Posted inUncategorized

Fesoterodine

July 24, 2017
Common Name

Fesoterodine Description

Fesoterodine is only found in individuals that have used or taken this drug. It is an antimuscarinic prodrug used for treating overactive bladder syndrome.Fesoterodine, once converted to its active metabolite, 5-hydroxymethyltolterodine, acts as a competitive antagonists at muscarinic receptors. This reslits in the inhibition of bladder contraction, decrease in detrusor pressure, and an incomplete emptying of the bladder. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Fesoterodine fumarateMeSH ToviazMeSH

Chemical Formlia

C26H37NO3 Average Molecliar Weight

411.5769 Monoisotopic Molecliar Weight

411.277344055 IUPAC Name

2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl 2-methylpropanoate Traditional Name

fesoterodine CAS Registry Number

286930-03-8 SMILES

CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(OC(=O)C(C)C)C=CC(CO)=C1)C(C)C

InChI Identifier

InChI=1S/C26H37NO3/c1-18(2)26(29)30-25-13-12-21(17-28)16-24(25)23(22-10-8-7-9-11-22)14-15-27(19(3)4)20(5)6/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3/t23-/m1/s1

InChI Key

DCCSDBARQIPTGU-HSZRJFAPSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Diphenylmethanes Alternative Parents

  • Phenol esters
  • Phenoxy compounds
  • Benzyl alcohols
  • Aralkylamines
  • Trialkylamines
  • Carboxylic acid esters
  • Amino acids and derivatives
  • Monocarboxylic acids and derivatives
  • Primary alcohols
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Aromatic alcohols

    • Substituents

  • Diphenylmethane
  • Phenol ester
  • Phenoxy compound
  • Benzyl alcohol
  • Aralkylamine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Aromatic alcohol
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Incontinence Agents
  • Antimuscarinics
  • Antispasmodics
  • Genitourinary Smooth Muscle Relaxants

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0021 mg/mLALOGPS logP5.45ALOGPS logP5.7ChemAxon logS-5.3ALOGPS pKa (Strongest Acidic)14.98ChemAxon pKa (Strongest Basic)10.64ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area49.77 Å2ChemAxon Rotatable Bond Count11ChemAxon Refractivity124.08 m3·mol-1ChemAxon Polarizability48.29 Å3ChemAxon Number of Rings2ChemAxon Bioavailability0ChemAxon 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

  • 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 DB06702

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06702

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06702 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

    5293755 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Fesoterodine NuGOwiki Link

