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    Trospium

    ACTIVE PHARMA INGREDIENTS

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    PharmaCompass
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    2D Structure
    Also known as: Trospium cation, 47608-32-2, Trospium ion, T4y8ork057, [(1s,5r)-spiro[8-azoniabicyclo[3.2.1]octane-8,1'-azolidin-1-ium]-3-yl] 2-hydroxy-2,2-diphenylacetate, Ncgc00167438-01
    Molecular Formula
    C25H30NO3+
    Molecular Weight
    392.5  g/mol
    InChI Key
    OYYDSUSKLWTMMQ-AIZNXBIQSA-N
    FDA UNII
    T4Y8ORK057
    Trospium is an antispasmodic agent used to treat the symptoms of overactive bladder, a condition that causes the bladder muscles to contract uncontrollably. An overactive bladder leads to an increased urge to urinate, frequent urination, and sometimes, loss of control over urination. Trospium is manufactured by Indevus Pharmaceutical Inc. and was granted FDA approval in 2007.
    Trospium is a Cholinergic Muscarinic Antagonist. The mechanism of action of trospium is as a Cholinergic Muscarinic Antagonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(1R,5S)-spiro[8-azoniabicyclo[3.2.1]octane-8,1'-azolidin-1-ium]-3-yl] 2-hydroxy-2,2-diphenylacetate
    2.1.2 InChI
    InChI=1S/C25H30NO3/c27-24(25(28,19-9-3-1-4-10-19)20-11-5-2-6-12-20)29-23-17-21-13-14-22(18-23)26(21)15-7-8-16-26/h1-6,9-12,21-23,28H,7-8,13-18H2/q+1/t21-,22+,23?
    2.1.3 InChI Key
    OYYDSUSKLWTMMQ-AIZNXBIQSA-N
    2.1.4 Canonical SMILES
    C1CC[N+]2(C1)C3CCC2CC(C3)OC(=O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O
    2.1.5 Isomeric SMILES
    C1CC[N+]2(C1)[C@@H]3CC[C@H]2CC(C3)OC(=O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O
    2.2 Other Identifiers
    2.2.1 UNII
    T4Y8ORK057
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Trospium Cation

    2. 47608-32-2

    3. Trospium Ion

    4. T4y8ork057

    5. [(1s,5r)-spiro[8-azoniabicyclo[3.2.1]octane-8,1'-azolidin-1-ium]-3-yl] 2-hydroxy-2,2-diphenylacetate

    6. Ncgc00167438-01

    7. Ncgc00167438-02

    8. Unii-t4y8ork057

    9. Tropsium Cation

    10. Tropsium Ion

    11. Trospium [vandf]

    12. Trospium [who-dd]

    13. Schembl119810

    14. Schembl2447242

    15. Chembl1888176

    16. Chebi:145791

    17. Zinc12503068

    18. 3alpha-hydroxyspiro(1alphah,5alphah-nortropane-8,1'-pyrrolidinium) Benzilate

    19. Zinc100016084

    20. Zinc100371992

    21. Am84314

    22. Db00209

    23. Ab01274814-01

    24. Ab01274814_02

    25. 3.alpha.-hydroxyspiro(1.alpha.h,5.alpha.h-nortropane-8,1'-pyrrolidinium) Benzilate

    26. (1alpha,3beta,5alpha)-3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-spiro[8-azoniabicyclo[3.2.1]octane-8,1'-pyrrolidinium]

    27. (1alpha,5alpha)-3beta-[(hydroxydiphenylacetyl)oxy]spiro[8-azoniabicyclo[3.2.1]octane-8,1'-pyrrolidinium]

    28. (1s,3r,5r)-3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-8lambda(5)-azaspiro[bicyclo[3.2.1]octane-8,1'-pyrrolidin]-8-ylium

    29. Spiro(8-azoniabicyclo(3.2.1)octane-8,1'-pyrrolidinium), 3-((hydroxydiphenylacetyl)oxy)-, (1.alpha.,3.beta.,5.alpha.)-

    2.4 Create Date
    2005-11-20
    3 Chemical and Physical Properties
    Molecular Weight 392.5 g/mol
    Molecular Formula C25H30NO3+
    XLogP34.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass392.22256882 g/mol
    Monoisotopic Mass392.22256882 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count29
    Formal Charge1
    Complexity553
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency, detrusor instability and frequency of micturition.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Trospium is an antispasmodic, antimuscarinic agent indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency. According to receptor assays, it displays higher affinity towards muscarininc receptors compared to nicotinic receptors at therapeutic concentrations.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    TROSPIUM
    5.2.2 FDA UNII
    T4Y8ORK057
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Cholinergic Muscarinic Antagonists
    5.3 ATC Code

    G04BD09

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    G - Genito urinary system and sex hormones

    G04 - Urologicals

    G04B - Urologicals

    G04BD - Drugs for urinary frequency and incontinence

    G04BD09 - Trospium

    5.4 Absorption, Distribution and Excretion

    Absorption

    9.6%

    Route of Elimination

    After administration of oral 14C-trospium chloride, the majority of the dose (85.2%) was recovered in feces and a smaller amount (5.8% of the dose) was recovered in urine; 60% of the radioactivity excreted in urine was unchanged trospium. Trospium mainly undergoes elimination via active tubular secretion, as indicated by the mean renal clearance of 29.07 L/hour, which is about 4-fold higher than average glomerular filtration rate. Trospium is metabolized by ester hydrolysis and excreted by the kidneys by a combination of tubular secretion and glomerular filtration.

    Volume of Distribution

    395 140 L

    Clearance

    Renal cl=29.07 L/hour

    5.5 Metabolism/Metabolites

    Not fully defined

    5.6 Biological Half-Life

    20 hours

    5.7 Mechanism of Action

    Trospium antagonizes the effect of acetylcholine on muscarinic receptors in cholinergically innervated organs. Its parasympatholytic action reduces the tonus of smooth muscle in the bladder.