Ritodrin
4-[2-[[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol
Grundinformationen
- CAS
26652-09-5- Standard-SMILES
C[C@@H](NCCc1ccc(O)cc1)[C@@H](O)c1ccc(O)cc1- InChIKey
IOVGROKTTNBUGK-SJKOYZFVSA-N- Summenformel
- C17H21NO3
- Durchschnittliche Molmasse
- 287,35 g/mol
- Monoisotopische Masse
- 287,15214353
Überblick
(1S,2R)-ritodrine is a 4-[2-[[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol that has (1S,2R)-configuration. It is an enantiomer of a (1R,2S)-ritodrine.
Namen und Bezeichner
- Bevorzugter Name
- 4-[2-[[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol
- IUPAC
- 4-[2-[[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol
- Lokaler Name
- Ritodrin
- Englischer Name
- RITODRINE
- Summenformel
- C17H21NO3
- Molmasse
- 287.35
Namen und Synonyme
4-[2-[[(1S,2R)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenolrel-RITODRINERitodrina [INN-Spanish]Ritodrinium [INN-Latin]RitodriniumRitodrine [USAN:INN:BAN]UNII-I0Q6O6740J(+)-ritodrineEINECS 247-879-9BRN 2388728(1S,2R)-ritodrineRITODRINE [INN]
Weitere Namen anzeigen
LavopaPremarRITODRINEritodrinaFormoterol-dRITODRINE USP/EP/BPPhenoxybenzamine hydrochlRitodrine Impurity 2 (Ritodrine)(1R,2S)-2-(4-Hydroxyphenethylamino)-1-(4-hydroxyphenyl)-1-propanol4-[(1R,2S)-1-Hydroxy-2-[2-(4-hydroxyphenyl)ethylamino]propyl]phenol
RITODRINE [MI]RITODRINE [USAN]RITODRINE [VANDF]RITODRINE [WHO-DD]Lopac0_001041CHEMBL489553orb16894502-(4-Hydroxyphenethylamino)-1-(4-hydroxyphenyl)propanol
Datenbank-Bezeichner
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,3
- Polarare Oberfläche (TPSA)
- 72,7 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 284
Experimentelle und physikochemische Eigenschaften
SolubilityComplete
Melting Point88-90 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 88 · 88-90 °C
- Siedepunkt
- 512.3 · 512.3±45.0 °C(Predicted)
- Dichte
- 1.213 · 1.213±0.06 g/cm3(Predicted)
- pka
- 9 · pKa 9.0 (Uncertain)
Chemie und Industrie
Pharmakologische Informationen
Protein Binding~56%
Pharmacodynamics
Beta-2 adrenergic receptors are located at sympathetic neuroeffector junctions of many organs, including uterus. Ritodrine is beta-2 adrenergic agonist. It stimulates beta-2 adrenergic receptor, increases cAMP level and decreases intracellular calcium concentration. The decrease of calcium concentration leads to a relaxation of uterine smooth muscle and, therefore, a decrease in premature uterine contractions.
Mechanism of Action
Ritodrine is beta-2 adrenergic agonist. It binds to beta-2 adrenergic receptors on outer membrane of myometrial cell, activates adenyl cyclase to increase the level of cAMP which decreases intracellular calcium and leads to a decrease of uterine contractions.
Biological Half-Life1.7-2.6 hours
Metabolism/MetabolitesHepatic, by both the mother and fetus
Anwendungen
BeschreibungRitodrine, 4-hydroxy-α-[1-[(4′-hydroxyphenethyl)amino]ethyl]benzylic alcohol (11.1.19), differs slightly from epinephrine, and in the given example only one hydroxyl group has been added to the aromatic ring of the phenylethylamino region of classic sympathomimetics. The second major difference between the examined series is the replacement of the traditionally terminal iso-propyl or tert-butylamine region with a p-hydroxyphenylethylamine. Finally, the third difference is the presence of a methyl group at the α-atom of the phenylethylamine region of sympathomimetics, which makes it similar to isoetharine.
VerwendenRitodrine is a selective β2-adrenoreceptor stimulant, predominantly of the urino-genital system. It is used as a tocolytic agent for problems associated with premature miscarriages, and only in specialized medical facilities.
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