塩酸オキシメタゾリン

関: oxymetazoline

WordNet

a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/09 12:16:20」(JST)

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Oxymetazoline is a selective α₁ adrenergic receptor agonist and α₂ adrenergic receptor partial agonist. It is a topical decongestant, used in the form of oxymetazoline hydrochloride in products such as Afrin, Dristan, Nasivin, Nezeril, Nostrilla, Logicin, Vicks Sinex, Visine L.R., Sudafed OM, Zicam, SinuFrin and Mucinex Sinus-Max. It was developed from xylometazoline at E. Merck Darmstadt by Fruhstorfer in 1961.^[1] Oxymetazoline is generally available as a nasal spray.

Clinical uses

Oxymetazoline is available over-the-counter as a topical decongestant in the form of oxymetazoline hydrochloride in nasal sprays such as Afrin, Operil, Dristan, Dimetapp, oxyspray, Facimin, Nasivin, Nostrilla, Sudafed OM, Vicks Sinex, Zicam, SinuFrin, and Mucinex Full Force.^[2]

Due to its vasoconstricting properties, oxymetazoline is also used to treat nose bleeds^[3]^[4] and eye redness due to minor irritation (marketed as Visine L.R. in the form of eye drops).^[5]

Pharmacokinetics

Imidazolines are sympathomimetic agents, with primary effects on α adrenergic receptors and little if any effect on β adrenergic receptors. Oxymetazoline is readily absorbed orally. Effects on α receptors from systemically absorbed oxymetazoline hydrochloride may persist for up to 7 hours after a single dose. The elimination half-life in humans is 5–8 hours. It is excreted unchanged both by the kidneys (30%) and in feces (10%).

Mechanism of action

Oxymetazoline is a sympathomimetic that selectively agonizes α₁ and, partially, α₂ adrenergic receptors.^[6] Since vascular beds widely express α₁ receptors, the action of oxymetazoline results in vasoconstriction. In addition, the local application of the drug also results in vasoconstriction due to its action on endothelial postsynaptic α₂ receptors; systemic application of α₂ agonists, in contrast, causes vasodilation because of centrally-mediated inhibition of sympathetic tone via presynaptic α₂ receptors.^[7] Vasoconstriction of vessels results in relief of nasal congestion in two ways: first, it increases the diameter of the airway lumen; second, it reduces fluid exudation from postcapillary venules.^[8] It can reduce nasal airway resistance (NAR) up to 35.7% and nasal mucosal blood flow up to 50%.^[9]

Side-effects and special considerations

Rebound congestion

It is recommended that oxymetazoline not be used for more than three days, as rebound congestion, or rhinitis medicamentosa, may occur.^[10] Patients who continue to use oxymetazoline beyond this point may become dependent on the medication to relieve their chronic congestion.

Effects of benzalkonium chloride

Some studies have found that benzalkonium chloride, a common additive to oxymetazoline nasal sprays, may damage nasal epithelia and exacerbate rhinitis medicamentosa. However, the majority of studies find benzalkonium chloride to be a safe preservative.^[11]

Use in pregnancy

The Food and Drug Administration places oxymetazoline in category C, indicating risk to the fetus cannot be ruled out. While it has been shown that a single dose does not significantly alter either maternal or fetal circulation,^[12] this subject has not been studied extensively enough to draw reliable conclusions.

Overdose

If accidentally ingested, standard methods to remove unabsorbed drugs should be considered. There is no specific antidote for oxymetazoline, although its pharmacological effects may be reversed by α adrenergic antagonists such as phentolamine. In the event of a possibly life-threatening overdose (such as a hypertensive crisis), benzodiazepines should be considered to decrease the likelihood of seizures and convulsions, as well as reduce anxiety and to lower blood pressure. In children, oxymetazoline may produce profound central nervous system depression due to stimulation of central α₂ receptors and imidazoline receptors, much like clonidine.^{[citation needed]}

