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)

HIDE SMILES / InChI

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 67 Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2752	120.0 nM [Ki]
Alpha-1b adrenergic receptor 45 Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2752	960.0 nM [Ki]
Alpha-1d adrenergic receptor 37 Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2752	660.0 nM [Ki]

PubMed

Title	Date	PubMed
Modulation of N-type calcium currents by presynaptic imidazoline receptor activation in rat superior cervical ganglion neurons.	2010-10	20696781
Attenuation of store-operated Ca2+ entry and enhanced expression of TRPC channels in caudal artery smooth muscle from Type 2 diabetic Goto-Kakizaki rats.	2010-07	20337661
Alpha1-adrenoceptors modulate citalopram-induced serotonin release.	2010-06	20043931
Impairment of α1-adrenoceptor-mediated contractile activity in caudal arterial smooth muscle from type 2 diabetic Goto-Kakizaki rats.	2010-03	19793102
The selective alpha1 adrenoceptor antagonist HEAT reduces L-DOPA-induced dyskinesia in a rat model of Parkinson's disease.	2010-02	19771592
Might adrenergic alpha2C-agonists/alpha2A-antagonists become novel therapeutic tools for pain treatment with morphine?	2009-11-26	19886609
Acute dilation to alpha(2)-adrenoceptor antagonists uncovers dual constriction and dilation mediated by arterial alpha(2)-adrenoceptors.	2009-11	19785657
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009-10-23	19725810
alpha(1A)- and alpha(1B)-adrenergic receptors differentially modulate antidepressant-like behavior in the mouse.	2009-08-18	19540213
alpha1-Adrenergic receptors regulate neurogenesis and gliogenesis.	2009-08	19487244
Dual regulation of heat-activated K+ channel in rat DRG neurons via alpha(1) and beta adrenergic receptors.	2009-07-17	19470391
Catecholaminergic automatic activity in the rat pulmonary vein: electrophysiological differences between cardiac muscle in the left atrium and pulmonary vein.	2009-07	19429824
Effects of a Western diet versus high glucose on endothelium-dependent relaxation in murine micro- and macro-vasculature.	2008-12-28	18996368
Evidence that some imidazoline derivatives inhibit peripherally the vasopressor sympathetic outflow in pithed rats.	2008-12-05	18774761
Enhanced alpha1 adrenergic sensitivity in sensorimotor gating deficits in neonatal ventral hippocampus-lesioned rats.	2008-12	18460229
Signal transduction and gene expression in cultured accessory olfactory bulb neurons.	2008-11-19	18848604
The adrenergic receptor subtypes present in frog (Rana esculenta) skin.	2008-08	18544474
Different response of ANP secretion to adrenoceptor stimulation in renal hypertensive rat atria.	2008-07	18378355
Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions.	2008-04-23	18431471
The effects of Cirazoline, an alpha-1 adrenoreceptor agonist, on the firing rates of thermally classified anterior hypothalamic neurons in rat brain slices.	2008-02-08	18184607
Alpha 1-adrenoceptor agonists protect against stress-induced death of neural progenitor cells.	2007-11-14	17643416
Mechanisms of modafinil: A review of current research.	2007-06	19300566
Presynaptic alpha-adrenoceptors in median preoptic nucleus modulate inhibitory neurotransmission from subfornical organ and organum vasculosum lamina terminalis.	2007-05	17218440
Medial prefrontal cortical alpha1 adrenoreceptor modulation of the nucleus accumbens dopamine response to stress in Long-Evans rats.	2007-04	17294052
Beta(2)-Adrenergic activation increases glycogen synthesis in L6 skeletal muscle cells through a signalling pathway independent of cyclic AMP.	2007-01	17119919
Increased Rho activation and PKC-mediated smooth muscle contractility in the absence of caveolin-1.	2006-12	17102036
Disruption of prepulse inhibition after stimulation of central but not peripheral alpha-1 adrenergic receptors.	2006-10	16407904
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.	2006-09	16814817
Iloperidone reduces sensorimotor gating deficits in pharmacological models, but not a developmental model, of disrupted prepulse inhibition in rats.	2006-09	16762376
Separable noradrenergic and dopaminergic regulation of prepulse inhibition in rats: implications for predictive validity and Tourette Syndrome.	2006-06	16583235
Pharmacological characterization of alpha1- and beta-adrenergic synergism of 5'DII activity in rat brown adipocytes.	2006-02	16754200
Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons.	2006-02	16249372
Imidazoline receptors in relaxation of acetylcholine-constricted isolated rat jejunum.	2005-11-25	17085862
Augmentation of alpha1-adrenoceptor-mediated contraction by warming without increased phosphorylation of myosin in rat caudal arterial smooth muscle.	2005-09	16127243
Effects of chloride substitution in isolated mesenteric blood vessels from Dahl normotensive and hypertensive rats.	2005-07	15965362
Yohimbine disrupts prepulse inhibition in rats via action at 5-HT1A receptors, not alpha2-adrenoceptors.	2005-07	15719216
Impaired alpha1-adrenergic responses in aged rat hearts.	2005-06	15910657
Impact of nitric oxide synthase inhibitor and chloride channel antagonist on mesenteric vascular conductance in anesthetized Dahl normotensive and hypertensive rats.	2005-06	15897785
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.	2005-03	15678090
alpha1A-adrenoceptors activate glucose uptake in L6 muscle cells through a phospholipase C-, phosphatidylinositol-3 kinase-, and atypical protein kinase C-dependent pathway.	2005-02	15550506
Protein kinase C overactivity impairs prefrontal cortical regulation of working memory.	2004-10-29	15514161
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands.	2004-10	15451775
Noradrenergic inputs mediate state dependence of auditory responses in the avian song system.	2004-09-01	15342742
Neurotensin agonists block the prepulse inhibition deficits produced by a 5-HT2A and an alpha1 agonist.	2004-09	15107967
Cold adaptation modulates Ca2+ signaling in brown preadipocytes.	2004-07	15514722
Adrenergic stimulation of lipoprotein lipase gene expression in rat brown adipocytes differentiated in culture: mediation via beta3- and alpha1-adrenergic receptors.	1997-02-01	9032464
Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes.	1995-09	8564227
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.	1994-11	7969082
Effects of staurosporine on the pressor responses to alpha-adrenoceptor agonists in pithed rats: a comparison with nifedipine.	1991	1685570
Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist.	1982-07	6123592

Name

Type

Language

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

Preferred Name

English

CIRAZOLINE

Official Name

English

cirazoline [INN]

Common Name

English

LD-3098

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709