Identification

Name
Nabiximols
Accession Number
DB14011
Type
Small Molecule
Groups
Approved, Investigational
Description

Nabiximols (tradename Sativex®) is a whole plant extract from the Cannabis species Cannabis sativa L. that has been purified into the active components CBD (cannabidiol) and THC (delta-9-tetrahydrocannabinol). For trademark purposes, purified CBD is branded as Nabidiolex®, while THC is purified as the product Tetrabinex®. Sativex® is available in a 1:1 formulation of THC:CBD as an oro-mucosal pump spray used for treatment of neuropathic pain from Multiple Sclerosis (MS) and for intractable cancer pain. Although still largely debated, Cannabis has been shown to have analgesic, anticonvulsant, muscle relaxant, anxiolytic, neuroprotective, anti-oxidant, and anti-psychotic activity [1, 2].

From a pharmacological perspective, Cannabis' diverse receptor profile explains its potential application for such a wide variety of medical conditions. Cannabis contains more than 400 different chemical compounds, of which 61 are considered cannabinoids, a class of compounds that act upon cannabinoid receptors of the body [A32584]. Tetrahydrocannabinol (THC) and cannabidiol (CBD) are two types of cannabinoids found naturally in the resin of the marijuana plant, both of which interact with the cannabinoid receptors found in the human body. While both CBD and THC are used for medicinal purposes, they have different receptor activity, function, and physiological effects. While cannabis in its natural plant form is currently used "off-label" for the management of many medical conditions, THC is currently commercially available in synthetic form as Nabilone, as purified isomer as Dronabinol, or in a 1:1 formulation with CBD from purified plant extract as Nabiximols.

The primary psychoactive component of Cannabis, delta 9-tetrahydrocannabinol (Δ9-THC), demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors. This activity results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. In contrast to THC's weak agonist activity, 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 [2]. Allosteric regulation is achieved through the modulation of receptor activity 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 [2].

In Canada, Sativex® has received a Notice of Compliance (NOC) for use as an as adjunctive treatment for symptomatic relief of spasticity in patients with multiple sclerosis (MS) who have not responded adequately to other therapy and who demonstrate meaningful improvement during an initial trial of therapy.

Sativex® has also received a Notice of Compliance with Conditions (NOC/c) for use as an adjunctive treatment for the symptomatic relief of neuropathic pain in adult patients with multiple sclerosis (MS) and 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.

Structure
Thumb
Synonyms
Not Available
External IDs
GW 1000 / GW 1000-02 / GW-1000 / GW1000 / SAB 378 / SAB-378
Categories
UNII
K4H93P747O
CAS number
56575-23-6
Weight
Average: 628.938
Monoisotopic: 628.449160412
Chemical Formula
C42H60O4
InChI Key
SSNHGLKFJISNTR-DYSNNVSPSA-N
InChI
InChI=1S/2C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15;1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,16-17,22H,5-10H2,1-4H3;11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t16-,17-;17-,18+/m10/s1
IUPAC Name
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol; 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
SMILES
[H][C@]1(CCC(C)=C[C@@]1([H])C1=C(O)C=C(CCCCC)C=C1O)C(C)=C.[H][C@@]12CCC(C)=C[C@@]1([H])C1=C(O)C=C(CCCCC)C=C1OC2(C)C

Pharmacology

Indication

In Canada, Sativex has received a Notice of Compliance (NOC) for use as an as adjunctive treatment for symptomatic relief of spasticity in patients with multiple sclerosis (MS) who have not responded adequately to other therapy and who demonstrate meaningful improvement during an initial trial of therapy.

Sativex has also received a Notice of Compliance with Conditions (NOC/c) for use as an adjunctive treatment for the symptomatic relief of neuropathic pain in adult patients with multiple sclerosis (MS) and 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.