References

^ German Patent 1,117,588
^ "Oxymetazoline: Drug Information Provided by Lexi-Comp: Merck Manual Professional". Merck.com. Retrieved 2013-04-15.
^ Katz, R.I.; et al. (1990). "A comparison of cocaine, lidocaine with epinephrine, and oxymetazoline for prevention of epistaxis on nasotracheal intubation". J Clin Anesth. 2 (1): 16–20. doi:10.1016/0952-8180(90)90043-3. PMID 2310576.
^ Krempl, G.A. & A.D. Noorily (1995). "Use of oxymetazoline in the management of epistaxis". Ann Otol Rhinol Laryngol. 104 (9 Pt 1): 704–6. PMID 7661519.
^ "VISINE® Original Red Eye Drops | VISINE® products". Visine.com. Retrieved 2013-04-15.
^ Westfall Thomas C, Westfall David P, "Chapter 6. Neurotransmission: The Autonomic and Somatic Motor Nervous Systems" (Chapter). Brunton LL, Lazo JS, Parker KL: Goodman & Gilman's The Pharmacological Basis of Therapeutics, 11e: http://www.accessmedicine.com/content.aspx?aID=954433.
^ Biaggioni Italo, Robertson David, "Chapter 9. Adrenoceptor Agonists & Sympathomimetic Drugs" (Chapter). Katzung BG: Basic & Clinical Pharmacology, 11e: http://www.accessmedicine.com/content.aspx?aID=4520412.
^ J. Widdicombe (1997). "Microvascular anatomy of the nose". Allergy. 52 (40 Suppl): 7–11. doi:10.1111/j.1398-9995.1997.tb04877.x. PMID 9353554.
^ The Journal of Laryngology & Otology, Volume 100 , Issue 03, pp 285-288
^ JT Ramey; E Bailen; RF Lockey (2006). "Rhinitis medicamentosa". J Investig Allergol Clin Immunol. 16 (3): 148–155. PMID 16784007.
^ Marple B, Roland P, Benninger M (2004). "Safety review of benzalkonium chloride used as a preservative in intranasal solutions: an overview of conflicting data and opinions". Otolaryngol Head Neck Surg. 130 (1): 131–141. doi:10.1016/j.otohns.2003.07.005. PMID 14726922.
^ Rayburn WF, Anderson JC, Smith CV, Appel LL, Davis SA (1990). "Uterine and fetal Doppler flow changes from a single dose of a long-acting intranasal decongestant". Obstet Gynecol. 76 (2): 180–182. PMID 2196495.

UpToDate Contents

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1. 小児における鼻出血のマネージメント management of epistaxis in children
2. 小児における鼻出血の評価 evaluation of epistaxis in children
3. アレルギー性鼻炎の薬物療法 pharmacotherapy of allergic rhinitis
4. OTC咳止め・かぜ薬：小児の中毒へのアプローチ over the counter cough and cold preparations approach to pediatric poisoning
5. 鼻腔内異物の診断およびマネージメント diagnosis and management of intranasal foreign bodies

English Journal

The investigation of the interaction between Oxymetazoline hydrochloride and mucin by spectroscopic approaches.

Yu X, Liu H, Yang Y, Lu S, Yao Q, Yi P.SourceKey Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China. Electronic address: yu_xianyong@163.com.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2012 Nov 16;103C:125-129. doi: 10.1016/j.saa.2012.11.019. [Epub ahead of print]
The fluorescence and ultraviolet spectroscopy were explored to study the interaction between Oxymetazoline hydrochloride (OMZH) and mucin under imitated physiological condition. The results demonstrated that the fluorescence quenching mechanism between OMZH and mucin is a combined quenching process.
PMID 23257339

UV derivative spectrophotometric and RP-HPLC methods for determination of imidapril hydrochloride in tablets and for its stability assessment in solid state.

Stanisz B, Regulska K, Kolasa K.SourceDepartment of Pharmaceutical Chemistry, University of Medical Science, 6 Grunwaldzka St., 60-780 Poznań, Poland. bstanisz@ump.edu.pl
Acta poloniae pharmaceutica.Acta Pol Pharm.2011 Sep-Oct;68(5):645-51.
Two methods for determination of imidapril hydrochloride (IMD) in the form of tablets were developed and the stability-indicative determination of IMD in solid state formulations by means of the proposed methods was investigated. IMD is not a pharmacopeial raw material, therefore there is no officia
PMID 21928708

Death related to aortic coarctation in a young female during sexual intercourse.

De-Giorgio F, Di-Giannantonio P, Vetrugno G, Arena V.SourceInstitute of Legal Medicine, Catholic University, Medical School, Largo F. Vito, 1, 00168 Rome, Italy. fabio.degiorgio@rm.unicatt.it
Journal of forensic sciences.J Forensic Sci.2011 Sep;56(5):1361-3. doi: 10.1111/j.1556-4029.2011.01799.x. Epub 2011 May 6.
Coarctation of the aorta (CA) is diagnosed mainly in pediatric patients, and therapy is conservative if asymptomatic, but surgical treatment is required if advanced arterial hypertension is present. Moderate to severe forms contraindicate any type of physical activity requiring cardiac effort. Here,
PMID 21554311

Japanese Journal

Construction and Analytical Applications of Plastic Membrane Electrode for Oxymetazoline Hydrochloride

ISSA Y. M.,ZAYED S. I. D.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20(2), 297-300, 2004-02-10
NAID 10012046797

α_<1B>-Adrenoceptor Subtype Mediating the Phenylephrine-Induced Contractile Response in Rabbit Corpus Cavernosum Penis

