Dexmedetomidine
Identification
- Summary
Dexmedetomidine is an alpha-2 agonist used for sedation during various procedures.
- Brand Names
- Dexdor, Precedex
- Generic Name
- Dexmedetomidine
- DrugBank Accession Number
- DB00633
- Background
An agonist of receptors, adrenergic alpha-2 that is used in veterinary medicine for its analgesic and sedative properties. It is the racemate of dexmedetomidine.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Dexmedetomidine (DB00633)
- Weight
- Average: 200.2795
Monoisotopic: 200.131348522 - Chemical Formula
- C13H16N2
- Synonyms
- (+)-4-((S)-alpha,2,3-Trimethylbenzyl)imidazole
- (+)-4-((S)-α,2,3-trimethylbenzyl)imidazole
- Dexmedetomidin
- Dexmedetomidina
- Dexmédétomidine
- Dexmedetomidine
- Dexmedetomidinum
- External IDs
- MPV 1440
- MPV-1440
- TPU 006
Pharmacology
- Indication
For sedation of initially intubated and mechanically ventilated patients during treatment in an intensive care setting, also used in pain relief; anxiety reduction and analgesia
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
- Associated Therapies
- 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
Dexmedetomidine activates 2-adrenoceptors, and causes the decrease of sympathetic tone, with attenuation of the neuroendocrine and hemodynamic responses to anesthesia and surgery; it reduces anesthetic and opioid requirements; and causes sedation and analgesia.
- Mechanism of action
Dexmedetomidine is a specific and selective alpha-2 adrenoceptor agonist. By binding to the presynaptic alpha-2 adrenoceptors, it inhibits the release if norepinephrine, therefore, terminate the propagation of pain signals. Activation of the postsynaptic alpha-2 adrenoceptors inhibits the sympathetic activity decreases blood pressure and heart rate.
Target Actions Organism AAlpha-2A adrenergic receptor agonistHumans - Absorption
Not Available
- Volume of distribution
- 118 L
- Protein binding
94%
- Metabolism
Hepatic
- Route of elimination
A mass balance study demonstrated that after nine days an average of 95% of the radioactivity, following intravenous administration of radiolabeled dexmedetomidine, was recovered in the urine and 4% in the feces. Fractionation of the radioactivity excreted in urine demonstrated that products of N-glucuronidation accounted for approximately 34% of the cumulative urinary excretion. The majority of metabolites are excreted in the urine.
- Half-life
2 hours
- Clearance
- 39 L/h [Healthy volunteers receiving IV infusion (0.2-0.7 mcg/kg/hr)]
- 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
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Dexmedetomidine is combined with 1,2-Benzodiazepine. Abacavir Dexmedetomidine may decrease the excretion rate of Abacavir which could result in a higher serum level. Acebutolol The therapeutic efficacy of Dexmedetomidine can be decreased when used in combination with Acebutolol. Aceclofenac Aceclofenac may decrease the excretion rate of Dexmedetomidine which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Dexmedetomidine which could result in a higher serum level. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Dexmedetomidine. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Dexmedetomidine. Acetazolamide The risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Acetophenazine. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Dexmedetomidine which could result in a higher serum level. 
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- No interactions found.
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- Product Ingredients
Ingredient UNII CAS InChI Key Dexmedetomidine hydrochloride 1018WH7F9I 145108-58-3 VPNGEIHDPSLNMU-MERQFXBCSA-N - Product Images
- International/Other Brands
- Dexdor (Orion) / Dexem (Themis Medicare)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dexdor Injection, solution, concentrate 100 mcg/ml Intravenous Orion Corporation 2021-01-12 Not applicable EU 
Dexdor Injection, solution, concentrate 100 mcg/ml Intravenous Orion Corporation 2021-01-12 Not applicable EU Dexdor Injection, solution, concentrate 100 mcg/ml Intravenous Orion Corporation 2021-01-12 Not applicable EU Dexdor Injection, solution, concentrate 100 mcg/ml Intravenous Orion Corporation 2021-01-12 Not applicable EU Dexdor Injection, solution, concentrate 100 mcg/ml Intravenous Orion Corporation 2021-01-12 Not applicable EU Dexmedetomidine Accord Injection, solution, concentrate 100 ?g/ml Intravenous Accord Healthcare S.L.U. 2020-12-16 Not applicable EU Dexmedetomidine Accord Injection, solution, concentrate 100 ?g/ml Intravenous Accord Healthcare S.L.U. 2020-12-16 Not applicable EU Dexmedetomidine Accord Injection, solution, concentrate 100 ?g/ml Intravenous Accord Healthcare S.L.U. 2020-12-16 Not applicable EU Dexmedetomidine Accord Injection, solution, concentrate 100 ?g/ml Intravenous Accord Healthcare S.L.U. 2020-12-16 Not applicable EU Dexmedetomidine Accord Injection, solution, concentrate 100 ?g/ml Intravenous Accord Healthcare S.L.U. 2020-12-16 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dexmedetomidine Injection, solution 200 ug/2mL Intravenous Piramal Critical Care Inc 2021-05-01 Not applicable US 
Dexmedetomidine Injection, solution, concentrate 100 ug/1mL Intravenous Jiangsu Hengrui Medicine Co., Ltd. 2017-09-19 Not applicable US Dexmedetomidine Injection, solution 100 ug/1mL Intravenous Accord Healthcare Inc. 2018-08-31 Not applicable US Dexmedetomidine Injection, solution 100 ug/1mL Intravenous AuroMedics Pharma LLC 2016-03-17 Not applicable US Dexmedetomidine Injection, solution, concentrate 100 ug/1mL Intravenous Mylan Institutional LLC 2014-08-18 Not applicable US Dexmedetomidine Injection, solution, concentrate 100 ug/1mL Intravenous Medical Purchasing Solutions, LLC. 2018-03-01 Not applicable US Dexmedetomidine Injection, solution 200 ug/2mL Intravenous Piramal Critical Care Inc 2021-01-19 Not applicable US Dexmedetomidine Injection, solution 100 ug/1mL Intravenous Accord Healthcare Inc. 2016-12-21 Not applicable US Dexmedetomidine Injection, solution, concentrate 100 ug/1mL Intravenous Athenex Pharmaceutical Division, Llc. 2018-03-01 Not applicable US Dexmedetomidine Injection, solution 100 ug/1mL Intravenous Meitheal Pharmaceuticals Inc. 2019-01-18 Not applicable US
Categories
- ATC Codes
- N05CM18 — Dexmedetomidine
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-2 Receptor Agonists
- Adrenergic alpha-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anesthetics
- Anesthetics, General
- Bradycardia-Causing Agents
- Central alpha-2 Adrenergic Agonist
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Hypnotics and Sedatives
- Hypotensive Agents
- Imidazoles
- Miscellaneous Anxiolytics Sedatives and Hypnotics
- Nervous System
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Psycholeptics
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as o-xylenes. These are aromatic compounds that contain a o-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 2-positions.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Xylenes
- Direct Parent
- o-Xylenes
- Alternative Parents
- Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / O-xylene / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- medetomidine (CHEBI:4466)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 67VB76HONO
- CAS number
- 113775-47-6
- InChI Key
- CUHVIMMYOGQXCV-NSHDSACASA-N
- InChI
- InChI=1S/C13H16N2/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13/h4-8,11H,1-3H3,(H,14,15)/t11-/m0/s1
- IUPAC Name
- 4-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole
- SMILES
- C[C@H](C1=CNC=N1)C1=C(C)C(C)=CC=C1
References
- Synthesis Reference
Inese Reine, Armands Zandersons, "METHOD FOR PREPARING MEDETOMIDINE AND ITS SALTS.." U.S. Patent US20100048915, issued February 25, 2010.
US20100048915- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014771
- KEGG Drug
- D00514
- KEGG Compound
- C07450
- PubChem Compound
- 5311068
- PubChem Substance
- 46507406
- ChemSpider
- 4470605
- BindingDB
- 50085683
- 48937
- ChEBI
- 4466
- ChEMBL
- CHEMBL778
- ZINC
- ZINC000004632106
- Therapeutic Targets Database
- DAP000233
- PharmGKB
- PA449256
- PDBe Ligand
- CZX
- RxList
- RxList Drug Page
- Wikipedia
- Dexmedetomidine
- PDB Entries
- 6k41 / 6k42
- FDA label
- Download (43.9 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Hospira inc
- Packagers
- Hospira Inc.
- Orion Corporation
- Dosage Forms
Form Route Strength Injection, solution, concentrate Parenteral Injection, solution, concentrate Intravenous 100 mcg/ml Solution Solution, concentrate Intravenous 200 mcg Solution, concentrate Intravenous 1000 mcg Injection, solution, concentrate Intravenous Solution Parenteral Solution Intravenous 0.236 mg Solution Intravenous 0.2 mg Injection, solution Intravenous Injection, solution, concentrate Intravenous; Parenteral Injection, solution Intravenous 100 ug/1mL Injection, solution Intravenous 200 ug/2mL Injection, solution, concentrate Intravenous 100 ?g/ml Injection Intravenous 100 ug/1mL Injection Intravenous 200 ug/50mL Injection Intravenous 4 ug/1mL Injection Intravenous 400 ug/100mL Injection, solution Intravenous 200 ug/50mL Injection, solution Intravenous 4 ug/1mL Injection, solution Intravenous 400 ug/100mL Injection, solution, concentrate Intravenous 100 ug/1mL Solution Intravenous 100 mcg Solution Intravenous 200 mcg / 50 mL Solution Intravenous 400 mcg / 100 mL Solution Intravenous Solution Intravenous 0.4 mg Solution Intravenous 200 cg Injection, solution, concentrate Intravenous 100 mcg/1ml Injection Intravenous Injection, solution Intravenous 100 mcg/1ml Solution Intravenous 100 mcg / mL Solution Intravenous 4 mcg / mL Solution Intravenous 200 mcg Solution Intravenous 400 mcg - Prices
Unit description Cost Unit Precedex 200 mcg/2 ml vial 41.32USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5344840 No 1994-09-06 2011-09-06 US CA2326339 No 2008-12-23 2019-03-31 Canada 
CA1337659 No 1995-11-28 2012-11-28 Canada US8455527 Yes 2013-06-04 2032-07-04 US US6716867 Yes 2004-04-06 2019-10-01 US US8242158 Yes 2012-08-14 2032-07-04 US US8338470 Yes 2012-12-25 2032-07-04 US US8648106 Yes 2014-02-11 2032-07-04 US US9320712 Yes 2016-04-26 2032-07-04 US US9616049 Yes 2017-04-11 2032-07-04 US US9649296 No 2017-05-16 2036-04-20 US US9717796 No 2017-08-01 2036-04-20 US US10016396 No 2018-07-10 2032-01-04 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Freely soluble in water Not Available logP 2.8 Not Available pKa 7.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.174 mg/mL ALOGPS logP 3.28 ALOGPS logP 3.39 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 14.09 ChemAxon pKa (Strongest Basic) 6.54 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 28.68 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 62.98 m3·mol-1 ChemAxon Polarizability 23.32 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9928 Blood Brain Barrier + 0.9663 Caco-2 permeable + 0.5471 P-glycoprotein substrate Non-substrate 0.7118 P-glycoprotein inhibitor I Non-inhibitor 0.8925 P-glycoprotein inhibitor II Non-inhibitor 0.9845 Renal organic cation transporter Non-inhibitor 0.824 CYP450 2C9 substrate Non-substrate 0.8067 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7558 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.5083 CYP450 2D6 inhibitor Non-inhibitor 0.8218 CYP450 2C19 inhibitor Inhibitor 0.8564 CYP450 3A4 inhibitor Inhibitor 0.5684 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6714 Ames test Non AMES toxic 0.6167 Carcinogenicity Non-carcinogens 0.9178 Biodegradation Not ready biodegradable 0.948 Rat acute toxicity 2.4712 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9581 hERG inhibition (predictor II) Non-inhibitor 0.9236
