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
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)
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227 |
120.0 nM [Ki] | ||
Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227 |
960.0 nM [Ki] | ||
Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227 |
660.0 nM [Ki] |
PubMed
Title | Date | PubMed |
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Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist. | 1982 Jul |
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Orthostatic hypotension occurs following alpha 2-adrenoceptor blockade in chronic prazosin-pretreated conscious spontaneously hypertensive rats. | 1992 Aug |
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Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes. | 1994 Nov |
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Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes. | 1995 Sep |
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Adrenergic stimulation of lipoprotein lipase gene expression in rat brown adipocytes differentiated in culture: mediation via beta3- and alpha1-adrenergic receptors. | 1997 Feb 1 |
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The release of noradrenaline in the locus coeruleus and prefrontal cortex studied with dual-probe microdialysis. | 2001 Jul 6 |
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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 |
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Agmatine and putrescine uptake in the human glioma cell line SK-MG-1. | 2001 Jun |
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Noradrenaline release-inhibiting receptors on PC12 cells devoid of alpha(2(-)) and CB(1) receptors: similarities to presynaptic imidazoline and edg receptors. | 2002 Feb |
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A comparative study of the effects of Cl(-) channel blockers on mesenteric vascular conductance in anaesthetized rat. | 2002 Jul 12 |
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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 |
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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 |
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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 |
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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
Edited
Sun Dec 18 18:28:21 UTC 2022
by
admin
on
Sun Dec 18 18:28:21 UTC 2022
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Record UNII |
QK318GVY3Y
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Record Status |
Validated (UNII)
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Record Version |
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-
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English |
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NCI_THESAURUS |
C29709
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admin on Sun Dec 18 18:28:21 UTC 2022 , Edited by admin on Sun Dec 18 18:28:21 UTC 2022
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Code System | Code | Type | Description | ||
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CHEMBL13852
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SUB07478MIG
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59939-16-1
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DB09202
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C014282
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C77294
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DTXSID4045131
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2765
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CIRAZOLINE
Created by
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4221
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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
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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ACTIVE MOIETY |