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Identification
NameRitodrine
Accession NumberDB00867  (APRD00541)
TypeSmall Molecule
GroupsApproved
Description

Adrenergic beta-agonist used to control premature labor. [PubChem]

Structure
Thumb
Synonyms
DU-21220
Ritodrina
Ritodrine
Ritodrinium
Yutopar
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Yutopar Inj 50mg/5mlliquid10 mgintravenousBristol Labs Division Of Bristol Myers Squibb1984-12-312001-07-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Yutopar Tab 10mgtablet10 mgoralBristol Labs Division Of Bristol Myers Squibb1984-12-312001-07-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
YutoparNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ritodrine Hydrochloride
Thumb
  • InChI Key: IDLSITKDRVDKRV-UHFFFAOYNA-N
  • Monoisotopic Mass: 323.128821282
  • Average Mass: 323.814
DBSALT000489
Categories
UNIII0Q6O6740J
CAS number26652-09-5
WeightAverage: 287.3535
Monoisotopic: 287.152143543
Chemical FormulaC17H21NO3
InChI KeyInChIKey=IOVGROKTTNBUGK-SJCJKPOMSA-N
InChI
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-/m0/s1
IUPAC Name
4-(2-{[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)phenol
SMILES
C[C@H](NCCC1=CC=C(O)C=C1)[C@H](O)C1=CC=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenylpropane
  • Phenethylamine
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment and prophylaxis of premature labour
PharmacodynamicsBeta-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 actionRitodrine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding~56%
Metabolism

Hepatic, by both the mother and fetus

Route of eliminationNot Available
Half life1.7-2.6 hours
ClearanceNot Available
ToxicityLD50=64mg/kg (mice, IV); LD50=540 mg/kg (mice, oral); LD50=85 mg/kg (rat, IV)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9871
Blood Brain Barrier-0.8115
Caco-2 permeable-0.5546
P-glycoprotein substrateSubstrate0.692
P-glycoprotein inhibitor INon-inhibitor0.953
P-glycoprotein inhibitor IINon-inhibitor0.8732
Renal organic cation transporterNon-inhibitor0.6134
CYP450 2C9 substrateNon-substrate0.6367
CYP450 2D6 substrateSubstrate0.5054
CYP450 3A4 substrateNon-substrate0.5874
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9442
CYP450 2D6 inhibitorNon-inhibitor0.6034
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8351
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7277
Ames testNon AMES toxic0.7799
CarcinogenicityNon-carcinogens0.9177
BiodegradationNot ready biodegradable0.8862
Rat acute toxicity2.2303 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7534
hERG inhibition (predictor II)Inhibitor0.5409
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Abraxis pharmaceutical products
  • Hospira inc
  • Astrazeneca lp
Packagers
Dosage forms
FormRouteStrength
Liquidintravenous10 mg
Tabletoral10 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point88-90 °CNot Available
water solubilityCompleteNot Available
logP2.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.179 mg/mLALOGPS
logP1.53ALOGPS
logP1.82ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.02 m3·mol-1ChemAxon
Polarizability31.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Naoki Yamazaki, Yoshimasa Fukuda, Yoshiaki Shibazaki, Tetsutarou Niizato, Isao Kosugi, Shin Yoshioka, “(-)-ritodrine, therapeutic compositions and use, and method of preparation.” U.S. Patent US5449694, issued July, 1992.

US5449694
General ReferencesNot Available
External Links
ATC CodesG02CA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (48 KB)
Interactions
Drug Interactions
Drug
AcetaminophenThe risk or severity of adverse effects can be increased when Ritodrine is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Ritodrine is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Aminophylline.
AmphetamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Ritodrine is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Ritodrine.
BenzphetamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Benzphetamine.
ButalbitalThe risk or severity of adverse effects can be increased when Ritodrine is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Caffeine.
CocaineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Cocaine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Ritodrine is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dopamine.
DoxapramThe risk or severity of adverse effects can be increased when Ritodrine is combined with Doxapram.
DronabinolDronabinol may increase the tachycardic activities of Ritodrine.
DyphyllineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Epinephrine.
FenoterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Fenoterol.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Ritodrine is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Formoterol.
IndacaterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ritodrine.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Ritodrine is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Ritodrine is combined with Isometheptene.
LevonordefrinThe risk or severity of adverse effects can be increased when Ritodrine is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Ritodrine.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Lisdexamfetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Mepivacaine.
MethamphetamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Ritodrine is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Ritodrine is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Ritodrine.
NaphazolineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Naphazoline.
NorepinephrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Olodaterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Oxymetazoline.
PhendimetrazineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Phendimetrazine.
PheniramineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Pheniramine.
PhentermineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Phenylephrine.
PirbuterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Pirbuterol.
PropylhexedrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Racepinephrine.
SalbutamolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Salmeterol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Ritodrine.
TerbutalineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Theophylline.
TriprolidineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Vilanterol.
Food InteractionsNot Available

Targets

1. Beta-2 adrenergic receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. Tanaka N, Tamai T, Mukaiyama H, Hirabayashi A, Muranaka H, Akahane S, Miyata H, Akahane M: Discovery of novel N-phenylglycine derivatives as potent and selective beta(3)-adrenoceptor agonists for the treatment of frequent urination and urinary incontinence. J Med Chem. 2001 Apr 26;44(9):1436-45. Pubmed
  2. Schwarz MK, Page P: Preterm labour: an overview of current and emerging therapeutics. Curr Med Chem. 2003 Aug;10(15):1441-68. Pubmed
  3. Lye SJ, Dayes BA, Freitag CL, Brooks J, Casper RF: Failure of ritodrine to prevent preterm labor in the sheep. Am J Obstet Gynecol. 1992 Nov;167(5):1399-408. Pubmed
  4. Bianchetti A, Manara L: In vitro inhibition of intestinal motility by phenylethanolaminotetralines: evidence of atypical beta-adrenoceptors in rat colon. Br J Pharmacol. 1990 Aug;100(4):831-9. Pubmed
  5. Lenselink DR, Kuhlmann RS, Lawrence JM, Kolesari GL: Cardiovascular teratogenicity of terbutaline and ritodrine in the chick embryo. Am J Obstet Gynecol. 1994 Aug;171(2):501-6. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. 6-phosphogluconate dehydrogenase, decarboxylating

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
6-phosphogluconate dehydrogenase, decarboxylating P52209 Details

References:

  1. Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Mar 17. Pubmed
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12