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
Orthostatic hypotension occurs following alpha 2-adrenoceptor blockade in chronic prazosin-pretreated conscious spontaneously hypertensive rats.	1992 Aug	1355091
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
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
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
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands.	2004 Oct	15451775
Neurotensin agonists block the prepulse inhibition deficits produced by a 5-HT2A and an alpha1 agonist.	2004 Sep	15107967
Noradrenergic inputs mediate state dependence of auditory responses in the avian song system.	2004 Sep 1	15342742
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
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
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
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	18184607
Different response of ANP secretion to adrenoceptor stimulation in renal hypertensive rat atria.	2008 Jul	18378355
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
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009 Oct 23	19725810
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:21:19 GMT 2023` Edited by `admin` on `Sat Dec 16 16:21:19 GMT 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