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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
Structure of CANNABIDIOL

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

HIDE SMILES / InChI

Molecular Formula C21H30O2
Molecular Weight 314.4617
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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 TargetPharmacologyConditionPotency
3.2 µM [EC50]
11.0 nM [Ki]
445.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
SATIVEX
Primary
SATIVEX
Primary
EPIDIOLEX
Primary
EPIDIOLEX
Primary
EPIDIOLEX

Cmax

ValueDoseCo-administeredAnalytePopulation
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

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
1500 mg single, oral
CANNABIDIOL plasma
Homo sapiens
6%
6000 mg single, oral
CANNABIDIOL plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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
Substance Class Chemical
Record UNII
19GBJ60SN5
Record Status Validated (UNII)
Record Version