Grundinformationen
- CAS
26652-09-5- Standard-SMILES
C[C@H](NCCc1ccc(O)cc1)[C@H](O)c1ccc(O)cc1- InChIKey
IOVGROKTTNBUGK-SJCJKPOMSA-N- Summenformel
- C17H21NO3
- Durchschnittliche Molmasse
- 287,35 g/mol
- Monoisotopische Masse
- 287,15214353
Überblick
Adrenergic beta-agonist used to control premature labor.
Namen und Bezeichner
- Bevorzugter Name
- Ritodrine
- IUPAC
- 4-[2-[[(1R,2S)-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
ritodrineRitodrinap-Hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)benzyl alcohol4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenolDU-21220DTXSID70485344-(2-{[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)phenol4-[2-[[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol4-(2-(((1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl)amino)ethyl)phenolritodrinum4-((1R,2S)-1-hydroxy-2-((2-(4-hydroxyphenyl)ethyl)amino)propyl)phenolDU21220
Weitere Namen anzeigen
LavopaPremarFormoterol-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
Benzenemethanol, 4-hydroxy-alpha-(1-((2-(4-hydroxyphenyl)ethyl)amino)ethyl)-, (R*,S*)-RefChem:883660G02CA01DTXCID801508631247-879-926652-09-5DU 21220I0Q6O6740J
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
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.4
Solubility
Complete
1.79e-01 g/L
Human DrugsPharmaceuticals
Melting Point
88-90 °C
88 - 90 °C
Physical DescriptionSolid
Collision Cross Section
165.17 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
165.8 Ų [M+H]+ [CCS Type: TW]
163.25 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 88 · 88-90 °C
- Siedepunkt
- 512.3 · 512.3±45.0 °C(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
RITODRINE
DILI Positive
Oral, Intravenous
DOI:10.1016/j.drudis.2019.09.022
Chemie und Industrie
Pharmakologische Informationen
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
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
MeSH Pharmacological Classification
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 LocationsCytoplasm
Zugehörige Reaktionen
2
Notizen zur Verbindung
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