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Details

Stereochemistry RACEMIC
Molecular Formula C17H21NO3
Molecular Weight 287.3542
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RITODRINE

SMILES

C[C@]([H])([C@]([H])(c1ccc(cc1)O)O)NCCc2ccc(cc2)O

InChI

InChIKey=IOVGROKTTNBUGK-SJKOYZFVSA-N
InChI=1S/C17H21NO3/c1-12(17(21)14-4-8-16(20)9-5-14)18-11-10-13-2-6-15(19)7-3-13/h2-9,12,17-21H,10-11H2,1H3/t12-,17-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00867 | https://www.drugs.com/mmx/ritodrine-hydrochloride.html | https://www.ncbi.nlm.nih.gov/pubmed/11311067

Ritodrine (trade name Yutopar) is beta-2 adrenergic agonist used to stop premature labor. Ritodrine binds to beta-2 adrenergic receptors on the outer membrane of the myometrial cell, activates adenyl cyclase to increase the level of cAMP which decreases intracellular calcium and leads to a decrease of uterine contractions. In addition to stimulating the beta-2–adrenergic receptors of the uterine smooth muscle, ritodrine stimulates beta-adrenergic receptors of bronchial and vascular smooth muscles. The cardiostimulatory effects, including increased cardiac output, increased maternal and fetal heart rates, and widening of the maternal pulse pressure, are probably due to relaxation of the vascular smooth muscle. Relaxation of vascular smooth muscle stimulates the beta-1–adrenergic receptors and the reflex response to blood pressure. Also, during intravenous administration, ritodrine transiently increases maternal and fetal blood glucose and maternal plasma insulin concentrations. Other metabolic changes include increased cAMP, lactic acid, and free fatty acids, and decreased serum potassium concentration. Most side effects of β2 agonists result from their concurrent β1 activity and include the increase in heart rate, rise in systolic pressure, decrease in diastolic pressure, chest pain secondary to myocardial infarction, 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 heart failure. In addition, they increase gluconeogenesis in the liver and muscle resulting in hyperglycemia, which increases insulin requirements in diabetic patients. The passage of β agonists through the placenta does occur and may be responsible for fetal tachycardia, as well as hypoglycemia or hyperglycemia at birth.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
24.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RITODRINE HYDROCHLORIDE IN DEXTROSE 5% IN PLASTIC CONTAINER

Approved Use

Unknown

Launch Date

6.645024E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.06 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RITODRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
24.03 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RITODRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.3 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RITODRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg multiple, intramuscular (starting)
Dose: 10 mg
Route: intramuscular
Route: multiple
Dose: 10 mg
Sources:
unhealthy, 29.8 year
n = 21
Health Status: unhealthy
Condition: preterm labor
Age Group: 29.8 year
Sex: F
Population Size: 21
Sources:
100 mg/min multiple, intravenous (starting)
Dose: 100 mg/min
Route: intravenous
Route: multiple
Dose: 100 mg/min
Sources:
unhealthy, 31 years
n = 24
Health Status: unhealthy
Condition: preterm labor
Age Group: 31 years
Sex: F
Population Size: 24
Sources:
Disc. AE: Pulmonary edema, Shortness of breath...
AEs leading to
discontinuation/dose reduction:
Pulmonary edema (3 patients)
Shortness of breath (3 patients)
Tachycardia (3 patients)
Fetal tachycardia (3 patients)
Sources:
6.4 mg/h 1 times / day multiple, intravenous (starting)
Dose: 6.4 mg/h, 1 times / day
Route: intravenous
Route: multiple
Dose: 6.4 mg/h, 1 times / day
Sources:
unhealthy, 31.6 years (range: 21–57 years)
n = 177
Health Status: unhealthy
Condition: preterm labor
Age Group: 31.6 years (range: 21–57 years)
Sex: F
Population Size: 177
Sources:
Disc. AE: Chest discomfort, Palpitation...
AEs leading to
discontinuation/dose reduction:
Chest discomfort (3 patients)
Palpitation (3 patients)
Pulmonary edema (1 patient)
Sources:
120 mg 1 times / day multiple, oral
Studied dose
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: preterm labor
Sex: F
Sources:
0.15 mg/min multiple, intravenous
Dose: 0.15 mg/min
Route: intravenous
Route: multiple
Dose: 0.15 mg/min
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: preterm labor
Sex: F
Population Size: 1
Sources:
Disc. AE: Absolute neutrophil count decreased...
AEs leading to
discontinuation/dose reduction:
Absolute neutrophil count decreased
Sources:
AEs

