General
Preferred name
CANNABIDIOL
Synonyms
Sativex-cannabidiol ()
GWP42003 ()
GWP-42003-P ()
Cardiolrx ()
(-)-trans-cannabidiol ()
BTX-1503 ()
Cannabidiol solution ()
(-)-cannabidiol ()
CBD ()
GWP42003-P ()
.delta.1(2)-trans-cannabidiol ()
Epidiolex ()
(-)-cbd ()
BTX-1204 ()
GWP-42003 ()
Cannabidiol-d9 (CRM) ()
(±)-Cannabidiol ()
Cannabidiol-d3 (CRM) ()
P&D ID
PD016236
CAS
13956-29-1
3956-29-1
1246819-21-5
3556-78-3
1435783-16-6
Tags
natural product
drug
available
Approved by
EMA
FDA
First approval
2018
Drug Status
investigational
approved
Drug indication
Dravet syndrome
Infantile spasm
Epilepsy
LennoxGastaut syndrome
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Cannabidiol (CBD) is a natural extract from cannabis plants (a 'cannabinoid'), which is being investigated in various orphan pediatric epilepsy syndromes. The major advantage of CBD over other cannabinoids such as , is that it is devoid of psychoactive activity, whilst retaining analgesic and anti-inflammatory actions.
CBD is also commonly represented with the structure shown by CID 26346.
MOA The exact mechanism of action of CBD and THC is not currently fully understood. However, it is known that CBD acts on cannabinoid (CB) receptors of the endocannabinoid system, which are found in numerous areas of the body, including the peripheral and central nervous systems, including the brain. The endocannabinoid system regulates many physiological responses of the body including pain, memory, appetite, and mood. More specifically, CB1 receptors can be found within the pain pathways of the brain and spinal cord where they may affect CBD-induced analgesia and anxiolysis, and CB2 receptors have an effect on immune cells, where they may affect CBD-induced anti-inflammatory processes. ; ; CBD has been shown to act as a negative allosteric modulator of the cannabinoid CB1 receptor, the most abundant G-Protein Coupled Receptor (GPCR) in the body [A32469]. Allosteric regulation of a receptor is achieved through the modulation of the activity of a receptor on a functionally distinct site from the agonist or antagonist binding site. The negative allosteric modulatory effects of CBD are therapeutically important as direct agonists are limited by their psychomimetic effects while direct antagonists are limited by their depressant effects [A32469].
DESCRIPTION Cannabidiol (CBD) is a natural extract from Cannabis plants (a 'cannabinoid'), which has recently been approved as a much needed therapy for the treatment of orphan pediatric epilepsy syndromes. It may also have benefit in schizophrenia or post-traumatic stress disorder. The major advantage of CBD over other cannabinoids such as , is that it is devoid of psychotropic effects, whilst retaining analgesic, anti-inflammatory and other beneficial actions.
CBD is also commonly represented with the structure shown by CID 26346. (GtoPdb)
ABSORPTION Following a single buccal administration, maximum plasma concentrations of both CBD and THC typically occur within two to four hours. When administered buccally,; blood levels of THC and other cannabinoids are lower compared with inhalation of smoked cannabis. The resultant concentrations in the blood are lower than those obtained by inhaling the same dose because absorption is slower, redistribution into fatty tissues is rapid and additionally some of the THC undergoes hepatic first pass metabolism to 11-OH-THC, a psycho-active metabolite. ; ; The CBD component of sublingual Sativex was found to have a Tmax of 1.63hr and a Cmax of 2.50ng/mL, while buccal Sativex was found to have a Tmax of 2.80hr and a Cmax of 3.02ng/mL.
INDICATION When used in combination with delta-9-tetrahydrocannabinol as the product Sativex, cannabidiol was given a standard marketing authorization (ie. a Notice of Compliance (NOC)) by Health Canada for the following indications: ; 1) as adjunctive treatment for symptomatic relief of spasticity in adult patients with multiple sclerosis (MS) who have not responded adequately to other therapy and who demonstrate meaningful improvement during an initial trial of therapy [L886];; ; Due to the need for confirmatory studies to verify the clinical benefit coupled with the promising nature of the clinical evidence, Sativex was also given a Notice of Compliance with Conditions (NOC/c) by Health Canada for the following indications: ; 1) as adjunctive treatment for the symptomatic relief of neuropathic pain in adult patients with multiple sclerosis; ; 2) as adjunctive analgesic treatment in adult patients with advanced cancer who experience moderate to severe pain during the highest tolerated dose of strong opioid therapy for persistent background pain [L886].
Cell lines
9
Organisms
1
Compound Sets
22
Axon Medchem Screening Library
1234
Cayman Chemical Bioactives
9003741
90080
16203
33075
ChEMBL Approved Drugs
CHEMBL190461
ChEMBL Drugs
CHEMBL190461
Concise Guide to Pharmacology 2017/18
4150
Concise Guide to Pharmacology 2019/20
4150
Concise Guide to Pharmacology 2021/22
4150
Concise Guide to Pharmacology 2023/24
4150
DrugBank
DB09061
DrugBank Approved Drugs
DB09061
DrugCentral
5288
DrugCentral Approved Drugs
5288
DrugMAP
DM0659E
DrugMAP Approved Drugs
DM0659E
Guide to Pharmacology
4150
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL190461
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
19GBJ60SN5
Novartis Chemogenetic Library (NIBR MoA Box)
ReFrame library
TargetMol Bioactive Compound Library
TWS0414
ZINC Tool Compounds
ZINC000004097406
External IDs
47
Properties
(calculated by RDKit )
Molecular Weight
314.22
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
2
Rotatable Bonds
6
Ring Count
2
Aromatic Ring Count
1
cLogP
5.85
TPSA
40.46
Fraction CSP3
0.52
Chiral centers
2.0
Largest ring
6.0
QED
0.51
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
GPCR/G protein
Endocrinology/Hormones
Neuroscience
Target
GPR55 Antagonist
CB1 antagonist
CB2 inverse agonist
VR1
Member status
virtual
MOA
Inducible Nitric Oxide Synthase (NOS-2) Inhibitors
Cannabinoid Receptor Agonists
Antioxidants
p38 MAPK Inhibitors
beta-Amyloid (Abeta) Protein Neurotoxicity Inhibitors
Biosynthetic Origin
Terpenoid
Therapeutic Indication
Neuropathic Pain
Therapeutic Class
CNS & PNS
Source data