Dexmedetomidine

Identification

Name
Dexmedetomidine
Accession Number
DB00633
Description

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
Thumb
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

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

TargetActionsOrganism
AAlpha-2A adrenergic receptor
agonist
Humans
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
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
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
AbacavirDexmedetomidine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Dexmedetomidine which could result in a higher serum level.
AcebutololThe therapeutic efficacy of Dexmedetomidine can be decreased when used in combination with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Dexmedetomidine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Dexmedetomidine which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Dexmedetomidine.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Dexmedetomidine.
AcetazolamideThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Acetophenazine.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Dexmedetomidine which could result in a higher serum level.
Additional Data Available
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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dexmedetomidine hydrochloride1018WH7F9I145108-58-3VPNGEIHDPSLNMU-MERQFXBCSA-N
International/Other Brands
Dexdor (Orion) / Dexem (Themis Medicare)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dexmedetomidine HydrochlorideInjection4 ug/1mLIntravenousWG Critical Care, LLC2016-04-19Not applicableUS flag
Dexmedetomidine HydrochlorideInjection, solution, concentrate100 ug/1mLIntravenousWG Critical Care, LLC2016-04-19Not applicableUS flag
Dexmedetomidine HydrochlorideInjection4 ug/1mLIntravenousWG Critical Care, LLC2016-04-19Not applicableUS flag
Dexmedetomidine HydrochlorideInjection, solution, concentrate100 ug/1mLIntravenousWG Critical Care, LLC2016-04-19Not applicableUS flag
Dexmedetomidine Hydrochloride for InjectionSolutionIntravenousAccord Healthcare Inc2019-03-29Not applicableCanada flag
Dexmedetomidine Hydrochloride for InjectionSolution100 mcgIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Dexmedetomidine Hydrochloride for InjectionSolutionIntravenousAuro Pharma Inc2019-10-10Not applicableCanada flag
Dexmedetomidine Hydrochloride for Injection, USPSolutionIntravenousJuno Pharmaceuticals Corp.2019-01-15Not applicableCanada flag
Dexmedetomidine Hydrochloride InjectionSolutionIntravenousJuno Pharmaceuticals Corp.2020-09-30Not applicableCanada flag
Dexmedetomidine Hydrochloride InjectionSolutionIntravenousJuno Pharmaceuticals Corp.2020-09-30Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
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    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
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DexmedetomidineInjection, solution, concentrate100 ug/1mLIntravenousMedical Purchasing Solutions, LLC.2018-03-01Not applicableUS flag
DexmedetomidineInjection, solution, concentrate100 ug/1mLIntravenousJiangsu Hengrui Medicine Co., Ltd.2017-09-19Not applicableUS flag
DexmedetomidineInjection, solution, concentrate100 ug/1mLIntravenousMylan Institutional LLC2014-08-18Not applicableUS flag
DexmedetomidineInjection, solution100 ug/1mLIntravenousAccord Healthcare Inc.2016-12-21Not applicableUS flag
DexmedetomidineInjection, solution, concentrate100 ug/1mLIntravenousAkorn, Inc.2014-11-24Not applicableUS flag
DexmedetomidineInjection, solution100 ug/1mLIntravenousAccord Healthcare Inc.2018-08-31Not applicableUS flag
DexmedetomidineInjection, solution, concentrate100 ug/1mLIntravenousAthenex Pharmaceutical Division, Llc.2018-03-01Not applicableUS flag
DexmedetomidineInjection, solution100 ug/1mLIntravenousAuroMedics Pharma LLC2016-03-17Not applicableUS flag
Dexmedetomidine HClInjection100 ug/1mLIntravenousHikma Pharmaceuticals USA Inc.2017-04-26Not applicableUS flag
Dexmedetomidine HClInjection100 ug/1mLIntravenousMedical Purchasing Solutions, Llc2017-04-26Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
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  • Product Code
    Product Code
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Categories

ATC Codes
N05CM18 — Dexmedetomidine
Drug Categories
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)

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[[email protected]](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
Human Metabolome Database
HMDB0014771
KEGG Drug
D00514
KEGG Compound
C07450
PubChem Compound
5311068
PubChem Substance
46507406
ChemSpider
4470605
BindingDB
50085683
RxNav
48937
ChEBI
4466
ChEMBL
CHEMBL778
ZINC
ZINC000004632106
Therapeutic Targets Database
DAP000233
PharmGKB
PA449256
PDBe Ligand
CZX
RxList
RxList Drug Page
Wikipedia
Dexmedetomidine
AHFS Codes
  • 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics
PDB Entries
6k41 / 6k42
FDA label
Download (43.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingHealth Services ResearchCerebral Palsy (CP) / Developmental Delays / Epilepsies1
4Active Not RecruitingOtherSurgery Ambulatory1
4Active Not RecruitingPreventionAnalgesia / Dexmedetomidine / Elderly / Long-term Outcome / Orthopedic Procedures / Postoperative Delirium1
4Active Not RecruitingPreventionCognitive Impairments / Delirium / Depression / Dexmedetomidine / Postoperative Cognitive Dysfunction1
4Active Not RecruitingPreventionOverall Survival1
4Active Not RecruitingTreatmentAcute Lung Injury (ALI) / Acute Respiratory Distress Syndrome (ARDS) / Illness, Critical / Sleep1
4Active Not RecruitingTreatmentEffect of Sedation on Heart Rate Variability1
4Active Not RecruitingTreatmentHeart Diseases1
4CompletedNot AvailableAdministration Related Reaction / Chloral Hydrate Adverse Reaction / Failed Moderate Sedation During Procedure1
4CompletedNot AvailableAgeing / Dose-Response Relationship / Drugs1