FURUKAWA Katsuo,CHESS-WILLIAMS Russell,UCHIYAMA Toshimitsu
The Japanese journal of pharmacology 71(4), 325-331, 1996-08-01
… WB4101 ((2-(2, 6-dimethoxy-phenoxyethyl)-aminomethyl-l, 4-benzodioxane) hydrochloride), 5-methylurapidil and tamsulosin concentration-dependently produced a parallel rightward shift of the concentration-response curve to phenylephrine, yielding pK<SUB>B</SUB> … Oxymetazoline (1 μM), which initially caused a small contraction, produced a parallel rightward shift of the concentration-response curve to phenylephrine with an apparent pK<SUB>B</SUB> …
NAID 10008189311

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★リンクテーブル★

リンク元	「オキシメタゾリン」
関連記事	「hydrochloride」

「オキシメタゾリン」

Oxymetazoline
Systematic (IUPAC) name
	3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethyl-6-tert-butyl-phenol
Clinical data
Trade names	Afrin, Ocuclear, Drixine
AHFS/Drugs.com	Monograph
Pregnancy; category	C;
Dependence; liability	Moderate
Routes of; administration	Intranasal
Legal status
Legal status	UK: General sales list (GSL, OTC); US: OTC;
Pharmacokinetic data
Metabolism	Kidney (30%), fecal (10%)
Biological half-life	5–6 hours
Identifiers
CAS Number	1491-59-4
ATC code	R01AA05 (WHO); R01AB07 (WHO) (combinations), S01GA04 (WHO)
PubChem	CID 4636
IUPHAR/BPS	124
DrugBank	DB00935
ChemSpider	4475
UNII	8VLN5B44ZY
KEGG	D08322
ChEBI	CHEBI:7862
ChEMBL	CHEMBL762
Chemical data
Formula	C16H24N2O
Molar mass	260.375 g·mol−1
	SMILES Oc1c(c(c(cc1C(C)(C)C)C)CC/2=N/CCN\2)C ;
	InChI InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18) ; Key:WYWIFABBXFUGLM-UHFFFAOYSA-N ;
Physical data
Melting point	301.5 °C (574.7 °F)
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　　[★]

英: oxymetazoline
化: 塩酸オキシメタゾリン oxymetazoline hydrochloride
商: ナシビン、Afrin, Nostrilla
関: 耳鼻科用剤

α1刺激薬、末梢血管収縮

「hydrochloride」

　　[★] 塩酸塩、ハイドロクロライド　

[1] German Patent 1,117,588

[2] "Oxymetazoline: Drug Information Provided by Lexi-Comp: Merck Manual Professional". Merck.com. Retrieved 2013-04-15.

[3] Katz, R.I.; et al. (1990). "A comparison of cocaine, lidocaine with epinephrine, and oxymetazoline for prevention of epistaxis on nasotracheal intubation". J Clin Anesth. 2 (1): 16–20. doi:10.1016/0952-8180(90)90043-3. PMID 2310576.

[4] Krempl, G.A. & A.D. Noorily (1995). "Use of oxymetazoline in the management of epistaxis". Ann Otol Rhinol Laryngol. 104 (9 Pt 1): 704–6. PMID 7661519.

[5] "VISINE® Original Red Eye Drops | VISINE® products". Visine.com. Retrieved 2013-04-15.

[adrenomimetic-6] Westfall Thomas C, Westfall David P, "Chapter 6. Neurotransmission: The Autonomic and Somatic Motor Nervous Systems" (Chapter). Brunton LL, Lazo JS, Parker KL: Goodman & Gilman's The Pharmacological Basis of Therapeutics, 11e: http://www.accessmedicine.com/content.aspx?aID=954433.

[alpha-7] Biaggioni Italo, Robertson David, "Chapter 9. Adrenoceptor Agonists & Sympathomimetic Drugs" (Chapter). Katzung BG: Basic & Clinical Pharmacology, 11e: http://www.accessmedicine.com/content.aspx?aID=4520412.

[8] J. Widdicombe (1997). "Microvascular anatomy of the nose". Allergy. 52 (40 Suppl): 7–11. doi:10.1111/j.1398-9995.1997.tb04877.x. PMID 9353554.

[9] The Journal of Laryngology & Otology, Volume 100 , Issue 03, pp 285-288

[10] JT Ramey; E Bailen; RF Lockey (2006). "Rhinitis medicamentosa". J Investig Allergol Clin Immunol. 16 (3): 148–155. PMID 16784007.

[11] Marple B, Roland P, Benninger M (2004). "Safety review of benzalkonium chloride used as a preservative in intranasal solutions: an overview of conflicting data and opinions". Otolaryngol Head Neck Surg. 130 (1): 131–141. doi:10.1016/j.otohns.2003.07.005. PMID 14726922.

[12] Rayburn WF, Anderson JC, Smith CV, Appel LL, Davis SA (1990). "Uterine and fetal Doppler flow changes from a single dose of a long-acting intranasal decongestant". Obstet Gynecol. 76 (2): 180–182. PMID 2196495.

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oxymetazoline hydrochloride