Identification

Name
Trospium
Accession Number
DB00209  (APRD00393)
Type
Small Molecule
Groups
Approved
Description

Trospium is a urinary antispasmodic. It is sold under the brand name Sanctura in the US, and as Trosec in Canada. [Wikipedia]

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Trospium chloride1E6682427E10405-02-4RVCSYOQWLPPAOA-QKYUOBHYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SancturaTablet20 mg/1OralAllergan2007-12-012015-09-19Us
Sanctura XRCapsule, extended release60 mg/1OralAllergan2007-12-012015-03-04Us0023 935020180907 15195 31zrgu
Sanctura XRCapsule, extended release60 mg/1OralEsprit Pharmaceuticals2007-08-012008-05-01Us
Sanctura XRCapsule, extended release60 mg/1OralPhysicians Total Care, Inc.2010-09-152013-06-30Us
Sanctura XRCapsule, extended release60 mgOralAllergan2010-01-202016-04-13Canada
TrosecTablet20 mgOralSunovion2006-04-04Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Trospium ChlorideTablet, film coated20 mg/1OralPaddock Laboratories, Inc.2010-11-17Not applicableUs0574 014520180907 15195 187lv38
Trospium ChlorideTablet20 mg/1OralAvKARE, Inc.2016-10-06Not applicableUs
Trospium ChlorideTablet20 mg/1OralGolden State Medical Supply2013-02-08Not applicableUs60505 3454 06 nlmimage10 714338c9
Trospium ChlorideCapsule, extended release60 mg/1OralBlue Point Laboratories2014-03-11Not applicableUs
Trospium ChlorideTablet, film coated20 mg/1OralExelan Pharmaceuticals, Inc.2017-07-11Not applicableUs
Trospium ChlorideTablet, film coated20 mg/1OralCipla Limited2016-09-23Not applicableUs
Trospium ChlorideTablet20 mg/1OralBiomes Pharmaceuticals2010-08-13Not applicableUs
Trospium ChlorideTablet20 mg/1OralApotex Corporation2012-10-15Not applicableUs60505 345420180907 15195 1o3r2bt
Trospium ChlorideTablet, film coated20 mg/1OralGlenmark Pharmaceuticals Inc.,Usa2010-08-13Not applicableUs68462 0461 60 nlmimage10 b73d5b9a
Trospium ChlorideTablet20 mg/1OralAmerincan Health Packaging2014-12-152015-07-09Us
International/Other Brands
Flotros / Regurin / Spasmex / Spasmolyt / Spasmoplex / Tropez OD
Categories
UNII
T4Y8ORK057
CAS number
47608-32-2
Weight
Average: 392.518
Monoisotopic: 392.22202025
Chemical Formula
C25H30NO3
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

Pharmacology

Indication

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

Associated Conditions
Pharmacodynamics

Trospium is an antispasmodic, antimuscarinic agent indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency. Receptor assays showed that trospium has negligible affinity for nicotinic receptors as compared to muscarinic receptors at concentrations obtained from therapeutic doses.

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
Human
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. The mean renal clearance for trospium (29.07 L/hour) is 4-fold higher than average glomerular filtration rate, indicating that active tubular secretion is a major route of elimination for trospium. SANCTURA ® 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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(2-benzhydryloxyethyl)diethyl-methylammonium iodideThe risk or severity of adverse effects can be increased when Trospium is combined with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
1,10-PhenanthrolineThe therapeutic efficacy of Trospium can be decreased when used in combination with 1,10-Phenanthroline.
AclidiniumThe risk or severity of adverse effects can be increased when Trospium is combined with Aclidinium.
AgmatineThe risk or severity of adverse effects can be increased when Trospium is combined with Agmatine.
Ajulemic acidThe risk or severity of Tachycardia and drowsiness can be increased when Trospium is combined with Ajulemic acid.
AlcuroniumThe risk or severity of adverse effects can be increased when Trospium is combined with Alcuronium.
AlfentanilThe risk or severity of adverse effects can be increased when Trospium is combined with Alfentanil.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Trospium is combined with Alphacetylmethadol.
AlphaprodineThe risk or severity of adverse effects can be increased when Trospium is combined with Alphaprodine.
AmantadineThe risk or severity of adverse effects can be increased when Trospium is combined with Amantadine.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D01103
PubChem Compound
5284632
PubChem Substance
46506398
ChemSpider
10482307
ChEBI
32270
ChEMBL
CHEMBL1888176
Therapeutic Targets Database
DAP000342
PharmGKB
PA164748976
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Trospium
ATC Codes
A03DA06 — Trospium and analgesicsG04BD09 — Trospium
AHFS Codes
  • 86:12.04 — Antimuscarinics
FDA label
Download (249 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentSchizophrenic Disorders1
2RecruitingTreatmentSchizophrenic Disorders1
3CompletedTreatmentUrge Urinary Incontinence / Urinary Bladder, Overactive1
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
Not AvailableActive Not RecruitingNot AvailableUrinary Bladder, Overactive1
Not AvailableCompletedNot AvailableUrinary Bladder Diseases / Urinary Bladder, Overactive / Urologic Diseases1
Not AvailableRecruitingNot AvailableUrinary Bladder, Overactive1
Not AvailableUnknown StatusNot AvailableUrinary Bladder, Overactive1

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
Capsule, extended releaseOral60 mg
Capsule, extended releaseOral60 mg/1
TabletOral20 mg
TabletOral20 mg/1
Tablet, film coatedOral20 mg/1
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)
CA2537103No2010-01-192024-11-04Canada
US7759359No2004-11-042024-11-04Us
US7763635No2004-11-042024-11-04Us
US7781448No2004-11-042024-11-04Us
US7781449No2004-11-042024-11-04Us
US7410978No2005-02-012025-02-01Us

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

Taxonomy

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
Diphenylmethane / Piperidine / N-alkylpyrrolidine / Pyrrolidine / Quaternary ammonium salt / Tertiary alcohol / Tetraalkylammonium salt / Carboxylic acid ester / Organoheterocyclic compound / Azacycle
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Enzymes

Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:10628907]

Drug created on June 13, 2005 07:24 / Updated on October 15, 2018 04:36