Identification

Name
Nabilone
Accession Number
DB00486
Description

Nabilone (marketed as Cesamet) is a synthetic form of delta-9-tetrahydrocannabinol (Δ⁹-THC), the primary psychoactive component of cannabis (marijuana). Although structurally distinct from THC, nabilone mimics THC's structure and pharmacological activity through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, however it is considered to be twice as active as Δ⁹-THC. Nabilone is approved by the FDA 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 5. 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 Nabilone or Dronabinol), 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 6. 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 7. 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 8.

In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the United States FDA for treatment of chemotherapy-induced nausea and vomiting that has not responded to conventional antiemetics. Though it was approved by the FDA in 1985, the drug only began marketing in the United States in 2006. It is also approved for use in treatment of anorexia and weight loss in patients with AIDS.

Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 372.5408
Monoisotopic: 372.266445018
Chemical Formula
C24H36O3
Synonyms
  • Nabilon
  • Nabilona
  • Nabilone
  • Nabilonum
External IDs
  • Cpd 109514
  • LY 109 514

Pharmacology

Indication

Nabilone is indicated for the treatment of the nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments. This restriction is required because a substantial proportion of any group of patients treated with Nabilone can be expected to experience disturbing psychotomimetic reactions not observed with other antiemetic agents.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Nabilone is a cannabinoid with therapeutic uses. It is an analog of dronabinol (also known as tetrahydrocannabinol or THC), the psychoactive ingredient in cannabis. Although structurally distinct from THC, nabilone mimics THC's structure and pharmacological activity through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, however it is considered to be twice as active as Δ⁹-THC.

Mechanism of action

Nabilone is an orally active synthetic cannabinoid which, like other cannabinoids, has complex effects on the central nervous system (CNS). It has been suggested that the antiemetic effect of nabilone is caused by interaction with the cannabinoid receptor system, i.e., the CB (1) receptor, which is a component of the endocannabinoid system of the body.

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 7. 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 8.

TargetActionsOrganism
ACannabinoid receptor 2
partial agonist
Humans
ACannabinoid receptor 1
partial agonist
Humans
Absorption

Nabilone appears to be completely absorbed from the human gastrointestinal tract when administered orally. Following oral administration of a 2 mg dose of radiolabeled nabilone, peak plasma concentrations of approximately 2 ng/mL nabilone and 10 ng equivalents/mL total radioactivity are achieved within 2.0 hours.

Volume of distribution

The apparent volume of distribution of nabilone is about 12.5 L/kg.

Protein binding
Not Available
Metabolism

Hepatic. Two metabolic pathways have been suggested. The major pathway probably involves the direct oxidation of Nabilone to produce hydroxylic and carboxylic analogues. These compounds are thought to account for the remaining plasma radioactivity when carbinol metabolites have been extracted.

Route of elimination

The route and rate of the elimination of nabilone and its metabolites are similar to those observed with other cannabinoids, including delta-9-THC (dronabinol). When nabilone is administered intravenously, the drug and its metabolites are eliminated mainly in the feces (approximately 67%) and to a lesser extent in the urine (approximately 22%) within 7 days. Of the 67% recovered from the feces, 5% corresponded to the parent compound and 16% to its carbinol metabolite. Following oral administration about 60% of nabilone and its metabolites were recovered in the feces and about 24% in urine. Therefore, it appears that the major excretory pathway is the biliary system.

Half-life

The plasma half-life (T1/2) values for nabilone and total radioactivity of identified and unidentified metabolites are about 2 and 35 hours, respectively.

Clearance
Not Available
Adverse Effects
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Toxicity

Symptoms of overdose include difficulty in breathing, hallucinations, mental changes (severe), nervousness or anxiety (severe). Monkeys treated with Nabilone at doses as high as 2mg/kg/day for a year experienced no significant adverse events. This result contrasts with the finding in a planned 1-year dog study that was prematurely terminated because of deaths associated with convulsions in dogs receiving as little as 0.5mg/kg/day. The earliest deaths, however, occurred at 56 days in dogs receiving 2mg/kg/day. The unusual vulnerability of the dog is not understood; it is hypothesised, however, that the explanation lies in the fact that the dog differs markedly from other species (including humans) in its metabolism of Nabilone.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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.
DrugInteraction
AcebutololThe risk or severity of Tachycardia can be increased when Nabilone is combined with Acebutolol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Nabilone.
AcetaminophenNabilone may increase the hepatotoxic activities of Acetaminophen.
AcetazolamideNabilone may increase the central nervous system depressant (CNS depressant) activities of Acetazolamide.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Nabilone.
AcetophenazineNabilone may increase the central nervous system depressant (CNS depressant) activities of Acetophenazine.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Nabilone.
AclidiniumThe risk or severity of Tachycardia and drowsiness can be increased when Aclidinium is combined with Nabilone.
AdenosineThe risk or severity of Tachycardia can be increased when Nabilone is combined with Adenosine.
AgomelatineNabilone may increase the central nervous system depressant (CNS depressant) activities of Agomelatine.
Additional Data Available
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  • Action
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Food Interactions
  • Avoid alcohol.
  • Take with or without food. Food does not significantly affect absorption.

Products

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International/Other Brands
Nabilone (Meda)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CesametCapsule1 mg/1OralMEDA Pharmaceuticals2010-03-012020-03-31US flag
CesametCapsule1 mg/1OralValeant Pharmaceuticals North America2009-11-012017-11-13US flag
CesametCapsule1 mg/1OralBausch Health US LLC2020-03-09Not applicableUS flag
CesametCapsule1 mg/1OralValeant Pharmaceuticals North America2017-11-122017-11-13US flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
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Categories

ATC Codes
A04AD11 — Nabilone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Naphthopyrans
Sub Class
Naphthopyranones
Direct Parent
Naphthopyranones
Alternative Parents
2,2-dimethyl-1-benzopyrans / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Cyclic ketones / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
Substituents
1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2,2-dimethyl-1-benzopyran / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Carbonyl group / Chromane
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
2N4O9L084N
CAS number
51022-71-0
InChI Key
GECBBEABIDMGGL-RTBURBONSA-N
InChI
InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1
IUPAC Name
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one
SMILES
[H][[email protected]@]12CC(=O)CC[[email protected]@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC

References

General References
  1. Cunningham D, Bradley CJ, Forrest GJ, Hutcheon AW, Adams L, Sneddon M, Harding M, Kerr DJ, Soukop M, Kaye SB: A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. Eur J Cancer Clin Oncol. 1988 Apr;24(4):685-9. [PubMed:2838294]
  2. Niiranen A, Mattson K: Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy. Am J Clin Oncol. 1987 Aug;10(4):325-9. [PubMed:3039831]
  3. Herman TS, Einhorn LH, Jones SE, Nagy C, Chester AB, Dean JC, Furnas B, Williams SD, Leigh SA, Dorr RT, Moon TE: Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. N Engl J Med. 1979 Jun 7;300(23):1295-7. [PubMed:375088]
  4. Einhorn LH, Nagy C, Furnas B, Williams SD: Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):64S-69S. [PubMed:6271844]
  5. 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. [PubMed:16199061]
  6. Sharma P, Murthy P, Bharath MM: Chemistry, metabolism, and toxicology of cannabis: clinical implications. Iran J Psychiatry. 2012 Fall;7(4):149-56. [PubMed:23408483]
  7. 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. [PubMed:26015168]
  8. Kaur R, Ambwani SR, Singh S: Endocannabinoid System: A Multi-Facet Therapeutic Target. Curr Clin Pharmacol. 2016;11(2):110-7. [PubMed:27086601]
Human Metabolome Database
HMDB0014629
KEGG Drug
D05099
PubChem Compound
5284592
PubChem Substance
46505171
ChemSpider
4447641
BindingDB
50287941
RxNav
31447
ChEMBL
CHEMBL947
ZINC
ZINC000001542930
Therapeutic Targets Database
DAP000067
PharmGKB
PA164746998
Drugs.com
Drugs.com Drug Page
Wikipedia
Nabilone
AHFS Codes
  • 56:22.92 — Miscellaneous Antiemetics
FDA label
Download (94.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAntineoplastic Combined Chemotherapy Protocols / Peripheral neuropathy1
4CompletedTreatmentDiabetic Neuropathies1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentDisseminated Sclerosis / Pain, Neuropathic1
4TerminatedTreatmentNausea and vomiting1
3Not Yet RecruitingTreatmentAgitation / Alzheimer's Disease (AD)1
3RecruitingTreatmentParkinson's Disease (PD)1
3Unknown StatusTreatmentDiabetic Neuropathies1
2CompletedPreventionPost Operative Nausea and Vomiting (PONV)1
2CompletedTreatmentFibromyalgia1

