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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/06 20:23:35」(JST)

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Oxymetazoline is a selective alpha-1 agonist and partial alpha-2 agonist 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 and SinuFrin. It was developed from xylometazoline at E. Merck Darmstadt by Fruhstorfer in 1961. 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.^[1] It was developed from xylometazoline at E. Merck Darmstadt by Fruhstorfer in 1961.^[2]

Due to its vasoconstricting properties, oxymetazoline is also used to treat nose bleed^[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 hr after a single dose. The elimination half-life in people is 5–8 hr. 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 reliant 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 alpha 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 alpha-2 receptors and imidazoline receptors, much like clonidine.^{[citation needed]}

Chemistry

Oxymetazoline is synthesized by chloromethylation of 6-tert-butyl-2,4-dimethylphenol and the further transformation of the resulting chloromethyl derivative into a nitrile.^[13]^[14] The reaction of this with ethylene diamine gives oxymetazoline.

References

^ "Oxymetazoline: Drug Information Provided by Lexi-Comp: Merck Manual Professional". Merck.com. Retrieved 2013-04-15.
^ German Patent 1,117,588
^ 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. and 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.
^ W. Fruhstorher, H. Muller-Calgan, U.S. Patent 3,147,275 (1964)
^ W. Fruhstorher, H. Muller-Calgan, DE 1117588 (1961).

UpToDate Contents

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1. 成人における急性副鼻腔炎および鼻副鼻腔炎：治療 acute sinusitis and rhinosinusitis in adults treatment
2. 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
3. 小児における鼻出血のマネージメント management of epistaxis in children
4. 小児における鼻出血の評価 evaluation of epistaxis in children
5. 妊娠中のアレルギー疾患の認識およびマネージメント recognition and management of allergic disease during pregnancy

English Journal

Staining intraoperative topical solutions with fluorescein: enhancing the safety of sinus surgery.

Yao WC1, Regone RM, Takashima M.
International forum of allergy & rhinology.Int Forum Allergy Rhinol.2015 Apr 9. doi: 10.1002/alr.21531. [Epub ahead of print]
BACKGROUND: Oxymetazoline HCl 0.05%, 1:100,000 lidocaine with epinephrine (lido+epi), and 1:1000 epinephrine are all colorless solutions employed in sinus surgery. Because lido+epi is injected whereas others are not, care must be taken to label all solutions to avoid inadvertent injection of oxymeta
PMID 25856496

[Topical anesthesia in flexible nasofibrolaryngoscopy].

Chiesa Estomba CM1, Ossa Echeverri CC2, Araujo da Costa AS2, Rivera Schmitz T2, Castro Ruiz P2, Santidrián Hidalgo C2.
Acta otorrinolaringológica española.Acta Otorrinolaringol Esp.2015 Mar-Apr;66(2):83-6. doi: 10.1016/j.otorri.2014.03.009. Epub 2014 Jul 18.
INTRODUCTION: The emergence of flexible nasofibrolaryngoscopy in recent decades has facilitated the development of Otolaryngology and the nasofibrolaryngoscope has become an essential diagnostic tool for the otolaryngologist. However, its use is not without discomfort for the patient, which is why v
PMID 25042017

Systemic side effects of locally used oxymetazoline.

Dokuyucu R1, Gokce H2, Sahan M3, Sefil F1, Tas ZA2, Tutuk O1, Ozturk A1, Tumer C1, Cevik C4.
International journal of clinical and experimental medicine.Int J Clin Exp Med.2015 Feb 15;8(2):2674-8. eCollection 2015.
OBJECTIVES: The object of the study is to experimentally investigate the possible systemic side effects of Oxymetazoline including its nasal spray which has been in use for a long time both by the physicians and patients. There is no study in the literature to address the damages of oxymetazoline on
PMID 25932218

Japanese Journal

Oxymetazoline Inhibits and Resolves Inflammatory Reactions in Human Neutrophils

BECK-SPEIER Ingrid,OSWALD Barbara,MAIER Konrad L.,KARG Erwin,RAMSEGER Rene
Journal of pharmacological sciences 110(3), 276-284, 2009-07-20
… The nasal decongestant oxymetazoline (OMZ) exhibits anti-oxidative and anti-inflammatory properties (I. …
NAID 10025737513

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

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★リンクテーブル★

リンク元	「オキシメタゾリン」
拡張検索	「oxymetazoline 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;
Legal status	UK: General sales list (GSL, OTC); US: OTC;
Dependence; liability	Moderate
Routes of; administration	intranasal
Pharmacokinetic data
Metabolism	Kidney (30%), Fecal (10%)
Half-life	5-6 hours
Identifiers
CAS Registry Number	1491-59-4
ATC code	R01AA05; R01AB07 (combinations), S01GA04
PubChem	CID 4636
IUPHAR ligand	124
DrugBank	DB00935
ChemSpider	4475
UNII	8VLN5B44ZY
KEGG	D08322
ChEBI	CHEBI:7862
ChEMBL	CHEMBL762
Chemical data
Formula	C16H24N2O
Molecular 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

「oxymetazoline hydrochloride」

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塩酸オキシメタゾリン

関: oxymetazoline

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

[2] German Patent 1,117,588

[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. and 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.

[13] W. Fruhstorher, H. Muller-Calgan, U.S. Patent 3,147,275 (1964)

[14] W. Fruhstorher, H. Muller-Calgan, DE 1117588 (1961).

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oxymetazoline