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Details

Stereochemistry ACHIRAL
Molecular Formula C13H16N2O
Molecular Weight 216.2789
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIRAZOLINE

SMILES

C(OC1=C(C=CC=C1)C2CC2)C3=NCCN3

InChI

InChIKey=YAORIDZYZDUZCM-UHFFFAOYSA-N
InChI=1S/C13H16N2O/c1-2-4-12(11(3-1)10-5-6-10)16-9-13-14-7-8-15-13/h1-4,10H,5-9H2,(H,14,15)

HIDE SMILES / InChI

Molecular Formula C13H16N2O
Molecular Weight 216.2789
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Cirazoline is an agonist of alpha1A adrenergic receptor, a partial agonist of alpha1B and alpha1D receptors, and an antagonist of alpha2 adrenergic receptors. Cirazoline was used to study the biologic function of adrenergic receptors. Injection of cirazoline into to the paravenricular hypothalamic nucleus of rats suppressed food and water intake. Cirazoline caused a large renal vasopressor response in rats. Systemic administration of cirazoline impaired spatial working memory in monkeys.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
120.0 nM [Ki]
960.0 nM [Ki]
660.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist.
1982 Jul
Orthostatic hypotension occurs following alpha 2-adrenoceptor blockade in chronic prazosin-pretreated conscious spontaneously hypertensive rats.
1992 Aug
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
1994 Nov
Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes.
1995 Sep
Adrenergic stimulation of lipoprotein lipase gene expression in rat brown adipocytes differentiated in culture: mediation via beta3- and alpha1-adrenergic receptors.
1997 Feb 1
The release of noradrenaline in the locus coeruleus and prefrontal cortex studied with dual-probe microdialysis.
2001 Jul 6
Phe-308 and Phe-312 in transmembrane domain 7 are major sites of alpha 1-adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists.
2001 Jul 6
Agmatine and putrescine uptake in the human glioma cell line SK-MG-1.
2001 Jun
Noradrenaline release-inhibiting receptors on PC12 cells devoid of alpha(2(-)) and CB(1) receptors: similarities to presynaptic imidazoline and edg receptors.
2002 Feb
A comparative study of the effects of Cl(-) channel blockers on mesenteric vascular conductance in anaesthetized rat.
2002 Jul 12
A novel pathway for adrenergic stimulation of cAMP-response-element-binding protein (CREB) phosphorylation: mediation via alpha1-adrenoceptors and protein kinase C activation.
2002 May 15
Identification and characterization of the imidazoline I2b-binding sites in the hamster brown adipose tissue as a study model for imidazoline receptors.
2003 Apr
Regulation of the release of serotonin in the dorsal raphe nucleus by alpha1 and alpha2 adrenoceptors.
2003 Oct
Cold adaptation modulates Ca2+ signaling in brown preadipocytes.
2004 Jul
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands.
2004 Oct
Noradrenergic inputs mediate state dependence of auditory responses in the avian song system.
2004 Sep 1
Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons.
2006 Feb
Medial prefrontal cortical alpha1 adrenoreceptor modulation of the nucleus accumbens dopamine response to stress in Long-Evans rats.
2007 Apr
Mechanisms of modafinil: A review of current research.
2007 Jun
The adrenergic receptor subtypes present in frog (Rana esculenta) skin.
2008 Aug
Effects of a Western diet versus high glucose on endothelium-dependent relaxation in murine micro- and macro-vasculature.
2008 Dec 28
Evidence that some imidazoline derivatives inhibit peripherally the vasopressor sympathetic outflow in pithed rats.
2008 Dec 5
Signal transduction and gene expression in cultured accessory olfactory bulb neurons.
2008 Nov 19
alpha1-Adrenergic receptors regulate neurogenesis and gliogenesis.
2009 Aug
alpha(1A)- and alpha(1B)-adrenergic receptors differentially modulate antidepressant-like behavior in the mouse.
2009 Aug 18
Catecholaminergic automatic activity in the rat pulmonary vein: electrophysiological differences between cardiac muscle in the left atrium and pulmonary vein.
2009 Jul
Dual regulation of heat-activated K+ channel in rat DRG neurons via alpha(1) and beta adrenergic receptors.
2009 Jul 17
Acute dilation to alpha(2)-adrenoceptor antagonists uncovers dual constriction and dilation mediated by arterial alpha(2)-adrenoceptors.
2009 Nov
Might adrenergic alpha2C-agonists/alpha2A-antagonists become novel therapeutic tools for pain treatment with morphine?
2009 Nov 26
The selective alpha1 adrenoceptor antagonist HEAT reduces L-DOPA-induced dyskinesia in a rat model of Parkinson's disease.
2010 Feb
Attenuation of store-operated Ca2+ entry and enhanced expression of TRPC channels in caudal artery smooth muscle from Type 2 diabetic Goto-Kakizaki rats.
2010 Jul
Alpha1-adrenoceptors modulate citalopram-induced serotonin release.
2010 Jun
Impairment of α1-adrenoceptor-mediated contractile activity in caudal arterial smooth muscle from type 2 diabetic Goto-Kakizaki rats.
2010 Mar
Modulation of N-type calcium currents by presynaptic imidazoline receptor activation in rat superior cervical ganglion neurons.
2010 Oct
Substance Class Chemical
Created
by admin
on Sun Dec 18 18:28:21 UTC 2022
Edited
by admin
on Sun Dec 18 18:28:21 UTC 2022
Record UNII
QK318GVY3Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIRAZOLINE
INN  
INN  
Official Name English
2-((O-CYCLOPROPYLPHENOXY)METHYL)-2-IMIDAZOLINE
Common Name English
cirazoline [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL13852
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
EVMPD
SUB07478MIG
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
CAS
59939-16-1
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
DRUG BANK
DB09202
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
MESH
C014282
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
NCI_THESAURUS
C77294
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
EPA CompTox
DTXSID4045131
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
PUBCHEM
2765
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
WIKIPEDIA
CIRAZOLINE
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
INN
4221
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
FDA UNII
QK318GVY3Y
Created by admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY