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
Structure for Cirazoline (DB09202)
- Weight
- Average: 216.284
Monoisotopic: 216.126263143 - Chemical Formula
- C13H16N2O
- Synonyms
- Cirazoline
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AAlpha-1A adrenergic receptor agonistHumans AAlpha-1B adrenergic receptor partial agonistHumans AAlpha-1D adrenergic receptor partial agonistHumans AAlpha-2 adrenergic receptors antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Cirazoline can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Cirazoline. Acemetacin The risk or severity of hypertension can be increased when Cirazoline is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Cirazoline. Aclidinium The risk or severity of Tachycardia can be increased when Aclidinium is combined with Cirazoline. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Cirazoline. Alclofenac The risk or severity of hypertension can be increased when Cirazoline is combined with Alclofenac. Alfentanil The risk or severity of hypertension can be increased when Alfentanil is combined with Cirazoline. Alfuzosin The therapeutic efficacy of Cirazoline can be decreased when used in combination with Alfuzosin. Aliskiren Cirazoline may decrease the antihypertensive activities of Aliskiren. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- 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]
- 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]
- 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]
- External Links
- PubChem Compound
- 2765
- PubChem Substance
- 310265110
- ChemSpider
- 2663
- BindingDB
- 50027060
- ChEBI
- 92950
- ChEMBL
- CHEMBL13852
- ZINC
- ZINC000000001160
- Wikipedia
- Cirazoline
Clinical Trials
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
Property Value Source Water Solubility 0.389 mg/mL ALOGPS logP 2.62 ALOGPS logP 1.67 Chemaxon logS -2.7 ALOGPS pKa (Strongest Basic) 9.26 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 33.62 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 62.7 m3·mol-1 Chemaxon Polarizability 24.21 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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:
| Name | UniProt ID |
|---|---|
| Alpha-2A adrenergic receptor | P08913 |
| Alpha-2B adrenergic receptor | P18089 |
| Alpha-2C adrenergic receptor | P18825 |
References
- 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]
- 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