CANNABIDIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H30O2
Molecular Weight	314.4617
Optical Activity	( - )
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 171 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16258853	Agonist 2637
Vanilloid receptor 49 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11606325	Agonist 2637	3.2 µM [EC50]
Dopamine D2 receptor 290 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27754480	Partial Agonist 283	11.0 nM [Ki]
G-protein coupled receptor 55 6 Target ID: CHEMBL1075322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17876302	Antagonist 2737	445.0 nM [IC50]
Glycine receptor subunit alpha-3 10 Target ID: CHEMBL1075092 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22585736	Binding Agent 1037

Conditions

Condition	Modality	Highest Phase	Product
Multiple sclerosis 101 Sources: http://sativex.co.uk/static/media/images/pdf/pil_uk.pdf	Palliative	Approved 8307	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 607 Sources: http://omr.bayer.ca/omr/online/sativex-dhcpl-lapds-08-01-2007-en.pdf	Primary	Approved 8307	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 651	EPIDIOLEX Approved Use Unknown
Dravet syndrome 5 Sources: https://www.gwpharm.com/epilepsy-patients-caregivers/patients	Primary	Phase III 651	EPIDIOLEX Approved Use Unknown
Tuberous sclerosis complex 1 Sources: https://www.gwpharm.com/epilepsy-patients-caregivers/patients	Primary	Phase III 651	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 1670 inhibitor 1532 inducer 753	inhibitor 1695		inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 691 CYP2C19 1410 CYP1A2 1463 CYP2B6 770 CYP2C8 869 UGT1A9 115 UGT2B7 145 P-gp 1401 OAT1 584 OAT3 625 OCT2 630 MATE1 302 MATE2 259 OATP1B1 770 BSEP 392 OCT1 498 BCRP 678	CYP2C19 955 UGT1A7 235 UGT1A9 378 UGT2B7 387 P-gp 1491 OATP1B1 389 OATP1B3 333 BCRP 545	CYP1A2 671 CYP2B6 521

Drug as perpetrator

Target	Modality	Activity	Metabolite
BCRP 751	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
BCRP 751	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
BSEP 393	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
BSEP 393	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
BSEP 393	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
MATE1 304	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
MATE1 304	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
MATE1 304	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
MATE2 259	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
MATE2 259	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
MATE2 259	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OAT1 588	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OAT1 588	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OAT1 588	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OAT3 627	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OAT3 627	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OAT3 627	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OATP1B1 785	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B1 785	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B1 785	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OATP1B3 700	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B3 700	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B3 700	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OCT1 513	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OCT1 513	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OCT1 513	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
OCT2 631	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OCT2 631	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OCT2 631	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
P-gp 1588	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
P-gp 1588	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-OH-CBD 1
CYP1A2 1620	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP1A2 1620	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2B6 946	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2B6 946	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2C19 1484	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	yes
CYP2C8 923	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP2C9 1747	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP3A4 1857	inducer 1515 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
CYP3A4 1857	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
UGT1A9 120	inhibitor 3185 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	yes
UGT2B7 156	inhibitor 3185 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 545	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
BCRP 545	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B1 389	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B1 389	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
OATP1B3 333	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
OATP1B3 333	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no	7-COOH-CBD 1
P-gp 1491	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=21 Page: 21.0	no
UGT1A7 235	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
UGT1A9 378	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
UGT2B7 387	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210365Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
CYP2C19 955	substrate 3264 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 1670	substrate 3264 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 1603	inhibitor 1584 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
Synthesis and pharmacological evaluation in mice of halogenated cannabidiol derivatives.	1999 Nov	10605059
Cannabinoid CB(1) receptor agonists produce cerebellar dysfunction in mice.	2001 May	11303052
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
Cannabidiol: an overview of some chemical and pharmacological aspects. Part I: chemical aspects.	2002 Dec 31	12505688
(-)-Cannabidiol antagonizes cannabinoid receptor agonists and noradrenaline in the mouse vas deferens.	2002 Dec 5	12450575
Cannabinol enhancement of interleukin-2 (IL-2) expression by T cells is associated with an increase in IL-2 distal nuclear factor of activated T cell activity.	2002 Feb	11809870
Fully automated determination of cannabinoids in hair samples using headspace solid-phase microextraction and gas chromatography-mass spectrometry.	2002 Nov-Dec	12501912
Medicinal cannabis: is delta9-tetrahydrocannabinol necessary for all its effects?	2003 Dec	14738597
Cannabidiol-transdermal delivery and anti-inflammatory effect in a murine model.	2003 Dec 12	14644587
Nonpsychotropic cannabinoid receptors regulate microglial cell migration.	2003 Feb 15	12598628
Safety, tolerability, and efficacy of orally administered cannabinoids in MS.	2003 Feb 25	12601130
[Weather-induced changes in cannabinoid content of hair].	2003 Jan-Feb	12635486
Post-ischemic treatment with cannabidiol prevents electroencephalographic flattening, hyperlocomotion and neuronal injury in gerbils.	2003 Jul 31	12850548
Simultaneous detection of some drugs of abuse in saliva samples by SPME technique.	2003 Jun 24	12842356
G protein-coupled endothelial receptor for atypical cannabinoid ligands modulates a Ca2+-dependent K+ current.	2003 Nov 14	12952947
Evidence for cannabinoid receptor-dependent and -independent mechanisms of action in leukocytes.	2003 Sep	12805480
An open-label pilot study of cannabis-based extracts for bladder dysfunction in advanced multiple sclerosis.	2004 Aug	15327041
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
Differential effects of THC- or CBD-rich cannabis extracts on working memory in rats.	2004 Dec	15567426
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
Effect of cannabinoids on lithium-induced vomiting in the Suncus murinus (house musk shrew).	2004 Jan	13680081
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
NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa.	2004 Nov-Dec	15595449
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
Gene ancestry of the cannabinoid receptor family.	2005 Dec	16118055
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

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