBL390	IC50	4.19	4.19	65000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	3.2	mL.min-1.kg-1	Homo sapiens
F	20.0	%	Homo sapiens
F	15.0	%	Homo sapiens
Fu	0.03	-	-
Fu	0.001	-	-
Fu	0.03	-	Homo sapiens
Fu	0.05	-	Homo sapiens
MRT	46.0	hr	Homo sapiens
t1/2	-	-	Rattus norvegicus
T1/2	33.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cannabinoid receptor 2	EC50	=	1.42	nM	8.85	Agonist activity at human CB2 receptor expressed in CHO-K1 cells assessed as act...	38885438
Cannabinoid receptor 2	EC50	=	1.5	nM	8.82	Agonist activity at cloned human CB2 receptor in Sf9 cells assessed as stimulati...	18522867
Cannabinoid receptor 1	IC50	=	2.8	nM	8.55	Displacement of [3H]CP55940 from human recombinant CB1 receptor expressed in HEK...	21999614
Cannabinoid receptor 1	Ki	=	2.9	nM	8.54	Displacement of [3H]CP-55940 from human CB1 receptor	18522867
Cannabinoid receptor 2	Ki	=	3.3	nM	8.48	Binding affinity to human CB2 receptor	17531479
Cannabinoid receptor 1	Ki	=	3.88	nM	8.41	Displacement of [3H]-CP55,940 from human CB1 receptor transfected in CHOK1 cells	23679955
Cannabinoid receptor 1	Ki	=	3.88	nM	8.41	Displacement of [3H]CP55,940 from human recombinant CB1 receptor expressed in CH...	-
Mus musculus	IC50	=	4.0	nM	8.4	Concentration required to inhibit electrically induced contractions in isolated ...	7636873
Mus musculus	IC50	=	4.0	nM	8.4	In vitro inhibition of electrically induced contractions in isolated mouse vas d...	-
Cannabinoid receptor 1	IC50	=	5.8	nM	8.24	Concentration of compound required to inhibit 50% of [3H]WIN-55212 binding to Ca...	7636873
Cannabinoid receptor	IC50	=	5.8	nM	8.24	Compound was evaluated for the inhibition of [3H]WIN-55212-2 binding in rat cere...	-
Cannabinoid receptor 1	EC50	=	6.73	nM	8.17	Agonist activity at human CB1 receptor expressed in CHO-K1 cells assessed as act...	38885438
Cannabinoid receptor 2	EC50	=	7.3	nM	8.14	Inverse agonist activity at mouse CB2 receptor expressed in HEK293 cells assesse...	29939744
Cannabinoid receptor 2	Ki	=	9.2	nM	8.04	Binding affinity to mouse CB2 receptor	17531479
Cannabinoid receptor 2	IC50	=	9.5	nM	8.02	Displacement of [3H]CP55940 from human recombinant CB2 receptor expressed in HEK...	21999614
Cannabinoid receptor 1	Ki	=	10.0	nM	8.0	Displacement of [3H]-CP55,940 from human CB1 receptor expressed in HEK293 cells	22284817
D(3) dopamine receptor	EC50	=	10.2	nM	7.99	Agonist activity at recombinant human CB1 receptor expressed in CHO-K1 cells ass...	28182408
Cannabinoid receptor 1	EC50	=	11.0	nM	7.96	Effective concentration for inhibition of Cannabinoid receptor 1-mediated adenyl...	9379442
Cannabinoid receptor 2	EC50	=	12.0	nM	7.92	Partial agonist activity at human CB2 receptor transfected in CHO cells incubate...	34304557
Cannabinoid receptor 2	EC50	=	12.3	nM	7.91	Partial agonist activity at human cannabinoid CB2 receptor expressed in CHO-K1 c...	25072877

Literature References

PubMed	DOI	Target Context	# Activities
2158563	10.1021/jm00167a025	Mus musculus	32
16472241	10.2174/1570163043334794	Hepatotoxicity	18
37411021	10.1021/acs.jnatprod.3c00064	Unchecked	18
26000707	10.1021/acs.jnatprod.5b00065	Mus musculus	15
817021	10.1021/jm00226a003	Rattus norvegicus	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
37411021	10.1021/acs.jnatprod.3c00064	Staphylococcus aureus	9
6296389	10.1021/jm00354a011	Mus musculus	8
20966043	10.1124/dmd.110.035105	Nuclear receptor subfamily 1 group I member 2	7
2989518	10.1021/jm00383a016	Mus musculus	7
6681843	10.1021/jm00356a031	Rattus norvegicus	7
18681481	10.1021/np8002673	Staphylococcus aureus	6
7086846	10.1021/jm00347a021	Oryctolagus cuniculus	6
817021	10.1021/jm00226a003	Mus musculus	5
6296389	10.1021/jm00354a011	Canis familiaris	5
1659638	10.1021/jm00115a023	Mus musculus	5
12061889	10.1021/jm0200409	ADMET	5
8057304	10.1021/jm00042a015	Mus musculus	4
817021	10.1021/jm00226a003	Felis catus	4
18426954	10.1124/dmd.108.020479	ADMET	4

Data from ChEMBL 36 via Core Engine