You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameRitodrine
Accession NumberDB00867  (APRD00541)
TypeSmall Molecule
GroupsApproved
DescriptionAdrenergic beta-agonist used to control premature labor. [PubChem]
Structure
Thumb
Synonyms
DU-21220
Ritodrina
Ritodrine
Ritodrinium
Yutopar
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Yutopar Inj 50mg/5mlliquid10 mgintravenousBristol Labs Division Of Bristol Myers Squibb1984-12-312001-07-30Canada
Yutopar Tab 10mgtablet10 mgoralBristol Labs Division Of Bristol Myers Squibb1984-12-312001-07-30Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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[[email protected]](NCCC1=CC=C(O)C=C1)[[email protected]](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.
Related Articles
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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Ritodrine.
AcebutololThe risk or severity of adverse effects can be increased when Ritodrine is combined with Acebutolol.
AlprenololAlprenolol may decrease the bronchodilatory activities of Ritodrine.
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Ritodrine.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Ritodrine.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ritodrine.
AtenololAtenolol may decrease the bronchodilatory activities of Ritodrine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Ritodrine.
AtosibanThe risk or severity of adverse effects can be increased when Ritodrine is combined with Atosiban.
BendroflumethiazideRitodrine may increase the hypokalemic activities of Bendroflumethiazide.
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Ritodrine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Ritodrine.
BetahistineThe therapeutic efficacy of Ritodrine can be decreased when used in combination with Betahistine.
BetaxololBetaxolol may decrease the bronchodilatory activities of Ritodrine.
BisoprololBisoprolol may decrease the bronchodilatory activities of Ritodrine.
BopindololBopindolol may decrease the bronchodilatory activities of Ritodrine.
BumetanideRitodrine may increase the hypokalemic activities of Bumetanide.
BupranololBupranolol may decrease the bronchodilatory activities of Ritodrine.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Ritodrine.
CarteololCarteolol may decrease the bronchodilatory activities of Ritodrine.
CeliprololThe risk or severity of adverse effects can be increased when Ritodrine is combined with Celiprolol.
ChlorothiazideRitodrine may increase the hypokalemic activities of Chlorothiazide.
ChlorphentermineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Chlorphentermine.
ChlorthalidoneRitodrine may increase the hypokalemic activities of Chlorthalidone.
ClenbuterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Clenbuterol.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Ritodrine.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Ritodrine.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Ritodrine.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Ritodrine.
DopamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dopamine.
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Ritodrine.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Ritodrine.
DoxofyllineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Ritodrine.
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 Epinephrine is combined with Ritodrine.
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Ritodrine.
EsmololEsmolol may decrease the bronchodilatory activities of Ritodrine.
Etacrynic acidRitodrine may increase the hypokalemic activities of Etacrynic acid.
EtilefrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Etilefrine.
FenoterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Fenoterol.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Ritodrine.
FurosemideRitodrine may increase the hypokalemic activities of Furosemide.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Ritodrine.
HydrochlorothiazideRitodrine may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideRitodrine may increase the hypokalemic activities of Hydroflumethiazide.
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Ritodrine is combined with Hydroxyamphetamine hydrobromide.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Ritodrine.
IndapamideRitodrine may increase the hypokalemic activities of Indapamide.
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Ritodrine.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Ritodrine.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Ritodrine.
IsoprenalineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Isoprenaline.
IsoxsuprineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Isoxsuprine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Ritodrine.
LinezolidLinezolid may increase the hypertensive activities of Ritodrine.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Ritodrine.
MephentermineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Mephentermine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ritodrine.
MethamphetamineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Methamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Ritodrine.
MethyclothiazideRitodrine may increase the hypokalemic activities of Methyclothiazide.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Ritodrine.
MetolazoneRitodrine may increase the hypokalemic activities of Metolazone.
MetoprololMetoprolol may decrease the bronchodilatory activities of Ritodrine.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Ritodrine.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Ritodrine.
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Ritodrine.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Ritodrine.
NabiloneNabilone may increase the tachycardic activities of Ritodrine.
NadololNadolol may decrease the bronchodilatory activities of Ritodrine.
NebivololNebivolol may decrease the bronchodilatory activities of Ritodrine.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Ritodrine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Ritodrine.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Ritodrine.
NylidrinThe risk or severity of adverse effects can be increased when Ritodrine is combined with Nylidrin.
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Ritodrine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Ritodrine.
OxprenololOxprenolol may decrease the bronchodilatory activities of Ritodrine.
OxymetazolineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Oxymetazoline.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Ritodrine.
PenbutololPenbutolol may decrease the bronchodilatory activities of Ritodrine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Ritodrine.
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Ritodrine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Ritodrine.
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Ritodrine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Ritodrine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Ritodrine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Ritodrine.
PindololPindolol may decrease the bronchodilatory activities of Ritodrine.
PiretanideRitodrine may increase the hypokalemic activities of Piretanide.
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Ritodrine.
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Ritodrine.
PolythiazideRitodrine may increase the hypokalemic activities of Polythiazide.
ProcaterolThe risk or severity of adverse effects can be increased when Ritodrine is combined with Procaterol.
PropranololPropranolol may decrease the bronchodilatory activities of Ritodrine.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Ritodrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Pseudoephedrine.
QuinethazoneRitodrine may increase the hypokalemic activities of Quinethazone.
RacepinephrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Racepinephrine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Ritodrine.
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Ritodrine.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Ritodrine.
SotalolSotalol may decrease the bronchodilatory activities of Ritodrine.
SynephrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Synephrine.
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.
TetryzolineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Tetryzoline.
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Ritodrine.
TimololTimolol may decrease the bronchodilatory activities of Ritodrine.
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Ritodrine.
TorasemideRitodrine may increase the hypokalemic activities of Torasemide.
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Ritodrine.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Ritodrine.
TrichlormethiazideRitodrine may increase the hypokalemic activities of Trichlormethiazide.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Ritodrine.
TyramineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Tyramine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
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:11311067 ]
  2. Schwarz MK, Page P: Preterm labour: an overview of current and emerging therapeutics. Curr Med Chem. 2003 Aug;10(15):1441-68. [PubMed:12871140 ]
  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:1332478 ]
  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:1976401 ]
  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:8059831 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Phosphogluconate dehydrogenase (decarboxylating) activity
Specific Function:
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH.
Gene Name:
PGD
Uniprot ID:
P52209
Molecular Weight:
53139.56 Da
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 Aug;25(4):476-9. doi: 10.3109/14756360903257900. [PubMed:20235752 ]
  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:10592235 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23