Dronabinol
Identification
- Summary
Dronabinol is a synthetic delta-9-THC used in the treatment of anorexia and weight loss in HIV patients as well as nausea and vomiting in cancer chemotherapy.
- Brand Names
- Marinol, Sativex, Syndros
- Generic Name
- Dronabinol
- DrugBank Accession Number
- DB00470
- Background
Dronabinol (marketed as Marinol) is a synthetic form of delta-9-tetrahydrocannabinol (Δ⁹-THC), the primary psychoactive component of cannabis (marijuana). THC demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, which results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. Due to its evidence as an appetite stimulant and an anti-nauseant, Dronabinol is approved for use in anorexia associated with weight loss in patients with AIDS and for the treatment of nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments Label.
Tetrahydrocannabinol (THC) and cannabidiol (CBD) are the two most abundant cannabinoids found naturally in the resin of the marijuana plant, both of which are pharmacologically active due to their interaction with cannabinoid receptors that are found throughout the body 4. While both CBD and THC are used for medicinal purposes, they have different receptor activity, function, and physiological effects. If not provided in their activated form (such as through synthetic forms like Dronabinol or Nabilone), THC and CBD are obtained through conversion from their precursors, tetrahydrocannabinolic acid-A (THCA-A) and cannabidiolic acid (CBDA), through decarboxylation reactions. This can be achieved through heating, smoking, vaporization, or baking of dried unfertilized female cannabis flowers.
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 endogenous cannabinoid receptors of the body 1. The endocannabinoid system is widely distributed throughout the central and peripheral nervous system (via the Cannabinoid Receptors CB1 and CB2) and plays a role in many physiological processes such as inflammation, cardiovascular function, learning, pain, memory, stress and emotional regulation, and the sleep/wake cycle among many others 2. CB1 receptors are found in both the central and peripheral nervous system, and are most abundant in the hippocampus and amygdala, which are the areas of the brain responsible for short-term memory storage and emotional regulation. CB2 receptors are mainly located in the peripheral nervous system and can be found on lymphoid tissue where they are involved in regulation of immune function 3.
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Dronabinol (DB00470)
- Weight
- Average: 314.4617
Monoisotopic: 314.224580204 - Chemical Formula
- C21H30O2
- Synonyms
- (-)-delta9-trans-Tetrahydrocannabinol
- 1-trans-delta-9-Tetrahydrocannabinol
- 3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-ol
- 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
- delta-9-tetrahydrocannabinol
- delta-9-THC
- delta(1)-tetrahydrocannabinol
- delta(9)-THC
- delta9-tetrahydrocannabinol
- Dronabinol
- Dronabinolum
- Tetrahydrocannabinol
- THC
- Δ9-tetrahydrocannabinol
- External IDs
- Abbott 40566
- ABBOTT-40566
- Dea No. 7369
- Dea No. 7370
- J882F
- NSC-134454
- QCD 84924
- QCD-84924
- SP 104
- SP-104
Pharmacology
- Indication
For the treatment of anorexia associated with weight loss in patients with AIDS, and nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Associated Conditions
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Marinol may has complex effects on the central nervous system (CNS), including cannabinoid receptors. Dronabinol may inhibit endorphins in the emetic center, suppress prostaglandin synthesis, and/or inhibit medullary activity through an unspecified cortical action.
- Mechanism of action
Dronabinol is a synthetic form of delta-9-tetrahydrocannabinol (Δ⁹-THC), the primary psychoactive component of cannabis (marijuana). THC demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, which results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes.
Target Actions Organism ACannabinoid receptor 1 agonistHumans UCannabinoid receptor 2 agonistHumans - Absorption
Dronabinol capsules are almost completely absorbed (90 to 95%) after single oral doses. Due to the combined effects of first pass hepatic metabolism and high lipid solubility, only 10 to 20% of the administered dose reaches the systemic circulation. After oral administration, dronabinol has an onset of action of approximately 0.5 to 1 hours and peak effect at 2 to 4 hours. Following BID dosing of 2.5mg of dronabinol, Cmax was found to be 1.32ng/mL with a median Tmax of 1.00 hr.
- Volume of distribution
Dronabinol has a large apparent volume of distribution, approximately 10 L/kg, because of its lipid solubility.
- Protein binding
The plasma protein binding of dronabinol and its metabolites is approximately 97%.
- Metabolism
THC is primarily metabolized in the liver by microsomal hydroxylation and oxidation reactions catalyzed by Cytochrome P450 enzymes. 11-hydroxy-▵9-tetrahydrocannabinol (11-OH-THC) is the primary active metabolite, capable of producing psychological and behavioural effects, which is then metabolized into 11-nor-9-carboxy-▵ 9-tetrahydrocannabinol (THC-COOH), THC's primary inactive metabolite 1. Dronabinol and its principal active metabolite, 11-OH-delta-9-THC, are present in approximately equal concentrations in plasma. Concentrations of both parent drug and metabolite peak at approximately 0.5 to 4 hours after oral dosing and decline over several days Label.
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- Route of elimination
Dronabinol and its biotransformation products are excreted in both feces and urine. Because of its large volume of distribution, dronabinol and its metabolites may be excreted at low levels for prolonged periods of time. Following single dose administration, low levels of dronabinol metabolites have been detected for more than 5 weeks in the urine and feces.
- Half-life
The elimination phase of dronabinol can be described using a two compartment model with an initial (alpha) half-life of about 4 hours and a terminal (beta) half-life of 25 to 36 hours.
- Clearance
Values for clearance average about 0.2 L/kg-hr, but are highly variable due to the complexity of cannabinoid distribution.
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C9 CYP2C9*2 Not Available 430C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*3 Not Available 1075A>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*4 Not Available 1076T>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*5 Not Available 1080C>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*8 Not Available 449G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*11 Not Available 1003C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*12 Not Available 1465C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*13 Not Available 269T>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*14 Not Available 374G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*16 Not Available 895A>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*18 Not Available 1075A>C / 1190A>C … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*26 Not Available 389C>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*28 Not Available 641A>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*30 Not Available 1429G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*33 Not Available 395G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*6 Not Available 818delA Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*15 Not Available 485C>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*25 Not Available 353_362delAGAAATGGAA Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*35 Not Available 374G>T / 430C>T Effect Inferred Poor drug metabolizer. Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine Dronabinol may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine. Abametapir The serum concentration of Dronabinol can be increased when it is combined with Abametapir. Abatacept The metabolism of Dronabinol can be increased when combined with Abatacept. Abemaciclib Dronabinol may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Abiraterone The metabolism of Dronabinol can be decreased when combined with Abiraterone. Acebutolol The risk or severity of Tachycardia can be increased when Dronabinol is combined with Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Dronabinol. Acetazolamide Dronabinol may increase the central nervous system depressant (CNS depressant) activities of Acetazolamide. Acetohexamide The metabolism of Dronabinol can be decreased when combined with Acetohexamide. Acetophenazine Dronabinol may increase the central nervous system depressant (CNS depressant) activities of Acetophenazine. 
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- Avoid alcohol.
- Take with or without food. The absorption is unaffected by food.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dronabinol Capsule 2.5 mg/1 Oral Major Pharmaceuticals 2017-05-10 Not applicable US 
Dronabinol Capsule 5 mg/1 Oral Actavis Pharma, Inc. 2005-06-07 2019-05-31 US Dronabinol Capsule 2.5 mg/1 Oral Ascend Laboratories, LLC 2017-05-10 2021-09-30 US Dronabinol Capsule 5 mg/1 Oral Major Pharmaceuticals 2021-03-03 Not applicable US Dronabinol Capsule 5 mg/1 Oral Ascend Laboratories, LLC 2021-03-03 Not applicable US Dronabinol Capsule 10 mg/1 Oral Actavis Pharma, Inc. 1994-08-11 2019-09-30 US Dronabinol Capsule 10 mg/1 Oral Ascend Laboratories, LLC 2017-05-10 2021-09-30 US Dronabinol Capsule 2.5 mg/1 Oral Major Pharmaceuticals 2021-03-03 Not applicable US Dronabinol Capsule 2.5 mg/1 Oral Ascend Laboratories, LLC 2021-03-03 Not applicable US Dronabinol Capsule 2.5 mg/1 Oral Actavis Pharma, Inc. 1994-08-11 2019-05-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dronabinol Capsule 2.5 mg/1 Oral AvKARE 2020-03-16 Not applicable US Dronabinol Capsule 5 mg/1 Oral American Health Packaging 2018-08-09 Not applicable US Dronabinol Capsule 5 mg/1 Oral Rhodes Pharmaceuticals L.P. 2018-06-26 Not applicable US Dronabinol Capsule 5 mg/1 Oral Par Pharmaceutical, Inc. 2008-06-27 Not applicable US Dronabinol Capsule 5 mg/1 Oral Akorn, Inc. 2014-06-20 Not applicable US Dronabinol Capsule 2.5 mg/1 Oral Camber Pharmaceuticals Inc 2020-02-10 Not applicable US Dronabinol Capsule, liquid filled 5 mg/1 Oral Mylan Pharmaceuticals 2011-11-01 2016-06-30 US Dronabinol Capsule 5 mg/1 Oral Major Pharmaceuticals 2018-06-26 Not applicable US Dronabinol Capsule 5 mg/1 Oral Lannett Company, Inc. 2018-05-18 Not applicable US Dronabinol Capsule 2.5 mg/1 Oral American Health Packaging 2010-06-02 2020-01-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image SATIVEX Dronabinol (27 mg) + Cannabidiol (25 mg) Solution Buccal; Oral GW PHARMA LTD 2016-08-17 Not applicable Colombia 
Sativex Dronabinol (2.7 mg / act) + Cannabidiol (2.5 mg / act) Spray Buccal Gw Pharma Limited 2005-06-22 Not applicable Canada 
Categories
- ATC Codes
- A04AD10 — Dronabinol
- Drug Categories
- Agents producing tachycardia
- Alimentary Tract and Metabolism
- Analgesics
- Analgesics, Non-Narcotic
- Antiemetics and Antinauseants
- BCRP/ABCG2 Inhibitors
- Cannabinoid Receptor Agonists
- Cannabinoids and similars
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Hallucinogens
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Miscellaneous Antiemetics
- Neurotransmitter Agents
- P-glycoprotein inhibitors
- Peripheral Nervous System Agents
- Psychotropic Drugs
- Sensory System Agents
- Terpenes
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrans
- Sub Class
- 1-benzopyrans
- Direct Parent
- 2,2-dimethyl-1-benzopyrans
- Alternative Parents
- Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Oxacyclic compounds / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2,2-dimethyl-1-benzopyran / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenoid / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- polyketide, diterpenoid, phytocannabinoid, benzochromene (CHEBI:66964) / Cannabinoids (C06972)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7J8897W37S
- CAS number
- 1972-08-3
- InChI Key
- CYQFCXCEBYINGO-IAGOWNOFSA-N
- InChI
- InChI=1S/C21H30O2/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/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
- IUPAC Name
- (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
- SMILES
- [H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=C2C(O)=CC(CCCCC)=C1
References
- Synthesis Reference
Fabio E.S. SOUZA, Jason E. FIELD, Ming PAN, "INTERMEDIATE COMPOUNDS IN THE SYNTHESIS OF DRONABINOL." U.S. Patent US20080312465, issued December 18, 2008.
US20080312465- General References
- Sharma P, Murthy P, Bharath MM: Chemistry, metabolism, and toxicology of cannabis: clinical implications. Iran J Psychiatry. 2012 Fall;7(4):149-56. [Article]
- Baron EP: Comprehensive Review of Medicinal Marijuana, Cannabinoids, and Therapeutic Implications in Medicine and Headache: What a Long Strange Trip It's Been .... Headache. 2015 Jun;55(6):885-916. doi: 10.1111/head.12570. Epub 2015 May 25. [Article]
- Kaur R, Ambwani SR, Singh S: Endocannabinoid System: A Multi-Facet Therapeutic Target. Curr Clin Pharmacol. 2016;11(2):110-7. [Article]
- Elsohly MA, Slade D: Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci. 2005 Dec 22;78(5):539-48. doi: 10.1016/j.lfs.2005.09.011. Epub 2005 Sep 30. [Article]
- Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
- External Links
- Human Metabolome Database
- HMDB0014613
- KEGG Drug
- D00306
- KEGG Compound
- C06972
- PubChem Compound
- 16078
- PubChem Substance
- 46508472
- ChemSpider
- 15266
- BindingDB
- 60994
- 10402
- ChEBI
- 66964
- ChEMBL
- CHEMBL465
- ZINC
- ZINC000001530625
- Therapeutic Targets Database
- DAP000207
- PharmGKB
- PA449421
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- TCI
- RxList
- RxList Drug Page
- Wikipedia
- Dronabinol
- PDB Entries
- 3ls4 / 6mp4
- FDA label
- Download (414 KB)
- MSDS
- Download (51.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Healthy Volunteers 1 4 Completed Basic Science Post Traumatic Stress Disorder (PTSD) 1 4 Completed Treatment Chest Pain 1 4 Completed Treatment Disseminated Sclerosis / Spasticity 1 4 Completed Treatment Medical Abortion / Pain 1 4 Enrolling by Invitation Treatment Postoperative pain 1 4 Not Yet Recruiting Basic Science Accidents, Traffic / Alcohol, Drinking / Cannabis 1 4 Recruiting Diagnostic Intoxication Alcohol / Intoxication Combined Alcohol THC / Intoxication THC 1 4 Recruiting Other Cannabis Use / Pregnancy Related 1 4 Recruiting Supportive Care Head and Neck Carcinoma / Lung Cancers / Malignant Neoplasm of Pancreas / Nutrition Poor / Oncologic Complications / Quality of Life 1
Pharmacoeconomics
- Manufacturers
- Svc pharma lp
- Abbott products inc
- Roxane Laboratories,Inc.
- Packagers
- Banner Pharmacaps Inc.
- GW Pharma Ltd.
- Par Pharmaceuticals
- Pharmaceutics International Inc.
