Ritodrine

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Ritodrine
Systematic (IUPAC) name
4-(2-((1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-ylamino)ethyl)phenol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy cat. ?
Legal status ?
RoutesOral, parenteral
Pharmacokinetic data
Protein binding~56%
Half-life1.7-2.6 hours
Identifiers
CAS number26652-09-5
ATC codeG02CA01
PubChemCID 33572
DrugBankDB00867
ChemSpider30971 YesY
UNIII0Q6O6740J YesY
KEGGD02359 YesY
ChEMBLCHEMBL785 YesY
Chemical data
FormulaC17H21NO3 
Mol. mass287.354 g/mol
 YesY (what is this?)  (verify)
 
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Ritodrine
Systematic (IUPAC) name
4-(2-((1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-ylamino)ethyl)phenol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy cat. ?
Legal status ?
RoutesOral, parenteral
Pharmacokinetic data
Protein binding~56%
Half-life1.7-2.6 hours
Identifiers
CAS number26652-09-5
ATC codeG02CA01
PubChemCID 33572
DrugBankDB00867
ChemSpider30971 YesY
UNIII0Q6O6740J YesY
KEGGD02359 YesY
ChEMBLCHEMBL785 YesY
Chemical data
FormulaC17H21NO3 
Mol. mass287.354 g/mol
 YesY (what is this?)  (verify)

Ritodrine (dicontinued preparation: Yutopar) is a tocolytic drug, used to stop premature labor.[1] This drug has been removed from the US market, according to FDA Orange Book. It was available in oral tablets or as an injection and was typically used as the hydrochloride salt, ritodrine hydrochloride.

Mechanism[edit]

Ritodrine is a beta-2 adrenergic receptor agonist - a class of medication used for smooth muscle relaxation (other similar drugs are used in asthma or other pulmonary diseases such as salbutamol). Since ritodrine has a bulky N-substituent, it has high β2-selectivity. Also, the 4'-hydroxy on the benzene ring is important for activity as it is needed to form hydrogen bonds. However, the 4'-hydroxy makes it susceptible to metabolism by COMT. Since it is β2-selective it is used for premature labor.[2]

Side effects and potential contraindications[edit]

Most side effects of beta-2 agonists result from their concurrent beta-1 activity, and include increase in heart rate, rise in systolic pressure, decrease in diastolic pressure, chest pain secondary to MI, and arrhythmia. Beta agonists may also cause fluid retention secondary to decrease in water clearance, which when added to the tachycardia and increased myocardial work, may result in cardiac failure. In addition, they increase gluconeogenesis in the liver and muscle resulting in hyperglycemia, which increases insulin requirements in diabetic patients. The passage of beta-agonists through the placenta does occur and may be responsible for fetal tachycardia, as well as hypoglycemia or hyperglycemia at birth.

Patients with type 2 diabetes, high blood pressure or migraines should bring this to their doctor's attention before receiving care.

It has also been associated with post-partum hemorrhage.[citation needed]

References[edit]

  1. ^ Li X, Zhang Y, Shi Z (February 2005). "Ritodrine in the treatment of preterm labour: a meta-analysis". The Indian journal of medical research 121 (2): 120–7. PMID 15756046. 
  2. ^ Medicinal Chemistry of Adrenergics and Cholinergics