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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

9.4538878E11
PubMed

PubMed

TitleDatePubMed
Noradrenergic regulation of hippocampal place cells.
2001
Contribution of alpha(2) receptor subtypes to nerve injury-induced pain and its regulation by dexmedetomidine.
2001 Apr
[Medetomidine-butorphanol combination anesthesia in the dog].
2001 Dec
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
Effect of dexmedetomidine, an alpha2-adrenoceptor agonist, on human pupillary reflexes during general anaesthesia.
2001 Jan
Effects of preemptive atropine administration on incidence of medetomidine-induced bradycardia in dogs.
2001 Jan 1
Use of medetomidine and ketamine for immobilization of free-ranging giraffes.
2001 Jan 15
Use of medetomidine-zolazepam-tiletamine with and without atipamezole reversal to immobilize captive California sea lions.
2001 Jul
Sedative but not analgesic alpha2 agonist tolerance is blocked by NMDA receptor and nitric oxide synthase inhibitors.
2001 Jul
Comparison of medetomidine and dexmedetomidine as premedicants in dogs undergoing propofol-isoflurane anesthesia.
2001 Jul
Anaesthesia of gemsbok (Oryx gazella) with a combination of A3080, medetomidine and ketamine.
2001 Jun
Anaesthesia of roan antelope (Hippotragus equinus) with a combination of A3080, medetomidine and ketamine.
2001 Mar
Comparison of medetomidine and dexmedetomidine as premedication in isoflurane anaesthesia for orthopaedic surgery in domestic sheep.
2001 May
Dexmedetomidine, a novel alpha 2-adrenergic agonist for short-term 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
Benzodiazepines in the intensive care unit.
2001 Oct
Noradrenergic modulation of serotonin release in rat dorsal and median raphé nuclei via alpha(1) and alpha(2A) adrenoceptors.
2001 Sep
Anesthetic effects of ketamine or isoflurane induction prior to isoflurane anesthesia in medetomidine-premedicated dogs.
2001 Sep-Oct
Down-regulation of the alpha-2C adrenergic receptor: involvement of a serine/threonine motif in the third cytoplasmic loop.
2002 Apr 2
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
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
Hemodynamics of anesthetized ventilated mouse models: aspects of anesthetics, fluid support, and strain.
2002 Jun
Quantitative electroencephalography of medetomidine, medetomidine-midazolam and medetomidine-midazolam-butorphanol in dogs.
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
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
Related Record Type Details
METABOLITE -> PARENT
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ACTIVE MOIETY