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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

Molecular Formula C17H21NO3
Molecular Weight 287.3542
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Influence of maternal magnesium sulphate and ritodrine treatment on the neonate: a study with six-month follow-up.
1999 Oct
Double-blind, randomized, controlled trial of atosiban and ritodrine in the treatment of preterm labor: a multicenter effectiveness and safety study.
2000 May
Asymmetric septal hypertrophy in an infant exposed to ritodrine in utero.
2000 Sep 15
Betamimetics for suspected impaired fetal growth.
2001
Discovery of novel N-phenylglycine derivatives as potent and selective beta(3)-adrenoceptor agonists for the treatment of frequent urination and urinary incontinence.
2001 Apr 26
Spectrophotometric methods for the determination of ritodrine hydrochloride and its application to pharmaceutical preparations.
2001 Aug
Tocolysis with beta-adrenergic receptor agonists.
2001 Aug
Use of molecularly imprinted polymers in the solid-phase extraction of clenbuterol from animal feeds and biological matrices.
2001 Aug 5
Effectiveness and safety of the oxytocin antagonist atosiban versus beta-adrenergic agonists in the treatment of preterm labour. The Worldwide Atosiban versus Beta-agonists Study Group.
2001 Feb
Prenatal diagnosis of persistent fetal bradycardia: report of four cases.
2001 Jan
Ritodrine-induced skin rash.
2001 Jan
A new fetal rat model of gastroschisis: development and early characterization.
2001 Jan
Changes in fetal hemodynamics with ritodrine tocolysis.
2001 Jul
Effect of maternal tocolysis on the incidence of severe periventricular/intraventricular haemorrhage in very low birthweight infants.
2001 Jul
Can a cyclo-oxygenase type-2 selective tocolytic agent avoid the fetal side effects of indomethacin?
2001 Mar
Tocolysis with nifedipine or beta-adrenergic agonists: a meta-analysis.
2001 May
Pharmacological characterization of KUR-1246, a selective uterine relaxant.
2001 May
Invasive pulmonary aspergillosis in a puerperant with drug-induced agranulocytosis.
2001 Nov
Influence of maternal magnesium sulphate and ritodrine treatment on cerebral blood flow velocity of the preterm newborn.
2001 Sep
Rebound perioperative hyperkalemia in six patients after cessation of ritodrine for premature labor.
2001 Sep
Rhabdomyolysis during prolonged intravenous tocolytic therapy.
2002
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
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
Tocolysis: an update for the practitioner.
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
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
KUR-1246, a novel beta(2)-adrenoceptor agonist, as a tocolytic agent.
2002 Sep
Rebound hyperkalemia after cessation of intravenous tocolytic therapy with terbutaline in the treatment of preterm labor: anesthetic implications.
2003 Aug
[External cephalic version for breech presentation at term: an effective procedure to reduce the caesarean section rate].
2003 Dec
Epinephrine inhibits tracheal occlusion induced lung growth in fetal sheep.
2003 Sep-Oct
Ritodrine-induced leukocytoclastic vasculitis in pregnancy.
2004 Jan
The combined maternal administration of magnesium sulfate and aminophylline reduces intraventricular hemorrhage in very preterm neonates.
2005 Feb
Tocolysis in term breech external cephalic version.
2005 Jan
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:01:30 UTC 2021
Edited
by admin
on Sat Jun 26 11:01:30 UTC 2021
Record UNII
I0Q6O6740J
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
TARGET -> AGONIST
SHORT-ACTING
Related Record Type Details
ACTIVE MOIETY