Marketing authorisations with conditions reflect the promising nature of the clinical evidence and the need for confirmatory studies to verify the clinical benefit. Patients should be advised of the conditional nature of the authorizations with conditions.

Pharmacodynamics

The principal pharmacological effects of THC include analgesic, muscle relaxant, antiemetic, appetite stimulant and psychoactive effects. CBD has analgesic, anticonvulsant, muscle relaxant, anxiolytic, neuroprotective, anti-oxidant and anti-psychotic activity.

Mechanism of action

The primary psychoactive component of Cannabis, delta 9-tetrahydrocannabinol (Δ9-THC), demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors. This activity results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. In contrast to THC's weak agonist activity, 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 [2]. Allosteric regulation is achieved through the modulation of receptor activity 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 [2].

There is further evidence that CBD also activates 5-HT1A serotonergic and TRPV1–2 vanilloid receptors, antagonizes alpha-1 adrenergic and µ-opioid receptors, inhibits synaptosomal uptake of noradrenaline, dopamine, serotonin and gaminobutyric acid and cellular uptake of anandamide, acts on mitochondria Ca2 stores, blocks low-voltage-activated (T-type) Ca2 channels, stimulates activity of the inhibitory glycine-receptor, and inhibits activity of fatty amide hydrolase (FAAH) [3, 4].

TargetActionsOrganism
ACannabinoid receptor 1Not AvailableHuman
ACannabinoid receptor 2Not AvailableHuman
UG-protein coupled receptor 12
inverse agonist
Human
UGlycine receptor subunit alpha-1Not AvailableHuman
UGlycine receptor (alpha-1/beta)Not AvailableHuman
UGlycine receptor subunit alpha-3Not AvailableHuman
UN-arachidonyl glycine receptorNot AvailableHuman
UG-protein coupled receptor 55Not AvailableHuman
U5-hydroxytryptamine receptor 1ANot AvailableHuman
U5-hydroxytryptamine receptor 2ANot AvailableHuman
UNeuronal acetylcholine receptor subunit alpha-7Not AvailableHuman
UDelta-type opioid receptorNot AvailableHuman
UMu-type opioid receptorNot AvailableHuman
UPeroxisome proliferator-activated receptor gammaNot AvailableHuman
UTransient receptor potential cation channel subfamily V member 1Not AvailableHuman
UVoltage-dependent T-type calcium channel subunit alpha-1GNot AvailableHuman
UVoltage-dependent T-type calcium channel subunit alpha-1HNot AvailableHuman
UVoltage-dependent T-type calcium channel subunit alpha-1INot AvailableHuman
UTransient receptor potential cation channel subfamily A member 1Not AvailableHuman
UTransient receptor potential cation channel subfamily M member 8Not AvailableHuman
UTransient receptor potential cation channel subfamily V member 2Not AvailableHuman
UTransient receptor potential cation channel subfamily V member 3Not AvailableHuman
UTransient receptor potential cation channel subfamily V member 4Not AvailableHuman
UVoltage-dependent anion-selective channel protein 1Not AvailableHuman
Absorption

Individual subject plasma concentration data and pharmacokinetic parameters show a high degree of inter-subject variability.

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.

Volume of distribution

Cannabinoids are distributed throughout the body; they are highly lipid soluble and accumulate in fatty tissue. The release of cannabinoids from fatty tissue is responsible for the prolonged terminal elimination half-life.

Protein binding
Not Available
Metabolism

THC and CBD are metabolized in the liver by a number of cytochrome P450 isoenzymes, including CYP2C9, CYP2C19, CYP2D6 and CYP3A4. They may be stored for as long as four weeks in the fatty tissues from which they are slowly released at sub-therapeutic levels back into the blood stream and metabolized via the renal and biliary systems.

Route of elimination

Nabiximols is excreted in the urine and faeces.