    HMDB15648 Metagene Link

    HMDB15648 METLIN ID

    Not Available PubChem Compound

    6918558 PDB ID

    Not Available ChEBI ID

    775715

    Product: Niclosamide (monohydrate)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Malhotra B, Dickins M, Alvey C, Jumadilova Z, Li X, Duczynski G, Gandelman K: Effects of the moderate CYP3A4 inhibitor, fluconazole, on the pharmacokinetics of fesoterodine in healthy subjects. Br J Clin Pharmacol. 2011 Aug;72(2):263-9. doi: 10.1111/j.1365-2125.2011.04007.x. [PubMed:21545485 ]
    2. Malhotra B, Gandelman K, Sachse R, Wood N, Michel MC: The design and development of fesoterodine as a prodrug of 5-hydroxymethyl tolterodine (5-HMT), the active metabolite of tolterodine. Curr Med Chem. 2009;16(33):4481-9. [PubMed:19835561 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Malhotra B, Guan Z, Wood N, Gandelman K: Pharmacokinetic profile of fesoterodine. Int J Clin Pharmacol Ther. 2008 Nov;46(11):556-63. [PubMed:19000553 ]
    2. Malhotra B, Dickins M, Alvey C, Jumadilova Z, Li X, Duczynski G, Gandelman K: Effects of the moderate CYP3A4 inhibitor, fluconazole, on the pharmacokinetics of fesoterodine in healthy subjects. Br J Clin Pharmacol. 2011 Aug;72(2):263-9. doi: 10.1111/j.1365-2125.2011.04007.x. [PubMed:21545485 ]
    3. Malhotra B, Sachse R, Wood N: Evaluation of drug-drug interactions with fesoterodine. Eur J Clin Pharmacol. 2009 Jun;65(6):551-60. doi: 10.1007/s00228-009-0648-1. Epub 2009 Apr 4. [PubMed:19347334 ]
    4. Malhotra BK, Wood N, Sachse R: Influence of age, gender, and race on pharmacokinetics, pharmacodynamics, and safety of fesoterodine. Int J Clin Pharmacol Ther. 2009 Sep;47(9):570-8. [PubMed:19761716 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
    Gene Name:
    CYP2D6
    Uniprot ID:
    P10635
    Molecular weight:
    55768.94
    References
    1. Malhotra B, Guan Z, Wood N, Gandelman K: Pharmacokinetic profile of fesoterodine. Int J Clin Pharmacol Ther. 2008 Nov;46(11):556-63. [PubMed:19000553 ]
    2. Malhotra B, Dickins M, Alvey C, Jumadilova Z, Li X, Duczynski G, Gandelman K: Effects of the moderate CYP3A4 inhibitor, fluconazole, on the pharmacokinetics of fesoterodine in healthy subjects. Br J Clin Pharmacol. 2011 Aug;72(2):263-9. doi: 10.1111/j.1365-2125.2011.04007.x. [PubMed:21545485 ]
    3. Malhotra B, Sachse R, Wood N: Evaluation of drug-drug interactions with fesoterodine. Eur J Clin Pharmacol. 2009 Jun;65(6):551-60. doi: 10.1007/s00228-009-0648-1. Epub 2009 Apr 4. [PubMed:19347334 ]
    4. Malhotra BK, Wood N, Sachse R: Influence of age, gender, and race on pharmacokinetics, pharmacodynamics, and safety of fesoterodine. Int J Clin Pharmacol Ther. 2009 Sep;47(9):570-8. [PubMed:19761716 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
    Gene Name:
    CHRM3
    Uniprot ID:
    P20309
    Molecular weight:
    66127.4
    References
    1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    2. Nilvebrant L: Tolterodine and its active 5-hydroxymethyl metabolite: pure muscarinic receptor antagonists. Pharmacol Toxicol. 2002 May;90(5):260-7. [PubMed:12076307 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
    Gene Name:
    CHRM1
    Uniprot ID:
    P11229
    Molecular weight:
    51420.4
    References
    1. Nilvebrant L: Tolterodine and its active 5-hydroxymethyl metabolite: pure muscarinic receptor antagonists. Pharmacol Toxicol. 2002 May;90(5):260-7. [PubMed:12076307 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
    Gene Name:
    CHRM2
    Uniprot ID:
    P08172
    Molecular weight:
    51714.6
    References
    1. Mansfield KJ, Chandran JJ, Vaux KJ, Millard RJ, Christopoulos A, Mitchelson FJ, Burcher E: Comparison of receptor binding characteristics of commonly used muscarinic antagonists in human bladder detrusor and mucosa. J Pharmacol Exp Ther. 2009 Mar;328(3):893-9. doi: 10.1124/jpet.108.145508. Epub 2008 Nov 24. [PubMed:19029429 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
    Gene Name:
    CHRM4
    Uniprot ID:
    P08173
    Molecular weight:
    53048.7
    References
    1. Mansfield KJ, Chandran JJ, Vaux KJ, Millard RJ, Christopoulos A, Mitchelson FJ, Burcher E: Comparison of receptor binding characteristics of commonly used muscarinic antagonists in human bladder detrusor and mucosa. J Pharmacol Exp Ther. 2009 Mar;328(3):893-9. doi: 10.1124/jpet.108.145508. Epub 2008 Nov 24. [PubMed:19029429 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
    Gene Name:
    CHRM5
    Uniprot ID:
    P08912
    Molecular weight:
    60073.2
    References
    1. Mansfield KJ, Chandran JJ, Vaux KJ, Millard RJ, Christopoulos A, Mitchelson FJ, Burcher E: Comparison of receptor binding characteristics of commonly used muscarinic antagonists in human bladder detrusor and mucosa. J Pharmacol Exp Ther. 2009 Mar;328(3):893-9. doi: 10.1124/jpet.108.145508. Epub 2008 Nov 24. [PubMed:19029429 ]

    PMID: 22049072

    Last updated on