DEXMEDETOMIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H16N2
Molecular Weight	200.28
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cc1cccc(c1C)[C@]([H])(C)c2cnc[nH]2

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

Molecular Formula	C13H16N2
Molecular Weight	200.28
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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-2 109 Target ID: CHEMBL2095158 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf	Agonist 2470

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 580 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf	Preventing		Approved 8043	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
Dextromethorphan and dexmedetomidine: new agents for the control of perioperative pain.	2001 Aug	11716440
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
Use of medetomidine-zolazepam-tiletamine with and without atipamezole reversal to immobilize captive California sea lions.	2001 Jul	11504231
Reversible immobilization of eurasian otters with a combination of ketamine and medetomidine.	2001 Jul	11504230
Effects of reduced sympathetic activity on myocardial metaiodobenzylguanidine (MIBG) washout.	2001 Jun	11844024
Anaesthesia of gemsbok (Oryx gazella) with a combination of A3080, medetomidine and ketamine.	2001 Jun	11513265
Anaesthesia of roan antelope (Hippotragus equinus) with a combination of A3080, medetomidine and ketamine.	2001 Mar	11563714
Comparison between dexmedetomidine and propofol for sedation in the intensive care unit: patient and clinician perceptions.	2001 Nov	11878517
Dexmedetomidine: a real innovation or more of the same?	2001 Nov	11878514
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
Cardiopulmonary evaluation of the use of medetomidine hydrochloride in cats.	2001 Nov	11703018
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
Benzodiazepines in the intensive care unit.	2001 Oct	11762264
Dexmedetomidine infusion and somatosensory evoked potentials.	2001 Oct	11733664
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 medetomidine and buprenorphine administered for sedation in dogs.	2001 Sep	11570387
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
Controlled hypotension in children: a critical review of available agents.	2002	12083972
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
Effect of the alpha2-agonist dexmedetomidine on cerebral neurotransmitter concentrations during cerebral ischemia in rats.	2002 Feb	11818781
Neurohormonal and metabolic effects of medetomidine compared with xylazine in beagle dogs.	2002 Jan	11858648
alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy.	2002 Jan	11752127
Reliability of goniometry in Labrador Retrievers.	2002 Jul	12118679
Evaluation of the perioperative stress response in dogs administered medetomidine or acepromazine as part of the preanesthetic medication.	2002 Jul	12118677
Effects of medetomidine-midazolam, midazolambutorphanol, or acepromazine-butorphanol as premedicants for mask induction of anesthesia with sevoflurane in dogs.	2002 Jul	12118664
Effect of synthesis parameters of the sol-gel-processed spray-dried silica gel microparticles on the release rate of dexmedetomidine.	2002 Jul	12059031
In vivo regulation of dopamine and noradrenaline release by alpha2A-adrenoceptors in the mouse prefrontal cortex.	2002 Jun	12081658
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
New agents, new monitors, same unanswered questions.	2002 May	12006825
Bispectral index-guided sedation with dexmedetomidine in intensive care: a prospective, randomized, double blind, placebo-controlled phase II study.	2002 May	12006795
alpha(2B)-Adrenergic receptors activate MAPK and modulate proliferation of primary cultured proximal tubule cells.	2002 May	11934705
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

Substance Class	Chemical Created by `admin` on `Sat Jun 26 14:43:14 UTC 2021` Edited by `admin` on `Sat Jun 26 14:43:14 UTC 2021`
Record UNII	67VB76HONO
Record Status	`Validated (UNII)`
Record Version

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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 [GREEN BOOK]

Common Name

English

DEXMEDETOMIDINE [VANDF]

Common Name

English

DEXMEDETOMIDINE [MI]

Common Name

English

DEXMEDETOMIDINE [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05CM18