Half life

Elimination from plasma is bi-exponential with an initial half-life of one to two hours. The terminal elimination half-lives are of the order of 24 to 36 hours or longer.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe metabolism of Nabiximols can be decreased when combined with Abiraterone.Approved
Acetyl sulfisoxazoleThe metabolism of Nabiximols can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AmiodaroneThe metabolism of Nabiximols can be decreased when combined with Amiodarone.Approved, Investigational
ApalutamideThe serum concentration of Nabiximols can be decreased when it is combined with Apalutamide.Approved, Investigational
AprepitantThe serum concentration of Nabiximols can be increased when it is combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Nabiximols can be decreased when combined with Armodafinil.Approved, Investigational
AtazanavirThe metabolism of Nabiximols can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Nabiximols can be decreased when combined with Atomoxetine.Approved
BoceprevirThe metabolism of Nabiximols can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Nabiximols can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Nabiximols can be decreased when it is combined with Bosentan.Approved, Investigational
CapecitabineThe metabolism of Nabiximols can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Nabiximols can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Nabiximols can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Nabiximols can be decreased when combined with Chloramphenicol.Approved, Vet Approved
CholecalciferolThe metabolism of Nabiximols can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Nabiximols can be decreased when combined with Cimetidine.Approved, Investigational
CitalopramThe metabolism of Nabiximols can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Nabiximols can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Nabiximols can be decreased when combined with Clemastine.Approved, Investigational
ClotrimazoleThe metabolism of Nabiximols can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Nabiximols can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Nabiximols.Approved, Investigational
CrisaboroleThe metabolism of Nabiximols can be decreased when combined with Crisaborole.Approved, Investigational
CrizotinibThe metabolism of Nabiximols can be decreased when combined with Crizotinib.Approved
CurcuminThe metabolism of Nabiximols can be decreased when combined with Curcumin.Approved, Investigational
CyclosporineThe metabolism of Nabiximols can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Nabiximols can be decreased when it is combined with Dabrafenib.Approved, Investigational
DarunavirThe metabolism of Nabiximols can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Nabiximols can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Nabiximols can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Nabiximols can be decreased when combined with Delavirdine.Approved
DihydroergotamineThe metabolism of Nabiximols can be decreased when combined with Dihydroergotamine.Approved, Investigational
DiltiazemThe metabolism of Nabiximols can be decreased when combined with Diltiazem.Approved, Investigational
DosulepinThe metabolism of Nabiximols can be decreased when combined with Dosulepin.Approved
DoxycyclineThe metabolism of Nabiximols can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Nabiximols can be decreased when combined with Dronedarone.Approved
EfavirenzThe metabolism of Nabiximols can be decreased when combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Nabiximols can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Nabiximols can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
Eslicarbazepine acetateThe metabolism of Nabiximols can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Nabiximols can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe metabolism of Nabiximols can be decreased when combined with Etravirine.Approved
FloxuridineThe metabolism of Nabiximols can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Nabiximols can be decreased when combined with Fluconazole.Approved, Investigational
FluorouracilThe metabolism of Nabiximols can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Nabiximols can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe metabolism of Nabiximols can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Nabiximols can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Nabiximols can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Nabiximols can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Nabiximols can be increased when combined with Fosphenytoin.Approved, Investigational
Fusidic AcidThe serum concentration of Nabiximols can be increased when it is combined with Fusidic Acid.Approved, Investigational
GemfibrozilThe metabolism of Nabiximols can be decreased when combined with Gemfibrozil.Approved
IdelalisibThe metabolism of Nabiximols can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Nabiximols can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Nabiximols can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Nabiximols can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoleThe serum concentration of Nabiximols can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Nabiximols can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Nabiximols can be decreased when combined with Isoniazid.Approved, Investigational
IsradipineThe metabolism of Nabiximols can be decreased when combined with Isradipine.Approved, Investigational
ItraconazoleThe metabolism of Nabiximols can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Nabiximols can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Nabiximols can be decreased when combined with Ketoconazole.Approved, Investigational
LeflunomideThe metabolism of Nabiximols can be decreased when combined with Leflunomide.Approved, Investigational
