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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

Trospium

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 Formula	C₂₅H₃₀NO₃+
Molecular Weight	392.5 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	392.22256882 g/mol
Monoisotopic Mass	392.22256882 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	29
Formal Charge	1
Complexity	553
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

Drugs in Development