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

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

SMILES

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

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
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

1999
PubMed

PubMed

TitleDatePubMed
Noradrenergic regulation of hippocampal place cells.
2001
Dextromethorphan and dexmedetomidine: new agents for the control of perioperative pain.
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
Comparison between dexmedetomidine and propofol for sedation in the intensive care unit: patient and clinician perceptions.
2001 Nov
Dexmedetomidine: a real innovation or more of the same?
2001 Nov
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
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
Controlled hypotension in children: a critical review of available agents.
2002
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
Initial experience with dexmedetomidine in paediatric-aged patients.
2002 Feb
Some factors influencing the level of clinical sedation induced by medetomidine in rabbits.
2002 Feb
The use of alpha2-agonists during off-pump coronary artery bypass and the effects of hypothermia.
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
Effects of medetomidine-midazolam, midazolambutorphanol, or acepromazine-butorphanol as premedicants for mask induction of anesthesia with sevoflurane in dogs.
2002 Jul
Effect of synthesis parameters of the sol-gel-processed spray-dried silica gel microparticles on the release rate of dexmedetomidine.
2002 Jul
In vivo regulation of dopamine and noradrenaline release by alpha2A-adrenoceptors in the mouse prefrontal cortex.
2002 Jun
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
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
N-Glucuronidation of some 4-arylalkyl-1H-imidazoles by rat, dog, and human liver microsomes.
2002 Mar
Postoperative pain control in cats: clinical trials with medetomidine and butorphanol.
2002 Mar-Apr
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
alpha 2B-adrenergic receptor activates MAPK via a pathway involving arachidonic acid metabolism, matrix metalloproteinases, and epidermal growth factor receptor transactivation.
2002 May 31
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
Name Type Language
DEXMEDETOMIDINE HYDROCHLORIDE
EMA EPAR   GREEN BOOK   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   WHO-DD  
USAN  
Official 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
DEXMEDETOMIDINE HCL
VANDF  
Common Name English
4-[(S)-α,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]
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS CEPEDEX (AUTHORISED)
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS SEDADEX [AUTHORIZED]
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS SILEO [AUTHORIZED]
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS DEXDOMITOR (AUTHORISED)
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
EMA ASSESSMENT REPORTS DEXDOR (AUTHORIZED: CONSCIOUS SEDATION)
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS DEXDOMITOR (AUTHORISED)
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS CEPEDEX (AUTHORISED)
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1179333
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
CHEBI
31472
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
EVMPD
SUB20317
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
PUBCHEM
6918081
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
RXCUI
228054
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID40873215
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL778
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
SMS_ID
100000092060
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
CAS
145108-58-3
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
DRUG BANK
DBSALT001013
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
FDA UNII
1018WH7F9I
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
NCI_THESAURUS
C72738
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
MERCK INDEX
m4218
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY Merck Index
DAILYMED
1018WH7F9I
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY
USAN
LL-19
Created by admin on Fri Dec 15 15:52:10 GMT 2023 , Edited by admin on Fri Dec 15 15:52:10 GMT 2023
PRIMARY