Pharmacoeconomics

Manufacturers
  • Meda pharmaceuticals inc
Packagers
  • Meda AB
  • Valeant Ltd.
Dosage Forms
FormRouteStrength
CapsuleOral1 mg
CapsuleOral0.25 mg
CapsuleOral0.5 mg
CapsuleOral1 mg/1
CapsuleOral
Prices
Unit descriptionCostUnit
Cesamet 1 mg capsule13.99USD capsule
Cesamet 0.5 mg Capsule3.49USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP6.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000493 mg/mLALOGPS
logP7.5ALOGPS
logP6.36ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.2 m3·mol-1ChemAxon
Polarizability44.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9954
Blood Brain Barrier+0.9575
Caco-2 permeable+0.7787
P-glycoprotein substrateSubstrate0.8103
P-glycoprotein inhibitor INon-inhibitor0.7926
P-glycoprotein inhibitor IIInhibitor0.6054
Renal organic cation transporterNon-inhibitor0.836
CYP450 2C9 substrateNon-substrate0.7385
CYP450 2D6 substrateNon-substrate0.8433
CYP450 3A4 substrateSubstrate0.6842
CYP450 1A2 substrateNon-inhibitor0.6601
CYP450 2C9 inhibitorNon-inhibitor0.714
CYP450 2D6 inhibitorNon-inhibitor0.9059
CYP450 2C19 inhibitorNon-inhibitor0.6521
CYP450 3A4 inhibitorNon-inhibitor0.8654
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7642
Ames testNon AMES toxic0.8337
CarcinogenicityNon-carcinogens0.8598
BiodegradationNot ready biodegradable0.9948
Rat acute toxicity2.5397 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9159
hERG inhibition (predictor II)Non-inhibitor0.7654
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial 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
  1. Conti S, Costa B, Colleoni M, Parolaro D, Giagnoni G: Antiinflammatory action of endocannabinoid palmitoylethanolamide and the synthetic cannabinoid nabilone in a model of acute inflammation in the rat. Br J Pharmacol. 2002 Jan;135(1):181-7. [PubMed:11786493]
  2. Mendizabal VE, Adler-Graschinsky E: Cannabinoids as therapeutic agents in cardiovascular disease: a tale of passions and illusions. Br J Pharmacol. 2007 Jun;151(4):427-40. Epub 2007 Apr 23. [PubMed:17450170]
  3. 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. [PubMed:17139494]
  4. Kraft B, Kress HG: [Cannabinoids and the immune system. Of men, mice and cells]. Schmerz. 2004 Jun;18(3):203-10. [PubMed:15221424]
  5. Darmani NA: The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2. Eur J Pharmacol. 2001 Oct 26;430(1):49-58. [PubMed:11698062]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial 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
  1. 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. [PubMed:17139494]
  2. Darmani NA: The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2. Eur J Pharmacol. 2001 Oct 26;430(1):49-58. [PubMed:11698062]
  3. Hirst RA, Almond SL, Lambert DG: Characterisation of the rat cerebella CB1 receptor using SR141716A, a central cannabinoid receptor antagonist. Neurosci Lett. 1996 Dec 13;220(2):101-4. [PubMed:8981483]
  4. Pertwee RG: Cannabis and cannabinoids: pharmacology and rationale for clinical use. Forsch Komplementarmed. 1999 Oct;6 Suppl 3:12-5. [PubMed:10575283]
  5. Pertwee RG, Fernando SR: Evidence for the presence of cannabinoid CB1 receptors in mouse urinary bladder. Br J Pharmacol. 1996 Aug;118(8):2053-8. [PubMed:8864542]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Nabilone FDA Label [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
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

Drug created on June 13, 2005 07:24 / Updated on November 23, 2020 09:08

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