CIRAZOLINE

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 Search

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)

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227 | https://www.ncbi.nlm.nih.gov/pubmed/6123592 | https://www.ncbi.nlm.nih.gov/pubmed/1350985 | https://www.ncbi.nlm.nih.gov/pubmed/9264070

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

Primary Target	Pharmacology	Potency
Alpha-1a adrenergic receptor 66 Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2678	120.0 nM [Ki]
Alpha-1b adrenergic receptor 44 Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2678	960.0 nM [Ki]
Alpha-1d adrenergic receptor 36 Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2678	660.0 nM [Ki]

PubMed

Title	Date	PubMed
Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist.	1982 Jul	6123592
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.	1994 Nov	7969082
Adrenergic stimulation of lipoprotein lipase gene expression in rat brown adipocytes differentiated in culture: mediation via beta3- and alpha1-adrenergic receptors.	1997 Feb 1	9032464
The release of noradrenaline in the locus coeruleus and prefrontal cortex studied with dual-probe microdialysis.	2001 Jul 6	11430860
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	11331292
Agmatine and putrescine uptake in the human glioma cell line SK-MG-1.	2001 Jun	11414662
Cholesterol depletion disrupts caveolae and differentially impairs agonist-induced arterial contraction.	2002 Aug 1	12171786
Noradrenaline release-inhibiting receptors on PC12 cells devoid of alpha(2(-)) and CB(1) receptors: similarities to presynaptic imidazoline and edg receptors.	2002 Feb	11738482
Alpha2-adrenoreceptors profile modulation and high antinociceptive activity of (S)-(-)-2-[1-(biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole.	2002 Jan 3	11754577
Effect of nitric oxide synthase inhibitor N(omega) nitro-L-arginine methyl ester on relaxant responses to calcium channel antagonists in isolated aortic rings from Dahl normotensive and hypertensive rats.	2002 Mar	11862114
Opposite effects of alpha 1- and beta-adrenoceptor stimulation on both glutamate- and gamma-aminobutyric acid-mediated spontaneous transmission in cultured rat hippocampal neurons.	2003 Feb 15	12548707
Regulation of the release of serotonin in the dorsal raphe nucleus by alpha1 and alpha2 adrenoceptors.	2003 Oct	12872296
Cold adaptation modulates Ca2+ signaling in brown preadipocytes.	2004 Jul	15514722
Preoptic alpha 1- and alpha 2-noradrenergic agonists induce, respectively, PGE2-independent and PGE2-dependent hyperthermic responses in guinea pigs.	2004 Jun	14962823
Effects of chloride substitution on electromechanical responses in the pulmonary artery of Dahl normotensive and hypertensive rats.	2004 Mar	14993100
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands.	2004 Oct	15451775
Protein kinase C overactivity impairs prefrontal cortical regulation of working memory.	2004 Oct 29	15514161
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	15550506
Impaired alpha1-adrenergic responses in aged rat hearts.	2005 Jun	15910657
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	15678090
Increased Rho activation and PKC-mediated smooth muscle contractility in the absence of caveolin-1.	2006 Dec	17102036
Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons.	2006 Feb	16249372
Medial prefrontal cortical alpha1 adrenoreceptor modulation of the nucleus accumbens dopamine response to stress in Long-Evans rats.	2007 Apr	17294052
Alpha 1-adrenoceptor agonists protect against stress-induced death of neural progenitor cells.	2007 Nov 14	17643416
Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions.	2008 Apr 23	18431471
Enhanced alpha1 adrenergic sensitivity in sensorimotor gating deficits in neonatal ventral hippocampus-lesioned rats.	2008 Dec	18460229
Effects of a Western diet versus high glucose on endothelium-dependent relaxation in murine micro- and macro-vasculature.	2008 Dec 28	18996368
Different response of ANP secretion to adrenoceptor stimulation in renal hypertensive rat atria.	2008 Jul	18378355
Catecholaminergic automatic activity in the rat pulmonary vein: electrophysiological differences between cardiac muscle in the left atrium and pulmonary vein.	2009 Jul	19429824
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	20337661
Modulation of N-type calcium currents by presynaptic imidazoline receptor activation in rat superior cervical ganglion neurons.	2010 Oct	20696781

Name

Type

Language

CIRAZOLINE

Official Name

English

2-((O-CYCLOPROPYLPHENOXY)METHYL)-2-IMIDAZOLINE

Common Name

English

cirazoline [INN]

Common Name

English

LD-3098

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709