- Physicians Total Care Inc.
- Southwood Pharmaceuticals
- UNIMED
- Unimed Pharmaceuticals Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Capsule Oral 10 mg/1 Capsule Oral 5 mg/1 Capsule, liquid filled Oral 10 mg/1 Capsule, liquid filled Oral 2.5 mg/1 Capsule, liquid filled Oral 5 mg/1 Capsule Oral 2.5 mg/1 Capsule Oral 2.5 mg Capsule Oral 5 mg Capsule Oral 10 mg Solution Buccal; Oral Spray Buccal Spray, metered Transmucosal Solution Oral 5 mg/1mL - Prices
Unit description Cost Unit Marinol 10 mg capsule 29.86USD capsule Dronabinol 10 mg capsule 19.26USD capsule Marinol 5 mg capsule 16.0USD capsule Dronabinol 5 mg capsule 11.8USD capsule Marinol 2.5 mg capsule 8.02USD capsule Dronabinol 2.5 mg capsule 5.11USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6703418 No 2004-03-09 2011-02-26 US US8222292 No 2012-07-17 2028-08-06 US US9345771 No 2016-05-24 2028-08-06 US US10265293 No 2019-04-23 2028-08-06 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 200 °C at 2.00E-02 mm Hg Not Available water solubility 2800 mg/L (at 23 °C) NIH NTP Reports web-site logP 5.648 Not Available pKa 10.6 PHYSICIAN'S DESK REFERENCE (1998) - Predicted Properties
Property Value Source Water Solubility 0.00263 mg/mL ALOGPS logP 7.29 ALOGPS logP 5.94 ChemAxon logS -5.1 ALOGPS pKa (Strongest Acidic) 9.34 ChemAxon pKa (Strongest Basic) -4.9 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 29.46 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 96.73 m3·mol-1 ChemAxon Polarizability 38.96 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9949 Blood Brain Barrier + 0.9685 Caco-2 permeable + 0.7607 P-glycoprotein substrate Substrate 0.8458 P-glycoprotein inhibitor I Non-inhibitor 0.5548 P-glycoprotein inhibitor II Inhibitor 0.7191 Renal organic cation transporter Non-inhibitor 0.8169 CYP450 2C9 substrate Non-substrate 0.7522 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7199 CYP450 1A2 substrate Inhibitor 0.6567 CYP450 2C9 inhibitor Inhibitor 0.5352 CYP450 2D6 inhibitor Non-inhibitor 0.7307 CYP450 2C19 inhibitor Inhibitor 0.7683 CYP450 3A4 inhibitor Non-inhibitor 0.6771 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8349 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.8947 Biodegradation Not ready biodegradable 0.9725 Rat acute toxicity 2.5940 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7714 hERG inhibition (predictor II) Non-inhibitor 0.8136
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-01pp-4792000000-06532e533cb7794b7c37 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Pryce G, Giovannoni G, Baker D: Mifepristone or inhibition of 11beta-hydroxylase activity potentiates the sedating effects of the cannabinoid receptor-1 agonist Delta(9)-tetrahydrocannabinol in mice. Neurosci Lett. 2003 May 1;341(2):164-6. [Article]
- Tsai SJ, Wang YC, Hong CJ: Association study of a cannabinoid receptor gene (CNR1) polymorphism and schizophrenia. Psychiatr Genet. 2000 Sep;10(3):149-51. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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
References
- Davis M, Maida V, Daeninck P, Pergolizzi J: The emerging role of cannabinoid neuromodulators in symptom management. Support Care Cancer. 2007 Jan;15(1):63-71. Epub 2006 Dec 1. [Article]
- Pertwee RG: Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411. doi: 10.1111/j.1476-5381.2008.00048.x. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Bland TM, Haining RL, Tracy TS, Callery PS: CYP2C-catalyzed delta9-tetrahydrocannabinol metabolism: kinetics, pharmacogenetics and interaction with phenytoin. Biochem Pharmacol. 2005 Oct 1;70(7):1096-103. doi: 10.1016/j.bcp.2005.07.007. [Article]
- Sachse-Seeboth C, Pfeil J, Sehrt D, Meineke I, Tzvetkov M, Bruns E, Poser W, Vormfelde SV, Brockmoller J: Interindividual variation in the pharmacokinetics of Delta9-tetrahydrocannabinol as related to genetic polymorphisms in CYP2C9. Clin Pharmacol Ther. 2009 Mar;85(3):273-6. doi: 10.1038/clpt.2008.213. Epub 2008 Nov 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Cannabinoids can cause dysregulation of P-glycoprotein but at higher concentrations than are normally present in cannabis smokers.
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [Article]
- Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [Article]
Drug created on June 13, 2005 13:24 / Updated on July 23, 2021 16:03