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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 of CIRAZOLINE

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

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

Targets

Primary TargetPharmacologyConditionPotency
120.0 nM [Ki]
960.0 nM [Ki]
660.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist.
1982 Jul
Adrenergic stimulation of lipoprotein lipase gene expression in rat brown adipocytes differentiated in culture: mediation via beta3- and alpha1-adrenergic receptors.
1997 Feb 1
Cholesterol depletion disrupts caveolae and differentially impairs agonist-induced arterial contraction.
2002 Aug 1
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
Identification and characterization of the imidazoline I2b-binding sites in the hamster brown adipose tissue as a study model for imidazoline receptors.
2003 Apr
A photosensitive vascular smooth muscle store of nitric oxide in mouse aorta: no dependence on expression of endothelial nitric oxide synthase.
2003 Mar
Regulation of the release of serotonin in the dorsal raphe nucleus by alpha1 and alpha2 adrenoceptors.
2003 Oct
Preoptic alpha 1- and alpha 2-noradrenergic agonists induce, respectively, PGE2-independent and PGE2-dependent hyperthermic responses in guinea pigs.
2004 Jun
Effects of chloride substitution on electromechanical responses in the pulmonary artery of Dahl normotensive and hypertensive rats.
2004 Mar
Increased Rho activation and PKC-mediated smooth muscle contractility in the absence of caveolin-1.
2006 Dec
Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons.
2006 Feb
Separable noradrenergic and dopaminergic regulation of prepulse inhibition in rats: implications for predictive validity and Tourette Syndrome.
2006 Jun
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
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 Thu Jul 06 21:51:15 UTC 2023
Edited
by admin
on Thu Jul 06 21:51:15 UTC 2023
Record UNII
QK318GVY3Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIRAZOLINE
INN  
INN  
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
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL13852
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
EVMPD
SUB07478MIG
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
CAS
59939-16-1
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
DRUG BANK
DB09202
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
MESH
C014282
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
NCI_THESAURUS
C77294
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID4045131
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
PUBCHEM
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
PRIMARY
WIKIPEDIA
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
PRIMARY
INN
4221
Created by admin on Thu Jul 06 21:51:16 UTC 2023 , Edited by admin on Thu Jul 06 21:51:16 UTC 2023
PRIMARY
FDA UNII
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
PRIMARY
SMS_ID
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
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Ki
TARGET -> AGONIST
TARGET -> AGONIST
Ki
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY