Trospium chloride information

Trospium chloride
Clinical data
Trade names	Regurin, Sanctura, many generics
AHFS/Drugs.com	Monograph
Pregnancy; category	C;
Routes of; administration	By mouth (tablets, capsules)
ATC code	G04BD09 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	50–85%
Elimination half-life	20 hours
Identifiers
	IUPAC name 3‑(2‑Hydroxy-2,2‑diphenylacetoxy)spiro[bicyclo[3.2.1]octane-8,1'‑pyrrolidin]-1'‑ium chloride;
CAS Number	10405-02-4;
PubChem CID	107979;
DrugBank	DB00209;
ChemSpider	10482307 ;
UNII	1E6682427E;
ChEBI	CHEBI:32270;
ChEMBL	ChEMBL1201344;
CompTox Dashboard (EPA)	DTXSID7023724 ;
ECHA InfoCard	100.030.784
Chemical and physical data
Formula	C25H30ClNO3
Molar mass	427.97 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC(c1ccccc1)(c2ccccc2)C(=O)O[C@@H]3C[C@@H]5CC[C@H](C3)[N+]45CCCC4;
	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+ ; Key:OYYDSUSKLWTMMQ-JKHIJQBDSA-N ;
	(verify)

Trospium chloride is a muscarinic antagonist used to treat overactive bladder.^[2] 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.^[3] It is in pregnancy category C and is excreted in breast milk.^[4]

Chemically it is a quaternary ammonium cation which causes it to stay in periphery rather than crossing the blood–brain barrier.^[5] It works by causing the smooth muscle in the bladder to relax.^[2]

It was patented in 1966 and approved for medical use in 1974.^[6] It was first approved in the US in 2004, and an extended release version with once-daily dosing was brought to market in 2007. It became generic in Europe in 2009 and in the US the first extended-release generic was approved in 2012.

^ Cite error: The named reference brands was invoked but never defined (see the help page).
^ ^a ^b "Regurin XL 60mg". UK eMC. 3 July 2015.
^ Biastre K, Burnakis T (February 2009). "Trospium chloride treatment of overactive bladder". Ann Pharmacother. 43 (2): 283–95. doi:10.1345/aph.1L160. PMID 19193592. S2CID 20102756.
^ FDA "Trospium chloride label" (PDF). U.S. Food and Drug Administration. January 2011.
^ Pak RW, Petrou SP, Staskin DR (December 2003). "Trospium chloride : a quaternary amine with unique pharmacologic properties". Curr Urol Rep. 4 (6): 436–40. doi:10.1007/s11934-003-0023-1. PMID 14622495. S2CID 4512769.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 446. ISBN 9783527607495.

[brands-1] Cite error: The named reference brands was invoked but never defined (see the help page).

[emcXLlabel-2] "Regurin XL 60mg". UK eMC. 3 July 2015.

[2009rev-3] Biastre K, Burnakis T (February 2009). "Trospium chloride treatment of overactive bladder". Ann Pharmacother. 43 (2): 283–95. doi:10.1345/aph.1L160. PMID 19193592. S2CID 20102756.

[FDAlabel-4] FDA "Trospium chloride label" (PDF). U.S. Food and Drug Administration. January 2011.

[Quat2003-5] Pak RW, Petrou SP, Staskin DR (December 2003). "Trospium chloride : a quaternary amine with unique pharmacologic properties". Curr Urol Rep. 4 (6): 436–40. doi:10.1007/s11934-003-0023-1. PMID 14622495. S2CID 4512769.

[6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 446. ISBN 9783527607495.

Trospium chloride information

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Trospium chloride

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Clinical data

Trade names	Regurin, Sanctura, many generics^[1]
AHFS/Drugs.com	Monograph
Pregnancy category	C
Routes of administration	By mouth (tablets, capsules)
ATC code	G04BD09 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	50–85%
Elimination half-life	20 hours
Identifiers
IUPAC name 3‑(2‑Hydroxy-2,2‑diphenylacetoxy)spiro[bicyclo[3.2.1]octane-8,1'‑pyrrolidin]-1'‑ium chloride
CAS Number	10405-02-4
PubChem CID	107979
DrugBank	DB00209
ChemSpider	10482307^Y
UNII	1E6682427E
ChEBI	CHEBI:32270
ChEMBL	ChEMBL1201344
CompTox Dashboard (EPA)	DTXSID7023724
ECHA InfoCard	100.030.784
Chemical and physical data
Formula	C₂₅H₃₀ClNO₃
Molar mass	427.97 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES OC(c1ccccc1)(c2ccccc2)C(=O)O[C@@H]3C[C@@H]5CC[C@H](C3)[N+]45CCCC4
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+^Y Key:OYYDSUSKLWTMMQ-JKHIJQBDSA-N^Y
(verify)