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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
RitodrinaSpanishINN
RitodriniumLatinINN
Salts
Name/CAS Structure Properties
Ritodrine Hydrochloride
Thumb
  • InChI Key: IDLSITKDRVDKRV-UHFFFAOYNA-N
  • Monoisotopic Mass: 323.128821282
  • Average Mass: 323.814
DBSALT000489
Brand names
NameCompany
YutoparNot Available
Brand mixturesNot Available
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-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol
SMILES
C[C@H](NCCC1=CC=C(O)C=C1)[C@H](O)C1=CC=C(O)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsPhenols and Derivatives; Secondary Alcohols; 1,2-Aminoalcohols; Polyols; Enols; Dialkylamines; Polyamines
Substituentsphenol derivative; 1,2-aminoalcohol; secondary alcohol; polyol; polyamine; secondary amine; secondary aliphatic amine; enol; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
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
Property Value Probability
Human Intestinal Absorption + 0.9871
Blood Brain Barrier - 0.8115
Caco-2 permeable - 0.5546
P-glycoprotein substrate Substrate 0.692
P-glycoprotein inhibitor I Non-inhibitor 0.953
P-glycoprotein inhibitor II Non-inhibitor 0.8732
Renal organic cation transporter Non-inhibitor 0.6134
CYP450 2C9 substrate Non-substrate 0.6367
CYP450 2D6 substrate Substrate 0.5054
CYP450 3A4 substrate Non-substrate 0.5874
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9442
CYP450 2D6 substrate Non-inhibitor 0.6034
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8351
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7277
Ames test Non AMES toxic 0.7799
Carcinogenicity Non-carcinogens 0.9177
Biodegradation Not ready biodegradable 0.8862
Rat acute toxicity 2.2303 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7534
hERG inhibition (predictor II) Inhibitor 0.5409
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 solubility1.79e-01 g/lALOGPS
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 area72.72ChemAxon
rotatable bond count6ChemAxon
refractivity83.02ChemAxon
polarizability31.56ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD02359
KEGG CompoundC07239
PubChem Compound33572
PubChem Substance46505273
ChemSpider30971
Therapeutic Targets DatabaseDAP000937
PharmGKBPA451258
Drug Product Database550140
Drugs.comhttp://www.drugs.com/cons/ritodrine-oral-intravenous.html
WikipediaRitodrine
ATC CodesG02CA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(48 KB)
Interactions
Drug InteractionsNot Available
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