DEXMEDETOMIDINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H16N2.ClH
Molecular Weight	236.74
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DEXMEDETOMIDINE HYDROCHLORIDE

Structure Search

SMILES

Cl.C[C@H](C1=CN=CN1)C2=CC=CC(C)=C2C

InChI

InChIKey=VPNGEIHDPSLNMU-MERQFXBCSA-N

InChI=1S/C13H16N2.ClH/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);1H/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-2 114 Target ID: CHEMBL2095158 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021038s027lbl.pdf	Preventing		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
2.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30427948/	1 μg/kg bw single, intravenous dose: 1 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		DEXMEDETOMIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
107.58 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30427948/	1 μg/kg bw single, intravenous dose: 1 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		DEXMEDETOMIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
138 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30427948/	1 μg/kg bw single, intravenous dose: 1 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		DEXMEDETOMIDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

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
Reliability of goniometry in Labrador Retrievers.	2002-07	12118679
Evaluation of the perioperative stress response in dogs administered medetomidine or acepromazine as part of the preanesthetic medication.	2002-07	12118677
Effects of medetomidine-midazolam, midazolambutorphanol, or acepromazine-butorphanol as premedicants for mask induction of anesthesia with sevoflurane in dogs.	2002-07	12118664
Effect of synthesis parameters of the sol-gel-processed spray-dried silica gel microparticles on the release rate of dexmedetomidine.	2002-07	12059031
In vivo regulation of dopamine and noradrenaline release by alpha2A-adrenoceptors in the mouse prefrontal cortex.	2002-06	12081658
Dual alpha(2)-adrenergic agonist and alpha(1)-adrenergic antagonist actions of dexmedetomidine on human isolated endothelium-denuded gastroepiploic arteries.	2002-06	12032002
Hemodynamics of anesthetized ventilated mouse models: aspects of anesthetics, fluid support, and strain.	2002-06	12003817
alpha 2B-adrenergic receptor activates MAPK via a pathway involving arachidonic acid metabolism, matrix metalloproteinases, and epidermal growth factor receptor transactivation.	2002-05-31	11891218
Cardiopulmonary effects of a medetomidine-ketamine combination administered intravenously in gopher tortoises.	2002-05-15	12018381
Quantitative electroencephalography of medetomidine, medetomidine-midazolam and medetomidine-midazolam-butorphanol in dogs.	2002-05	12069256
Pharmacokinetics of dexmedetomidine infusions for sedation of postoperative patients requiring intensive caret.	2002-05	12067004
Altered presynaptic function in monoaminergic neurons of monoamine oxidase-A knockout mice.	2002-05	12028362
New agents, new monitors, same unanswered questions.	2002-05	12006825
Bispectral index-guided sedation with dexmedetomidine in intensive care: a prospective, randomized, double blind, placebo-controlled phase II study.	2002-05	12006795
alpha(2B)-Adrenergic receptors activate MAPK and modulate proliferation of primary cultured proximal tubule cells.	2002-05	11934705
Activation of the peroxisome proliferator-activated receptor alpha protects against myocardial ischaemic injury and improves endothelial vasodilatation.	2002-04-09	11940253
Down-regulation of the alpha-2C adrenergic receptor: involvement of a serine/threonine motif in the third cytoplasmic loop.	2002-04-02	11926967
Anesthesia of boma-captured Lichtenstein's hartebeest (Sigmoceros lichtensteinii) with a combination of thiafentanil, medetomidine, and ketamine.	2002-04	12038149
Postoperative pain control in cats: clinical trials with medetomidine and butorphanol.	2002-03-09	11884953
Use of medetomidine for capture and restraint of cassowaries (Casuarius casuaris).	2002-03	12019701
Dexmedetomidine may be effective, but is it safe?	2002-03	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.	2002-03	11914589
N-Glucuronidation of some 4-arylalkyl-1H-imidazoles by rat, dog, and human liver microsomes.	2002-03	11854148
Initial experience with dexmedetomidine in paediatric-aged patients.	2002-02	11882231
Some factors influencing the level of clinical sedation induced by medetomidine in rabbits.	2002-02	11874525
The use of alpha2-agonists during off-pump coronary artery bypass and the effects of hypothermia.	2002-02	11854895
Alpha 2-adrenoceptors in the enteric nervous system: a study in alpha 2A-adrenoceptor-deficient mice.	2002-02	11834617
Effect of the alpha2-agonist dexmedetomidine on cerebral neurotransmitter concentrations during cerebral ischemia in rats.	2002-02	11818781
Neurohormonal and metabolic effects of medetomidine compared with xylazine in beagle dogs.	2002-01	11858648
Effects of alpha(2)-adrenoceptor agonists on perinatal excitotoxic brain injury: comparison of clonidine and dexmedetomidine.	2002-01	11753013
alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy.	2002-01	11752127
Controlled hypotension in children: a critical review of available agents.	2002	12083972
Interactions between cutaneous afferent inputs to a withdrawal reflex in the decerebrated rabbit and their control by descending and segmental systems.	2002	12074898
[Medetomidine-butorphanol combination anesthesia in the dog].	2001-12	11776718
alpha2A-adrenoceptor stimulation reduces capsaicin-induced glutamate release from spinal cord synaptosomes.	2001-12	11714880
Dexmedetomidine decreases extracellular dopamine concentrations in the rat nucleus accumbens.	2001-11-16	11689170
Comparison between dexmedetomidine and propofol for sedation in the intensive care unit: patient and clinician perceptions.	2001-11	11878517
Dexmedetomidine: a real innovation or more of the same?	2001-11	11878514
Effect of medetomidine on electroencephalography and use of a quantitative electroencephalograph for evaluating sedation levels in dogs.	2001-11	11765809
Cardiopulmonary effects of three different anaesthesia protocols in cats.	2001-11	11765236
Cardiopulmonary evaluation of the use of medetomidine hydrochloride in cats.	2001-11	11703018
Optimization of intraperitoneal injection anesthesia in mice: drugs, dosages, adverse effects, and anesthesia depth.	2001-10	11924805
New agents for sedation in the intensive care unit.	2001-10	11762266
Use of propofol and other nonbenzodiazepine sedatives in the intensive care unit.	2001-10	11762265
Benzodiazepines in the intensive care unit.	2001-10	11762264
Dexmedetomidine infusion and somatosensory evoked potentials.	2001-10	11733664
Clinical comparison of preanaesthetic intramuscular medetomidine and dexmedetomidine in domestic sheep.	2001-10	11721587
Dextromethorphan and dexmedetomidine: new agents for the control of perioperative pain.	2001-08	11716440
Effects of reduced sympathetic activity on myocardial metaiodobenzylguanidine (MIBG) washout.	2001-06	11844024
Noradrenergic regulation of hippocampal place cells.	2001	11811674

