CANNABIDIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H30O2
Molecular Weight	314.4617
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1

InChI

InChIKey=QHMBSVQNZZTUGM-ZWKOTPCHSA-N

InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1

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Description

Cannabidiol is the major nonpsychoactive ingredient in cannabis. Cannabidiol demonstrates a range of effects that may be therapeutically useful, including anti-seizure, antioxidant, neuroprotective, anti-inflammatory, analgesic, anti-tumor, anti-psychotic, and anti-anxiety properties. Exact mechanism of action of cannabidiol is not known, but may include effects on the orphan G-protein-coupled receptor GPR55; the transient receptor potential of vanilloid type-1 channel; the 5-HT1a receptor; and the α3 glycine receptors. GW Pharmaceuticals successfully developed the world’s first prescription medicine derived from the cannabis plant, Sativex® (buccal spray containing delta-9-tetrahydrocannabinol and cannabidiol) now approved in over 29 countries outside of the United States for the treatment of spasticity due to Multiple Sclerosis. GW Pharmaceuticals is developing Epidiolex® (a liquid formulation of pure plant-derived cannabidiol) for certain rare and severe early-onset, drug-resistant epilepsy syndromes.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 172	Agonist 2,678
Vanilloid receptor 53	Agonist 2,678	3.2 µM [EC50]
Dopamine D2 receptor 297	Partial Agonist 290	11.0 nM [Ki]
G-protein coupled receptor 55 6	Antagonist 2,778	445.0 nM [IC50]
Glycine receptor subunit alpha-3 10	Binding Agent 1,064

Conditions

Condition	Modality	Highest Phase	Product
Multiple sclerosis 104	Palliative	Approved 8,429	SATIVEX
Pain 614	Primary	Approved 8,429	SATIVEX
Lennox-Gastaut syndrome 4	Primary	Phase III 656	EPIDIOLEX
Dravet syndrome 5	Primary	Phase III 656	EPIDIOLEX
Tuberous sclerosis complex 1	Primary	Phase III 656	EPIDIOLEX

C_max

Value	Dose	Analyte	Population
330.3 ng/mL	750 mg 2 times / day multiple, oral	CANNABIDIOL plasma	Homo sapiens
541.2 ng/mL	1500 mg 2 times / day multiple, oral	CANNABIDIOL plasma	Homo sapiens
292.4 ng/mL	1500 mg single, oral	CANNABIDIOL plasma	Homo sapiens
327 ng/mL	1500 mg single, oral	CANNABIDIOL plasma	Homo sapiens
782 ng/mL	6000 mg single, oral	CANNABIDIOL plasma	Homo sapiens
1588 ng/mL	1500 mg single, oral	CANNABIDIOL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1745 ng × h/mL	750 mg 2 times / day multiple, oral	CANNABIDIOL plasma	Homo sapiens
3236 ng × h/mL	1500 mg 2 times / day multiple, oral	CANNABIDIOL plasma	Homo sapiens
1618 ng × h/mL	1500 mg single, oral	CANNABIDIOL plasma	Homo sapiens
2198 ng × h/mL	1500 mg single, oral	CANNABIDIOL plasma	Homo sapiens
3900 ng × h/mL	6000 mg single, oral	CANNABIDIOL plasma	Homo sapiens
8670 ng × h/mL	1500 mg single, oral	CANNABIDIOL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
56.41 h	750 mg 2 times / day multiple, oral	CANNABIDIOL plasma	Homo sapiens
60.54 h	1500 mg 2 times / day multiple, oral	CANNABIDIOL plasma	Homo sapiens
14.43 h	1500 mg single, oral	CANNABIDIOL plasma	Homo sapiens
15.42 h	6000 mg single, oral	CANNABIDIOL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
6%	1500 mg single, oral		CANNABIDIOL plasma	Homo sapiens
6%	6000 mg single, oral		CANNABIDIOL plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 mg/kg/day 1 times / day multiple, oral Recommended	unhealthy, 14 years (range: 2 - 48 years) n = 75	Disc. AE: Transaminases increased... Other AEs: Transaminases increased, Decreased appetite...
20 mg/kg/day 1 times / day multiple, oral Recommended	unhealthy, 14 years (range: 2 - 48 years) n = 238	Disc. AE: Transaminases increased... Other AEs: Transaminases increased, Decreased appetite...
50 mg/kg/day 1 times / day multiple, oral	healthy, adult n = 5

