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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
SynonymLanguageCode
DU-21220Not AvailableNot Available
RitodrinaSpanishINN
RitodrineNot AvailableNot Available
RitodriniumLatinINN
YutoparNot AvailableNot Available
Prescription ProductsNot Available
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
CAS number26652-09-5
WeightAverage: 287.3535
Monoisotopic: 287.152143543
Chemical FormulaC17H21NO3
InChI KeyIOVGROKTTNBUGK-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 substrateNon-inhibitor0.9442
CYP450 2D6 substrateNon-inhibitor0.6034
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Abraxis pharmaceutical products
  • Hospira inc
  • Astrazeneca lp
Packagers
Dosage formsNot Available
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 ReferenceNot Available
External Links
ATC CodesG02CA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (48 KB)
Interactions
Drug Interactions
Drug
AminophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ArformoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
armodafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
ArticaineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineAtoMOXetine may enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
CaffeineMay enhance the adverse/toxic effect of other Sympathomimetics.
CocaineMay enhance the adverse/toxic effect of other Sympathomimetics.
DexmethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
DextroamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DiethylpropionMay enhance the adverse/toxic effect of other Sympathomimetics.
DihydrocodeineMay enhance the adverse/toxic effect of other Sympathomimetics.
DipivefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DoxapramMay enhance the adverse/toxic effect of other Sympathomimetics.
DronabinolCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Fluticasone furoateMay enhance the adverse/toxic effect of other Sympathomimetics.
FormoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IndacaterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IobenguaneMay diminish the therapeutic effect of Iobenguane I 123.
Ipratropium bromideMay enhance the adverse/toxic effect of other Sympathomimetics.
IsomethepteneMay enhance the adverse/toxic effect of other Sympathomimetics.
LevonordefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidLinezolid may enhance the hypertensive effect of Sympathomimetics.
LisdexamfetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
ModafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
NabiloneCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
OxymetazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhendimetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PheniramineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PirbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
PropylhexedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PseudoephedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalbutamolMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Tedizolid PhosphateTedizolid may enhance the hypertensive effect of Sympathomimetics. Tedizolid may enhance the tachycardic effect of Sympathomimetics.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
TheophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
TriprolidineMay enhance the adverse/toxic effect of other Sympathomimetics.
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