NAV

Cirazoline

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

Identification

Generic Name
Cirazoline
DrugBank Accession Number
DB09202
Background

Cirazoline acts on a number of α adrenergic receptors. It is an agonist of α1A, partial agonist of α1B and α1D, and a nonselective antagonist of α2. 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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 216.284
Monoisotopic: 216.126263143
Chemical Formula
C13H16N2O
Synonyms
  • Cirazoline
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Humans
AAlpha-1B adrenergic receptor
partial agonist
Humans
AAlpha-1D adrenergic receptor
partial agonist
Humans
AAlpha-2 adrenergic receptors
antagonist
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AcebutololThe therapeutic efficacy of Cirazoline can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Cirazoline.
AcemetacinThe risk or severity of hypertension can be increased when Cirazoline is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Cirazoline.
AclidiniumThe risk or severity of Tachycardia can be increased when Aclidinium is combined with Cirazoline.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-imidazoline / Alkyl aryl ether / Amidine / Aromatic heteromonocyclic compound / Azacycle / Carboximidamide / Carboxylic acid amidine / Ether / Hydrocarbon derivative / Imidolactam
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
QK318GVY3Y
CAS number
59939-16-1
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

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. [Article]
  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. [Article]
  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. [Article]
PubChem Compound
2765
PubChem Substance
310265110
ChemSpider
2663
BindingDB
50027060
ChEBI
92950
ChEMBL
CHEMBL13852
ZINC
ZINC000000001160
Wikipedia
Cirazoline

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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/MSsplash10-014i-0090000000-8f1c42f855da23872714
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-0970000000-d424d5d6a86cda21b1a8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3290000000-f7761eb8ffdebd9e987c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3900000000-1817e4bdcceaf551bf07
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-6900000000-e684129cfa4ff8471326
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-067i-9420000000-dc1f4f2436c47494a790
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-159.6135986
predicted
DarkChem Lite v0.1.0
[M-H]-144.99522
predicted
DeepCCS 1.0 (2019)
[M+H]+160.3443986
predicted
DarkChem Lite v0.1.0
[M+H]+147.3908
predicted
DeepCCS 1.0 (2019)
[M+Na]+159.6456986
predicted
DarkChem Lite v0.1.0
[M+Na]+153.7824
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Alpha-1A adrenergic receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details2. Alpha-1B adrenergic receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details3. Alpha-1D adrenergic receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details4. Alpha-2 adrenergic receptors (Protein Group)
Kind
Protein group
Organism
Humans
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:
NameUniProt ID
Alpha-2A adrenergic receptorP08913
Alpha-2B adrenergic receptorP18089
Alpha-2C adrenergic receptorP18825
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. [Article]
  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. [Article]

Drug created at October 19, 2015 16:26 / Updated at February 21, 2021 18:52