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Details

Stereochemistry ACHIRAL
Molecular Formula C13H16N2O
Molecular Weight 216.2794
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIRAZOLINE

SMILES

c1ccc(c(c1)C2CC2)OCC3=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 216.2794
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
Effects of staurosporine on the pressor responses to alpha-adrenoceptor agonists in pithed rats: a comparison with nifedipine.
1991
Orthostatic hypotension occurs following alpha 2-adrenoceptor blockade in chronic prazosin-pretreated conscious spontaneously hypertensive rats.
1992 Aug
Effects on ingestive behavior in rats of the alpha 1-adrenoceptor agonist cirazoline.
1992 Jan 7
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
Identification and characterization of the imidazoline I2b-binding sites in the hamster brown adipose tissue as a study model for imidazoline receptors.
2003 Apr
Atypical [(3)H]clonidine binding sites in human caudate and platelets on cryostat-cut sections.
2003 Dec
Identification and pharmacological characterization of a specific agmatine transport system in human tumor cell lines.
2003 Dec
Stimulation of alpha1-adrenoceptors in the rat medial prefrontal cortex increases the local in vivo 5-hydroxytryptamine release: reversal by antipsychotic drugs.
2003 Nov
Tempol, an antioxidant, restores endothelium-derived hyperpolarizing factor-mediated vasodilation during hypertension.
2003 Nov 14
Regulation of the release of serotonin in the dorsal raphe nucleus by alpha1 and alpha2 adrenoceptors.
2003 Oct
Noradrenaline inhibits autonomous activity in the isolated guinea pig bladder.
2004 Feb
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
Protein kinase C overactivity impairs prefrontal cortical regulation of working memory.
2004 Oct 29
Neurotensin agonists block the prepulse inhibition deficits produced by a 5-HT2A and an alpha1 agonist.
2004 Sep
Noradrenergic inputs mediate state dependence of auditory responses in the avian song system.
2004 Sep 1
alpha1A-adrenoceptors activate glucose uptake in L6 muscle cells through a phospholipase C-, phosphatidylinositol-3 kinase-, and atypical protein kinase C-dependent pathway.
2005 Feb
Effects of chloride substitution in isolated mesenteric blood vessels from Dahl normotensive and hypertensive rats.
2005 Jul
Yohimbine disrupts prepulse inhibition in rats via action at 5-HT1A receptors, not alpha2-adrenoceptors.
2005 Jul
Impaired alpha1-adrenergic responses in aged rat hearts.
2005 Jun
Impact of nitric oxide synthase inhibitor and chloride channel antagonist on mesenteric vascular conductance in anesthetized Dahl normotensive and hypertensive rats.
2005 Jun
Addition of a signal peptide sequence to the alpha1D-adrenoceptor gene increases the density of receptors, as determined by [3H]-prazosin binding in the membranes.
2005 Mar
Increased Rho activation and PKC-mediated smooth muscle contractility in the absence of caveolin-1.
2006 Dec
Discriminative stimulus properties of the selective and highly potent alpha2-adrenoceptor agonist, S18616, in rats: mediation by the alpha2A subtype, and blockade by the atypical antidepressants, mirtazapine and mianserin.
2006 Sep
Iloperidone reduces sensorimotor gating deficits in pharmacological models, but not a developmental model, of disrupted prepulse inhibition in rats.
2006 Sep
Imidazoline receptors in relaxation of acetylcholine-constricted isolated rat jejunum.
2006 Sep-Oct
Medial prefrontal cortical alpha1 adrenoreceptor modulation of the nucleus accumbens dopamine response to stress in Long-Evans rats.
2007 Apr
Beta(2)-Adrenergic activation increases glycogen synthesis in L6 skeletal muscle cells through a signalling pathway independent of cyclic AMP.
2007 Jan
Mechanisms of modafinil: A review of current research.
2007 Jun
Presynaptic alpha-adrenoceptors in median preoptic nucleus modulate inhibitory neurotransmission from subfornical organ and organum vasculosum lamina terminalis.
2007 May
Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions.
2008 Apr 23
The adrenergic receptor subtypes present in frog (Rana esculenta) skin.
2008 Aug
Enhanced alpha1 adrenergic sensitivity in sensorimotor gating deficits in neonatal ventral hippocampus-lesioned rats.
2008 Dec
Evidence that some imidazoline derivatives inhibit peripherally the vasopressor sympathetic outflow in pithed rats.
2008 Dec 5
The effects of Cirazoline, an alpha-1 adrenoreceptor agonist, on the firing rates of thermally classified anterior hypothalamic neurons in rat brain slices.
2008 Feb 8
Different response of ANP secretion to adrenoceptor stimulation in renal hypertensive rat atria.
2008 Jul
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
Might adrenergic alpha2C-agonists/alpha2A-antagonists become novel therapeutic tools for pain treatment with morphine?
2009 Nov 26
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
2009 Oct 23
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
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 Fri Jun 25 23:44:15 UTC 2021
Edited
by admin
on Fri Jun 25 23:44:15 UTC 2021
Record UNII
QK318GVY3Y
Record Status Validated (UNII)
Record Version
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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 Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL13852
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
EVMPD
SUB07478MIG
Created by admin on Fri Jun 25 23:44:15 UTC 2021 , Edited by admin on Fri Jun 25 23:44:15 UTC 2021
PRIMARY
CAS
59939-16-1
Created by admin on Fri Jun 25 23:44:15 UTC 2021 , Edited by admin on Fri Jun 25 23:44:15 UTC 2021
PRIMARY
DRUG BANK
DB09202
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
MESH
C014282
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
NCI_THESAURUS
C77294
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
EPA CompTox
59939-16-1
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
PUBCHEM
2765
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
WIKIPEDIA
CIRAZOLINE
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
INN
4221
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
FDA UNII
QK318GVY3Y
Created by admin on Fri Jun 25 23:44:16 UTC 2021 , Edited by admin on Fri Jun 25 23:44:16 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY