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Ritodrine

July 24, 2017
Common Name

Ritodrine Description

Ritodrine is only found in individuals that have used or taken this drug. It is an adrenergic beta-agonist used to control premature labor. [PubChem]Ritodrine 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 intracellliar calcium and leads to a decrease of uterine contractions. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source DU-21220RitodrineChEMBL PreParMeSH Astra brand OF ritodrine hydrochlorideMeSH Janssen brand OF ritodrine hydrochlorideMeSH Pre-parMeSH Solvay brand OF ritodrine hydrochlorideMeSH Ritodrine hydrochlorideMeSH Hydrochloride, ritodrineMeSH Pre parMeSH YutoparMeSH

Chemical Formlia

C17H21NO3 Average Molecliar Weight

287.3535 Monoisotopic Molecliar Weight

287.152143543 IUPAC Name

4-(2-{[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)phenol Traditional Name

PrePar CAS Registry Number

26652-09-5 SMILES

C[C@H](NCCC1=CC=C(O)C=C1)[C@H](O)C1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

IOVGROKTTNBUGK-SJCJKPOMSA-N Chemical Taxonomy Description

This 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. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Phenethylamines Direct Parent

Phenethylamines Alternative Parents

  • Phenylpropanes
  • Aralkylamines
  • 1-hydroxy-2-unsubstituted benzenoids
  • Secondary alcohols
  • 1,2-aminoalcohols
  • Dialkylamines
  • Organopnictogen compounds
  • Hydrocarbon derivatives
  • Aromatic alcohols

    • Substituents

  • Phenethylamine
  • Phenylpropane
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Amine
  • Aromatic alcohol
  • Alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • amphetamines (CHEBI:8872 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic beta-Agonists
  • Sympathomimetic
  • Sympathomimetics
  • Tocolytic Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point88 – 90 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.79e-01 g/LNot Available LogP2.4Not Available

    Predicted Properties

    Property Value Source Water Solubility0.18 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00867

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00867

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00867 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    30971 KEGG Compound ID

    C07239 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Ritodrine NuGOwiki Link

    HMDB15005 Metagene Link

    HMDB15005 METLIN ID

    Not Available PubChem Compound

    33572 PDB ID

    Not Available ChEBI ID

    147138

    Product: Tiadinil

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
    Gene Name:
    PGD
    Uniprot ID:
    P52209
    Molecular weight:
    53139.56
    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 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    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:
    46458.3
    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 ]

    PMID: 16834754

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