LobeglitazoneThe metabolism of Nabiximols can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Nabiximols can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Nabiximols can be increased when it is combined with Lorpiprazole.Approved
LosartanThe metabolism of Nabiximols can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Nabiximols can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Nabiximols can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Nabiximols can be decreased when it is combined with Lumacaftor.Approved
ManidipineThe metabolism of Nabiximols can be decreased when combined with Manidipine.Approved, Investigational
MidostaurinThe metabolism of Nabiximols can be decreased when combined with Midostaurin.Approved, Investigational
MifepristoneThe serum concentration of Nabiximols can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Nabiximols can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Nabiximols can be decreased when combined with Moclobemide.Approved, Investigational
ModafinilThe metabolism of Nabiximols can be decreased when combined with Modafinil.Approved, Investigational
NabiloneThe metabolism of Nabiximols can be decreased when combined with Nabilone.Approved, Investigational
NefazodoneThe metabolism of Nabiximols can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Nabiximols can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Nabiximols can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Nabiximols can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Nabiximols can be decreased when combined with Nicardipine.Approved, Investigational
NilotinibThe metabolism of Nabiximols can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Nabiximols can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Nabiximols can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Nabiximols can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Nabiximols can be increased when it is combined with Palbociclib.Approved, Investigational
PantoprazoleThe metabolism of Nabiximols can be decreased when combined with Pantoprazole.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Nabiximols.Approved
PentobarbitalThe metabolism of Nabiximols can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PhenobarbitalThe metabolism of Nabiximols can be increased when combined with Phenobarbital.Approved, Investigational
PhenytoinThe metabolism of Nabiximols can be increased when combined with Phenytoin.Approved, Vet Approved
PitolisantThe serum concentration of Nabiximols can be decreased when it is combined with Pitolisant.Approved, Investigational
PosaconazoleThe metabolism of Nabiximols can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Nabiximols can be increased when combined with Primidone.Approved, Vet Approved
PyrimethamineThe metabolism of Nabiximols can be decreased when combined with Pyrimethamine.Approved, Investigational, Vet Approved
QuinineThe metabolism of Nabiximols can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Nabiximols can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Nabiximols can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Nabiximols can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Nabiximols can be increased when combined with Rifapentine.Approved, Investigational
RucaparibThe metabolism of Nabiximols can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Nabiximols can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Nabiximols can be decreased when used in combination with Sarilumab.Approved, Investigational
SecobarbitalThe metabolism of Nabiximols can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Nabiximols can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Nabiximols can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Nabiximols can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Nabiximols can be increased when it is combined with Simeprevir.Approved
SorafenibThe metabolism of Nabiximols can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Nabiximols can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Nabiximols can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Nabiximols can be decreased when combined with Sulfadiazine.Approved, Investigational, Vet Approved
SulfamethoxazoleThe metabolism of Nabiximols can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Nabiximols can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Nabiximols can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Nabiximols can be decreased when combined with Telithromycin.Approved
TicagrelorThe metabolism of Nabiximols can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Nabiximols can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Nabiximols can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Nabiximols can be decreased when combined with Tolbutamide.Approved, Investigational
TopiramateThe metabolism of Nabiximols can be decreased when combined with Topiramate.Approved
TopiroxostatThe metabolism of Nabiximols can be decreased when combined with Topiroxostat.Approved, Investigational
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Nabiximols.Approved, Investigational
TranylcypromineThe metabolism of Nabiximols can be decreased when combined with Tranylcypromine.Approved, Investigational
TrimethoprimThe metabolism of Nabiximols can be decreased when combined with Trimethoprim.Approved, Vet Approved
Valproic AcidThe metabolism of Nabiximols can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Nabiximols can be decreased when combined with Valsartan.Approved, Investigational
VemurafenibThe serum concentration of Nabiximols can be decreased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Nabiximols can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Nabiximols can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Nabiximols can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Nabiximols can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Nabiximols can be decreased when combined with Ziprasidone.Approved
ZucapsaicinThe metabolism of Nabiximols can be decreased when combined with Zucapsaicin.Approved, Investigational
Food Interactions
Not Available

