CHEBI:32270 - trospium chloride

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ChEBI Name trospium chloride
ChEBI ID CHEBI:32270
Definition An organic chloride salt of trospium. It is an antispasmodic drug used for the treatment of overactive bladder.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6481397, eMolecules:29936590, Selleckchem:Trospium-chloride-Sanctura
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Trospium chloride is a muscarinic antagonist used to treat overactive bladder. It has side effects typical of this class of drugs, namely dry mouth, stomach upset, and constipation; these side effects cause problems with people taking their medicine as directed. However it doesn't cause central nervous system side effects like some other muscarinic antagonists. Chemically it is a quaternary ammonium cation which causes it to stay in periphery rather than crossing the blood–brain barrier. It works by causing the smooth muscle in the bladder to relax. It was patented in 1966 and approved for medical use in 1974. It was first approved in the US in 2004, and an extended release version was brought to market in 2007. It became generic in the EU in 2009, and the first extended-release generic was approved in the US in 2012.
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Formula C25H30NO3.Cl
Net Charge 0
Average Mass 427.970
Monoisotopic Mass 427.19142
InChI InChI=1S/C25H30NO3.ClH/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;1H/q+1;/p-1/t21-,22+,23+;
InChIKey RVCSYOQWLPPAOA-QKYUOBHYSA-M
SMILES [N+]12([C@]3(C[C@H](OC(C(C4=CC=CC=C4)(C5=CC=CC=C5)O)=O)C[C@@]1(CC3)[H])[H])CCCC2.[Cl-]
Roles Classification
Biological Role(s): muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
Application(s): antispasmodic drug
A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trospium chloride (CHEBI:32270) has part trospium (CHEBI:145791)
trospium chloride (CHEBI:32270) has role antispasmodic drug (CHEBI:53784)
trospium chloride (CHEBI:32270) has role muscarinic antagonist (CHEBI:48876)
trospium chloride (CHEBI:32270) is a organic chloride salt (CHEBI:36094)
trospium chloride (CHEBI:32270) is a quaternary ammonium salt (CHEBI:35273)
IUPAC Name
(1S,3R,5R)-3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-5-azaspiro[bicyclo[3.2.1]octane-8,1'-pyrrolidin]-8-ylium chloride
INNs Sources
chlorure de trospium WHO MedNet
cloruro de trospio WHO MedNet
trospii chloridum WHO MedNet
trospium chloride WHO MedNet
Synonyms Sources
IP-631 ChEBI
IP631 ChemIDplus
Trospium chloride KEGG DRUG
trospium Cl ChemIDplus
Brand Names Sources
Regurin ChEBI
Relaspium ChemIDplus
Sanctura ChemIDplus
Sanctura XR ChemIDplus
Santura ChemIDplus
Spasmed ChEBI
Spasmex KEGG DRUG
Spasmo 3 ChemIDplus
Spasmo-lyt ChemIDplus
Spasmolyt ChEBI
Spasmoplex KEGG DRUG
Trofame ChEBI
Trosec DrugBank
Trospikan ChEBI
Uraplex ChemIDplus
Manual Xrefs Databases
2776 DrugCentral
D01103 KEGG DRUG
DBSALT000883 DrugBank
Trospium_chloride Wikipedia
View more database links
Registry Number Type Source
10405-02-4 CAS Registry Number ChemIDplus
Citations
Abebe BT, Weiss M, Modess C, Tadken T, Wegner D, Meyer MJ, Schwantes U, Neumeister C, Scheuch E, Schulz HU, Tzvetkov M, Siegmund W (2020)
Pharmacokinetic Drug-Drug Interactions Between Trospium Chloride and Ranitidine Substrates of Organic Cation Transporters in Healthy Human Subjects.
Journal of clinical pharmacology 60, 312-323 [PubMed:31542894]
[show Abstract]
Murgas S, Adolf D (2019)
Evaluation of real-world persistence of propiverine and trospium chloride in treatment of overactive bladder in Germany.
