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

Structure Search

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

Description
Sources: https://www.drugabuse.gov/about-nida/legislative-activities/testimony-to-congress/2016/biology-potential-therapeutic-effects-cannabidiol
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24854329 | https://www.gwpharm.com/products-pipeline

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 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16258853	Agonist 2678
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11606325	Agonist 2678	3.2 µM [EC50]
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27754480	Partial Agonist 290	11.0 nM [Ki]
G-protein coupled receptor 55 6 Target ID: CHEMBL1075322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17876302	Antagonist 2778	445.0 nM [IC50]
Glycine receptor subunit alpha-3 10 Target ID: CHEMBL1075092 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22585736	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Multiple sclerosis 104 Sources: http://sativex.co.uk/static/media/images/pdf/pil_uk.pdf	Palliative	Approved 8429	SATIVEX Approved Use Sativex is used in multiple sclerosis (MS) to improve symptoms related to muscle stiffness. This is also called “spasticity”. Spasticity means there is an increase in ‘muscle tone’ which makes the muscles feel more stiff or rigid. This means it is more difficult than normal to move the muscle. Sativex is used when other medicines have not helped your muscle stiffness.
Pain 614 Sources: http://omr.bayer.ca/omr/online/sativex-dhcpl-lapds-08-01-2007-en.pdf	Primary	Approved 8429	SATIVEX Approved Use SATIVEX® buccal spray is indicated 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.
Lennox-Gastaut syndrome 4 Sources: https://www.gwpharm.com/epilepsy-patients-caregivers/patients	Primary	Phase III 656	EPIDIOLEX Approved Use Unknown
Dravet syndrome 5 Sources: https://www.gwpharm.com/epilepsy-patients-caregivers/patients	Primary	Phase III 656	EPIDIOLEX Approved Use Unknown
Tuberous sclerosis complex 1 Sources: https://www.gwpharm.com/epilepsy-patients-caregivers/patients	Primary	Phase III 656	EPIDIOLEX Approved Use Unknown

C_max

Value	Dose	Analyte	Population
330.3 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	750 mg 2 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
541.2 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg 2 times / day multiple, oral dose: 1500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
292.4 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
327 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
782 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	6000 mg single, oral dose: 6000 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1588 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
1745 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	750 mg 2 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3236 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg 2 times / day multiple, oral dose: 1500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1618 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2198 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3900 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	6000 mg single, oral dose: 6000 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8670 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
56.41 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	750 mg 2 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
60.54 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg 2 times / day multiple, oral dose: 1500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
14.43 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
15.42 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	6000 mg single, oral dose: 6000 mg route of administration: Oral experiment type: SINGLE co-administered:	CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:		CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6% OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf	6000 mg single, oral dose: 6000 mg route of administration: Oral experiment type: SINGLE co-administered:		CANNABIDIOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
10 mg/kg/day 1 times / day multiple, oral Recommended Dose: 10 mg/kg/day, 1 times / day Route: oral Route: multiple Dose: 10 mg/kg/day, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf	unhealthy, 14 years (range: 2 - 48 years) n = 75 Health Status: unhealthy Condition: seizures associated with Lennox-Gastaut syndrome or Dravet syndrome Age Group: 14 years (range: 2 - 48 years) Sex: M+F Population Size: 75 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf	Disc. AE: Transaminases increased... Other AEs: Transaminases increased, Decreased appetite... AEs leading to discontinuation/dose reduction: Transaminases increased (1.3%) Other AEs: Transaminases increased (8%) Decreased appetite (16%) Diarrhea (9%) Weight decreased (3%) Abdominal discomfort (3%) Somnolence (23%) Sedation (3%) Lethargy (4%) Fatigue (11%) Malaise (11%) Asthenia (11%) Irritability (9%) Agitation (9%) Insomnia (11%) Sleep disorder (11%) Poor quality sleep (11%) Aggression (3%) Anger (3%) Drooling (1%) Salivary hypersecretion (1%) Gait disturbance (3%) Infection viral (7%) Pneumonia (8%) Fungal infection (1%) Infection NOS (25%) Rash (7%) Hypoxia (3%) Respiratory failure (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf
20 mg/kg/day 1 times / day multiple, oral Recommended Dose: 20 mg/kg/day, 1 times / day Route: oral Route: multiple Dose: 20 mg/kg/day, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf	unhealthy, 14 years (range: 2 - 48 years) n = 238 Health Status: unhealthy Condition: seizures associated with Lennox-Gastaut syndrome or Dravet syndrome Age Group: 14 years (range: 2 - 48 years) Sex: M+F Population Size: 238 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf	Disc. AE: Transaminases increased... Other AEs: Transaminases increased, Decreased appetite... AEs leading to discontinuation/dose reduction: Transaminases increased (5.9%) Other AEs: Transaminases increased (16%) Decreased appetite (22%) Diarrhea (20%) Weight decreased (5%) Abdominal discomfort (3%) Somnolence (25%) Sedation (6%) Lethargy (8%) Fatigue (12%) Malaise (12%) Asthenia (12%) Irritability (5%) Agitation (5%) Aggression (5%) Anger (5%) Drooling (4%) Salivary hypersecretion (4%) Gait disturbance (2%) Infection viral (11%) Pneumonia (5%) Fungal infection (3%) Infection NOS (21%) Rash (13%) Hypoxia (3%) Gastroenteritis (4%) Insomnia (5%) Sleep disorder (5%) Poor quality sleep (5%) Respiratory failure (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210365lbl.pdf
50 mg/kg/day 1 times / day multiple, oral Dose: 50 mg/kg/day, 1 times / day Route: oral Route: multiple Dose: 50 mg/kg/day, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26724101	healthy, adult n = 5 Health Status: healthy Age Group: adult Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/26724101	Sources: https://pubmed.ncbi.nlm.nih.gov/26724101