References

General References
  1. Pertwee RG: The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin. Br J Pharmacol. 2008 Jan;153(2):199-215. doi: 10.1038/sj.bjp.0707442. Epub 2007 Sep 10. [PubMed:17828291]
  2. Laprairie RB, Bagher AM, Kelly ME, Denovan-Wright EM: Cannabidiol is a negative allosteric modulator of the cannabinoid CB1 receptor. Br J Pharmacol. 2015 Oct;172(20):4790-805. doi: 10.1111/bph.13250. Epub 2015 Oct 13. [PubMed:26218440]
  3. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
  4. Zhornitsky S, Potvin S: Cannabidiol in humans-the quest for therapeutic targets. Pharmaceuticals (Basel). 2012 May 21;5(5):529-52. doi: 10.3390/ph5050529. [PubMed:24281562]
External Links
KEGG Drug
D09317
ChemSpider
8027901
ChEMBL
CHEMBL3833333
Drugs.com
Drugs.com Drug Page
Wikipedia
Nabiximols

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentCancer, Advanced / Pain2
3RecruitingTreatmentGilles de la Tourette's Syndrome / Tic Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0126 mg/mLALOGPS
logP6.1ALOGPS
logP5.94ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.73 m3·mol-1ChemAxon
Polarizability38.97 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
General Function
Drug binding
Specific Function
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered l...
Gene Name
CNR1
Uniprot ID
P21554
Uniprot Name
Cannabinoid receptor 1
Molecular Weight
52857.365 Da
References
  1. Laprairie RB, Bagher AM, Kelly ME, Denovan-Wright EM: Cannabidiol is a negative allosteric modulator of the cannabinoid CB1 receptor. Br J Pharmacol. 2015 Oct;172(20):4790-805. doi: 10.1111/bph.13250. Epub 2015 Oct 13. [PubMed:26218440]
Kind
Protein
Organism
Human
Pharmacological action
Yes
General Function
Cannabinoid receptor activity
Specific Function
Heterotrimeric G protein-coupled receptor for endocannabinoid 2-arachidonoylglycerol mediating inhibition of adenylate cyclase. May function in inflammatory response, nociceptive transmission and b...
Gene Name
CNR2
Uniprot ID
P34972
Uniprot Name
Cannabinoid receptor 2
Molecular Weight
39680.275 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inverse agonist
General Function
Promotes neurite outgrowth and blocks myelin inhibition in neurons (By similarity). Receptor with constitutive G(s) signaling activity that stimulates cyclic AMP production.
Specific Function
G-protein coupled receptor activity
Gene Name
GPR12
Uniprot ID
P47775
Uniprot Name
G-protein coupled receptor 12
Molecular Weight
36729.785 Da
References
  1. Laprairie RB, Bagher AM, Kelly ME, Denovan-Wright EM: Cannabidiol is a negative allosteric modulator of the cannabinoid CB1 receptor. Br J Pharmacol. 2015 Oct;172(20):4790-805. doi: 10.1111/bph.13250. Epub 2015 Oct 13. [PubMed:26218440]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transmitter-gated ion channel activity
Specific Function
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name
GLRA1
Uniprot ID
P23415
Uniprot Name
Glycine receptor subunit alpha-1
Molecular Weight
52623.35 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
General Function
Transmitter-gated ion channel activity
Specific Function
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).

