Basic information
- CAS
26652-09-5- Standard SMILES
C[C@@H](NCCc1ccc(O)cc1)[C@@H](O)c1ccc(O)cc1- InChIKey
IOVGROKTTNBUGK-SJKOYZFVSA-N- Molecular formula
- C17H21NO3
- Average molar mass
- 287.35 g/mol
- Monoisotopic mass
- 287.15214353
Overview
(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.
Names & identifiers
- Preferred 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
- English name
- RITODRINE
- Molecular formula
- C17H21NO3
- Molecular weight
- 287.35
Names & synonyms
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]
Show more names
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
Database identifiers
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 72.7 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 284
Experimental & physicochemical properties
SolubilityComplete
Melting Point88-90 °C
Physicochemical properties
- Melting point
- 88 · 88-90 °C
- Boiling point
- 512.3 · 512.3±45.0 °C(Predicted)
- Density
- 1.213 · 1.213±0.06 g/cm3(Predicted)
- pka
- 9 · pKa 9.0 (Uncertain)
- FDA UNII
- 0 Q6O6740J · I0Q6O6740J
- ATC code
- 2 CA01 · G02CA01
Chemistry & industry
Pharmacology
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
Applications
DescriptionRitodrine, 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.
UsesRitodrine 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.
UsesRelaxant (smooth muscle).
Ritodrine is a selective β2-agonist that wasdeveloped specifically for use as a uterine relaxant. Its uterineinhibitory effects are more sustained than its effects onthe cardiovascular system, which are minimal comparedwith those caused by nonselective β-agonists. The cardiovasculareffects usually associated with its administrationare mild tachycardia and slight diastolic pressure decrease.Usually, it is administered initially by intravenous infusionto stop premature labor and subsequently it may be givenorally.
Related reactions
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Compound notes
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