Trospium

Identification

Summary

Trospium is an antimuscarinic agent used to treat the symptoms of overactive bladder (OAB).

Brand Names
Trosec
Generic Name
Trospium
DrugBank Accession Number
DB00209
Background

Trospium is an antispasmodic agent used to treat the symptoms of overactive bladder, a condition that causes the bladder muscles to contract uncontrollably.1 An overactive bladder leads to an increased urge to urinate, frequent urination, and sometimes, loss of control over urination.1 Trospium is manufactured by Indevus Pharmaceutical Inc. and was granted FDA approval in 2007.2

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 392.518
Monoisotopic: 392.22202025
Chemical Formula
C25H30NO3
Synonyms
Not Available

Pharmacology

Indication

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

Pharmacology
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Drug Discovery
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

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.

TargetActionsOrganism
UMuscarinic acetylcholine receptor M1
antagonist
Humans
UMuscarinic acetylcholine receptor M3Not AvailableHumans
Absorption

9.6%

Volume of distribution
  • 395 ± 140 L
Protein binding

50-85%

Metabolism

Not fully defined

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.

Half-life

20 hours

Clearance
  • Renal cl=29.07 L/hour
Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Trospium.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Trospium.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Trospium.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Trospium.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Trospium.
AclidiniumThe risk or severity of adverse effects can be increased when Trospium is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Trospium is combined with Adenosine.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Trospium.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Trospium.
AlimemazineAlimemazine may increase the central nervous system depressant (CNS depressant) activities of Trospium.
Interactions
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Food Interactions
  • Take on an empty stomach. Take at least 1 hour before food as the Cmax and AUC of trospium are reduced by 70-80% when taken with a high fat meal.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Trospium chloride1E6682427E10405-02-4RVCSYOQWLPPAOA-QKYUOBHYSA-M
Product Images
International/Other Brands
Flotros / Regurin / Spasmex / Spasmolyt / Spasmoplex / Tropez OD
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SancturaTablet20 mg/1OralAllergan2007-12-012015-09-19US flag
Sanctura XRCapsule, extended release60 mg/1OralEsprit Pharmaceuticals2007-08-012008-05-01US flag
Sanctura XRCapsule, extended release60 mgOralAllergan2010-01-202016-04-13Canada flag
Sanctura XRCapsule, extended release60 mg/1OralPhysicians Total Care, Inc.2010-09-152013-06-30US flag
Sanctura XRCapsule, extended release60 mg/1OralAllergan2007-12-012015-03-04US flag0023 935020180907 15195 31zrgu
TrosecTabletOralSunovion2006-04-04Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-trospiumTabletOralAccel Pharma IncNot applicableNot applicableCanada flag
Jamp TrospiumTabletOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Mar-trospiumTabletOralMarcan Pharmaceuticals Inc2019-06-21Not applicableCanada flag
Trospium ChlorideTablet, film coated20 mg/1OralGlenmark Pharmaceuticals Inc., USA2010-08-13Not applicableUS flag68462 0461 60 nlmimage10 b73d5b9a
Trospium ChlorideCapsule, extended release60 mg/1OralActavis Pharma, Inc.2012-10-12Not applicableUS flag00591 3636 30 nlmimage10 9241c94e
Trospium ChlorideCapsule, extended release60 mg/1OralGolden State Medical Supply, Inc.2014-07-18Not applicableUS flag60429 009820210416 32485 1bd63cj
Trospium ChlorideCapsule, extended release60 mg/1OralBluePoint Laboratories2020-07-10Not applicableUS flag
Trospium ChlorideTablet, film coated20 mg/1OralHeritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc.2016-08-30Not applicableUS flag
Trospium ChlorideTablet20 mg/1OralAvKARE2016-10-06Not applicableUS flag
Trospium ChlorideTablet20 mg/1OralAmerincan Health Packaging2014-12-152015-07-09US flag

Categories

ATC Codes
A03DA06 — Trospium and analgesicsG04BD09 — Trospium
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds 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
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Piperidines / N-alkylpyrrolidines / Tetraalkylammonium salts / Tertiary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts / Organic oxides
show 5 more
Substituents
Alcohol / Amine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Diphenylmethane / Hydrocarbon derivative
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
T4Y8ORK057
CAS number
47608-32-2
InChI Key
OYYDSUSKLWTMMQ-JKHIJQBDSA-N
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+
IUPAC Name
(1S,3R,5R)-3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-8λ⁵-azaspiro[bicyclo[3.2.1]octane-8,1'-pyrrolidin]-8-ylium
SMILES
[H][C@]12CC[C@]([H])(C[C@@H](C1)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1)[N+]21CCCC1

