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Wikipedia

Fenoterol

January 01, 1970

Not to be confused with Formoterol.

Fenoterol is a β adrenoreceptor agonist. It is classed as sympathomimetic β2 agonist and an inhaled bronchodilator asthma medication.

Fenoterol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • AU: A
Routes of
administration		Inhalation (MDI)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
Elimination half-life6.5 hours approximately [1][2][3][4]
Identifiers
  • (RR,SS)-5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol
CAS Number
  • 13392-18-2
PubChem CID
  • 3343
IUPHAR/BPS
  • 557
DrugBank
  • DB01288 Y
ChemSpider
  • 3226 Y
UNII
  • 22M9P70OQ9
KEGG
  • D04157 Y
ChEBI
  • CHEBI:149226 Y
ChEMBL
  • ChEMBL32800 Y
CompTox Dashboard (EPA)
  • DTXSID4023046
ECHA InfoCard100.205.960
Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 g·mol−1
3D model (JSmol)
  • Interactive image
  • Oc1cc(cc(O)c1)C(O)CNC(C)Cc2ccc(O)cc2
  • 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 Y
  • Key:LSLYOANBFKQKPT-UHFFFAOYSA-N Y
  (verify)

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

It was patented in 1962 and came into medical use in 1971[5] but, in the 1980s, concerns emerged about its safety and its use being associated with an increased risk of death (see below).

Adverse effects and toxicity edit

 
Fenoterol branded as Berotec

Fenoterol is a short-acting β2 agonist that also stimulates β1 receptors. Fenoterol has more cardiovascular toxicity than isoprenaline or salbutamol.[6][7] Fenoterol was widely used in New Zealand in the late 1970s and the 1980s until it was removed from the New Zealand drug tariff in 1989 because its introduction and widespread use was associated with an epidemic of asthma deaths.[8] A series of case-control studies demonstrated that asthmatics using fenoterol were more likely to die of asthma compared with controls treated with alternative beta agonists; this risk of asthma deaths was particularly high in severe asthmatics.[9][10] The mortality rate declined following withdrawal of fenoterol[11] without evidence supporting an alternative explanation for the abrupt rise and fall in asthma deaths.[12] Data did not support confounding by severity as the explanation for the excess mortality.[13] There are alternative short-acting beta agonists that have not been associated with increased mortality e.g. salbutamol.

Stereoisomers edit

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)-, (R,S)-, (S,R)- and (S,S)-stereoisomers (see the figure below). 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.[14]

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

References edit

  1. ^ . Drugs.com. 1996-01-01. Archived from the original on 2019-08-25. Retrieved 2018-06-11.
  2. ^ "Fenoterol - Drug Monograph". DrugInfoSys.com. 2016-10-27. Retrieved 2018-06-11.
  3. ^ "Berotec Inhalation Solution (Fenoterol HBr)". RxMed.com. Retrieved 2018-06-11.
  4. ^ Svedmyr N (1985-05-06). "Fenoterol: A Beta2-adrenergic Agonist for Use in Asthma; Pharmacology, Pharmacokinetics, Clinical Efficacy and Adverse Effects". Pharmacotherapy. 5 (3). Wiley: 109–126. doi:10.1002/j.1875-9114.1985.tb03409.x. ISSN 0277-0008. PMID 2991865. S2CID 189746.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 542. ISBN 9783527607495.
  6. ^ Crane J, Burgess C, Beasley R (February 1989). "Cardiovascular and hypokalaemic effects of inhaled salbutamol, fenoterol, and isoprenaline". Thorax. 44 (2): 136–40. doi:10.1136/thx.44.2.136. PMC 461717. PMID 2928998.
  7. ^ Burgess CD, Windom HH, Pearce N, Marshall S, Beasley R, Siebers RW, Crane J (February 1991). "Lack of evidence for beta-2 receptor selectivity: a study of metaproterenol, fenoterol, isoproterenol, and epinephrine in patients with asthma". The American Review of Respiratory Disease. 143 (2): 444–6. doi:10.1164/ajrccm/143.2.444. PMID 1671326.
  8. ^ 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.
  9. ^ Crane J, Pearce N, Flatt A, Burgess C, Jackson R, Kwong T, Ball M, Beasley R (April 1989). "Prescribed fenoterol and death from asthma in New Zealand, 1981-83: case-control study". Lancet. 1 (8644): 917–22. doi:10.1016/s0140-6736(89)92505-1. PMID 2565417. S2CID 22765551.
  10. ^ Pearce N, Grainger J, Atkinson M, Crane J, Burgess C, Culling C, Windom H, Beasley R (March 1990). "Case-control study of prescribed fenoterol and death from asthma in New Zealand, 1977-81". Thorax. 45 (3): 170–5. doi:10.1136/thx.45.3.170. PMC 462377. PMID 2330548.
  11. ^ 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.
  12. ^ Pearce N, Beasley R, Crane J, Burgess C, Jackson R (January 1995). "End of the New Zealand asthma mortality epidemic". Lancet. 345 (8941): 41–4. doi:10.1016/s0140-6736(95)91159-6. PMID 7799709. S2CID 13287788.
  13. ^ Beasley R, Burgess C, Pearce N, Woodman K, Crane J (July 1994). "Confounding by severity does not explain the association between fenoterol and asthma death". Clinical and Experimental Allergy. 24 (7): 660–8. doi:10.1111/j.1365-2222.1994.tb00970.x. PMID 7953948. S2CID 24043007.
  14. ^ Beale JP, Stephenson NC (April 1972). "X-ray analysis of Th 1165a* and salbutamol". Journal of Pharmacy and Pharmacology. 24 (4): 277–280. doi:10.1111/j.2042-7158.1972.tb08986.x. PMID 4402834. S2CID 42668199.

January 01, 1970
fenoterol, confused, with, formoterol, adrenoreceptor, agonist, classed, sympathomimetic, agonist, inhaled, bronchodilator, asthma, medication, clinical, dataahfs, drugs, commicromedex, detailed, consumer, informationpregnancycategoryau, aroutes, ofadministrat. Not to be confused with Formoterol Fenoterol is a b adrenoreceptor agonist It is classed as sympathomimetic b2 agonist and an inhaled bronchodilator asthma medication FenoterolClinical dataAHFS Drugs comMicromedex Detailed Consumer InformationPregnancycategoryAU ARoutes ofadministrationInhalation MDI ATC codeR03AC04 WHO G02CA03 WHO Legal statusLegal statusAU S4 Prescription only Pharmacokinetic dataElimination half life6 5 hours approximately 1 2 3 4 IdentifiersIUPAC name RR SS 5 1 hydroxy 2 2 4 hydroxyphenyl 1 methylethyl amino ethyl benzene 1 3 diolCAS Number13392 18 2PubChem CID3343IUPHAR BPS557DrugBankDB01288 YChemSpider3226 YUNII22M9P70OQ9KEGGD04157 YChEBICHEBI 149226 YChEMBLChEMBL32800 YCompTox Dashboard EPA DTXSID4023046ECHA InfoCard100 205 960Chemical and physical dataFormulaC 17H 21N O 4Molar mass303 358 g mol 13D model JSmol Interactive imageSMILES Oc1cc cc O c1 C O CNC C Cc2ccc O cc2InChI 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 YKey LSLYOANBFKQKPT UHFFFAOYSA N Y verify Fenoterol is produced and sold by Boehringer Ingelheim as Berotec N and in combination with ipratropium as Berodual N It was patented in 1962 and came into medical use in 1971 5 but in the 1980s concerns emerged about its safety and its use being associated with an increased risk of death see below Adverse effects and toxicity edit nbsp Fenoterol branded as Berotec Fenoterol is a short acting b2 agonist that also stimulates b1 receptors Fenoterol has more cardiovascular toxicity than isoprenaline or salbutamol 6 7 Fenoterol was widely used in New Zealand in the late 1970s and the 1980s until it was removed from the New Zealand drug tariff in 1989 because its introduction and widespread use was associated with an epidemic of asthma deaths 8 A series of case control studies demonstrated that asthmatics using fenoterol were more likely to die of asthma compared with controls treated with alternative beta agonists this risk of asthma deaths was particularly high in severe asthmatics 9 10 The mortality rate declined following withdrawal of fenoterol 11 without evidence supporting an alternative explanation for the abrupt rise and fall in asthma deaths 12 Data did not support confounding by severity as the explanation for the excess mortality 13 There are alternative short acting beta agonists that have not been associated with increased mortality e g salbutamol Stereoisomers edit5 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 R S S R and S S stereoisomers see the figure below 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 14 nbsp Four stereoisomers of 5 1 hydroxy 2 2 4 hydroxyphenyl 1 methylethyl amino ethyl benzene 1 3 diolReferences edit Fenoterol Hydrobromide Drug Information Professional Drugs com 1996 01 01 Archived from the original on 2019 08 25 Retrieved 2018 06 11 Fenoterol Drug Monograph DrugInfoSys com 2016 10 27 Retrieved 2018 06 11 Berotec Inhalation Solution Fenoterol HBr RxMed com Retrieved 2018 06 11 Svedmyr N 1985 05 06 Fenoterol A Beta2 adrenergic Agonist for Use in Asthma Pharmacology Pharmacokinetics Clinical Efficacy and Adverse Effects Pharmacotherapy 5 3 Wiley 109 126 doi 10 1002 j 1875 9114 1985 tb03409 x ISSN 0277 0008 PMID 2991865 S2CID 189746 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 542 ISBN 9783527607495 Crane J Burgess C Beasley R February 1989 Cardiovascular and hypokalaemic effects of inhaled salbutamol fenoterol and isoprenaline Thorax 44 2 136 40 doi 10 1136 thx 44 2 136 PMC 461717 PMID 2928998 Burgess CD Windom HH Pearce N Marshall S Beasley R Siebers RW Crane J February 1991 Lack of evidence for beta 2 receptor selectivity a study of metaproterenol fenoterol isoproterenol and epinephrine in patients with asthma The American Review of Respiratory Disease 143 2 444 6 doi 10 1164 ajrccm 143 2 444 PMID 1671326 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 Crane J Pearce N Flatt A Burgess C Jackson R Kwong T Ball M Beasley R April 1989 Prescribed fenoterol and death from asthma in New Zealand 1981 83 case control study Lancet 1 8644 917 22 doi 10 1016 s0140 6736 89 92505 1 PMID 2565417 S2CID 22765551 Pearce N Grainger J Atkinson M Crane J Burgess C Culling C Windom H Beasley R March 1990 Case control study of prescribed fenoterol and death from asthma in New Zealand 1977 81 Thorax 45 3 170 5 doi 10 1136 thx 45 3 170 PMC 462377 PMID 2330548 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 Pearce N Beasley R Crane J Burgess C Jackson R January 1995 End of the New Zealand asthma mortality epidemic Lancet 345 8941 41 4 doi 10 1016 s0140 6736 95 91159 6 PMID 7799709 S2CID 13287788 Beasley R Burgess C Pearce N Woodman K Crane J July 1994 Confounding by severity does not explain the association between fenoterol and asthma death Clinical and Experimental Allergy 24 7 660 8 doi 10 1111 j 1365 2222 1994 tb00970 x PMID 7953948 S2CID 24043007 Beale JP Stephenson NC April 1972 X ray analysis of Th 1165a and salbutamol Journal of Pharmacy and Pharmacology 24 4 277 280 doi 10 1111 j 2042 7158 1972 tb08986 x PMID 4402834 S2CID 42668199 Retrieved from https en wikipedia org w index php title Fenoterol amp oldid 1213041408, wikipedia, wiki, book, books, library,

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