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 HYDROCHLORIDE

Official Name

English

DEXMEDETOMIDINE HCL

Preferred Name

English

DEXDOMITOR

Common Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [GREEN BOOK]

Common Name

English

CEPEDEX

Brand Name

English

1H-IMIDAZOLE, 4-(1-(2,3-DIMETHYLPHENYL)ETHYL)-, MONOHYDROCHLORIDE, (S)-

Common Name

English

DEXMEDETOMIDINE HCL [VANDF]

Common Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [USAN]

Common Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [MART.]

Common Name

English

PRECEDEX

Brand Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [EMA EPAR]

Common Name

English

SILEO

Brand Name

English

4-[(S)-?,2,3-Trimethylbenzyl]imidazole monohydrochloride

Systematic Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

DEXMEDETOMIDINE HYDROCHLORIDE (EMA EPAR: VETERINARY)

Common Name

English

DEXDOR

Brand Name

English

SEDADEX

Brand Name

English

Dexmedetomidine hydrochloride [WHO-DD]

Common Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [USP-RS]

Common Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [JAN]

Common Name

English

IGALMI

Brand Name

English

DEXMEDETOMIDINE HYDROCHLORIDE [MI]

Common Name

English

Classification Tree Code System Code

EMA VETERINARY ASSESSMENT REPORTS

SEDADEX [AUTHORIZED]