Components:
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transmitter-gated ion channel activity
Specific Function
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name
GLRA3
Uniprot ID
O75311
Uniprot Name
Glycine receptor subunit alpha-3
Molecular Weight
53799.775 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled receptor activity
Specific Function
Receptor for N-arachidonyl glycine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. May contribute to regulation of the immune system.
Gene Name
GPR18
Uniprot ID
Q14330
Uniprot Name
N-arachidonyl glycine receptor
Molecular Weight
38133.27 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled receptor activity
Specific Function
May be involved in hyperalgesia associated with inflammatory and neuropathic pain (By similarity). Receptor for L-alpha-lysophosphatidylinositol (LPI). LPI induces Ca(2+) release from intracellular...
Gene Name
GPR55
Uniprot ID
Q9Y2T6
Uniprot Name
G-protein coupled receptor 55
Molecular Weight
36637.12 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transmembrane signaling receptor activity
Specific Function
Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular aci...
Gene Name
TRPV1
Uniprot ID
Q8NER1
Uniprot Name
Transient receptor potential cation channel subfamily V member 1
Molecular Weight
94955.33 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
  2. Bisogno T, Hanus L, De Petrocellis L, Tchilibon S, Ponde DE, Brandi I, Moriello AS, Davis JB, Mechoulam R, Di Marzo V: Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide. Br J Pharmacol. 2001 Oct;134(4):845-52. doi: 10.1038/sj.bjp.0704327. [PubMed:11606325]
  3. Iannotti FA, Hill CL, Leo A, Alhusaini A, Soubrane C, Mazzarella E, Russo E, Whalley BJ, Di Marzo V, Stephens GJ: Nonpsychotropic plant cannabinoids, cannabidivarin (CBDV) and cannabidiol (CBD), activate and desensitize transient receptor potential vanilloid 1 (TRPV1) channels in vitro: potential for the treatment of neuronal hyperexcitability. ACS Chem Neurosci. 2014 Nov 19;5(11):1131-41. doi: 10.1021/cn5000524. Epub 2014 Jul 29. [PubMed:25029033]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Scaffold protein binding
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1G
Uniprot ID
O43497
Uniprot Name
Voltage-dependent T-type calcium channel subunit alpha-1G
Molecular Weight
262468.62 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Scaffold protein binding
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1H
Uniprot ID
O95180
Uniprot Name
Voltage-dependent T-type calcium channel subunit alpha-1H
Molecular Weight
259160.2 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1I
Uniprot ID
Q9P0X4
Uniprot Name
Voltage-dependent T-type calcium channel subunit alpha-1I
Molecular Weight
245100.8 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Temperature-gated cation channel activity
Specific Function
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in t...
Gene Name
TRPA1
Uniprot ID
O75762
Uniprot Name
Transient receptor potential cation channel subfamily A member 1
Molecular Weight
127499.88 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Calcium channel activity
Specific Function
Receptor-activated non-selective cation channel involved in detection of sensations such as coolness, by being activated by cold temperature below 25 degrees Celsius. Activated by icilin, eucalypto...
Gene Name
TRPM8
Uniprot ID
Q7Z2W7
Uniprot Name
Transient receptor potential cation channel subfamily M member 8
Molecular Weight
127684.035 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Calcium-permeable, non-selective cation channel with an outward rectification. Seems to be regulated, at least in part, by IGF-I, PDGF and neuropeptide head activator. May transduce physical stimuli in mast cells. Activated by temperatures higher than 52 degrees Celsius; is not activated by vanilloids and acidic pH.
Specific Function
Calcium channel activity
Gene Name
TRPV2
Uniprot ID
Q9Y5S1
Uniprot Name
Transient receptor potential cation channel subfamily V member 2
Molecular Weight
85980.335 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Calcium channel activity
Specific Function
Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 d...
