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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/03/15 16:30:13」(JST)

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Formoterol (INN) or eformoterol (former BAN) is a long-acting β₂ agonist (LABA) used in the management of asthma and COPD. It is marketed in three forms: a dry-powder inhaler, a metered-dose inhaler and an inhalation solution, under various trade names including Atock, Atimos/Atimos Modulite, Foradil/Foradile, Oxeze/Oxis, and Perforomist. It is also marketed in the combination formulations budesonide/formoterol and mometasone/formoterol.

Formoterol has an extended duration of action (up to 12 h) compared to short-acting β₂ agonists such as salbutamol (albuterol), which are effective for 4 h to 6 h. LABAs such as formoterol are used as "symptom controllers" to supplement prophylactic corticosteroid therapy. A "reliever" short-acting β₂ agonist (e.g., salbutamol) is still required, since LABAs are not recommended for the treatment of acute asthma.

Mechanism of action

Inhaled formoterol works like other β₂ agonists, causing bronchodilation by relaxing the smooth muscle in the airway so as to treat the exacerbation of asthma.

Safety

In November 2005, the US FDA released a health advisory alerting the public to findings that show the use of long-acting β₂ agonists could lead to a worsening of wheezing symptoms in some patients.^[1]

At the current time, available long-acting β₂ agonists include salmeterol, formoterol, bambuterol, and sustained-release oral salbutamol.

Combinations of inhaled steroids and long-acting bronchodilators are becoming more widespread – combination preparations include fluticasone/salmeterol and budesonide/formoterol.

Additional potential uses

Stimulation of mitochondrial biogenesis

Formoterol may also help stimulate mitochondrial biogenesis. Mitochondrial dysfunction is related to many degenerative diseases — particularly neurodegenerative disorders.^[2]

Treatment for Down syndrome

Preliminary research offers hope that formoterol may be a useful treatment in Down syndrome. In a mouse model of the disease, the drug strengthened nerve connections in the hippocampus, a brain center used for spatial navigation, paying attention and forming new memories.^[3]

Trade names

Inhaler for a powder based in budesonide and formoterol

Foradil/Foradile capsules for oral inhalation (Schering-Plough in the U.S., Novartis rest of world)
Oxeze/Oxis Turbuhaler DPI (AstraZeneca)
Atock (Astellas)
Atimos/Atimos Modulite MDI (Chiesi)
Perforomist inhalation solution (Mylan N.V.)

References

^ Center for Drug Evaluation and Research. "Advair Diskus, Advair HFA, Brovana, Foradil, Perforomist, Serevent Diskus, and Symbicort Information (Long Acting Beta Agonists)". Postmarket Drug Safety Information for Patients and Providers.
^ Wills, Lauren P; Trager, Richard E; Beeson, Gyda C; Lindsey, Christopher C; Peterson, Yuri K; Beeson, Craig C; Schnellmann, Rick G (April 6, 2012). "The β2-adrenoceptor agonist formoterol stimulates mitochondrial biogenesis". The Journal of Pharmacology and Experimental Therapeutics. 342 (1): 106–118. doi:10.1124/jpet.112.191528. ISSN 1521-0103. PMC 3383035 . PMID 22490378.
^ Dang, Van; Medina, Brian; Das, Devsmita; Moghadam, Sarah; Martin, Kara J.; Lin, Bill; Naik, Priyanka; Patel, Devan; Nosheny, Rachel; Wesson Ashford, John; Salehi, Ahmad (February 2014). "Formoterol, a Long-Acting β₂ Adrenergic Agonist, Improves Cognitive Function and Promotes Dendritic Complexity in a Mouse Model of Down Syndrome". Biological Psychiatry. 75 (3): 179–188. doi:10.1016/j.biopsych.2013.05.024. ISSN 1873-2402. PMID 23827853.

UpToDate Contents

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1. 喘息におけるβ刺激剤：長期使用に関する議論 beta agonists in asthma controversy regarding chronic use
2. Management of refractory chronic obstructive pulmonary disease
3. 喘息におけるβ刺激剤：急性期投与および予防的使用 beta agonists in asthma acute administration and prophylactic use
4. 青年や成人の中等度持続型喘息の治療 treatment of moderate persistent asthma in adolescents and adults
5. 安定した慢性閉塞性肺疾患（COPD）のマネージメント management of stable chronic obstructive pulmonary disease

English Journal

Evaluation of air-interfaced Calu-3 cell layers for investigation of inhaled drug interactions with organic cation transporters in vitro.

Mukherjee M, Pritchard DI, Bosquillon C.SourceDivision of Drug Delivery and Tissue Engineering, School of Pharmacy, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
International journal of pharmaceutics.Int J Pharm.2012 Apr 15;426(1-2):7-14. Epub 2012 Jan 13.
A physiologically pertinent in vitro model is urgently needed for probing interactions between inhaled drugs and the organic cation transporters (OCT) in the bronchial epithelium. This study evaluated OCT expression, functionality, inhibition by common inhaled drugs and impact on formoterol transepi
PMID 22265910

Cost-Effectiveness and Cost-Utility of Beclomethasone/Formoterol versus Fluticasone Propionate/Salmeterol in Patients with Moderate to Severe Asthma.