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	inhibitor 1767		inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 706 CYP2C19 1478 CYP1A2 1524 CYP2B6 810 CYP2C8 911 UGT1A9 116 UGT2B7 146 P-gp 1461 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 1537 OATP1B1 406 OATP1B3 350 BCRP 561	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity	Metabolite
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
BSEP 403	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
BSEP 403	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
BSEP 403	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
MATE1 308	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
MATE1 308	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
MATE1 308	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
MATE2 263	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
MATE2 263	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
MATE2 263	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OCT1 543	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OCT1 543	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OCT1 543	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	yes
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
UGT1A9 121	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
UGT2B7 157	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B3 350	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B3 350	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
UGT1A7 236	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
UGT1A9 380	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
UGT2B7 389	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes		likely Comment: Co-administration with moderate or strong inhibitors of CYP3A4 or CYP2C19 is predicted to increase CBD plasma concentrations which may increase the risk CBD toxicities. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes		likely Comment: Co-administration with moderate or strong inhibitors of CYP3A4 or CYP2C19 is predicted to increase CBD plasma concentrations which may increase the risk CBD toxicities. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000PharmR.pdf#page=20 Page: 20.0

Sourcing

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

PubMed

Title	Date	PubMed
Medicinal use of cannabis: history and current status.	2001 Summer	11854770
Cannabidiol, a non-psychoactive component of cannabis and its synthetic dimethylheptyl homolog suppress nausea in an experimental model with rats.	2002 Apr 16	11973447
Hair analysis for delta(9)-THC, delta(9)-THC-COOH, CBN and CBD, by GC/MS-EI. Comparison with GC/MS-NCI for delta(9)-THC-COOH.	2002 Aug 14	12208025
(-)-Cannabidiol antagonizes cannabinoid receptor agonists and noradrenaline in the mouse vas deferens.	2002 Dec 5	12450575
Resorcinol derivatives: a novel template for the development of cannabinoid CB(1)/CB(2) and CB(2)-selective agonists.	2002 May	11961073
Effects of pharmacological manipulations of cannabinoid receptors on severity of dystonia in a genetic model of paroxysmal dyskinesia.	2002 Nov 15	12421641
Therapeutic potential of cannabinoids in CNS disease.	2003	12617697
Automated headspace solid-phase dynamic extraction for the determination of cannabinoids in hair samples.	2003 Apr 23	12742687
The CB1 cannabinoid receptor agonist, HU-210, reduces levodopa-induced rotations in 6-hydroxydopamine-lesioned rats.	2003 Aug	12899667
Cannabidiol-transdermal delivery and anti-inflammatory effect in a murine model.	2003 Dec 12	14644587
Safety, tolerability, and efficacy of orally administered cannabinoids in MS.	2003 Feb 25	12601130
Gateways to clinical trials.	2003 Jun	12851663
G protein-coupled endothelial receptor for atypical cannabinoid ligands modulates a Ca2+-dependent K+ current.	2003 Nov 14	12952947
Oral cannabinoids for spasticity in multiple sclerosis: will attitude continue to limit use?	2003 Nov 8	14615102
Gamma-irradiation enhances apoptosis induced by cannabidiol, a non-psychotropic cannabinoid, in cultured HL-60 myeloblastic leukemia cells.	2003 Oct	14692532
Efficacy, safety and tolerability of an orally administered cannabis extract in the treatment of spasticity in patients with multiple sclerosis: a randomized, double-blind, placebo-controlled, crossover study.	2004 Aug	15327040
Pain reduction and lack of psychotropic effects with ajulemic acid: comment on the article by Sumariwalla et al.	2004 Dec	15593192
Efficacy of two cannabis based medicinal extracts for relief of central neuropathic pain from brachial plexus avulsion: results of a randomised controlled trial.	2004 Dec	15561385
(+)-Cannabidiol analogues which bind cannabinoid receptors but exert peripheral activity only.	2004 Dec 15	15588739
