Fenoterol
Grundinformationen
- CAS
13392-18-2- Standard-SMILES
CC(Cc1ccc(O)cc1)NCC(O)c1cc(O)cc(O)c1- InChIKey
LSLYOANBFKQKPT-UHFFFAOYSA-N- Summenformel
- C17H21NO4
- Durchschnittliche Molmasse
- 303,35 g/mol
- Monoisotopische Masse
- 303,14705815
Überblick
Fenoterol is a member of the class resorcinols that is 5-(1-hydroxyethyl)benzene-1,3-diol in which one of the methyl hydrogens is replaced by a 1-(4-hydroxyphenyl)propan-2-amino group. A beta2-adrenergic agonist, it is used (as the hydrobromide salt) as a bronchodilator in the management of reversible airway obstruction. It has a role as a beta-adrenergic agonist, a bronchodilator agent, a sympathomimetic agent and a tocolytic agent. It is a member of resorcinols, a secondary alcohol and a secondary amino compound.
Namen und Bezeichner
- Bevorzugter Name
- Fenoterol
- IUPAC
- 5-[1-hydroxy-2-[1-(4-hydroxyphenyl)propan-2-ylamino]ethyl]benzene-1,3-diol
- Englischer Name
- Fenoterol
- Summenformel
- C17H21NO4
- Molmasse
- 303.35
Namen und Synonyme
fenoterol13392-18-2PhenoterolFenoterolumBerotec5-(1-hydroxy-2-{[1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)benzene-1,3-diolDosberotecAirum1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethane5-[1-hydroxy-2-[1-(4-hydroxyphenyl)propan-2-ylamino]ethyl]benzene-1,3-diol1-(p-Hydroxyphenyl)-2-((beta-hydroxy-beta-(3',5'-dihydroxyphenyl))ethyl)aminopropane3,5-Dihydroxy-alpha-(((p-hydroxy-alpha-methylphenethyl)amino)methyl)benzyl alcohol
Weitere Namen anzeigen
lcoholTh 1165opropaneAURORA KA-7877Fenoterol MonomerFenoterol USP/EP/BPFenoterol (Th-1165aFenoterol & Fenoterol Hydrobromide
DTXSID4023046CHEBI:1492261,3-Benzenediol, 5-(1-hydroxy-2-((2-(4-hydroxyphenyl)-1-methylethyl)amino)ethyl)-5-{1-Hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-benzene-1,3-diolNSC-757811TH-11655-(1-hydroxy-2-(1-(4-hydroxyphenyl)propan-2-ylamino)ethyl)benzene-1,3-diolp-Hydroxyphenylorciprenaline
Datenbank-Bezeichner
- CAS
13392-18-2- PubChem CID
- 3343
- DTXSID
DTXSID4023046- ChEMBL
CHEMBL32800- ChEBI
CHEBI:149226- EC Number
- 680-817-2
- Nikkaji
- J8.104C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2
- Polarare Oberfläche (TPSA)
- 93 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 310
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals
LogP0.34
Solubility1.62e-01 g/L
Human DrugsPharmaceuticals
Melting Point222-223
Physical DescriptionSolid
Collision Cross Section
180.4 Ų [M+H]+ [CCS Type: TW]
169.04 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
168.94 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 181 · 181-183°C
- Siedepunkt
- 566 · 566.0±45.0 °C(Predicted)
- Dichte
- 1.289 · 1.289±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- pka
- 8.5 · pKa 8.5 (Uncertain);10.0 (Uncertain)
- Aggregatzustand
- Solid
- Farbe
- Light brown to brown
- CAS Datenbank
- 13392 · 13392-18-2(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory InformationREACH registered substance: 5-(1-Hydroxy-2-{[1-(4-hydroxyphenyl)-2-propanyl]amino}ethyl)-1,3-benzenediol (EC: 680-817-2)
Other Safety InformationIMAP assessments - 1,3-Benzenediol, 5-[1-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
fenoterol
DILI Positive
Oral; Respiratory (inhalation)
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
ATC Code
R03AL01
R - Respiratory system
R - Respiratory system
G - Genito urinary system and sex hormones
QR - Respiratory system
QG - Genito urinary system and sex hormones
PharmacodynamicsFenoterol is a beta agonist designed to open up the airways to the lungs by decreasing bronchconstriction.
Mechanism of ActionBeta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Agents that cause an increase in the expansion of a bronchus or bronchial tubes.
Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete.
Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS.
Cellular LocationsMembrane
Verwendung und Herstellung
UsesUse (kg; approx.) in Germany (2009): >50
Use ClassificationPharmaceuticals
Anwendungen
Verwendenantiinflammatory
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
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Ergänzende Hinweise
DefinitionChEBI: A member of the class resorcinols that is 5-(1-hydroxyethyl)benzene-1,3-diol in which one of the methyl hydrogens is replaced by a 1-(4-hydroxyphenyl)propan-2-amino group. A beta2-adrenergic agonist, it is used (as the ydrobromide salt) as a bronchodilator in the management of reversible airway obstruction.
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