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Identification
NameTrospium
Accession NumberDB00209  (APRD00393)
TypeSmall Molecule
GroupsApproved
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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sanctura XRcapsule (extended release)60 mgoralAllergan Inc2010-01-202016-04-13Canada
Trosectablet20 mgoralSunovion Pharmaceuticals Canada Inc2006-04-04Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Trospium Chloridecapsule, extended release60 mg/1oralBlue Point Laboratories2014-03-11Not applicableUs
Trospium Chloridetablet20 mg/1oralApotex Corp.2012-10-15Not applicableUs
Trospium Chloridetablet20 mg/1oralGolden State Medical Supply, Inc.2013-02-08Not applicableUs
Trospium Chloridecapsule, extended release60 mg/1oralGolden State Medical Supply, Inc.2014-07-18Not applicableUs
Trospium Chloridecapsule, extended release60 mg/1oralActavis Pharma, Inc.2012-10-12Not applicableUs
Trospium Chloridetablet20 mg/1oralAmerican Health Packaging2014-12-152015-12-29Us
Trospium Chloridetablet, film coated20 mg/1oralPaddock Laboratories, LLC2010-11-17Not applicableUs
Trospium Chloridetablet, film coated20 mg/1oralGlenmark Pharmaceuticals Inc., Usa2010-08-13Not applicableUs
Trospium Chloride ERcapsule, extended release60 mg/1oralPaddock Laboratories, LLC2013-06-07Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
FlotrosNot Available
RegurinNot Available
SpasmexNot Available
SpasmolytNot Available
SpasmoplexNot Available
Tropez ODNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Trospium chloride
10405-02-4
Thumb
  • InChI Key: RVCSYOQWLPPAOA-QKYUOBHYSA-M
  • Monoisotopic Mass: 427.1914215
  • Average Mass: 427.97
DBSALT000883
Categories
UNIIT4Y8ORK057
CAS number47608-32-2
WeightAverage: 392.518
Monoisotopic: 392.22202025
Chemical FormulaC25H30NO3
InChI KeyOYYDSUSKLWTMMQ-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Quaternary ammonium salt
  • Tertiary alcohol
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic alcohol
  • Organic oxide
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency, detrusor instability and frequency of micturition.
PharmacodynamicsTrospium 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 actionTrospium antagonizes the effect of acetylcholine on muscarinic receptors in cholinergically innervated organs. Its parasympatholytic action reduces the tonus of smooth muscle in the bladder.
Related Articles
Absorption9.6%
Volume of distribution
  • 395 ± 140 L
Protein binding50-85%
Metabolism

Not fully defined

Route of eliminationAfter 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 life20 hours
Clearance
  • Renal cl=29.07 L/hour
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Allergan inc
Packagers
Dosage forms
FormRouteStrength
Capsule (extended release)oral60 mg
Tabletoral20 mg
Tabletoral20 mg/1
Tablet, film coatedoral20 mg/1
Capsule, extended releaseoral60 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)
CA2537103 No2010-01-192024-11-04Canada
US7410978 No2005-02-012025-02-01Us
US7759359 No2004-11-042024-11-04Us
US7763635 No2004-11-042024-11-04Us
US7781448 No2004-11-042024-11-04Us
US7781449 No2004-11-042024-11-04Us
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA03DA06G04BD09
AHFS Codes
  • 86:12.00
PDB EntriesNot Available
FDA labelDownload (249 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AclidiniumAclidinium may increase the anticholinergic activities of Trospium.
Botulinum Toxin Type ATrospium may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BTrospium may increase the anticholinergic activities of Botulinum Toxin Type B.
Cimetropium BromideTrospium may increase the anticholinergic activities of Cimetropium Bromide.
DronabinolTrospium may increase the tachycardic activities of Dronabinol.
EluxadolineTrospium may increase the activities of Eluxadoline.
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Trospium.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Trospium is combined with Glucagon recombinant.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Trospium.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Trospium.
MetforminThe serum concentration of Trospium can be decreased when it is combined with Metformin.
MianserinMianserin may increase the anticholinergic activities of Trospium.
MirabegronThe risk or severity of adverse effects can be increased when Trospium is combined with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Trospium is combined with Morphine.
Potassium ChlorideTrospium may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Trospium.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Trospium.
RamosetronTrospium may increase the activities of Ramosetron.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Trospium.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Trospium.
TacrineThe therapeutic efficacy of Trospium can be decreased when used in combination with Tacrine.
TiotropiumTrospium may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Trospium is combined with Topiramate.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Trospium.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Trospium.
Food InteractionsNot 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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 ]
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Drug created on June 13, 2005 07:24 / Updated on July 29, 2016 01:51