AEs

AESignificanceDosePopulation
Fetal tachycardia 3 patients
Disc. AE
100 mg/min multiple, intravenous (starting)
Dose: 100 mg/min
Route: intravenous
Route: multiple
Dose: 100 mg/min
Sources:
unhealthy, 31 years
n = 24
Health Status: unhealthy
Condition: preterm labor
Age Group: 31 years
Sex: F
Population Size: 24
Sources:
Pulmonary edema 3 patients
Disc. AE
100 mg/min multiple, intravenous (starting)
Dose: 100 mg/min
Route: intravenous
Route: multiple
Dose: 100 mg/min
Sources:
unhealthy, 31 years
n = 24
Health Status: unhealthy
Condition: preterm labor
Age Group: 31 years
Sex: F
Population Size: 24
Sources:
Shortness of breath 3 patients
Disc. AE
100 mg/min multiple, intravenous (starting)
Dose: 100 mg/min
Route: intravenous
Route: multiple
Dose: 100 mg/min
Sources:
unhealthy, 31 years
n = 24
Health Status: unhealthy
Condition: preterm labor
Age Group: 31 years
Sex: F
Population Size: 24
Sources:
Tachycardia 3 patients
Disc. AE
100 mg/min multiple, intravenous (starting)
Dose: 100 mg/min
Route: intravenous
Route: multiple
Dose: 100 mg/min
Sources:
unhealthy, 31 years
n = 24
Health Status: unhealthy
Condition: preterm labor
Age Group: 31 years
Sex: F
Population Size: 24
Sources:
Pulmonary edema 1 patient
Disc. AE
6.4 mg/h 1 times / day multiple, intravenous (starting)
Dose: 6.4 mg/h, 1 times / day
Route: intravenous
Route: multiple
Dose: 6.4 mg/h, 1 times / day
Sources:
unhealthy, 31.6 years (range: 21–57 years)
n = 177
Health Status: unhealthy
Condition: preterm labor
Age Group: 31.6 years (range: 21–57 years)
Sex: F
Population Size: 177
Sources:
Chest discomfort 3 patients
Disc. AE
6.4 mg/h 1 times / day multiple, intravenous (starting)
Dose: 6.4 mg/h, 1 times / day
Route: intravenous
Route: multiple
Dose: 6.4 mg/h, 1 times / day
Sources:
unhealthy, 31.6 years (range: 21–57 years)
n = 177
Health Status: unhealthy
Condition: preterm labor
Age Group: 31.6 years (range: 21–57 years)
Sex: F
Population Size: 177
Sources:
Palpitation 3 patients
Disc. AE
6.4 mg/h 1 times / day multiple, intravenous (starting)
Dose: 6.4 mg/h, 1 times / day
Route: intravenous
Route: multiple
Dose: 6.4 mg/h, 1 times / day
Sources:
unhealthy, 31.6 years (range: 21–57 years)
n = 177
Health Status: unhealthy
Condition: preterm labor
Age Group: 31.6 years (range: 21–57 years)
Sex: F
Population Size: 177
Sources:
Absolute neutrophil count decreased Disc. AE
0.15 mg/min multiple, intravenous
Dose: 0.15 mg/min
Route: intravenous
Route: multiple
Dose: 0.15 mg/min
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: preterm labor
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
PubMed

