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 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf	Preventing		Approved 8429	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 1999

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
Preliminary UK experience of dexmedetomidine, a novel agent for postoperative sedation in the intensive care unit.	1999 Dec	10594409
Noradrenergic regulation of hippocampal place cells.	2001	11811674
[Medetomidine-butorphanol combination anesthesia in the dog].	2001 Dec	11776718
Effect of dexmedetomidine on propofol requirements in healthy subjects.	2001 Feb	11169534
Hematological and biochemical reference intervals for wild caught Eurasian otter from Spain.	2001 Jan	11272491
Effects of preemptive atropine administration on incidence of medetomidine-induced bradycardia in dogs.	2001 Jan 1	11149715
Sedative but not analgesic alpha2 agonist tolerance is blocked by NMDA receptor and nitric oxide synthase inhibitors.	2001 Jul	11465557
Effects of reduced sympathetic activity on myocardial metaiodobenzylguanidine (MIBG) washout.	2001 Jun	11844024
Anaesthesia of roan antelope (Hippotragus equinus) with a combination of A3080, medetomidine and ketamine.	2001 Mar	11563714
Clinical evaluation of established optimal immobilizing doses of medetomidine-ketamine in captive reindeer (Rangifer tarandus tarandus).	2001 Mar	11277207
Effects of dexmedetomidine on adrenocortical function, and the cardiovascular, endocrine and inflammatory responses in post-operative patients needing sedation in the intensive care unit.	2001 May	11575340
Comparison of medetomidine and dexmedetomidine as premedication in isoflurane anaesthesia for orthopaedic surgery in domestic sheep.	2001 May	11413983
Effect of medetomidine on electroencephalography and use of a quantitative electroencephalograph for evaluating sedation levels in dogs.	2001 Nov	11765809
Spatial working memory improvement by an alpha2-adrenoceptor agonist dexmedetomidine is not mediated through alpha2C-adrenoceptor.	2001 Nov	11642653
Dexmedetomidine infusion and somatosensory evoked potentials.	2001 Oct	11733664
Clinical comparison of preanaesthetic intramuscular medetomidine and dexmedetomidine in domestic sheep.	2001 Oct	11721587
Cardiopulmonary effects of prolonged anesthesia via propofol-medetomidine infusion in ponies.	2001 Sep	11560273
The effect of a combination of medetomidine-butorphanol and medetomidine, butorphanol, atropine on glomerular filtration rate in dogs.	2001 Sep-Oct	11678570
Anesthetic effects of ketamine or isoflurane induction prior to isoflurane anesthesia in medetomidine-premedicated dogs.	2001 Sep-Oct	11563439
Interactions between cutaneous afferent inputs to a withdrawal reflex in the decerebrated rabbit and their control by descending and segmental systems.	2002	12074898
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
Alpha 2-adrenoceptors in the enteric nervous system: a study in alpha 2A-adrenoceptor-deficient mice.	2002 Feb	11834617
Effect of the alpha2-agonist dexmedetomidine on cerebral neurotransmitter concentrations during cerebral ischemia in rats.	2002 Feb	11818781
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
Use of medetomidine for capture and restraint of cassowaries (Casuarius casuaris).	2002 Mar	12019701
Dexmedetomidine may be effective, but is it safe?	2002 Mar	11990287
N-Glucuronidation of some 4-arylalkyl-1H-imidazoles by rat, dog, and human liver microsomes.	2002 Mar	11854148
Pharmacokinetics of dexmedetomidine infusions for sedation of postoperative patients requiring intensive caret.	2002 May	12067004
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
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