References

General References
  1. Trospium [Link]
  2. FDA drug approval: Trospium [Link]
KEGG Drug
D01103
PubChem Compound
5284632
PubChem Substance
46506398
ChemSpider
10482307
RxNav
236778
ChEBI
145791
ChEMBL
CHEMBL1888176
ZINC
ZINC000100016084
Therapeutic Targets Database
DAP000342
PharmGKB
PA164748976
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Trospium_chloride
AHFS Codes
  • 86:12.04 — Antimuscarinics
FDA label
Download (249 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceCognitive Function / Mental Competency / Urinary Bladder, Overactive1
4CompletedTreatmentBMI >30 kg/m2 / Incontinence / Urinary Bladder, Overactive1
4CompletedTreatmentElderly / Pharmacokinetics / Urinary Bladder, Overactive1
4CompletedTreatmentNeurogenic Detrusor Overactivity / Spinal Cord Injuries (SCI)1
4CompletedTreatmentUrinary Bladder, Overactive2
4RecruitingOtherUrinary Urgency Incontinence1
3CompletedTreatmentUrinary Bladder, Overactive / Urinary Incontinence, Urge1
3Not Yet RecruitingTreatmentSchizophrenia1
3RecruitingTreatmentSchizophrenia1
3RecruitingTreatmentSchizophrenia / Schizophrenia; Psychosis2

Pharmacoeconomics

Manufacturers
  • Allergan inc
Packagers
  • Allergan Inc.
  • Catalent Pharma Solutions
  • Endo Pharmaceuticals Inc.
  • Esprit Pharma Inc.
  • Madaus GmbH
  • Murfreesboro Pharmaceutical Nursing Supply
  • Odyssey Pharmaceuticals Inc.
  • Redpharm Drug
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
TabletOral20 mg/1
Capsule, extended releaseOral60 mg/1
Tablet, coatedOral
Tablet, sugar coatedOral
TabletOral
Tablet, film coatedOral20 mg/1
CapsuleOral60 mg/1
Capsule, extended releaseOral
Capsule, extended releaseOral60 mg
Prices
Unit descriptionCostUnit
Sanctura XR 60 mg 24 Hour Capsule5.17USD capsule
Sanctura xr 60 mg capsule5.02USD capsule
Sanctura 20 mg tablet3.12USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2537103No2010-01-192024-11-04Canada flag
US7759359No2010-07-202024-11-04US flag
US7763635No2010-07-272024-11-04US flag
US7781448No2010-08-242024-11-04US flag
US7781449No2010-08-242024-11-04US flag
US7410978No2008-08-122025-02-01US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.68e-05 mg/mLALOGPS
logP2.86ALOGPS
logP-0.5ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)11.05ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.04 m3·mol-1ChemAxon
Polarizability43.25 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9469
Blood Brain Barrier+0.9418
Caco-2 permeable+0.6042
P-glycoprotein substrateSubstrate0.6431
P-glycoprotein inhibitor INon-inhibitor0.7783
P-glycoprotein inhibitor IINon-inhibitor0.9759
Renal organic cation transporterInhibitor0.7234
CYP450 2C9 substrateNon-substrate0.818
CYP450 2D6 substrateNon-substrate0.774
CYP450 3A4 substrateSubstrate0.5716
CYP450 1A2 substrateNon-inhibitor0.9005
CYP450 2C9 inhibitorNon-inhibitor0.89
CYP450 2D6 inhibitorNon-inhibitor0.7317
CYP450 2C19 inhibitorNon-inhibitor0.9147
CYP450 3A4 inhibitorNon-inhibitor0.8121
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9567
Ames testNon AMES toxic0.8238
CarcinogenicityNon-carcinogens0.9458
BiodegradationNot ready biodegradable0.8128
Rat acute toxicity2.8407 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9135
hERG inhibition (predictor II)Non-inhibitor0.6933
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Rovner ES: Trospium chloride in the management of overactive bladder. Drugs. 2004;64(21):2433-46. doi: 10.2165/00003495-200464210-00005. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor activity
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Hesch K: Agents for treatment of overactive bladder: a therapeutic class review. Proc (Bayl Univ Med Cent). 2007 Jul;20(3):307-14. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase 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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Beckmann-Knopp S, Rietbrock S, Weyhenmeyer R, Bocker RH, Beckurts KT, Lang W, Fuhr U: Inhibitory effects of trospium chloride on cytochrome P450 enzymes in human liver microsomes. Pharmacol Toxicol. 1999 Dec;85(6):299-304. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 07, 2021 21:05