Gene Name
TRPV3
Uniprot ID
Q8NET8
Uniprot Name
Transient receptor potential cation channel subfamily V member 3
Molecular Weight
90635.115 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Non-selective calcium permeant cation channel involved in osmotic sensitivity and mechanosensitivity. Activation by exposure to hypotonicity within the physiological range exhibits an outward rectification (PubMed:18826956, PubMed:18695040). Also activated by heat, low pH, citrate and phorbol esters (PubMed:18826956, PubMed:18695040). Increase of intracellular Ca(2+) potentiates currents. Channel activity seems to be regulated by a calmodulin-dependent mechanism with a negative feedback mechanism (PubMed:12724311, PubMed:18826956). Promotes cell-cell junction formation in skin keratinocytes and plays an important role in the formation and/or maintenance of functional intercellular barriers (By similarity). Acts as a regulator of intracellular Ca(2+) in synoviocytes (PubMed:19759329). Plays an obligatory role as a molecular component in the nonselective cation channel activation induced by 4-alpha-phorbol 12,13-didecanoate and hypotonic stimulation in synoviocytes and also regulates production of IL-8 (PubMed:19759329). Together with PKD2, forms mechano- and thermosensitive channels in cilium (PubMed:18695040). Negatively regulates expression of PPARGC1A, UCP1, oxidative metabolism and respiration in adipocytes (By similarity). Regulates expression of chemokines and cytokines related to proinflammatory pathway in adipocytes (By similarity). Together with AQP5, controls regulatory volume decrease in salivary epithelial cells (By similarity). Required for normal development and maintenance of bone and cartilage (PubMed:26249260).
Specific Function
Actin binding
Gene Name
TRPV4
Uniprot ID
Q9HBA0
Uniprot Name
Transient receptor potential cation channel subfamily V member 4
Molecular Weight
98280.2 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Voltage-gated anion channel activity
Specific Function
Forms a channel through the mitochondrial outer membrane and also the plasma membrane. The channel at the outer mitochondrial membrane allows diffusion of small hydrophilic molecules; in the plasma...
Gene Name
VDAC1
Uniprot ID
P21796
Uniprot Name
Voltage-dependent anion-selective channel protein 1
Molecular Weight
30772.39 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Plays a major role in ketone body metabolism.
Gene Name
ACAT1
Uniprot ID
P24752
Uniprot Name
Acetyl-CoA acetyltransferase, mitochondrial
Molecular Weight
45199.2 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
N-acetyltransferase activity
Gene Name
AANAT
Uniprot ID
F1T0I5
Uniprot Name
Arylalkylamine N-acetyltransferase
Molecular Weight
23343.8 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia c...
Gene Name
CAT
Uniprot ID
P04040
Uniprot Name
Catalase
Molecular Weight
59755.82 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Campone M, Rademaker-Lakhai JM, Bennouna J, Howell SB, Nowotnik DP, Beijnen JH, Schellens JH: Phase I and pharmacokinetic trial of AP5346, a DACH-platinum-polymer conjugate, administered weekly for three out of every 4 weeks to advanced solid tumor patients. Cancer Chemother Pharmacol. 2007 Sep;60(4):523-33. Epub 2007 Feb 17. [PubMed:17308894]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
DAGLA
Uniprot ID
F5GY58
Uniprot Name
Sn1-specific diacylglycerol lipase alpha
Molecular Weight
19005.05 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Fatty acid amide hydrolase activity
Specific Function
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of t...
Gene Name
FAAH
Uniprot ID
O00519
Uniprot Name
Fatty-acid amide hydrolase 1
Molecular Weight
63065.28 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Maintains high levels of reduced glutathione in the cytosol.
Gene Name
GSR
Uniprot ID
P00390
Uniprot Name
Glutathione reductase, mitochondrial
Molecular Weight
56256.565 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sh3 domain binding
Specific Function
Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name
GPX1
Uniprot ID
P07203
Uniprot Name
Glutathione peroxidase 1
Molecular Weight