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AEs

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AE	Significance	Dose	Population
Drooling	1%	10 mg/kg/day 1 times / day multiple, oral Recommended	unhealthy, 14 years (range: 2 - 48 years) n = 75
Fungal infection	1%	10 mg/kg/day 1 times / day multiple, oral Recommended	unhealthy, 14 years (range: 2 - 48 years) n = 75
Salivary hypersecretion	1%	10 mg/kg/day 1 times / day multiple, oral Recommended	unhealthy, 14 years (range: 2 - 48 years) n = 75
Transaminases increased	1.3% Disc. AE	10 mg/kg/day 1 times / day multiple, oral Recommended	unhealthy, 14 years (range: 2 - 48 years) n = 75
Asthenia	11%	10 mg/kg/day 1 times / day multiple, oral Recommended	unhealthy, 14 years (range: 2 - 48 years) n = 75

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587 inducer 781	inhibitor 1,767		inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 706 CYP2C19 1,478 CYP1A2 1,524 CYP2B6 810 CYP2C8 911 UGT1A9 116 UGT2B7 146 P-gp 1,461 OAT1 599 OAT3 642 OCT2 647 MATE1 306 MATE2 263 OATP1B1 788 BSEP 402 OCT1 512 BCRP 699	CYP2C19 991 UGT1A7 236 UGT1A9 380 UGT2B7 389 P-gp 1,537 OATP1B1 406 OATP1B3 350 BCRP 561	CYP1A2 701 CYP2B6 547

Drug as perpetrator

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Target	Modality	Activity	Metabolite
BCRP 773	inhibitor 3,277	no	7-COOH-CBD 1
BCRP 773	inhibitor 3,277	no	7-OH-CBD 1
BSEP 403	inhibitor 3,277	no
BSEP 403	inhibitor 3,277	no	7-COOH-CBD 1
BSEP 403	inhibitor 3,277	no	7-OH-CBD 1

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Drug as victim

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Target	Modality	Activity	Metabolite
BCRP 561	substrate 3,367	no
BCRP 561	substrate 3,367	no	7-COOH-CBD 1
OATP1B1 406	substrate 3,367	no
OATP1B1 406	substrate 3,367	no	7-COOH-CBD 1
OATP1B3 350	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:69478	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:69478
ChemicalBook	CB7673434	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7673434
ZINC	ZINC000004097406	http://zinc15.docking.org/substances/ZINC000004097406
eMolecules	536311	https://www.emolecules.com/cgi-bin/more?vid=536311

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PubMed

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Title	Date	PubMed
Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.	2001 Oct	11606325
Medicinal use of cannabis: history and current status.	2001 Summer	11854770
The cannabinoids: an overview. Therapeutic implications in vomiting and nausea after cancer chemotherapy, in appetite promotion, in multiple sclerosis and in neuroprotection.	2001 Summer	11854768
Novel 1',1'-chain substituted Delta(8)-tetrahydrocannabinols.	2002 Dec 16	12443781
Resorcinol derivatives: a novel template for the development of cannabinoid CB(1)/CB(2) and CB(2)-selective agonists.	2002 May	11961073

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Patents

Sample Use Guides

In Vivo Use Guide

SATIVEX® is provided as a buccal spray in a 5.5 ml vial, with each 100 microlitre spray providing 2.7 mg delta-9-tetrahydrocannabinol (THC) and 2.5 mg cannabidiol (CBD). In patients with multiple sclerosis, the median daily dosage of SATIVEX® in the extension phase of the 4-week clinical trial was 5 sprays per day. The majority of patients required 12 sprays or less; dosage should be adjusted as needed and tolerated. There is limited experience with doses higher than 12 sprays per day. Some patients may require and may tolerate a higher number of sprays. In patients with pain in cancer, the median daily dosage of SATIVEX® was 8 actuations (sprays).

Route of Administration: Topical

In Vitro Use Guide

in vitro pre-treatment of Human Gingival Mesenchymal Stem Cells with 5 uM Cannabidiol (CBD) can influence their expression profile

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Name

Type

Language

CANNABIDIOL

Official Name

English

CANNABIDIOL [USAN]

Common Name