Effects of coadministration of cannabinoids and morphine on nociceptive behaviour, brain monoamines and HPA axis activity in a rat model of persistent pain.	2004 Feb	14984418
Determination of cannabinoids in hemp food products by use of headspace solid-phase microextraction and gas chromatography-mass spectrometry.	2004 Jan	14598006
Effect of cannabinoids on lithium-induced vomiting in the Suncus murinus (house musk shrew).	2004 Jan	13680081
Medicinal cannabis extracts for the treatment of multiple sclerosis.	2004 Jul	15298068
A comparative analysis of the potential of cannabinoids and ondansetron to suppress cisplatin-induced emesis in the Suncus murinus (house musk shrew).	2004 Jul	14740147
Synthesis and antitumor activity of quinonoid derivatives of cannabinoids.	2004 Jul 15	15239658
Cannabidiol increases Fos expression in the nucleus accumbens but not in the dorsal striatum.	2004 Jun 18	15158372
Human skin permeation of Delta8-tetrahydrocannabinol, cannabidiol and cannabinol.	2004 Mar	15025853
Antitumor effects of cannabidiol, a nonpsychoactive cannabinoid, on human glioma cell lines.	2004 Mar	14617682
6"-Azidohex-2"-yne-cannabidiol: a potential neutral, competitive cannabinoid CB1 receptor antagonist.	2004 Mar 8	15033394
Cannabidiol lacks the vanilloid VR1-mediated vasorespiratory effects of capsaicin and anandamide in anaesthetised rats.	2004 May 3	15140635
Determination of cannabinoids in cannabis products using liquid chromatography-ion trap mass spectrometry.	2004 Nov 26	15595662
NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa.	2004 Nov-Dec	15595449
Cannabidiol prevents infarction via the non-CB1 cannabinoid receptor mechanism.	2004 Oct 25	15640760
Cannabinoids in hair: strategy to prove marijuana/hashish consumption.	2004 Oct 29	15451086
Cannabis (marijuana) contamination of United States and foreign paper currency.	2004 Sep	15516293
Effect of low doses of delta9-tetrahydrocannabinol and cannabidiol on the extinction of cocaine-induced and amphetamine-induced conditioned place preference learning in rats.	2004 Sep	15138755
Cannabidiol inhibits human glioma cell migration through a cannabinoid receptor-independent mechanism.	2005 Apr	15700028
Cannabidiol inhibits the hyperlocomotion induced by psychotomimetic drugs in mice.	2005 Apr 11	15840405
Gene ancestry of the cannabinoid receptor family.	2005 Dec	16118055
The nonpsychoactive component of marijuana cannabidiol modulates chemotaxis and IL-10 and IL-12 production of murine macrophages both in vivo and in vitro.	2005 Feb	15652407
Marijuana extracts possess the effects like the endocrine disrupting chemicals.	2005 Jan 31	15588936
A rapid and simple procedure for the determination of cannabinoids in hemp food products by gas chromatography-mass spectrometry.	2005 Jan 4	15620517
Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L.	2005 Jan-Feb	15688956
The use of cannabinoids in multiple sclerosis.	2005 Jul	16022575
CB1 cannabinoid receptor-mediated modulation of food intake in mice.	2005 Jun	15778743
Cannabinoids provide neuroprotection against 6-hydroxydopamine toxicity in vivo and in vitro: relevance to Parkinson's disease.	2005 Jun-Jul	15837565
Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors.	2005 Mar 21	15750656
Cannabinoids in bipolar affective disorder: a review and discussion of their therapeutic potential.	2005 May	15888515
Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids.	2005 Sep	16148455
Cannabidiol reverses MK-801-induced disruption of prepulse inhibition in mice.	2006 Apr	16052245

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

Name

Type

Language

CANNABIDIOL

Official Name

English

CANNABIDIOL [USAN]

Common Name

English

CANNABIDIOL [USP-RS]

Common Name

English

.DELTA.1(2)-TRANS-CANNABIDIOL

Common Name

English

Cannabidiol [WHO-DD]

Common Name

English

(-)-CANNABIDIOL

Common Name

English

EPIDIOLEX

Brand Name

English

CANNABIDIOL [MART.]

Common Name

English

CARDIOLRX

Brand Name

English

2-((1R,6R)-3-METHYL-6-(PROP-1-EN-2-YL)CYCLOHEX-2-EN-1-YL)-5-PENTYLBENZENE-1,3-DIOL

Systematic Name

English

2-((1R,6R)-3-METHYL-6-(1-METHYLETHENYL)CYCLOHEX-2-ENYL)-5-PENTYLBENZENE-1,3-DIOL

Systematic Name

English

CANNABIDIOL [INCI]

Common Name

English

BTX-1503

Code

English

(-)-CBD

Common Name

English

GWP-42003

Code

English

CANNABIDIOL [MI]

Common Name

English

CBD

Common Name

English

BTX-1204

Code

English

CANNABIDIOL [ORANGE BOOK]

Common Name

English

1,3-BENZENEDIOL, 2-((1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL)-5-PENTYL-

Systematic Name

English

CANNABIDIOL SOLUTION [USP-RS]

Common Name

English

GWP-42003-P

Code

English

cannabidiol [INN]

Common Name

English

GWP42003

Code

English

(-)-TRANS-CANNABIDIOL

Common Name

English

GWP42003-P

Code

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/17/1959