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

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

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 64 Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2637	120.0 nM [Ki]
Alpha-1b adrenergic receptor 42 Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2637	960.0 nM [Ki]
Alpha-1d adrenergic receptor 34 Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2637	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
Orthostatic hypotension occurs following alpha 2-adrenoceptor blockade in chronic prazosin-pretreated conscious spontaneously hypertensive rats.	1992 Aug	1355091
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.	1994 Nov	7969082
Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes.	1995 Sep	8564227
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
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
A comparative study of the effects of Cl(-) channel blockers on mesenteric vascular conductance in anaesthetized rat.	2002 Jul 12	12126972
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	11988078
Identification and characterization of the imidazoline I2b-binding sites in the hamster brown adipose tissue as a study model for imidazoline receptors.	2003 Apr	12919003
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
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands.	2004 Oct	15451775
Noradrenergic inputs mediate state dependence of auditory responses in the avian song system.	2004 Sep 1	15342742
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
Mechanisms of modafinil: A review of current research.	2007 Jun	19300566
The adrenergic receptor subtypes present in frog (Rana esculenta) skin.	2008 Aug	18544474
Effects of a Western diet versus high glucose on endothelium-dependent relaxation in murine micro- and macro-vasculature.	2008 Dec 28	18996368
Evidence that some imidazoline derivatives inhibit peripherally the vasopressor sympathetic outflow in pithed rats.	2008 Dec 5	18774761
Signal transduction and gene expression in cultured accessory olfactory bulb neurons.	2008 Nov 19	18848604
alpha1-Adrenergic receptors regulate neurogenesis and gliogenesis.	2009 Aug	19487244
alpha(1A)- and alpha(1B)-adrenergic receptors differentially modulate antidepressant-like behavior in the mouse.	2009 Aug 18	19540213
Catecholaminergic automatic activity in the rat pulmonary vein: electrophysiological differences between cardiac muscle in the left atrium and pulmonary vein.	2009 Jul	19429824
Dual regulation of heat-activated K+ channel in rat DRG neurons via alpha(1) and beta adrenergic receptors.	2009 Jul 17	19470391
Acute dilation to alpha(2)-adrenoceptor antagonists uncovers dual constriction and dilation mediated by arterial alpha(2)-adrenoceptors.	2009 Nov	19785657
Might adrenergic alpha2C-agonists/alpha2A-antagonists become novel therapeutic tools for pain treatment with morphine?	2009 Nov 26	19886609
The selective alpha1 adrenoceptor antagonist HEAT reduces L-DOPA-induced dyskinesia in a rat model of Parkinson's disease.	2010 Feb	19771592
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
Alpha1-adrenoceptors modulate citalopram-induced serotonin release.	2010 Jun	20043931
Impairment of α1-adrenoceptor-mediated contractile activity in caudal arterial smooth muscle from type 2 diabetic Goto-Kakizaki rats.	2010 Mar	19793102
Modulation of N-type calcium currents by presynaptic imidazoline receptor activation in rat superior cervical ganglion neurons.	2010 Oct	20696781

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

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Name

Type

Language

CIRAZOLINE

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