Pharmacoeconomics

Manufacturers
  • Hospira inc
Packagers
  • Hospira Inc.
  • Orion Corporation
Dosage Forms
FormRouteStrength
SolutionIntravenous100 mcg
Injection, solution, concentrateParenteral200 mcg/2ml
Injection, solution, concentrateIntravenous100 Mikrogramm/ml
SolutionParenteral4 Mikrogramm/ml
SolutionIntravenous0.236 mg
SolutionIntravenous0.2 mg
Injection, solution, concentrateIntravenous100 MCG/ML
Injection, solution, concentrateIntravenous100 MICROGRAMMI/ML
Injection, solutionIntravenous100 ug/1mL
InjectionIntravenous100 ug/1mL
InjectionIntravenous200 ug/50mL
InjectionIntravenous4 ug/1mL
InjectionIntravenous400 ug/100mL
Injection, solutionIntravenous4 ug/1mL
Injection, solution, concentrateIntravenous100 ug/1mL
SolutionIntravenous
SolutionIntravenous0.1 mg/mL
SolutionIntravenous0.4 mg
SolutionIntravenous200 cg
Injection, solution, concentrateIntravenous200 mcg/2ml
SolutionIntravenous100 mcg/ml
InjectionIntravenous100 MCG/ML
Injection, solutionIntravenous100 mcg/ml
SolutionIntravenous4 mcg
SolutionIntravenous200 mcg/2ml
SolutionIntravenous400 mcg
SolutionIntravenous200 mcg
Injection, solutionIntravenous200 mcg/2ml
Prices
Unit descriptionCostUnit
Precedex 200 mcg/2 ml vial41.32USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5344840No1994-09-062011-09-06US flag
CA2326339No2008-12-232019-03-31Canada flag
CA1337659No1995-11-282012-11-28Canada flag
US8455527Yes2013-06-042032-07-04US flag
US6716867Yes2004-04-062019-10-01US flag
US8242158Yes2012-08-142032-07-04US flag
US8338470Yes2012-12-252032-07-04US flag
US8648106Yes2014-02-112032-07-04US flag
US9320712Yes2016-04-262032-07-04US flag
US9616049Yes2017-04-112032-07-04US flag
US9649296No2017-05-162036-04-20US flag
US9717796No2017-08-012036-04-20US flag
US10016396No2018-07-102032-01-04US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityFreely soluble in waterNot Available
logP2.8Not Available
pKa7.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.174 mg/mLALOGPS
logP3.28ALOGPS
logP3.39ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)6.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.98 m3·mol-1ChemAxon
Polarizability23.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9928
Blood Brain Barrier+0.9663
Caco-2 permeable+0.5471
P-glycoprotein substrateNon-substrate0.7118
P-glycoprotein inhibitor INon-inhibitor0.8925
P-glycoprotein inhibitor IINon-inhibitor0.9845
Renal organic cation transporterNon-inhibitor0.824
CYP450 2C9 substrateNon-substrate0.8067
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.5083
CYP450 2D6 inhibitorNon-inhibitor0.8218
CYP450 2C19 inhibitorInhibitor0.8564
CYP450 3A4 inhibitorInhibitor0.5684
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6714
Ames testNon AMES toxic0.6167
CarcinogenicityNon-carcinogens0.9178
BiodegradationNot ready biodegradable0.948
Rat acute toxicity2.4712 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9581
hERG inhibition (predictor II)Non-inhibitor0.9236
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
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
  1. 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. [PubMed:11752127]
  2. 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. [PubMed:11834617]
  3. 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. [PubMed:14583739]
  4. 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. [PubMed:15087625]
  5. 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. [PubMed:15306201]
  6. 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. [PubMed:17692748]

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
  1. 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. [PubMed:18638298]
  2. 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. [PubMed:20020418]
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
  1. 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. [PubMed:17973897]
  2. 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. [PubMed:16510159]
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
  1. 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. [PubMed:15627480]
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
  1. 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. [PubMed:9152607]

Drug created on June 13, 2005 07:24 / Updated on November 25, 2020 15:47

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