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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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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Cholesterol depletion disrupts caveolae and differentially impairs agonist-induced arterial contraction. | 2002 Aug 1 |
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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 |
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A photosensitive vascular smooth muscle store of nitric oxide in mouse aorta: no dependence on expression of endothelial nitric oxide synthase. | 2003 Mar |
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Regulation of the release of serotonin in the dorsal raphe nucleus by alpha1 and alpha2 adrenoceptors. | 2003 Oct |
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Preoptic alpha 1- and alpha 2-noradrenergic agonists induce, respectively, PGE2-independent and PGE2-dependent hyperthermic responses in guinea pigs. | 2004 Jun |
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Effects of chloride substitution on electromechanical responses in the pulmonary artery of Dahl normotensive and hypertensive rats. | 2004 Mar |
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Increased Rho activation and PKC-mediated smooth muscle contractility in the absence of caveolin-1. | 2006 Dec |
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Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons. | 2006 Feb |
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Separable noradrenergic and dopaminergic regulation of prepulse inhibition in rats: implications for predictive validity and Tourette Syndrome. | 2006 Jun |
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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 |
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Beta(2)-Adrenergic activation increases glycogen synthesis in L6 skeletal muscle cells through a signalling pathway independent of cyclic AMP. | 2007 Jan |
|
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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 21:51:15 UTC 2023
by
admin
on
Thu Jul 06 21:51:15 UTC 2023
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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 |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29709
Created by
admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
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Code System | Code | Type | Description | ||
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CHEMBL13852
Created by
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SUB07478MIG
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admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
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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
Created by
admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
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CIRAZOLINE
Created by
admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
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4221
Created by
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QK318GVY3Y
Created by
admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
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PRIMARY | |||
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100000081544
Created by
admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
Ki
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TARGET -> AGONIST | |||
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TARGET -> AGONIST |
Ki
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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