From Wikipedia, the free encyclopedia
Cirazoline
Names
Preferred IUPAC name
2-[(2-Cyclopropylphenoxy)methyl]-4,5-dihydro-1H -imidazole
Identifiers
ChEMBL
ChemSpider
MeSH
Cirazoline
UNII
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)
Y Key: YAORIDZYZDUZCM-UHFFFAOYSA-N
Y 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
O(c1c(cccc1)C2CC2)CC/3=N/CCN\3
Properties
C 13 H 16 N 2 O
Molar mass
216.284 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Cirazoline is a full
agonist at the
α1A adrenergic receptor , a
partial agonist at both the
α1B and
α1D 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] Administration of cirazoline also seemed to present impairment in the spatial memory of monkeys through the activation of the same receptors that showed decreased food intake in rats.
[4]
[5] However, in preliminary studies, through stimulation of α2 adrenoceptors, working memory is comparatively improved.
[4]
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 .
^
a
b 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 .
^
a
b Arnsten, A.F.T.; Jentsch, J.D. (September 1997).
"The Alpha-1 Adrenergic Agonist, Cirazoline, Impairs Spatial Working Memory Performance in Aged Monkeys" . Pharmacology Biochemistry and Behavior . 58 (1): 55–59.
doi :
10.1016/s0091-3057(96)00477-7 .
ISSN
0091-3057 .
PMID
9264070 .
S2CID
20663570 .
^ Imbery, Irdmusa, Speidell, Streer, Griffin, Ted E., Mitra S., Andrew P., Mark S., John D. (15 December 2007).
"The effects of Cirazoline, an alpha-1 adrenoreceptor agonist, on the firing rates of thermally classified anterior hypothalamic neurons in rat brain slices" . Brain Research . 1193 : 93–101.
doi :
10.1016/j.brainres.2007.12.016 .
PMC
2268753 .
PMID
18184607 . {{
cite journal }}
: CS1 maint: multiple names: authors list (
link )
α1
Agonists Antagonists
Abanoquil
Ajmalicine
Alfuzosin
Anisodamine
Anisodine
Atiprosin
Atypical antipsychotics (e.g.,
brexpiprazole ,
clozapine ,
olanzapine ,
quetiapine ,
risperidone )
Benoxathian
Beta blockers (e.g.,
adimolol ,
amosulalol ,
arotinolol ,
carvedilol ,
eugenodilol ,
labetalol )
Buflomedil
Bunazosin
Corynanthine
Dapiprazole
Domesticine
Doxazosin
Ergolines (e.g.,
acetergamine ,
ergotamine ,
dihydroergotamine ,
lisuride ,
nicergoline ,
terguride )
Etoperidone
Fenspiride
Hydroxyzine
Indoramin
Ketanserin
L-765,314
mCPP
Mepiprazole
Metazosin
Monatepil
Moxisylyte
Naftopidil
Nantenine
Neldazosin
Niaprazine
Niguldipine
Pardoprunox
Pelanserin
Perlapine
Phendioxan
Phenoxybenzamine
Phentolamine
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Piperoxan
Prazosin
Quinazosin
Quinidine
Silodosin
Spegatrine
Spiperone
Talipexole
Tamsulosin
Terazosin
Tiodazosin
Tolazoline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin )
Tricyclic antidepressants (e.g.,
amitriptyline ,
clomipramine ,
doxepin ,
imipramine ,
trimipramine )
Trimazosin
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Urapidil
WB-4101
Zolertine
α2
Agonists Antagonists
1-PP
Adimolol
Amesergide
Aptazapine
Atipamezole
Atypical antipsychotics (e.g.,
asenapine ,
brexpiprazole ,
clozapine ,
lurasidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
zotepine )
Azapirones (e.g.,
buspirone ,
gepirone ,
ipsapirone ,
tandospirone )
BRL-44408
Buflomedil
Cirazoline
Efaroxan
Esmirtazapine
Fenmetozole
Fluparoxan
Idazoxan
Ketanserin
Lisuride
mCPP
Mianserin
Mirtazapine
NAN-190
Pardoprunox
Phentolamine
Phenoxybenzamine
Piperoxan
Piribedil
Rauwolscine
Rotigotine
Setiptiline
Spegatrine
Spiroxatrine
Sunepitron
Terguride
Tolazoline
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Yohimbine
β