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

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

9.4538878E11
PubMed

PubMed

TitleDatePubMed
Noradrenergic regulation of hippocampal place cells.
2001
Effects of dexmedetomidine after transient and permanent occlusion of the middle cerebral artery in the rat.
2001
[Efficacy of oncologic surgery. Does anesthesia influence the postoperative outcome?].
2001 Apr
Sedative, analgesic, and cardiovascular effects of levomedetomidine alone and in combination with dexmedetomidine in dogs.
2001 Apr
Infusion of a combination of propofol and medetomidine for long-term anesthesia in ponies.
2001 Apr
Acid-base status and blood gas arterial values in free-ranging sika deer hinds immobilized with medetomidine and ketamine.
2001 Apr
Contribution of alpha(2) receptor subtypes to nerve injury-induced pain and its regulation by dexmedetomidine.
2001 Apr
Evaluation of the alpha2C-adrenoceptor as a neuropsychiatric drug target studies in transgenic mouse models.
2001 Apr 6
[Medetomidine-butorphanol combination anesthesia in the dog].
2001 Dec
Results of cystometry and urethral pressure profilometry in dogs sedated with medetomidine or xylazine.
2001 Feb
Alpha2-adrenoceptors modulating neuronal serotonin release: a study in alpha2-adrenoceptor subtype-deficient mice.
2001 Feb
Effect of dexmedetomidine on propofol requirements in healthy subjects.
2001 Feb
Hematological and biochemical reference intervals for wild caught Eurasian otter from Spain.
2001 Jan
Determination of optimal immobilizing doses of a medetomidine hydrochloride and ketamine hydrochloride combination in captive reindeer.
2001 Jan
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia.
2001 Jan
Use of medetomidine and ketamine for immobilization of free-ranging giraffes.
2001 Jan 15
Sedative but not analgesic alpha2 agonist tolerance is blocked by NMDA receptor and nitric oxide synthase inhibitors.
2001 Jul
Effects of reduced sympathetic activity on myocardial metaiodobenzylguanidine (MIBG) washout.
2001 Jun
Anaesthesia of gemsbok (Oryx gazella) with a combination of A3080, medetomidine and ketamine.
2001 Jun
The effects of topical tropicamide and systemic medetomidine, followed by atipamezole reversal, on pupil size and intraocular pressure in normal dogs.
2001 Mar
Clinical evaluation of established optimal immobilizing doses of medetomidine-ketamine in captive reindeer (Rangifer tarandus tarandus).
2001 Mar
Alpha(2) adrenoceptor agonists as potential analgesic agents. 3. Imidazolylmethylthiophenes.
2001 Mar 15
Minimal alveolar concentration of desflurane in combination with an infusion of medetomidine for the anaesthesia of ponies.
2001 Mar 3
The use of dexmedetomidine infusion for awake craniotomy.
2001 May
Modulation of ligand responses by coupling of alpha(2A)-adrenoceptors to diverse G(alpha)-proteins.
2001 May 1
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
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
Alkyl-substituted silica gel as a carrier in the controlled release of dexmedetomidine.
2001 Oct 19
Anesthetic effects of ketamine or isoflurane induction prior to isoflurane anesthesia in medetomidine-premedicated dogs.
2001 Sep-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
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
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
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
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
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
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
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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
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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
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PRIMARY
EVMPD
SUB07037MIG
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PRIMARY
NCI_THESAURUS
C47479
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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