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 66 Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2678	120.0 nM [Ki]
Alpha-1b adrenergic receptor 44 Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2678	960.0 nM [Ki]
Alpha-1d adrenergic receptor 36 Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8564227	Agonist 2678	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
Effects of staurosporine on the pressor responses to alpha-adrenoceptor agonists in pithed rats: a comparison with nifedipine.	1991	1685570
Effects on ingestive behavior in rats of the alpha 1-adrenoceptor agonist cirazoline.	1992 Jan 7	1350985
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
[Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons].	2001 Nov	11774707
Effect of nitric oxide synthase inhibitor N(omega) nitro-L-arginine methyl ester on relaxant responses to calcium channel antagonists in isolated aortic rings from Dahl normotensive and hypertensive rats.	2002 Mar	11862114
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
Identification and pharmacological characterization of a specific agmatine transport system in human tumor cell lines.	2003 Dec	15028572
Opposite effects of alpha 1- and beta-adrenoceptor stimulation on both glutamate- and gamma-aminobutyric acid-mediated spontaneous transmission in cultured rat hippocampal neurons.	2003 Feb 15	12548707
Contractile actions of imidazoline alpha-adrenoceptor agonists and effects of noncompetitive alpha1-adrenoceptor antagonists in human vas deferens.	2003 Feb 21	12591110
A photosensitive vascular smooth muscle store of nitric oxide in mouse aorta: no dependence on expression of endothelial nitric oxide synthase.	2003 Mar	12642395
Stimulation of alpha1-adrenoceptors in the rat medial prefrontal cortex increases the local in vivo 5-hydroxytryptamine release: reversal by antipsychotic drugs.	2003 Nov	14622114
Tempol, an antioxidant, restores endothelium-derived hyperpolarizing factor-mediated vasodilation during hypertension.	2003 Nov 14	14637180
Regulation of the release of serotonin in the dorsal raphe nucleus by alpha1 and alpha2 adrenoceptors.	2003 Oct	12872296
Noradrenaline inhibits autonomous activity in the isolated guinea pig bladder.	2004 Feb	14764146
Preoptic alpha 1- and alpha 2-noradrenergic agonists induce, respectively, PGE2-independent and PGE2-dependent hyperthermic responses in guinea pigs.	2004 Jun	14962823
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands.	2004 Oct	15451775
Protein kinase C overactivity impairs prefrontal cortical regulation of working memory.	2004 Oct 29	15514161
Neurotensin agonists block the prepulse inhibition deficits produced by a 5-HT2A and an alpha1 agonist.	2004 Sep	15107967
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	15550506
Yohimbine disrupts prepulse inhibition in rats via action at 5-HT1A receptors, not alpha2-adrenoceptors.	2005 Jul	15719216
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	15678090
Increased Rho activation and PKC-mediated smooth muscle contractility in the absence of caveolin-1.	2006 Dec	17102036
Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons.	2006 Feb	16249372
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	16814817
Medial prefrontal cortical alpha1 adrenoreceptor modulation of the nucleus accumbens dopamine response to stress in Long-Evans rats.	2007 Apr	17294052
Beta(2)-Adrenergic activation increases glycogen synthesis in L6 skeletal muscle cells through a signalling pathway independent of cyclic AMP.	2007 Jan	17119919
Mechanisms of modafinil: A review of current research.	2007 Jun	19300566
Presynaptic alpha-adrenoceptors in median preoptic nucleus modulate inhibitory neurotransmission from subfornical organ and organum vasculosum lamina terminalis.	2007 May	17218440
Alpha 1-adrenoceptor agonists protect against stress-induced death of neural progenitor cells.	2007 Nov 14	17643416
Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions.	2008 Apr 23	18431471
The adrenergic receptor subtypes present in frog (Rana esculenta) skin.	2008 Aug	18544474
Enhanced alpha1 adrenergic sensitivity in sensorimotor gating deficits in neonatal ventral hippocampus-lesioned rats.	2008 Dec	18460229
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
Different response of ANP secretion to adrenoceptor stimulation in renal hypertensive rat atria.	2008 Jul	18378355
alpha(1A)- and alpha(1B)-adrenergic receptors differentially modulate antidepressant-like behavior in the mouse.	2009 Aug 18	19540213
Might adrenergic alpha2C-agonists/alpha2A-antagonists become novel therapeutic tools for pain treatment with morphine?	2009 Nov 26	19886609
Alpha1-adrenoceptors modulate citalopram-induced serotonin release.	2010 Jun	20043931
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 `Sat Dec 16 16:21:19 UTC 2023` Edited by `admin` on `Sat Dec 16 16:21:19 UTC 2023`
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

LD-3098

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709