Gerzeli S, Rognoni C, Quaglini S, Cavallo MC, Cremonesi G, Papi A.SourceDepartment of Political and Social Sciences, University of Pavia, Pavia, Italy.
Clinical drug investigation.Clin Drug Investig.2012 Apr 1;32(4):253-65. doi: 10.2165/11598940-000000000-00000.
Background: Asthma is a chronic disease characterized by acute symptomatic episodes with variable severity and duration. Pharmacological asthma management aims to achieve and maintain control without side effects, thus improving quality of life and reducing the economic impact. Recently, a clinical
PMID 22352412

Japanese Journal

気管支喘息の維持療法におけるブデソニド/ホルモテロールフマル酸塩水和物吸入剤(シムビコートタービュヘイラー)の長期使用の安全性と有効性の検討 : 特定使用成績調査の報告

アレルギー・免疫 21(11), 1768-1786, 2014-11
NAID 40020240173

ブデソニド/ホルモテロールフマル酸塩水和物吸入剤(シムビコートタービュヘイラー)を気管支喘息維持療法として使用する場合の安全性と有効性の検討 : 使用成績調査の最終報告

アレルギー・免疫 21(2), 320-338, 2014-02
NAID 40019951704

使用実態下におけるブデソニド/ホルモテロールフマル酸塩水和物吸入剤(シムビコートタービュヘイラー)の安全性と有効性の検討 : 使用成績調査の中間解析結果の報告(第2報)

アレルギー・免疫 19(5), 808-828, 2012-05
NAID 40019302579

「ホルモテロール」

Formoterol
	Formoterol (top),; (R,R)-(−)-formoterol (center) and; (S,S)-(+)-formoterol (bottom)
Clinical data
Trade names	See below
AHFS/Drugs.com	Monograph
License data	EU EMA: by formoterol fumarate dihydrate;
Pregnancy; category	AU: B3; US: C (Risk not ruled out); ;
Routes of; administration	Inhalation (capsules for oral inhalation, DPI, MDI)
ATC code	R03AC13 (WHO);
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	61% to 64%
Metabolism	Hepatic demethylation and glucuronidation (CYP2D6, CYP2C19, CYP2C9 and CYP2A6 involved)
Biological half-life	10 h
Excretion	Renal and fecal
Identifiers
	IUPAC name (RR,SS)-N-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl] phenyl]formamide;
CAS Number	73573-87-2 ;
PubChem CID	3083544; 3034756;
IUPHAR/BPS	3465;
DrugBank	DB00983 ;
ChemSpider	2340731 ;
UNII	5ZZ84GCW8B;
KEGG	D07990 ;
ChEBI	CHEBI:408174 ;
ChEMBL	CHEMBL1363 ;
ECHA InfoCard	100.131.654
Chemical and physical data
Formula	C19H24N2O4
Molar mass	344.405 g/mol
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2 ;
	InChI InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1 ; Key:BPZSYCZIITTYBL-YJYMSZOUSA-N ;
(verify)

　　[★]

英: formoterol
同: フォルモテロール
化: フマル酸ホルモテロール, フマル酸フォルモテロール, formoterol fumarate
商: アトック、オーキシス、シムビコート
関: その他の呼吸器官用薬

「fumarate」

　　[★]

フマル酸、フマル酸塩、フマル酸エステル

関: fumaric acid

fumaric acid

[1] Center for Drug Evaluation and Research. "Advair Diskus, Advair HFA, Brovana, Foradil, Perforomist, Serevent Diskus, and Symbicort Information (Long Acting Beta Agonists)". Postmarket Drug Safety Information for Patients and Providers.

[2] Wills, Lauren P; Trager, Richard E; Beeson, Gyda C; Lindsey, Christopher C; Peterson, Yuri K; Beeson, Craig C; Schnellmann, Rick G (April 6, 2012). "The β2-adrenoceptor agonist formoterol stimulates mitochondrial biogenesis". The Journal of Pharmacology and Experimental Therapeutics. 342 (1): 106–118. doi:10.1124/jpet.112.191528. ISSN 1521-0103. PMC 3383035 . PMID 22490378.

[3] Dang, Van; Medina, Brian; Das, Devsmita; Moghadam, Sarah; Martin, Kara J.; Lin, Bill; Naik, Priyanka; Patel, Devan; Nosheny, Rachel; Wesson Ashford, John; Salehi, Ahmad (February 2014). "Formoterol, a Long-Acting β₂ Adrenergic Agonist, Improves Cognitive Function and Promotes Dendritic Complexity in a Mouse Model of Down Syndrome". Biological Psychiatry. 75 (3): 179–188. doi:10.1016/j.biopsych.2013.05.024. ISSN 1873-2402. PMID 23827853.

v t e Adrenergic receptor modulators
α₁	Agonists: 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Desglymidodrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., brexpiprazole, clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione) Piperoxan Prazosin Quinazosin Quinidine Ritanserin Silodosin 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: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rezatomidine Rilmenidine Romifidine Talipexole Tasipimidine Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Vatinoxan XP21279 Xylazine Xylometazoline Antagonists: 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, brexpiprazole, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, gepirone, ipsapirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine
β	Agonists: Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Colterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

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formoterol fumarate