Introduction：Basic information about FENOTEROL HYDROBROMIDE CAS 1944-12-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
FENOTEROL HYDROBROMIDE Basic informationin vivo
| Product Name: | FENOTEROL HYDROBROMIDE |
| Synonyms: | FENOTEROL HBR;FENOTEROL HYDROBROMIDE;2-[3,5-DIHYDROXYPHENYL]-2-HYDROXY-2'-[4-HYDROXYPHENYL]-1'-METHYLDIETHYLAMINE HYDROBROMIDE;1-(3,5-dihydroxy-phenyl)-2-((1-(4-hydroxybenzyl)ethyl)amino)-ethanolhydrobro;berotec;berotechydrobromide;fenoterolbromide;partusisten |
| CAS: | 1944-12-3 |
| MF: | C17H21NO4.BrH |
| MW: | 384.27 |
| EINECS: | 217-742-8 |
| Product Categories: | Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor |
| Mol File: | 1944-12-3.mol |
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FENOTEROL HYDROBROMIDE Chemical Properties
| Melting point | 226-228°C |
| storage temp. | 2-8°C |
| solubility | Soluble in water and in ethanol (96 per cent). |
| form | Solid |
| color | White to Off-White |
Safety Information
| 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) |
FENOTEROL HYDROBROMIDE Usage And Synthesis
| in vivo | Fenoterol (0.7 mg/kg; intraperitoneal injection; twice a day; for 3 weeks) treatment suppresses mechanical allodynia during chronic treatment. |
| 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 asolution of 714 grams (2.8 mols) of 1-p-methoxyphenyl-2-benzylaminopropanein 1,000 cc of benzene, and the resulting solution mixture wasrefluxed for 1 hour. The molar excess of 1-p-methoxy-phenyl-2-benzylaminopropaneprecipitated out as its hydrobromide. After separation of theprecipitated hydrobromide of the amino component, the hydrochloride of 1-pmethoxy-phenyl-2-(β-3',5'-diacetoxyphenyl-β-oxo)-ethyl-benzylamino-propanewas precipitated from the reaction solution by addition of an ethanolic solutionof hydrochloric acid. The precipitate was separated and, without furtherpurification, was deacetylated by boiling it in a mixture of 2 liters of aqueous10% hydrochloric acid and 1.5 liters of methanol.
The resulting solution was filtered through animal charcoal and, after additionof 2 liters of methanol, it was debenzylated by hydrogenation at 60°C overpalladinized charcoal as a catalyst. After removal of the catalyst by filtration,the filtrate was concentrated by evaporation, whereupon the hydrochloride of1-p-methoxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-oxo)-ethylamino-propane(MP 244°C) crystallized out. For the purpose of demethylation, the 350 gramsof the hydrochloride thus produced were refluxed for 2 hours with 3.5 liters ofaqueous 48% hydrobromic acid. Upon cooling of the reaction solution, 320grams 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, theresulting solution was boiled with activated charcoal, the charcoal was filteredoff and the filtrate was hydrogenated in the presence of Raney nickel at 60°Cand 5 atmospheres gauge. Thereafter, the catalyst was filtered off, themethanolic solution was admixed with a small amount of concentratedhydrobromic acid, and the mixture was evaporated to dryness in vacuo. Theresidue was stirred with acetone, the mixture was vacuum filtered and thefilter cake was recrystallized from a mixture of methanol and ether. The 1-phydroxyphenyl-2-(β-3',5'-dihydroxyphenyl-β-hydroxy)-ethylamino-propanehydrobromide 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 since1970. It is the p-hydroxyphenyl derivative of metaproteronol, and the combination of theresorcinol ring and the bulky p-hydroxyphenyl isopropyl group on the nitrogen gives fenoterolsignificant β2-receptor selectivity. It has approximately half the affinity for the β2-receptor ascompared to albuterol. The resorcinol ring is resistant to COMT metabolism, and the bulkynitrogen substituent greatly retards MOA metabolism as well giving fenoterol a reasonable oralbioavailability with pharmacokinetics similar to albuterol (i.e., rapid onset and a 4- to 6-hourduration of action after oral inhalation). |
FENOTEROL HYDROBROMIDE Preparation Products And Raw materials
| Raw materials | Hydrogen-->Hydrochloric acid-->Hydrogen bromide |
