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
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)
| 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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
Edited
Fri Jun 25 23:44:15 UTC 2021
by
admin
on
Fri Jun 25 23:44:15 UTC 2021
|
| Record UNII |
QK318GVY3Y
|
| Record Status |
Validated (UNII)
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| Record Version |
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-
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| Name | Type | Language | ||
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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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
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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CHEMBL13852
Created by
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SUB07478MIG
Created by
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59939-16-1
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DB09202
Created by
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C014282
Created by
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C77294
Created by
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59939-16-1
Created by
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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
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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
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4221
Created by
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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
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
TARGET -> AGONIST |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
