Dexmedetomidine

Identification

Summary

Dexmedetomidine is an alpha-2 agonist used for sedation during various procedures.

Brand Names
Dexdor, Igalmi, 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
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

Administered intravenously, dexmedetomidine is indicated for the sedation of initially intubated and mechanically ventilated patients during treatment in intensive care settings, and for the sedation of non-intubated patients prior to and/or during surgery and other procedures.1 It is also available as a buccally- or sublingually-administered dissolvable film for the acute treatment of agitation associated with schizophrenia or bipolar I or II disorder.2

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAgitation•••••••••••••••••••••
Treatment ofAgitation•••••••••••••••••••••
Adjunct therapy in treatment ofAlcohol withdrawal syndrome••• ••••••••••••••
Contraindications & Blackbox Warnings
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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
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Dexmedetomidine is combined with 1,2-Benzodiazepine.
AbacavirDexmedetomidine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbaloparatideThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Dexmedetomidine can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Dexmedetomidine is combined with Aceclofenac.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dexmedetomidine hydrochloride1018WH7F9I145108-58-3VPNGEIHDPSLNMU-MERQFXBCSA-N
Product Images
International/Other Brands
Dexdor (Orion) / Dexem (Themis Medicare)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DexdorInjection, solution, concentrate100 mcg/mlIntravenousOrion Corporation2021-01-12Not applicableEU flag
DexdorInjection, solution, concentrate100 mcg/mlIntravenousOrion Corporation2021-01-12Not applicableEU flag
DexdorInjection, solution, concentrate100 mcg/mlIntravenousOrion Corporation2021-01-12Not applicableEU flag
DexdorInjection, solution, concentrate100 mcg/mlIntravenousOrion Corporation2021-01-12Not applicableEU flag
DexdorInjection, solution, concentrate100 mcg/mlIntravenousOrion Corporation2021-01-12Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DexmedetomidineInjection, solution100 ug/1mLIntravenousGland Pharma Limited2021-06-28Not applicableUS flag
DexmedetomidineInjection, solution, concentrate100 ug/1mLIntravenousAkorn2014-11-24Not applicableUS flag
DexmedetomidineInjection, solution100 ug/1mLIntravenousMeitheal Pharmaceuticals Inc.2019-01-18Not applicableUS flag
DexmedetomidineInjection, solution100 ug/1mLIntravenousAccord Healthcare Inc.2018-08-31Not applicableUS flag
DexmedetomidineInjection, solution, concentrate100 ug/1mLIntravenousJiangsu Hengrui Medicine Co., Ltd.2017-09-19Not applicableUS flag

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)
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
  1. FDA Approved Drug Products: Precedex (dexmedetomidine hydrochloride) for intravenous injection [Link]
  2. FDA Approved Drug Products: Igalmi (dexmedetomidine) film for sublingual or buccal administration [Link]
  3. UIC Drug Information Group: What evidence is available on the off-label use of dexmedetomidine for alcohol withdrawal syndrome? [Link]
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
PDB Entries
6k41 / 6k42 / 7eja

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingOtherACL Injuries1
4Active Not RecruitingPreventionAbdominal Surgeries / Blood Pressures / Dexmedetomidine / High Risk Patients / Postoperative Complications1
4Active Not RecruitingPreventionAcute Kidney Injury (AKI) / Liver Disease1
4Active Not RecruitingPreventionAnalgesia / Dexmedetomidine / Elderly / Long-term Outcomes / Orthopedic Surgery / Postoperative Delirium (POD)1
4Active Not RecruitingPreventionChronic Postoperative Pain / Dexmedetomidine / Esketamine / Postoperative Analgesia / Scoliosis Correction1