PubMed

TitleDatePubMed
Acute coronary syndrome associated with oral administration of ritodrine hydrochloride during pregnancy: a case report.
2001 Dec
Fetal magnetocardiogram recordings and power spectra analysis in biomagnetic arrhythmic signals.
2001 Jul
Invasive pulmonary aspergillosis in a puerperant with drug-induced agranulocytosis.
2001 Nov
Fetal heart rate patterns in normal and ritodrine-treated pregnancies, detected by magnetocardiography.
2001 Oct
Nitric oxide donors for the treatment of preterm labour.
2002
The importance of oxytocin mechanisms in the control of mouse parturition.
2002 Apr
[A case of cardiac arrest at induction of anesthesia for postpartum hysterectomy].
2002 Dec
Tocolytic activity of formoterol against premature delivery in mice.
2002 Dec
Comparison of the effects of antenatal magnesium sulphate and ritodrine exposure on circulatory adaptation in preterm infants.
2002 Jan
[Management of pregnancy and delivery after augmentation cystoplasty].
2002 Jan
[Anesthetic experience of endoscopic umbilical cord ligation in a case of twin pregnancy with acardia].
2002 Jan
Periventricular haemorrhage and tocolytic therapies.
2002 Jan 19
Infantile renal dysfunction associated with intrauterine exposure to ritodrine and magnesium sulfate.
2002 Jun
Intrauterine left chamber myocardial infarction of the heart and hydrops fetalis in the recipient fetus due to twin-to-twin transfusion syndrome.
2002 Mar
Nitroglycerin as a uterine relaxant: a systematic review.
2002 May
[Successful resuscitation of a patient with prolonged tocolytic therapy and an emergency cesarean section].
2002 May-Jun
[Special management for threatened preterm delivery in multiple pregnancies].
2002 Nov
[Which tocolytic drugs in case of preterm labor?].
2002 Nov
Successful prenatal treatment of congenital heart block with ritodrine administered transplacentally.
2002 Nov
In vitro study of tocolytic effect of rofecoxib, a specific cyclo-oxygenase 2 inhibitor. Comparison and combination with other tocolytic agents.
2002 Sep
Beta2- and beta3-adrenoreceptor agonists: human myometrial selectivity and effects on umbilical artery tone.
2002 Sep
Successful treatment with doxycycline and nicotinamide of two cases of persistent pemphigoid gestationis.
2002 Sep
Effect of magnesium sulfate, isradipine, and ritodrine on contractions of myometrium: pregnant human and rat.
2002 Sep
KUR-1246, a novel beta(2)-adrenoceptor agonist, as a tocolytic agent.
2002 Sep
The in vitro effect of dual combinations of ritodrine, nicardipine and atosiban on contractility of pregnant rat myometrium.
2003 Aug
Preterm labour: an overview of current and emerging therapeutics.
2003 Aug
Administration of beta2-adrenergic agonists during the peri-implantation period does not improve implantation or pregnancy rates in intracytoplasmic sperm injection (ICSI) cycles.
2003 Dec
[External cephalic version for breech presentation at term: an effective procedure to reduce the caesarean section rate].
2003 Dec
Hemodynamic and metabolic effects after nifedipine and ritodrine tocolysis.
2003 Jul
Epinephrine inhibits tracheal occlusion induced lung growth in fetal sheep.
2003 Sep-Oct
Oral nifedipine maintenance therapy after acute intravenous tocolysis in preterm labor.
2004
Pulmonary edema after ritodrine therapy during pregnancy and subsequent cesarean section with epidural anesthesia.
2004
Management options for preterm labour in Canada.
2004 Apr
Tocolytic therapy in conservative management of symptomatic placenta previa.
2004 Feb
Maternal admission characteristics as risk factors for preterm birth.
2004 Jan 15
A GC-MS method for the determination of isoxsuprine in biological fluids of the horse utilizing electron impact ionization.
2004 Jan-Feb
Erythromycin treatment in idiopathic preterm labor.
2004 Jul
Pulmonary edema due to ritodrine.
2004 Jun
[Anesthetic management of three patients with myotonic dystrophy in a family].
2004 Mar
Glyceryl trinitrate vs. ritodrine for the treatment of preterm labor.
2004 May
Maternal complications from tocolytic treatment with ritodrine. Three cases of pulmonary edema.
2004 Oct
Betamimetics for inhibiting preterm labour.
2004 Oct 18
Ritodrine in the treatment of preterm labour: a meta-analysis.
2005 Feb
Progesterone enhances the tocolytic effect of ritodrine in isolated pregnant human myometrium.
2005 Feb
The combined maternal administration of magnesium sulfate and aminophylline reduces intraventricular hemorrhage in very preterm neonates.
2005 Feb
alpha- and beta-adrenergic receptor mechanisms in spontaneous contractile activity of rat ileal longitudinal smooth muscle.
2005 Feb
Tocolysis in term breech external cephalic version.
2005 Jan
[Pharmacoeconomic assessment of two tocolysis protocols for the inhibition of premature delivery].
2005 Jan-Feb
Determination of beta-agonist residues in bovine urine using liquid chromatography-tandem mass spectrometry.
2005 Jan-Feb
Use of beta agonists in preterm labor.
2005 Mar 1
Patents