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available 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
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Fairbanks CA, Stone LS, Kitto KF, Nguyen HO, Posthumus IJ, Wilcox GL: alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy. J Pharmacol Exp Ther. 2002 Jan;300(1):282-90. [Article]
- Scheibner J, Trendelenburg AU, Hein L, Starke K, Blandizzi C: Alpha 2-adrenoceptors in the enteric nervous system: a study in alpha 2A-adrenoceptor-deficient mice. Br J Pharmacol. 2002 Feb;135(3):697-704. [Article]
- Davies MF, Tsui J, Flannery JA, Li X, DeLorey TM, Hoffman BB: Activation of alpha2 adrenergic receptors suppresses fear conditioning: expression of c-Fos and phosphorylated CREB in mouse amygdala. Neuropsychopharmacology. 2004 Feb;29(2):229-39. [Article]
- Dawson C, Ma D, Chow A, Maze M: Dexmedetomidine enhances analgesic action of nitrous oxide: mechanisms of action. Anesthesiology. 2004 Apr;100(4):894-904. [Article]
- Ozdogan UK, Lahdesmaki J, Hakala K, Scheinin M: The involvement of alpha 2A-adrenoceptors in morphine analgesia, tolerance and withdrawal in mice. Eur J Pharmacol. 2004 Aug 23;497(2):161-71. [Article]
- Menon DV, Wang Z, Fadel PJ, Arbique D, Leonard D, Li JL, Victor RG, Vongpatanasin W: Central sympatholysis as a novel countermeasure for cocaine-induced sympathetic activation and vasoconstriction in humans. J Am Coll Cardiol. 2007 Aug 14;50(7):626-33. Epub 2007 Jul 30. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Avsaroglu H, Bull S, Maas-Bakker RF, Scherpenisse P, Van Lith HA, Bergwerff AA, Hellebrekers LJ, Van Zutphen LF, Fink-Gremmels J: Differences in hepatic cytochrome P450 activity correlate with the strain-specific biotransformation of medetomidine in AX/JU and IIIVO/JU inbred rabbits. J Vet Pharmacol Ther. 2008 Aug;31(4):368-77. doi: 10.1111/j.1365-2885.2008.00969.x. [Article]
- Duhamel MC, Troncy E, Beaudry F: Metabolic stability and determination of cytochrome P450 isoenzymes' contribution to the metabolism of medetomidine in dog liver microsomes. Biomed Chromatogr. 2010 Aug;24(8):868-77. doi: 10.1002/bmc.1379. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Konstandi M, Lang MA, Kostakis D, Johnson EO, Marselos M: Predominant role of peripheral catecholamines in the stress-induced modulation of CYP1A2 inducibility by benzo(alpha)pyrene. Basic Clin Pharmacol Toxicol. 2008 Jan;102(1):35-44. Epub 2007 Oct 31. [Article]
- Konstandi M, Kostakis D, Harkitis P, Johnson EO, Marselos M, Adamidis K, Lang MA: Benzo(alpha)pyrene-induced up-regulation of CYP1A2 gene expression: role of adrenoceptor-linked signaling pathways. Life Sci. 2006 Jun 20;79(4):331-41. Epub 2006 Feb 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Konstandi M, Kostakis D, Harkitis P, Marselos M, Johnson EO, Adamidis K, Lang MA: Role of adrenoceptor-linked signaling pathways in the regulation of CYP1A1 gene expression. Biochem Pharmacol. 2005 Jan 15;69(2):277-87. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Rodrigues AD, Roberts EM: The in vitro interaction of dexmedetomidine with human liver microsomal cytochrome P4502D6 (CYP2D6). Drug Metab Dispos. 1997 May;25(5):651-5. [Article]
Drug created on June 13, 2005 13:24 / Updated on July 29, 2021 06:27