This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Cirazoline
Accession Number
DB09202
Type
Small Molecule
Groups
Experimental
Description

Cirazoline is a full agonist at the alpha-1A (α1A) adrenergic receptor, a partial agonist at both the alpha-1B (α1B) adrenergic receptor and alpha-1D (α1D) adrenergic receptor, and a nonselective antagonist to the alpha-2 adrenergic receptor. It is believed that this combination of properties could make cirazoline an effective vasoconstricting agent. Cirazoline has also been shown to decrease food intake in rats, purportedly through activation of α1-adrenoceptors in the paraventricular nucleus in the hypothalamus of the brain.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
QK318GVY3Y
CAS number
59939-16-1
Weight
Average: 216.284
Monoisotopic: 216.126263143
Chemical Formula
C13H16N2O
InChI Key
YAORIDZYZDUZCM-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[(2-cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole
SMILES
[H]N1CCN=C1COC1=CC=CC=C1C1CC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-1B adrenergic receptor
partial agonist
Human
AAlpha-1D adrenergic receptor
partial agonist
Human
AAlpha-2 adrenergic receptors
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololThe therapeutic efficacy of Cirazoline can be decreased when used in combination with Acebutolol.
AcepromazineThe therapeutic efficacy of Cirazoline can be decreased when used in combination with Acepromazine.
AlfuzosinThe therapeutic efficacy of Cirazoline can be decreased when used in combination with Alfuzosin.
AlprenololThe therapeutic efficacy of Cirazoline can be decreased when used in combination with Alprenolol.
AmineptineAmineptine may increase the vasopressor activities of Cirazoline.
AmitriptylineAmitriptyline may increase the vasopressor activities of Cirazoline.
AmitriptylinoxideAmitriptylinoxide may increase the vasopressor activities of Cirazoline.
AmoxapineAmoxapine may increase the vasopressor activities of Cirazoline.
AnisodamineThe therapeutic efficacy of Cirazoline can be decreased when used in combination with Anisodamine.
AripiprazoleThe therapeutic efficacy of Cirazoline can be decreased when used in combination with Aripiprazole.
Food Interactions
Not Available

References

General References
  1. Horie K, Obika K, Foglar R, Tsujimoto G: Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes. Br J Pharmacol. 1995 Sep;116(1):1611-8. [PubMed:8564227]
  2. Ruffolo RR Jr, Waddell JE: Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist. J Pharmacol Exp Ther. 1982 Jul;222(1):29-36. [PubMed:6123592]
  3. Davies BT, Wellman PJ: Effects on ingestive behavior in rats of the alpha 1-adrenoceptor agonist cirazoline. Eur J Pharmacol. 1992 Jan 7;210(1):11-6. [PubMed:1350985]
External Links
PubChem Compound
2765
PubChem Substance
310265110
ChemSpider
2663
BindingDB
50027060
ChEBI
92950
ChEMBL
CHEMBL13852
Wikipedia
Cirazoline

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.389 mg/mLALOGPS
logP2.62ALOGPS
logP1.67ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)9.26ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.62 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.7 m3·mol-1ChemAxon
Polarizability24.21 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Alkyl aryl ethers / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Imidolactam / 2-imidazoline / Amidine / Carboxylic acid amidine / Ether / Carboximidamide
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Horie K, Obika K, Foglar R, Tsujimoto G: Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes. Br J Pharmacol. 1995 Sep;116(1):1611-8. [PubMed:8564227]
  2. Ruffolo RR Jr, Waddell JE: Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist. J Pharmacol Exp Ther. 1982 Jul;222(1):29-36. [PubMed:6123592]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Horie K, Obika K, Foglar R, Tsujimoto G: Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes. Br J Pharmacol. 1995 Sep;116(1):1611-8. [PubMed:8564227]
  2. Ruffolo RR Jr, Waddell JE: Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist. J Pharmacol Exp Ther. 1982 Jul;222(1):29-36. [PubMed:6123592]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
References
  1. Horie K, Obika K, Foglar R, Tsujimoto G: Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes. Br J Pharmacol. 1995 Sep;116(1):1611-8. [PubMed:8564227]
  2. Ruffolo RR Jr, Waddell JE: Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist. J Pharmacol Exp Ther. 1982 Jul;222(1):29-36. [PubMed:6123592]
Kind
Protein group
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...

Components:
References
  1. Horie K, Obika K, Foglar R, Tsujimoto G: Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes. Br J Pharmacol. 1995 Sep;116(1):1611-8. [PubMed:8564227]
  2. Ruffolo RR Jr, Waddell JE: Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist. J Pharmacol Exp Ther. 1982 Jul;222(1):29-36. [PubMed:6123592]

Drug created on October 19, 2015 10:26 / Updated on November 02, 2018 07:00