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

Details

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

SHOW SMILES / InChI
Structure of MEDETOMIDINE HYDROCHLORIDE

SMILES

Cl.CC(C1=CN=CN1)C2=C(C)C(C)=CC=C2

InChI

InChIKey=VPNGEIHDPSLNMU-UHFFFAOYSA-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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H16N2
Molecular Weight 200.2795
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/2571177

Domitor (medetomidine hydrochloride) is indicated for use in dogs: for restraint, sedation and analgesia associated with clinical examinations and procedures, minor surgery, pre-anaesthesia and as a premedicant before thiopentone-halothane general a naesthesiaand as a premedicant before general anaesthesia with propofol. In combination with butorphanol for sedation and analgesia, and as a premedicant prior to thiopentone anaesthesia. In cats: for restraint and sedation. Medetomidine is a potent and highly selective alpha2-adrenoreceptor agonist with both central and peripheral activity, and acting both presynaptically and postsynaptically. Its primary effects are sedative and analgesic resulting from its central depressant activity. It has no local anaesthetic properties. Like other compounds of its class there are secondary effects, including bradycardia. Blood pressure is increased but then returns to normal or just below. Body temperature is decreased in a dose dependent manner and intestinal motility is also reduced. The drug has been developed by Orion Pharma. It is currently approved for dogs in the United States, and distributed in the United States by Pfizer Animal Health and by Novartis Animal Health in Canada under the product name Domitor. The marketed product is a racemic mixture of two stereoisomers; dexmedetomidine is the isomer with more useful effects, and is now marketed as Dexdomitor.

CNS Activity

Curator's Comment: Medetomidine is a potent and highly selective alpha2-adrenoreceptor agonist with both central and peripheral activity, and acting both presynaptically and postsynaptically. Its primary effects are sedative and analgesic resulting from its central depressant activity. It has no local anaesthetic properties

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DOMITOR

Approved Use

Dogs: For restraint, sedation and analgesia associated with clinical examinations and procedures, minor surgery, pre-anaesthesia and as a premedicant before thiopentone-halothane general a naesthesiaand as a premedicant before general anaesthesia with propofol. Cats: For restraint and sedation.
PubMed

PubMed

TitleDatePubMed
Effects of anticholinergic treatment on the cardiac and respiratory systems in dogs sedated with medetomidine.
1991 Oct 5
Comparison of neurologic responses to the use of medetomidine as a sole agent or preanesthetic in laboratory beagles.
1992
Postoperative analgesic and cardiopulmonary effects in dogs of oxymorphone administered epidurally and intramuscularly, and medetomidine administered epidurally: a comparative clinical study.
1996 Jul-Aug
Reduced blood flow and oxygenation in SA-1 tumours after electrochemotherapy with cisplatin.
2002 Oct 21
The effect of cartilage and bone density of mushroom-shaped, photooxidized, osteochondral transplants: an experimental study on graft performance in sheep using transplants originating from different species.
2005 Dec 15
Evaluation of two combinations of Domitor, Zoletil 100, and Euthatal to obtain long-term nonrecovery anesthesia in Sprague-Dawley rats.
2005 Jun
Acute aortic rupture in a dog with spirocercosis following the administration of medetomidine.
2005 Sep
Training-induced plasticity of auditory localization in adult mammals.
2006 Apr
Light stimulus frequency dependence of activity in the rat visual system as studied with high-resolution BOLD fMRI.
2006 May
Estrogen sensitivity of target genes and expression of nuclear receptor co-regulators in rat prostate after pre- and postnatal exposure to the ultraviolet filter 4-methylbenzylidene camphor.
2007 Dec
Degradable gelatin microspheres as an embolic agent: an experimental study in a rabbit renal model.
2007 Sep-Oct
A cardiovascular monitoring system used in conscious cynomolgus monkeys for regulatory safety pharmacology. Part 2: Pharmacological validation.
2007 Sep-Oct
Vascular disrupting action of electroporation and electrochemotherapy with bleomycin in murine sarcoma.
2008 Jan 29
IFN-lambda (IFN-lambda) is expressed in a tissue-dependent fashion and primarily acts on epithelial cells in vivo.
2008 Mar 14
EphrinB2 induces tyrosine phosphorylation of NR2B via Src-family kinases during inflammatory hyperalgesia.
2008 Sep 22
Late treatment with imatinib mesylate ameliorates radiation-induced lung fibrosis in a mouse model.
2009 Dec 21
Retrograde adenoviral vector targeting of nociresponsive pontospinal noradrenergic neurons in the rat in vivo.
2009 Jan 10
Seizures during medetomindine sedation and local anaesthesia in two dogs undergoing skin biopsy.
2009 May
Nitric oxide synthase enzymes in the airways of mice exposed to ovalbumin: NOS2 expression is NOS3 dependent.
2010
The non-lemniscal auditory cortex in ferrets: convergence of corticotectal inputs in the superior colliculus.
2010
Melody, an ENU mutation in Caspase 3, alters the catalytic cysteine residue and causes sensorineural hearing loss in mice.
2010 Dec
Manufacturing and in vivo inner ear visualization of MRI traceable liposome nanoparticles encapsulating gadolinium.
2010 Dec 18
Sympathetic alpha(2)-adrenoceptors prevent cardiac hypertrophy and fibrosis in mice at baseline but not after chronic pressure overload.
2010 Jun 1
Adaptation to stimulus statistics in the perception and neural representation of auditory space.
2010 Jun 24
Microscopic mammalian retinal pigment epithelium lesions induce widespread proliferation with differences in magnitude between center and periphery.
2010 Mar 31
Creating a population-averaged standard brain template for Japanese macaques (M. fuscata).
2010 Oct 1
Physiology and mRNA expression in rainbow trout (Oncorhynchus mykiss) after long-term exposure to the new antifoulant medetomidine.
2011 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Intended for injection by intramuscular, intravenous and subcutaneous routes in the dog, and by the intramuscular or subcutaneous route in the cat.
for animals: Dog: 10-30 µg/kg Slight sedation; 30-80 µg/kg Moderate to deep sedation and analgesia; 10-20 µg/kg Pre-anaesthesia Cat: 50-100 µg/kg Moderate sedation; 100-150 µg/kg Deep sedation;
Route of Administration: Other
In Vitro Use Guide
Rat pineal glands were incubated in oxygenated Krebs-Ringer solution in perifusion chambers, and perifused for 30 min with alpha(2)-adrenoceptor ligands. The melatonin concentrations were measured from the perifusate by radioimmunoassay. Medetomidine (>/=10(-5) M) increased melatonin release.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:06:41 GMT 2023
Edited
by admin
on Fri Dec 15 16:06:41 GMT 2023
Record UNII
BH210P244U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEDETOMIDINE HYDROCHLORIDE
MART.   MI   USAN  
USAN  
Official Name English
MEDETOMIDINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
MEDETOMIDINE HCL
Common Name English
MEDETOMIDINE HYDROCHLORIDE [MI]
Common Name English
MEDETOMIDINE HYDROCHLORIDE [MART.]
Common Name English
MEDETOMIDINE HYDROCHLORIDE [USAN]
Common Name English
(±)-4-(.ALPHA.,2,3-TRIMETHYLBENZYL)IMIDAZOLE MONOHYDROCHLORIDE
Systematic Name English
4-(1-(2,3-DIMETHYLPHENYL)ETHYL)-, MONOHYDROCHLORIDE, (±)-
Common Name English
MPV-785
Code English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
CFR 21 CFR 522.1335
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
Code System Code Type Description
MERCK INDEX
m7128
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY Merck Index
FDA UNII
BH210P244U
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
USAN
Z-59
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL77921
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
NCI_THESAURUS
C81368
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
PUBCHEM
68601
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID3045691
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
CAS
86347-15-1
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
DRUG BANK
DBSALT002859
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
DAILYMED
BH210P244U
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
RXCUI
29428
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY RxNorm
SMS_ID
300000023831
Created by admin on Fri Dec 15 16:06:41 GMT 2023 , Edited by admin on Fri Dec 15 16:06:41 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY