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1944-12-3

1944-12-3 Structure

1944-12-3 Structure
IdentificationBack Directory
[Name]

FENOTEROL HYDROBROMIDE
[CAS]

1944-12-3
[Synonyms]

Airum
Ugacor
Emitex
berotec
th1165a
Siobetec
Dosberotec
partusisten
FENOTEROL HBR
fenoterolbromide
Fenoterol solution
berotechydrobromide
Fenoterolhydrobromid
Fenoterol in Methanol
FenoteroleHydrobromide
FENOTEROL HYDROBROMIDE
phenoterolhydrobromide
Fenoterol hydrobromide CRS
Fenoterol HydrobroMide USP
FENOTEROL HYDROBROMIDE USP/EP/BP
Fenoterol for peak identification CRS
Fenoterol HBr (Mixture of Diastereomers)
1-(3,5-dihydroxy-phenyl)-2-((1-(4-hydroxybenzyl)ethyl)amino)-ethanolhydrobro
1-(3,5-Dihydroxyphenyl)-2-[2-(3-p-hydroxyphenyl)propylamino]ethanol hydrobromide
3,5-Dihydroxy-α-[(p-hydroxy-α-methylphenethyl)amino]methylbenzyl alcohol hydrobromide
5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]resorcinol hydrobromide
1-(p-Hydroxyphenyl)-2-(β-3',5'-dihydroxyphenyl-β-hydroxy)ethylaminopropane hydrobromide
5-[1-hydroxy-2-[1-(4-hydroxyphenyl)propan-2-ylamino]ethyl]benzene-1,3-diol hydrobromide
3,5-Dihydroxy-α-[[(p-hydroxy-α-methylphenethyl)amino]methyl]benzyl alc. monohydrobromide
2-[3,5-DIHYDROXYPHENYL]-2-HYDROXY-2'-[4-HYDROXYPHENYL]-1'-METHYLDIETHYLAMINE HYDROBROMIDE
5-[1-Hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-1,3-benzenediol hydrobromide
1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-, hydrobromide
Benzyl alcohol, 3,5-dihydroxy-α-[[(p-hydroxy-α-methylphenethyl)amino]methyl]-, hydrobromide (8CI)
1,3-Benzenediol,5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-Methylethyl]aMino]ethyl]-, hydrobroMide(1:1)
Fenoterol hydrobromide,2-(3,5-Dihydroxyphenyl)-2-hydroxy-2′-(4-hydroxyphenyl)-1′-methyldiethylamine hydrobromide
[EINECS(EC#)]

217-742-8
[Molecular Formula]

C17H22BrNO4
[MDL Number]

MFCD00079288
[MOL File]

1944-12-3.mol
[Molecular Weight]

384.26
Chemical PropertiesBack Directory
[Melting point ]

226-228°C
[storage temp. ]

2-8°C
[solubility ]

Soluble in water and in ethanol (96 per cent).
[form ]

neat
[color ]

White to Off-White
Questions And AnswerBack Directory
[in vivo]

Fenoterol (0.7 mg/kg; intraperitoneal injection; twice a day; for 3 weeks) treatment suppresses mechanical allodynia during chronic treatment.
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[Safety Statements ]

36
[RIDADR ]

3249
[WGK Germany ]

3
[RTECS ]

DO1500000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29225090
[Toxicity]

LD50 in mice (mg/kg): 1100 s.c.; 1990 orally (Goldenthal)
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Originator]

Berotec,Boehringer Ingelheim,W. Germany,1972
[Uses]

An β2-adrenergic agonist. Bronchodilator; tocolytic.
[Definition]

ChEBI: The hydrobromide salt of fenoterol. A beta2-adrenergic agonist, it is used as a bronchodilator in the management of reversible airway obstruction.
[Manufacturing Process]

441 grams (1.4 mols) of 3,5-diacetoxy-α-bromo-acetophenone (MP 66°C), prepared by bromination of 3,5-diacetoxy-acetophenone, were added to a solution of 714 grams (2.8 mols) of 1-p-methoxyphenyl-2-benzylaminopropane in 1,000 cc of benzene, and the resulting solution mixture was refluxed for 1 hour. The molar excess of 1-p-methoxy-phenyl-2-benzylaminopropane precipitated out as its hydrobromide. After separation of the precipitated hydrobromide of the amino component, the hydrochloride of 1-pmethoxy- phenyl-2-(β-3',5'-diacetoxyphenyl-β-oxo)-ethyl-benzylamino-propane was precipitated from the reaction solution by addition of an ethanolic solution of hydrochloric acid. The precipitate was separated and, without further purification, was deacetylated by boiling it in a mixture of 2 liters of aqueous 10% hydrochloric acid and 1.5 liters of methanol.
The resulting solution was filtered through animal charcoal and, after addition of 2 liters of methanol, it was debenzylated by hydrogenation at 60°C over palladinized charcoal as a catalyst. After removal of the catalyst by filtration, the filtrate was concentrated by evaporation, whereupon the hydrochloride of 1-p-methoxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-oxo)-ethylamino-propane (MP 244°C) crystallized out. For the purpose of demethylation, the 350 grams of the hydrochloride thus produced were refluxed for 2 hours with 3.5 liters of aqueous 48% hydrobromic acid. Upon cooling of the reaction solution, 320 grams of 1-p-hydroxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-oxo)-ethylaminopropanehydrobromide (MP 220°C) crystallized out.
·220 grams of 1-p-hydroxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-oxo)- ethylamino-propane hydrobromide were dissolved in 1 liter of methanol, the resulting solution was boiled with activated charcoal, the charcoal was filtered off and the filtrate was hydrogenated in the presence of Raney nickel at 60°C and 5 atmospheres gauge. Thereafter, the catalyst was filtered off, the methanolic solution was admixed with a small amount of concentrated hydrobromic acid, and the mixture was evaporated to dryness in vacuo. The residue was stirred with acetone, the mixture was vacuum filtered and the filter cake was recrystallized from a mixture of methanol and ether. The 1-phydroxyphenyl- 2-(β-3',5'-dihydroxyphenyl-β-hydroxy)-ethylamino-propane hydrobromide thus obtained had a melting point of 222° to 223°C.
[Therapeutic Function]

Bronchodilator
[Clinical Use]

Fenoterol is an investigational drug in the United States that has been in use in Europe since 1970. It is the p-hydroxyphenyl derivative of metaproteronol, and the combination of the resorcinol ring and the bulky p-hydroxyphenyl isopropyl group on the nitrogen gives fenoterol significant β2-receptor selectivity. It has approximately half the affinity for the β2-receptor as compared to albuterol. The resorcinol ring is resistant to COMT metabolism, and the bulky nitrogen substituent greatly retards MOA metabolism as well giving fenoterol a reasonable oral bioavailability with pharmacokinetics similar to albuterol (i.e., rapid onset and a 4- to 6-hour duration of action after oral inhalation).
[storage]

Store at -20°C
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