DEXMEDETOMIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H16N2
Molecular Weight	200.2795
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](C1=CN=CN1)C2=C(C)C(C)=CC=C2

InChI

InChIKey=CUHVIMMYOGQXCV-NSHDSACASA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16369581
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf

Dexmedetomide (biologically active dextroisomer of medetomidine) is an alpha2-adrenergic agonist which was approved by FDA for the sedation purposes. Upon administration the drug activates the alpha2 receptors thus inhibiting the release of norepinephrine and terminating the propagation of pain signals. Also it inhibits sympathetic activity and thus can decrease blood pressure and heart rate.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf	Agonist 2637

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 607 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf	Preventing		Approved 8307	PRECEDEX Approved Use Dexmedetomidine hydrochloride injection is a relatively selective alpha2-adrenergic agonist indicated for: 1) Sedation of initially intubated and mechanically ventilated patients during treatment in an intensive care setting. Administer Precedex by continuous infusion not to exceed 24 hours. 2) Sedation of non-intubated patients prior to and/or during surgical and other procedures. Launch Date 9.4538878E11

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4466	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4466
ChemicalBook	CB41017166	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB41017166
MolPort	MolPort-035-395-718	https://www.molport.com/shop/molecule-link/MolPort-035-395-718
Selleck Chemicals	dexmedetomidine	http://www.selleckchem.com/products/dexmedetomidine.html
ZINC	ZINC000004632106	http://zinc15.docking.org/substances/ZINC000004632106

