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vasoconstrictor (trade names Privine and Sudafed) used in nasal sprays to treat symptoms of nasal congestion and in eyedrops to treat eye irritation (同)Privine, Sudafed

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/05/31 07:55:33」(JST)

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Naphazoline (in the hydrochloride form) is the common name for 2-(1-naphthylmethyl)-2-imidazoline hydrochloride. It is a sympathomimetic agent with marked alpha adrenergic activity. It is a vasoconstrictor with a rapid action in reducing swelling when applied to mucous membrane. It acts on alpha-receptors in the arterioles of the conjunctiva to produce constriction, resulting in decreased congestion. It is an active ingredient in several over-the-counter formulations including Clear Eyes and Naphcon eye drops.^[1]

The non-hydrochloride form of Naphazoline has the molecular formula C₁₄H₁₄N₂ and a molar mass of 210.28 g/mol. The HCl salt form has a molar mass of 246.73 g/mol.

Warnings and contraindications

A few warnings and contraindications that apply to all naphazoline-containing substances intended for medicinal use are:

Hypersensitivity to naphazoline
Patients taking MAO inhibitors can experience a severe hypertensive crisis if given a sympathomimetic drug such as naphazoline HCl
Use in infants and children can result in central nervous system depression, leading to coma and marked reduction in body temperature
Should be used with caution in patients with severe cardiovascular disease including cardiac arrhythmia and in patients with diabetes, especially those with a tendency toward diabetic ketoacidosis
Drug interactions can occur with anaesthetics that sensitize the myocardium to sympathomimetics (e.g. cyclopropane or halothane cautiously)
Exercise caution when applying prior to use of phenylephrine.
Extended use may cause rhinitis medicamentosa, a condition of rebound nasal congestion.

A possible association with stroke has been suggested.^[2]

References

^ Green, S. M. (2008). "Ophthalmology: Naphazoline". Tarascon Pocket Pharmacopoeia 2009. Jones and Bartlett. ISBN 0-7637-6572-4.
^ Zavala, J. A.; Pereira, E. R.; Zétola, V. H.; Teive, H. A.; Nóvak, E. M.; Werneck, L. C. (2004). "Hemorrhagic stroke after naphazoline exposition: case report". Arquivos de Neuro-Psiquiatria. 62 (3B): 889–891. doi:10.1590/S0004-282X2004000500030. PMID 15476091.

UpToDate Contents

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English Journal

Pharmacological characterization of a tyramine receptor from the southern cattle tick, Rhipicephalus (Boophilus) microplus.

Gross AD1, Temeyer KB2, Day TA3, Pérez de León AA2, Kimber MJ3, Coats JR4.
Insect biochemistry and molecular biology.Insect Biochem Mol Biol.2015 Aug;63:47-53. doi: 10.1016/j.ibmb.2015.04.008. Epub 2015 May 6.
The southern cattle tick (Rhipicephalus (Boophilus) microplus) is a hematophagous external parasite that vectors the causative agents of bovine babesiosis or cattle tick fever, Babesia bovis and B. bigemina, and anaplasmosis, Anaplasma marginale. The southern cattle tick is a threat to the livestock
PMID 25958152

Bilateral thalamic stroke due to nasal ephedrine and naphazoline use.

Liguori C1, Garaci F, Romigi A, Mercuri NB, Marciani MG, Placidi F.
Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology.Neurol Sci.2015 Jul;36(7):1285-6. doi: 10.1007/s10072-014-2030-z. Epub 2014 Dec 20.
PMID 25527367

Simultaneous determination of chloramphenicol, dexamethasone and naphazoline in ternary and quaternary mixtures by RP-HPLC, derivative and wavelet transforms of UV ratio spectra.

Hoang VD1, Hue NT2, Tho NH3, Nguyen HM4.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Mar 15;139:20-7. doi: 10.1016/j.saa.2014.11.101. Epub 2014 Dec 12.
The application of chemometrics-assisted UV spectrophotometry and RP-HPLC to the simultaneous determination of chloramphenicol, dexamethasone and naphazoline in ternary and quaternary mixtures is presented. The spectrophotometric procedure is based on the first-order derivative and wavelet transform
PMID 25546493

Japanese Journal

ナファゾリン含有殺菌消毒薬中毒による肺水腫の1例

山口充,間藤卓,大井秀則,中田一之,井口浩一,熊井戸邦佳,杉山聡
日本救急医学会雑誌 22(6), 291-296, 2011-06-15
NAID 10029368625

ナファゾリン含有殺菌消毒薬中毒による肺水腫の１例

山口充,間藤卓,大井秀則,中田一之,井口浩一,熊井戸邦佳,杉山聡
日本救急医学会雑誌 22(6), 291-296, 2011
患者は22歳の女性。自殺目的に薬局で購入した殺菌消毒薬を服用した。来院時，意識障害と頻呼吸，SpO<SUB>2</SUB>の低下が認められた。胸部X線写真では両側の肺うっ血が認められ，心エコーでは左室駆出率が25%と心機能の低下が認められた。ナファゾリンによる心不全，肺水腫と考え，dobutamine，phentolamine，olprinoneなどを投与した。症状は改善し …
NAID 130004542319

Simultaneous determination of dibucaine and naphazoline in human serum by monolithic silica spin column extraction and liquid chromatography-mass spectrometry

SAITO Takeshi,MORITA Seiji,KISHIYAMA Izumi,MIYAZAKI Shota,NAKAMOTO Akihiro,NISHIDA Manami,NAMERA Akira,NAGAO Masataka,INOKUCHI Sadaki
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 872(1), 186-190, 2008-09-01
NAID 10028006232

「ナファゾリン」

Naphazoline
Clinical data
Trade names	Naphcon-a
AHFS/Drugs.com	Monograph
Routes of; administration	Topical (solution)
ATC code	R01AA08 (WHO) S01GA01 (WHO);
Identifiers
	IUPAC name 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole;
CAS Number	835-31-4 ;
PubChem CID	4436;
IUPHAR/BPS	5509;
DrugBank	DB06711 ;
ChemSpider	4283 ;
UNII	H231GF11BV;
KEGG	D08253 ;
ChEMBL	CHEMBL761 ;
ECHA InfoCard	100.011.492
Chemical and physical data
Formula	C14H14N2
Molar mass	210.274
3D model (Jmol)	Interactive image;
	SMILES N\1=C(\NCC/1)Cc2cccc3c2cccc3 ;
	InChI InChI=1S/C14H14N2/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14/h1-7H,8-10H2,(H,15,16) ; Key:CNIIGCLFLJGOGP-UHFFFAOYSA-N ;
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