Patents

Sample Use Guides

For oral dosage form (extended-release capsules): Adults: In the first twenty-four hours after the doctor stops your intravenous ritodrine, your dose may be as high as 40 milligrams (mg) every eight hours. After that, the dose is usually 40 mg every eight to twelve hours. Your doctor may want you to take oral ritodrine up until it is time for you to deliver your baby or until your 37th week of pregnancy. For oral dosage form (tablets): Adults: In the first twenty-four hours after the doctor stops your intravenous ritodrine, your dose may be as high as 10 milligrams (mg) every two hours. After that, the dose is usually 10 to 20 mg every four to six hours. Your doctor may want you to take oral ritodrine up until it is time for you to deliver your baby or until your 37th week of pregnancy. For injection dosage form: Adults: 50 to 350 micrograms per minute, injected into a vein.
Route of Administration: Other
Uteri of pregnant SD rats (pregnancy day 21, 200-380 g in body weight) were isolated and longitudinal uterine muscle strips of approximately 15 mm in length and 5 mm in width were prepared. The experiment was performed according to the Magnus method. The preparations were exposed to Locke-Ringer solution maintained at 37 °C and continuously gassed with a mixture of 95% oxygen and 5% carbon dioxide under 0.5 g of tension. Spontaneous contractions of myometrium were measured isometrically with a force-displacement transducer (SB-1T; Nihon-Kohdan) and recorded on a rectigram (Rectigraph 8K; NEC San-ei). The drug was added cumulatively to the organ bath every 5 min. The Ritodrine efficacy was evaluated as the molar concentration of the drug required to produce 50% of the inhibition of uterine contraction as comparing the total degree of uterine contraction during 5 min before the addition of the drug (100%) with the total degree of uterine contraction during 5 min after the addition of the drug at various concentrations.
Name Type Language
RITODRINE
INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
RITODRINE [VANDF]
Common Name English
RITODRINE [WHO-DD]
Common Name English
RITODRINE [MI]
Common Name English
DU-21220
Code English
RITODRINE [INN]
Common Name English
RITODRINE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
WHO-ATC G02CA01
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
WHO-VATC QG02CA01
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
247-879-9
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
PUBCHEM
688570
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
MERCK INDEX
M9635
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY Merck Index
RXCUI
9392
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C61929
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
WIKIPEDIA
RITODRINE
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
EVMPD
SUB10340MIG
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
EPA CompTox
26652-09-5
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
INN
2608
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
CAS
26652-09-5
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
DRUG BANK
DB00867
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
FDA UNII
I0Q6O6740J
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
MESH
D012312
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL785
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
DRUG CENTRAL
2390
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY
IUPHAR
7294
Created by admin on Sat Jun 26 11:01:30 UTC 2021 , Edited by admin on Sat Jun 26 11:01:30 UTC 2021
PRIMARY