Pharmacoeconomics

Manufacturers
  • Hospira inc
Packagers
  • Hospira Inc.
  • Orion Corporation
Dosage Forms
FormRouteStrength
SolutionIntravenous236.400 mcg
Injection, solution, concentrateParenteral200 mcg/2ml
SolutionIntravenous200.000 µg
Solution100 MCG/ML
Solution, concentrateIntravenous200 mcg
Solution, concentrateIntravenous1000 mcg
Injection, solution, concentrateIntravenous200 mcg/2mL
Injection, solution, concentrateIntravenous100 Mikrogramm/ml
SolutionParenteral4 Mikrogramm/ml
SolutionParenteral8 Mikrogramm/ml
Injection, solution, concentrateIntravenous
SolutionIntravenous0.236 mg
SolutionIntravenous4 mcg
SolutionIntravenous0.2 mg
Injection, solution, concentrateIntravenous100 mcg/ml
Injection, solutionIntravenous4 MICROGRAMMI/ML
Injection, solution, concentrateIntravenous100 MICROGRAMMI/ML
Injection, solution, concentrateIntravenous; Parenteral100 MICROGRAMMI/ML
Injection, solutionIntravenous100 ug/1mL
Injection, solutionIntravenous200 ug/2mL
Injection, solution, concentrateIntravenous100 ?g/ml
InjectionIntravenous100 ug/1mL
InjectionIntravenous200 ug/50mL
InjectionIntravenous400 ug/100mL
Injection, solutionIntravenous200 ug/50mL
Injection, solutionIntravenous4 ug/1mL
Injection, solutionIntravenous400 ug/100mL
Injection, solution, concentrateIntravenous100 ug/1mL
InjectionIntravenous4 ug/1mL
SolutionIntravenous200 mcg / 50 mL
SolutionIntravenous400 mcg / 100 mL
SolutionIntravenous0.1 mg/mL
SolutionIntravenous0.4 mg
SolutionIntravenous200 cg
Injection, solutionIntravenous200 mcg/2ml
SolutionIntravenous236.000 µg
SolutionIntravenous100.000 mcg
Injection, solution, concentrateIntravenous100 mcg/1ml
SolutionIntravenous
FilmSublingual120 ug/1
FilmSublingual180 ug/1
SolutionIntravenous236.000 mg
SolutionIntravenous200.000 mcg
SolutionIntravenous236.000 mcg
InjectionIntravenous
Injection, solutionIntravenous
Injection, solutionIntravenous100 mcg/1ml
SolutionIntravenous100 mcg / mL
SolutionIntravenous4 mcg / mL
SolutionIntravenous200 mcg/2ml
InjectionIntravenous100 mcg/ml
SolutionIntravenous200 mcg
SolutionIntravenous400 mcg
SolutionIntravenous100 mcg
SolutionIntravenous4 mcg/ml
Injection, solution, concentrate200 mcg/2ml
Injection, solutionIntravenous200 mcg/50ml
Injection, solutionIntravenous400 mcg/100ml
Solution118.000 M
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
US10792246No2020-10-062039-06-26US flag
US11497711No2019-06-262039-06-26US flag
US11478422No2019-06-262039-06-26US flag
US11517524No2019-06-262039-06-26US flag
US11786508No2017-12-292037-12-29US flag
US11806334No2023-01-122043-01-12US flag
US11839604No2017-12-292037-12-29US flag
US11890272No2020-07-172040-07-17US flag

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-MSsplash10-001r-3900000000-1af3ca78fb22ea06ac9d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0390000000-830ebe4b019878fb680f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001j-0900000000-4b281b6c3a9d9d3b2a0e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6t-9320000000-2d6e946efa256f0ab6e4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-fc901015a78caad6d8f0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-067i-5900000000-2b70a2b73dacc1115b5b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05o0-2900000000-89806c6093c4a5a71ac4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-154.0301544
predicted
DarkChem Lite v0.1.0
[M-H]-154.1502544
predicted
DarkChem Lite v0.1.0
[M-H]-149.81636
predicted
DeepCCS 1.0 (2019)
[M+H]+155.0281544
predicted
DarkChem Lite v0.1.0
[M+H]+155.0091544
predicted
DarkChem Lite v0.1.0
[M+H]+152.21193
predicted
DeepCCS 1.0 (2019)
[M+Na]+154.7270544
predicted
DarkChem Lite v0.1.0
[M+Na]+154.0196544
predicted
DarkChem Lite v0.1.0
[M+Na]+158.20319
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [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
  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. [Article]
  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. [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
  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. [Article]
  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. [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
  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. [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
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48