22087.94 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nadph binding
Specific Function
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including...
Gene Name
HMGCR
Uniprot ID
P04035
Uniprot Name
3-hydroxy-3-methylglutaryl-coenzyme A reductase
Molecular Weight
97475.155 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tryptophan 2,3-dioxygenase activity
Specific Function
Catalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, cont...
Gene Name
IDO1
Uniprot ID
P14902
Uniprot Name
Indoleamine 2,3-dioxygenase 1
Molecular Weight
45325.89 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Iron ion binding
Specific Function
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name
ALOX5
Uniprot ID
P09917
Uniprot Name
Arachidonate 5-lipoxygenase
Molecular Weight
77982.595 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatidylinositol-4,5-bisphosphate binding
Specific Function
Non-heme iron-containing dioxygenase that catalyzes the stereo-specific peroxidation of free and esterified polyunsaturated fatty acids generating a spectrum of bioactive lipid mediators. Converts ...
Gene Name
ALOX15
Uniprot ID
P16050
Uniprot Name
Arachidonate 15-lipoxygenase
Molecular Weight
74803.795 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Degrades bioactive fatty acid amides to their corresponding acids, with the following preference: N-palmitoylethanolamine > N-myristoylethanolamine > N-lauroylethanolamine = N-stearoylethanolamine > N-arachidonoylethanolamine > N-oleoylethanolamine. Also exhibits weak hydrolytic activity against the ceramides N-lauroylsphingosine and N-palmitoylsphingosine.
Specific Function
Hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
Gene Name
NAAA
Uniprot ID
Q02083
Uniprot Name
N-acylethanolamine-hydrolyzing acid amidase
Molecular Weight
40065.65 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Does not have alcohol dehydrogenase activity. Binds NADP and acts through a one-electron transfer process. Orthoquinones, such as 1,2-naphthoquinone or 9,10-phenanthrenequinone, are the best substr...
Gene Name
CRYZ
Uniprot ID
Q08257
Uniprot Name
Quinone oxidoreductase
Molecular Weight
35206.36 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Hydrolyzes N-acyl-phosphatidylethanolamines (NAPEs) to produce N-acylethanolamines (NAEs) and phosphatidic acid. Responsible for the generation of anandamide (N-arachidonoylethanolamine), the ligand of cannabinoid and vanilloid receptors (By similarity).
Specific Function
Identical protein binding
Gene Name
NAPEPLD
Uniprot ID
Q6IQ20
Uniprot Name
N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
Molecular Weight
45595.15 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
Gene Name
PLA2G1B
Uniprot ID
P04054
Uniprot Name
Phospholipase A2
Molecular Weight
16359.535 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid 17-alpha-monooxygenase activity
Specific Function
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
Gene Name
CYP17A1
Uniprot ID
P05093
Uniprot Name
Steroid 17-alpha-hydroxylase/17,20 lyase
Molecular Weight
57369.995 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name
SOD1
Uniprot ID
P00441
Uniprot Name
Superoxide dismutase [Cu-Zn]
Molecular Weight
15935.685 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sphingomyelin phosphodiesterase activity
Specific Function
Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic ac...
Gene Name
SMPD1
Uniprot ID
P17405
Uniprot Name
Sphingomyelin phosphodiesterase
Molecular Weight
69751.3 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Nucleoside transmembrane transporter activity
Specific Function
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR...
Gene Name
SLC29A1
Uniprot ID
Q99808
Uniprot Name
Equilibrative nucleoside transporter 1
Molecular Weight
50218.805 Da
References
  1. Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914]
  2. Carrier EJ, Auchampach JA, Hillard CJ: Inhibition of an equilibrative nucleoside transporter by cannabidiol: a mechanism of cannabinoid immunosuppression. Proc Natl Acad Sci U S A. 2006 May 16;103(20):7895-900. doi: 10.1073/pnas.0511232103. Epub 2006 May 3. [PubMed:16672367]

Drug created on April 17, 2018 10:41 / Updated on July 02, 2018 19:59