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    Chemistry

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    Also known as: 286930-03-8, Toviaz, (r)-fesoterodine fumarate, Spm 907, Spm 8272, Spm-907
    Molecular Formula
    C30H41NO7
    Molecular Weight
    527.6  g/mol
    InChI Key
    MWHXMIASLKXGBU-RNCYCKTQSA-N
    FDA UNII
    EOS72165S7
    Fesoterodine
    Fesoterodine Fumarate is the fumarate salt form of fesoterodine, a competitive muscarinic receptor antagonist with muscle relaxant and urinary antispasmodic properties. Fesoterodine is rapidly hydrolyzed in vivo into its active metabolite 5-hydroxy methyl tolterodine, which binds and inhibits muscarinic receptors on the bladder detrusor muscle, thereby preventing bladder contractions or spasms caused by acetylcholine. This results in the relaxation of bladder smooth muscle and greater bladder capacity, in addition to a reduction in involuntary muscle contractions and involuntary loss of urine. The active metabolite does not interact with alpha-adrenergic, serotonergic, histaminergic and excitatory amino acid receptors and is eliminated via renal excretion.
    1 2D Structure

    Fesoterodine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-but-2-enedioic acid;[2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate
    2.1.2 InChI
    InChI=1S/C26H37NO3.C4H4O4/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;5-3(6)1-2-4(7)8/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t23-;/m1./s1
    2.1.3 InChI Key
    MWHXMIASLKXGBU-RNCYCKTQSA-N
    2.1.4 Canonical SMILES
    CC(C)C(=O)OC1=C(C=C(C=C1)CO)C(CCN(C(C)C)C(C)C)C2=CC=CC=C2.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CC(C)C(=O)OC1=C(C=C(C=C1)CO)[C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2.C(=C/C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    EOS72165S7
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Fesoterodine

    2. Toviaz

    2.3.2 Depositor-Supplied Synonyms

    1. 286930-03-8

    2. Toviaz

    3. (r)-fesoterodine Fumarate

    4. Spm 907

    5. Spm 8272

    6. Spm-907

    7. Spm-8272

    8. Fesoterodine Maleate

    9. Fesoterodine (fumarate)

    10. Eos72165s7

    11. (e)-but-2-enedioic Acid;[2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

    12. Propanoic Acid, 2-methyl-, 2-[(1r)-3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl Ester, (2e)-2-butenedioate (1:1)

    13. 286930-03-8 (fumarate); 286930-02-7 (free Base)

    14. Fesoterodine Fumarate [usan]

    15. Unii-eos72165s7

    16. Fesoterodine Fumarate [usan:jan]

    17. (e)-but-2-enedioic Acid,[2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

    18. Toviaz (tn)

    19. (r)-fesoterodinefumarate

    20. Mls003915638

    21. Schembl814971

    22. Fesoterodine Fumarate - Toviaz

    23. Schembl1993632

    24. Chembl1201765

    25. Dtxsid00904655

    26. Bcpp000231

    27. Fesoterodine Fumarate (jan/usan)

    28. Fesoterodine Fumarate [mi]

    29. Hms3884d11

    30. Fesoterodine Fumarate [jan]

    31. Amy37611

    32. Hy-a0030

    33. Bdbm50248002

    34. Fesoterodine Fumarate [vandf]

    35. Mfcd12756004

    36. S2240

    37. Fesoterodine Fumarate [mart.]

    38. Akos005146248

    39. Akos015855886

    40. Fesoterodine Fumarate [who-dd]

    41. Ac-3486

    42. Bcp9000682

    43. Ccg-269901

    44. Cs-0822

    45. Ks-1298

    46. 2-((1r)-3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl Isobutyrate

    47. Fesoterodine Fumarate [ema Epar]

    48. 2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl 2-methylpropanoate Hydrogen (2e)-butenedioate (salt)

    49. Propanoic Acid, 2-methyl-, 2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl Ester, (2e)-2-butenedioate (1:1) (salt)

    50. Smr002544691

    51. Fesoterodine Fumarate [orange Book]

    52. Pf-00695838

    53. D08923

    54. 930f038

    55. A846296

    56. Q27277274

    57. 2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl 2-methylpropanoate Hydrogen(2e)-butenedioate (salt)

    58. Fesoterodinefumarate;(r)-fesoterodine Fumarate;2-methylpropanoic Acid 2-[(1r)-3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl Ester (2e)-2-butenedioate

    59. Propanoic Acid,2-methyl ,2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl Ester,(2e)-2-butenedioate (1:1)(salt)

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 527.6 g/mol
    Molecular Formula C30H41NO7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count13
    Exact Mass527.28830265 g/mol
    Monoisotopic Mass527.28830265 g/mol
    Topological Polar Surface Area124 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity610
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameToviaz
    PubMed HealthFesoterodine (By mouth)
    Drug ClassesUrinary Antispasmodic
    Drug LabelToviaz contains fesoterodine fumarate and is an extended-release tablet. Fesoterodine is rapidly de-esterified to its active metabolite (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol, or 5-hydroxymethyl tolterodine, which is a musca...
    Active IngredientFesoterodine fumarate
    Dosage FormTablet, extended release
    RouteOral
    Strength8mg; 4mg
    Market StatusPrescription
    CompanyPfizer

    2 of 2  
    Drug NameToviaz
    PubMed HealthFesoterodine (By mouth)
    Drug ClassesUrinary Antispasmodic
    Drug LabelToviaz contains fesoterodine fumarate and is an extended-release tablet. Fesoterodine is rapidly de-esterified to its active metabolite (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol, or 5-hydroxymethyl tolterodine, which is a musca...
    Active IngredientFesoterodine fumarate
    Dosage FormTablet, extended release
    RouteOral
    Strength8mg; 4mg
    Market StatusPrescription
    CompanyPfizer

    4.2 Drug Indication

    Treatment of the symptoms (increased urinary frequency and / or urgency and / or urgency incontinence) that may occur in patients with overactive-bladder syndrome.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Muscarinic Antagonists

    Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

    Urological Agents

    Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)

    5.2 ATC Code

    G04BD11

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