Cirazoline

Cirazoline
Names
	IUPAC name 2-[(2-cyclopropylphenoxy)methyl]-4,5-dihydro-1H-imidazole
Identifiers
CAS Number	59939-16-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL13852 ;
ChemSpider	2663 ;
IUPHAR/BPS	515;
MeSH	Cirazoline
PubChem CID	2765;
UNII	QK318GVY3Y ;
CompTox Dashboard (EPA)	DTXSID4045131 ;
	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) Key: YAORIDZYZDUZCM-UHFFFAOYSA-N ; InChI=1/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) Key: YAORIDZYZDUZCM-UHFFFAOYAV;
	SMILES O(c1c(cccc1)C2CC2)CC/3=N/CCN\3;
Properties
Chemical formula	C13H16N2O
Molar mass	216.279 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Cirazoline is a full agonist at the α_1A adrenergic receptor, a partial agonist at both the α_1B and α_1D adrenergic receptors,[1] and a nonselective antagonist to the α₂ adrenergic receptor.[2] It is believed that this combination of properties could make cirazoline an effective vasoconstricting agent.[2]

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.[3]

References

Horie, K; Obika, K; Foglar, R. (1995). "Selectivity of the imidazoline α-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned α₁-adrenoceptor subtypes". British Journal of Pharmacology. 116 (1): 1611–8. doi:10.1111/j.1476-5381.1995.tb16381.x. PMC 1908909. PMID 8564227.
Ruffolo, R. R. Jr.; Waddell, J. E. (1982). "Receptor interactions of imidazolines. IX. Cirazoline is an α₁ adrenergic agonist and an α₂ adrenergic antagonist". Journal of Pharmacology and Experimental Therapeutics. 222 (1): 29–36. PMID 6123592.
Davies, B. T.; Wellman, P. J. (1992). "Effects on ingestive behavior in rats of the α₁-adrenoceptor agonist cirazoline". European Journal of Pharmacology. 210 (1): 11–16. doi:10.1016/0014-2999(92)90645-K. PMID 1350985.

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[horie-1] Horie, K; Obika, K; Foglar, R. (1995). "Selectivity of the imidazoline α-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned α₁-adrenoceptor subtypes". British Journal of Pharmacology. 116 (1): 1611–8. doi:10.1111/j.1476-5381.1995.tb16381.x. PMC 1908909. PMID 8564227.

[ruffolo-2] Ruffolo, R. R. Jr.; Waddell, J. E. (1982). "Receptor interactions of imidazolines. IX. Cirazoline is an α₁ adrenergic agonist and an α₂ adrenergic antagonist". Journal of Pharmacology and Experimental Therapeutics. 222 (1): 29–36. PMID 6123592.

[davies-3] Davies, B. T.; Wellman, P. J. (1992). "Effects on ingestive behavior in rats of the α₁-adrenoceptor agonist cirazoline". European Journal of Pharmacology. 210 (1): 11–16. doi:10.1016/0014-2999(92)90645-K. PMID 1350985.