U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DEXMEDETOMIDINE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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

945388800000
PubMed

PubMed

TitleDatePubMed
Noradrenergic regulation of hippocampal place cells.
2001
Dextromethorphan and dexmedetomidine: new agents for the control of perioperative pain.
2001 Aug
Dexmedetomidine.
2001 Aug
[Medetomidine-butorphanol combination anesthesia in the dog].
2001 Dec
alpha2A-adrenoceptor stimulation reduces capsaicin-induced glutamate release from spinal cord synaptosomes.
2001 Dec
Effects of reduced sympathetic activity on myocardial metaiodobenzylguanidine (MIBG) washout.
2001 Jun
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
Effect of medetomidine on electroencephalography and use of a quantitative electroencephalograph for evaluating sedation levels in dogs.
2001 Nov
Cardiopulmonary effects of three different anaesthesia protocols in cats.
2001 Nov
Cardiopulmonary evaluation of the use of medetomidine hydrochloride in cats.
2001 Nov
The pharmacokinetics of dexmedetomidine in volunteers with severe renal impairment.
2001 Nov
Spatial working memory improvement by an alpha2-adrenoceptor agonist dexmedetomidine is not mediated through alpha2C-adrenoceptor.
2001 Nov
Dexmedetomidine decreases extracellular dopamine concentrations in the rat nucleus accumbens.
2001 Nov 16
Optimization of intraperitoneal injection anesthesia in mice: drugs, dosages, adverse effects, and anesthesia depth.
2001 Oct
New agents for sedation in the intensive care unit.
2001 Oct
Use of propofol and other nonbenzodiazepine sedatives in the intensive care unit.
2001 Oct
Benzodiazepines in the intensive care unit.
2001 Oct
Dexmedetomidine infusion and somatosensory evoked potentials.
2001 Oct
Clinical comparison of preanaesthetic intramuscular medetomidine and dexmedetomidine in domestic sheep.
2001 Oct
The synergistic antinociceptive interactions of endomorphin-1 with dexmedetomidine and/or S(+)-ketamine in rats.
2001 Oct
Determinants of mortality after hypothermic circulatory arrest in a chronic porcine model.
2001 Oct
Alkyl-substituted silica gel as a carrier in the controlled release of dexmedetomidine.
2001 Oct 19
Effects of medetomidine and buprenorphine administered for sedation in dogs.
2001 Sep
Effects of chronic tramadol on pre- and post-synaptic measures of monoamine function.
2001 Sep
The effect of a combination of medetomidine-butorphanol and medetomidine, butorphanol, atropine on glomerular filtration rate in dogs.
2001 Sep-Oct
Interactions between cutaneous afferent inputs to a withdrawal reflex in the decerebrated rabbit and their control by descending and segmental systems.
2002
Anesthesia of boma-captured Lichtenstein's hartebeest (Sigmoceros lichtensteinii) with a combination of thiafentanil, medetomidine, and ketamine.
2002 Apr
Down-regulation of the alpha-2C adrenergic receptor: involvement of a serine/threonine motif in the third cytoplasmic loop.
2002 Apr 2
Activation of the peroxisome proliferator-activated receptor alpha protects against myocardial ischaemic injury and improves endothelial vasodilatation.
2002 Apr 9
Some factors influencing the level of clinical sedation induced by medetomidine in rabbits.
2002 Feb
Alpha 2-adrenoceptors in the enteric nervous system: a study in alpha 2A-adrenoceptor-deficient mice.
2002 Feb
Effect of the alpha2-agonist dexmedetomidine on cerebral neurotransmitter concentrations during cerebral ischemia in rats.
2002 Feb
Neurohormonal and metabolic effects of medetomidine compared with xylazine in beagle dogs.
2002 Jan
Effects of alpha(2)-adrenoceptor agonists on perinatal excitotoxic brain injury: comparison of clonidine and dexmedetomidine.
2002 Jan
alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy.
2002 Jan
Reliability of goniometry in Labrador Retrievers.
2002 Jul
Evaluation of the perioperative stress response in dogs administered medetomidine or acepromazine as part of the preanesthetic medication.
2002 Jul
Effect of synthesis parameters of the sol-gel-processed spray-dried silica gel microparticles on the release rate of dexmedetomidine.
2002 Jul
Dual alpha(2)-adrenergic agonist and alpha(1)-adrenergic antagonist actions of dexmedetomidine on human isolated endothelium-denuded gastroepiploic arteries.
2002 Jun
Hemodynamics of anesthetized ventilated mouse models: aspects of anesthetics, fluid support, and strain.
2002 Jun
Use of medetomidine for capture and restraint of cassowaries (Casuarius casuaris).
2002 Mar
Dexmedetomidine may be effective, but is it safe?
2002 Mar
N-Glucuronidation of some 4-arylalkyl-1H-imidazoles by rat, dog, and human liver microsomes.
2002 Mar
Quantitative electroencephalography of medetomidine, medetomidine-midazolam and medetomidine-midazolam-butorphanol in dogs.
2002 May
Pharmacokinetics of dexmedetomidine infusions for sedation of postoperative patients requiring intensive caret.
2002 May
Altered presynaptic function in monoaminergic neurons of monoamine oxidase-A knockout mice.
2002 May
New agents, new monitors, same unanswered questions.
2002 May
Bispectral index-guided sedation with dexmedetomidine in intensive care: a prospective, randomized, double blind, placebo-controlled phase II study.
2002 May
alpha(2B)-Adrenergic receptors activate MAPK and modulate proliferation of primary cultured proximal tubule cells.
2002 May
Cardiopulmonary effects of a medetomidine-ketamine combination administered intravenously in gopher tortoises.
2002 May 15
Patents

Patents

Sample Use Guides

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
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
  • Download
Name Type Language
DEXMEDETOMIDINE
INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
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
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
NCI_THESAURUS C29709
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
NDF-RT N0000175975
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
NDF-RT N0000009918
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
CFR 21 CFR 522.558
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
NDF-RT N0000175554
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
WHO-ATC N05CM18
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL778
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
DRUG CENTRAL
835
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
IUPHAR
521
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
FDA UNII
67VB76HONO
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
LACTMED
Dexmedetomidine
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
RXCUI
48937
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY RxNorm
PUBCHEM
5311068
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
WIKIPEDIA
DEXMEDETOMIDINE
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
INN
6277
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
EVMPD
SUB07037MIG
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
NCI_THESAURUS
C47479
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
CAS
113775-47-6
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
DRUG BANK
DB00633
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
MESH
D020927
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY
MERCK INDEX
M4218
Created by admin on Sat Jun 26 14:43:15 UTC 2021 , Edited by admin on Sat Jun 26 14:43:15 UTC 2021
PRIMARY Merck Index
Related Record Type Details
TARGET -> AGONIST
SHORT-ACTING
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
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METABOLITE -> PARENT
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ACTIVE MOIETY