PubMed

Title	Date	PubMed
Noradrenergic regulation of hippocampal place cells.	2001	11811674
Calcification of the intervertebral discs and curvature of the radius and ulna: a radiographic survey of Finnish miniature dachshunds.	2001	11503367
Sedative, analgesic, and cardiovascular effects of levomedetomidine alone and in combination with dexmedetomidine in dogs.	2001 Apr	11327474
Contribution of alpha(2) receptor subtypes to nerve injury-induced pain and its regulation by dexmedetomidine.	2001 Apr	11309255
Evaluation of the alpha2C-adrenoceptor as a neuropsychiatric drug target studies in transgenic mouse models.	2001 Apr 6	11358337
Dextromethorphan and dexmedetomidine: new agents for the control of perioperative pain.	2001 Aug	11716440
Dexmedetomidine.	2001 Aug	11571417
A study of presynaptic alpha2-autoreceptors in alpha2A/D-, alpha2B- and alpha2C-adrenoceptor-deficient mice.	2001 Aug	11534851
[Medetomidine-butorphanol combination anesthesia in the dog].	2001 Dec	11776718
alpha2A-adrenoceptor stimulation reduces capsaicin-induced glutamate release from spinal cord synaptosomes.	2001 Dec	11714880
Sedative but not analgesic alpha2 agonist tolerance is blocked by NMDA receptor and nitric oxide synthase inhibitors.	2001 Jul	11465557
Comparison of medetomidine and dexmedetomidine as premedicants in dogs undergoing propofol-isoflurane anesthesia.	2001 Jul	11453483
Effects of reduced sympathetic activity on myocardial metaiodobenzylguanidine (MIBG) washout.	2001 Jun	11844024
In vitro release of dexmedetomidine from silica xerogel monoliths: effect of sol-gel synthesis parameters.	2001 Jun 19	11397572
Anaesthesia of roan antelope (Hippotragus equinus) with a combination of A3080, medetomidine and ketamine.	2001 Mar	11563714
Comparison of medetomidine and dexmedetomidine as premedication in isoflurane anaesthesia for orthopaedic surgery in domestic sheep.	2001 May	11413983
Dexmedetomidine, a novel alpha 2-adrenergic agonist for short-term sedation in the intensive care unit.	2001 May	11402470
Medetomidine-ketamine anesthesia in red-eared slider turtles (Trachemys scripta elegans).	2001 May	11353517
The use of dexmedetomidine infusion for awake craniotomy.	2001 May	11323355
Modulation of ligand responses by coupling of alpha(2A)-adrenoceptors to diverse G(alpha)-proteins.	2001 May 1	11301041
High-performance liquid chromatographic method combining radiochemical and ultraviolet detection for determination of low activities of uridine 5'-diphosphate-glucuronosyltransferase.	2001 May 15	11355849
Effect of medetomidine on electroencephalography and use of a quantitative electroencephalograph for evaluating sedation levels in dogs.	2001 Nov	11765809
Cardiopulmonary effects of three different anaesthesia protocols in cats.	2001 Nov	11765236
Spatial working memory improvement by an alpha2-adrenoceptor agonist dexmedetomidine is not mediated through alpha2C-adrenoceptor.	2001 Nov	11642653
Optimization of intraperitoneal injection anesthesia in mice: drugs, dosages, adverse effects, and anesthesia depth.	2001 Oct	11924805
New agents for sedation in the intensive care unit.	2001 Oct	11762266
Use of propofol and other nonbenzodiazepine sedatives in the intensive care unit.	2001 Oct	11762265
Benzodiazepines in the intensive care unit.	2001 Oct	11762264
Clinical comparison of preanaesthetic intramuscular medetomidine and dexmedetomidine in domestic sheep.	2001 Oct	11721587
Alkyl-substituted silica gel as a carrier in the controlled release of dexmedetomidine.	2001 Oct 19	11578738
Effects of chronic tramadol on pre- and post-synaptic measures of monoamine function.	2001 Sep	11565620
Cardiopulmonary effects of prolonged anesthesia via propofol-medetomidine infusion in ponies.	2001 Sep	11560273
Noradrenergic modulation of serotonin release in rat dorsal and median raphé nuclei via alpha(1) and alpha(2A) adrenoceptors.	2001 Sep	11543763
Anesthetic effects of ketamine or isoflurane induction prior to isoflurane anesthesia in medetomidine-premedicated dogs.	2001 Sep-Oct	11563439
Anesthesia of boma-captured Lichtenstein's hartebeest (Sigmoceros lichtensteinii) with a combination of thiafentanil, medetomidine, and ketamine.	2002 Apr	12038149
Down-regulation of the alpha-2C adrenergic receptor: involvement of a serine/threonine motif in the third cytoplasmic loop.	2002 Apr 2	11926967
Activation of the peroxisome proliferator-activated receptor alpha protects against myocardial ischaemic injury and improves endothelial vasodilatation.	2002 Apr 9	11940253
Initial experience with dexmedetomidine in paediatric-aged patients.	2002 Feb	11882231
Some factors influencing the level of clinical sedation induced by medetomidine in rabbits.	2002 Feb	11874525
Effects of alpha(2)-adrenoceptor agonists on perinatal excitotoxic brain injury: comparison of clonidine and dexmedetomidine.	2002 Jan	11753013
Effect of synthesis parameters of the sol-gel-processed spray-dried silica gel microparticles on the release rate of dexmedetomidine.	2002 Jul	12059031
Dual alpha(2)-adrenergic agonist and alpha(1)-adrenergic antagonist actions of dexmedetomidine on human isolated endothelium-denuded gastroepiploic arteries.	2002 Jun	12032002
Hemodynamics of anesthetized ventilated mouse models: aspects of anesthetics, fluid support, and strain.	2002 Jun	12003817
Dexmedetomidine may be effective, but is it safe?	2002 Mar	11990287
Infusion of alpha-2-adrenergic agents into the paraventricular and arcuate nuclei of the hypothalamus in the Siberian hamster: opposing effects on basal prolactin.	2002 Mar	11914589
Postoperative pain control in cats: clinical trials with medetomidine and butorphanol.	2002 Mar-Apr	11884953
Quantitative electroencephalography of medetomidine, medetomidine-midazolam and medetomidine-midazolam-butorphanol in dogs.	2002 May	12069256
Pharmacokinetics of dexmedetomidine infusions for sedation of postoperative patients requiring intensive caret.	2002 May	12067004
Cardiopulmonary effects of a medetomidine-ketamine combination administered intravenously in gopher tortoises.	2002 May 15	12018381
alpha 2B-adrenergic receptor activates MAPK via a pathway involving arachidonic acid metabolism, matrix metalloproteinases, and epidermal growth factor receptor transactivation.	2002 May 31	11891218

Patents

Sample Use Guides

In Vivo Use Guide

For Adult Intensive Care Unit Sedation: Generally initiate at one mcg/kg over 10 minutes, followed by a maintenance infusion of 0.2 to 0.7 mcg/kg/hour. For Adult Procedural Sedation: Generally initiate at one mcg/kg over 10 minutes, followed by a maintenance infusion initiated at 0.6 mcg/kg/hour and titrated to achieve desired clinical effect with doses ranging from 0.2 to 1 mcg/kg/hour.

Route of Administration: Intravenous

In Vitro Use Guide

Strips of pregnant human myometrium obtained from six individuals at elective caesarean section were incubated with dexmedetomidine (1x10(-11) to 1x10(-6) g/mL) and the in vitro effect was studied as the drug may be used in obstetric anaesthesia

Name

Type

Language

DEXMEDETOMIDINE

Official Name

English

MPV-1440

Code

English

DEXMEDETOMIDINE [USAN]

Common Name

English

dexmedetomidine [INN]

Common Name

English

MEDETOMIDINE, (S)-

Common Name

English

(+)-4-((S)-.ALPHA.,2,3-TRIMETHYLBENZYL)IMIDAZOLE

Systematic Name

English

Dexmedetomidine [WHO-DD]

Common Name

English

DEXMEDETOMIDINE [GREEN BOOK]

Common Name

English

DEXMEDETOMIDINE [VANDF]

Common Name

English

DEXMEDETOMIDINE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05CM18