Research and reports in urology 11, 9-13 [PubMed:30697533]
[show Abstract]
Ivchenko A, Bödeker RH, Neumeister C, Wiedemann A (2018)
Anticholinergic burden and comorbidities in patients attending treatment with trospium chloride for overactive bladder in a real-life setting: results of a prospective non-interventional study.
BMC urology 18, 80 [PubMed:30217174]
[show Abstract]
Abulseoud A, Moussa A, Abdelfattah G, Ibrahim I, Saba E, Hassouna M (2018)
Transcutaneous posterior tibial nerve electrostimulation with low dose trospium chloride: Could it be used as a second line treatment of overactive bladder in females.
Neurourology and urodynamics 37, 842-848 [PubMed:28792105]
[show Abstract]
Turkoglu AR, Parmak Yener N, Coban S, Guzelsoy M, Emul A, Demirbas M, Demirci H (2017)
Effect of trospium chloride therapy on intraocular pressure and tear secretion in overactive bladder patients.
Cutaneous and ocular toxicology 36, 331-335 [PubMed:28468509]
[show Abstract]
Geller EJ, Dumond JB, Bowling JM, Khandelwal CM, Wu JM, Wu JM, Busby-Whitehead J, Kaufer DI (2017)
Effect of Trospium Chloride on Cognitive Function in Women Aged 50 and Older: A Randomized Trial.
Female pelvic medicine & reconstructive surgery 23, 118-123 [PubMed:28067745]
[show Abstract]
Abdelhamid MH, Zayed AS, Ghoneima WE, Elmarakbi AA, El Sheemy MS, Aref A, Abdelbary A, Nour HH (2017)
Randomized, double-blind, placebo-controlled trial to compare solifenacin versus trospium chloride in the relief of double-J stent-related symptoms.
World journal of urology 35, 1261-1268 [PubMed:28050642]
[show Abstract]
Tadken T, Weiss M, Modess C, Wegner D, Roustom T, Neumeister C, Schwantes U, Schulz HU, Weitschies W, Siegmund W (2016)
Trospium chloride is absorbed from two intestinal "absorption windows" with different permeability in healthy subjects.
International journal of pharmaceutics 515, 367-373 [PubMed:27765726]
[show Abstract]
Bexten M, Oswald S, Grube M, Jia J, Graf T, Zimmermann U, Rodewald K, Zolk O, Schwantes U, Siegmund W, Keiser M (2015)
Expression of drug transporters and drug metabolizing enzymes in the bladder urothelium in man and affinity of the bladder spasmolytic trospium chloride to transporters likely involved in its pharmacokinetics.
Molecular pharmaceutics 12, 171-178 [PubMed:25466967]
[show Abstract]
Karaman A, Samdancı E, Sayın S, Karabulut I, Fadıllıoglu E (2013)
Effects of tolterodine and trospium chloride on renal damage induced by partial upper urinary tract obstruction.
Urology 82, 194-200 [PubMed:23453648]
[show Abstract]
Kranz J, Petzinger E, Geyer J (2013)
Brain penetration of the OAB drug trospium chloride is not increased in aged mice.
World journal of urology 31, 219-224 [PubMed:22120415]
[show Abstract]
Biastre K, Burnakis T (2009)
Trospium chloride treatment of overactive bladder.
The Annals of pharmacotherapy 43, 283-295 [PubMed:19193592]
[show Abstract]
Mazo EB, Babanina GA (2007)
[Trospium chloride (spasmex) in the treatment of lower urinary tract symptoms in patients with neurogenic hyperactive urinary bladder caused by vertebrogenic lesions].
Urologiia (Moscow, Russia : 1999)15-19 [PubMed:17722614]
[show Abstract]
(2005)
Trospium chloride (Sanctura): another anticholinergic for overactive bladder.
Obstetrics and gynecology 105, 431-432 [PubMed:15684176]
Gaines KK (2005)
Trospium chloride (Sanctura)--new to the U.S. for overactive bladder.
Urologic nursing 25, 64-5, 52 [PubMed:15779697]
(2004)
Trospium chloride (Sanctura): another anticholinergic for overactive bladder.
The Medical letter on drugs and therapeutics 46, 63-64 [PubMed:15289745]
Last Modified
17 January 2020