関: fenoterol hydrobromide

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/23 01:00:15」(JST)

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Fenoterol is a Beta 2 adrenergic agonist designed to open up the airways to the lungs. It is classed as sympathomimetic beta₂ agonist and asthma medication.

Fenoterol is produced and sold by Boehringer Ingelheim as Berotec N and in combination with ipratropium as Berodual N.

Side effects

Fenoterol is a short-acting beta₂-agonist, which also stimulates beta₁ receptors at doses above the recommended therapeutic doses. It was widely used in New Zealand in the early 1990s but withdrawn from that market^[1] because of its association with an excess number of deaths.

It is thought that the association of increased risk of death was because it was typically used in excessively large doses for severe acute asthma attacks^[2] in the absence of medical assistance. Instances were known of patients who had used up to 80 puffs before seeking medical attention. Both excessive prescribed doses and patient's excessive self-medication with beta-agonists in acute asthma not responding to usual doses, are now generally recognised as undesirable with all beta-agonist asthma inhalers.

Stereoisomers

5-(1-Hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol is a molecule with two different stereogenic centers. Thus, four stereoisomers may exist, the (R,R)-, (S,S)-, (R,S)-, and (S,R)-stereoisomers (Scheme). Fenoterol is a racemate of the (R,R)- and the (S,S)-enantiomers. This racemate is 9 to 20 times more effective, as compared to the racemate of the (R,S)- and (S,R)-enantiomers.^[3]

Four stereoisomers of 5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol

References

^ Beasley R, Pearce N, Crane J, Burgess C (1995). "Withdrawal of fenoterol and the end of the New Zealand asthma mortality epidemic". International archives of allergy and immunology 107 (1-3): 325–7. doi:10.1159/000237016. PMID 7613161.
^ Spitzer WO, Suissa S, Ernst P et al. (February 1992). "The use of beta-agonists and the risk of death and near death from asthma". The New England Journal of Medicine 326 (8): 501–6. doi:10.1056/NEJM199202203260801. PMID 1346340.
^ Beale J. P., Stephenson N.C. (1972). "X-ray analysis of Th 1165 and salbutamol". , Journal of Pharmacy and Pharmacology 24: 277–280.

UpToDate Contents

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1. 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
2. 12歳未満の小児における慢性喘息：初回評価および診断 asthma in children younger than 12 years rescue treatment for acute symptoms
3. 成人における喘息の急性増悪の治療 treatment of acute exacerbations of asthma in adults
4. 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

English Journal

The T/QRS ratio values in pregnancies complicated by threatened preterm labour treated with intravenous infusions of fenoterol.

Fuchs T, Pomorski M, Grobelak K, Zimmer M.
Journal of perinatal medicine.J Perinat Med.2015 Jul 1;43(4):467-72. doi: 10.1515/jpm-2014-0042.
AIMS: To evaluate values of foetal T/QRS ratios in pregnancies complicated by threatened preterm labour treated with intravenous infusions of fenoterol using non-invasive methods with transabdominal electrodes.MATERIALS AND METHODS: The study group consisted of 451 Caucasian women (63 preterm pregna
PMID 25153544

Simple and sensitive monitoring of β2-agonist residues in meat by liquid chromatography-tandem mass spectrometry using a QuEChERS with preconcentration as the sample treatment.

Xiong L1, Gao YQ2, Li WH2, Yang XL2, Shimo SP2.
Meat science.Meat Sci.2015 Jul;105:96-107. doi: 10.1016/j.meatsci.2015.03.013. Epub 2015 Mar 20.
A liquid chromatography with tandem mass spectrometric detection (LC-MS/MS) method was established for the simultaneous determination of the levels of 10 β2-agonists in meat. The samples were extracted using an aqueous acidic solution and cleaned up using a Quick, Easy, Cheap, Effective, Rugged and
PMID 25828164

Fenoterol inhibits LPS-induced AMPK activation and inflammatory cytokine production through β-arrestin-2 in THP-1 cell line.

Wang W1, Zhang Y2, Xu M3, Zhang YY3, He B4.
Biochemical and biophysical research communications.Biochem Biophys Res Commun.2015 Jun 26;462(2):119-23. doi: 10.1016/j.bbrc.2015.04.097. Epub 2015 Apr 28.
The AMP-activated protein kinase (AMPK) pathway is involved in regulating inflammation in several cell lines. We reported that fenoterol, a β2-adrenergic receptor (β2-AR) agonist, had anti-inflammatory effects in THP-1 cells, a monocytic cell line. Whether the fenoterol anti-inflammatory effect in
PMID 25930996

Japanese Journal

Determination of the Intrinsic Efficacies of β_2-adrenergic Agonists

BARBER Roger
Allergology international : official journal of the Japanese Society of Allergology 54(2), 245-250, 2005-06-01
NAID 10015655584

Differential Effects of β_2-Adrenoceptor Desensitization on the IgE-Dependent Release of Chemical Mediators from Cultured Human Mast Cells(Pharmacology)

Tsuji Toshikazu,Kato Toshinobu,Kimata Masahiro [他],MIURA Toru,SERIZAWA Isao,INAGAKI Naoki,NAGAI Hiroichi
Biological & pharmaceutical bulletin 27(10), 1549-1554, 2004-10-01
… In the present study, we examined the inhibitory effects of the β_2-adrenoceptor agonists isoproterenol, salbutamol, fenoterol, and clenbuterol, on the release of chemical mediators from cultured human mast cells after prolonged treatment with the agonists. …
NAID 110003608652

The β_2- and β_3-Adrenoceptor-Mediated Relaxation Induced by Fenoterol in Guinea Pig Taenia Caecum

AKIMOTO Yurie,HORINOUCHI Takahiro,TANAKA Yoshio,KOIKE Katsuo
日本平滑筋学会機関誌 38(4&5), 145-151, 2002-10
… Fenoterol, a β_2-adrenoceptor selective agonist, belongs to the arylethanolamine class. … To understand the receptor subtypes responsible for β-adrenoceptor-mediated relaxation of guinea pig taenia caecum, we investigated the effect of fenoterol. … Fenoterol caused concentration-dependent relaxation of the guinea pig taenia caecum. … Propranolol, bupranolol and butoxamine produced shifts of the concentration-response curve for fenoterol. …
NAID 110002954131

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Fenoterol
Systematic (IUPAC) name
	(RR,SS)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	US: B (No risk in non-human studies);
Legal status	AU: Pharmacist Only (S3); CA: ℞-only; UK: Prescription-only (POM); US: ℞-only;
Routes of; administration	Inhalation
Identifiers
CAS Registry Number	13392-18-2
ATC code	R03AC04 G02CA03
PubChem	CID 3343
IUPHAR ligand	557
DrugBank	DB01288
ChemSpider	3226
UNII	22M9P70OQ9
KEGG	D04157
ChEBI	CHEBI:149226
ChEMBL	CHEMBL32800
Chemical data
Formula	C17H21NO4
Molecular mass	303.35 g/mol
	SMILES Oc1cc(cc(O)c1)C(O)CNC(C)Cc2ccc(O)cc2;
	InChI InChI=1S/C17H21NO4/c1-11(6-12-2-4-14(19)5-3-12)18-10-17(22)13-7-15(20)9-16(21)8-13/h2-5,7-9,11,17-22H,6,10H2,1H3 ; Key:LSLYOANBFKQKPT-UHFFFAOYSA-N ;
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