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Details

Stereochemistry ACHIRAL
Molecular Formula C25H30NO3.Cl
Molecular Weight 427.964
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROSPIUM CHLORIDE

SMILES

[Cl-].OC(C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)[N@@+]23CCCC3)(C4=CC=CC=C4)C5=CC=CC=C5

InChI

InChIKey=RVCSYOQWLPPAOA-QKYUOBHYSA-M
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+;

HIDE SMILES / InChI
Molecular Formula C25H29NO3
Molecular Weight 391.5027
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00209

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. 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. Trospium is marketed under the brand name Sancturain the US, Tropez OD in India,Trosec in Canada, Regurin and Flotros in the United Kingdom and Spasmex in Germany, Russia, Turkey, Argentina, Chile and Israel.

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: Trospium chloride is hydrophilic and does not cross the normal blood-brain barrier in significant amounts and, therefore, has minimal central anticholinergic activity.

Originator

Approval Year

2004
210
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
SANCTURA

Approved Use

Trospium chloride tablets are a muscarinic antagonist indicated for the treatment of overactive bladder (OAB) with symptoms of urge urinary incontinence, urgency, and urinary frequency. Trospium chloride tablets are a muscarinic antagonist indicated for the treatment of overactive bladder (OAB) with symptoms of urge urinary incontinence, urgency, and urinary frequency. (1)

Launch Date

1.08570241E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.5 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TROSPIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
36.4 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TROSPIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18.3 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TROSPIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
32.5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TROSPIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
360 mg single, oral
Highest studied dose
Dose: 360 mg
Route: oral
Route: single
Dose: 360 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8494577
https://pubmed.ncbi.nlm.nih.gov/18360555
healthy
n = 8
Health Status: healthy
Sex: M
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/8494577
https://pubmed.ncbi.nlm.nih.gov/18360555
Sources:
https://pubmed.ncbi.nlm.nih.gov/8494577
https://pubmed.ncbi.nlm.nih.gov/18360555
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.3
unhealthy
n = 591
Health Status: unhealthy
Condition: Overactive bladder
Population Size: 591
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.3
Disc. AE: Dry mouth...
AEs leading to
discontinuation/dose reduction:
Dry mouth (1.9%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.3
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
Disc. AE: Face angioedema, Lip angioedema...
AEs leading to
discontinuation/dose reduction:
Face angioedema
Lip angioedema
Oedema tongue
Angioedema of larynx
Somnolence
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Dry mouth 1.9%
Disc. AE
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.3
unhealthy
n = 591
Health Status: unhealthy
Condition: Overactive bladder
Population Size: 591
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.3
Angioedema of larynx Disc. AE
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
Face angioedema Disc. AE
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
Lip angioedema Disc. AE
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
Oedema tongue Disc. AE
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
Somnolence Disc. AE
20 mg 2 times / day multiple, oral
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Overactive bladder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021595s009lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2A6
707

CYP2C19
1478

CYP2E1
882
esterase
72
CYP
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 inconclusive
CYP3A4
1925
 no [IC50 11928 uM]
CYP2E1
970
 no [IC50 14857 uM]
CYP2C19
1553
 no [IC50 1756.3 uM]
CYP2A6
739
 no [IC50 2000 uM]
CYP2C9
1819
 no [IC50 2600 uM]
CYP2D6
1891
 no [IC50 27 uM]
CYP1A2
1692
 no [IC50 8432 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
esterase
72
 likely
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:145791
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:145791
ZINC
ZINC000100016084
http://zinc15.docking.org/substances/ZINC000100016084
PubMed

PubMed

TitleDatePubMed
Patents

Patents

US20100221353
2

Sample Use Guides

In Vivo Use Guide
The recommended dose of SANCTURA (Trospium) is one 20 mg tablet twice daily. SANCTURA should be dosed with water on an empty stomach, at least one hour before a meal. For patients with severe renal impairment (creatinine clearance less than 30 mL/min), the recommended dose is 20 mg once daily at bedtime. In geriatric patients greater than or equal to 75 years of age, dose may be titrated down to 20 mg once daily based upon tolerability.
Route of Administration: Oral
In Vitro Use Guide
After cumulative administration of increasing concentrations of trospium (1, 3, and 5 uM), agonist-induced contractions decreased significantly in bladder strips.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:53:37 UTC 2023
Edited
by admin
on Sat Dec 16 16:53:37 UTC 2023
Record UNII
1E6682427E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TROSPIUM CHLORIDE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   WHO-DD  
USAN   INN  
Official Name English
SANCTURA
Brand Name English
SPIRO(8-AZONIABICYCLO(3.2.1)OCTANE-8,1'-PYRROLIDINIUM), 3-((HYDROXYDIPHENYLACETYL)OXY)-, CHLORIDE, (1.ALPHA., 3.BETA., 5.ALPHA.)
Common Name English
SPASMOLYT
Brand Name English
TROSPIUM CHLORIDE [ORANGE BOOK]
Common Name English
TROSPIUM CHLORIDE [MI]
Common Name English
RELASPIUM
Brand Name English
TROSPIUM CHLORIDE [USP-RS]
Common Name English
IP631
Code English
SPASMOPLEX
Brand Name English
trospium chloride [INN]
Common Name English
REGURIN
Brand Name English
TROSPIUM CHLORIDE [JAN]
Common Name English
TROSPIUM CHLORIDE [MART.]
Common Name English
3.ALPHA.-HYDROXY-SPIRO(1.ALPHA.H,5.ALPHA.H-NORTROPANE-8,1'-PYRROLIDINIUM) CHLORIDE BENZILATE
Common Name English
Trospium chloride [WHO-DD]
Common Name English
TROSPIUM CHLORIDE [USP MONOGRAPH]
Common Name English
IP-631
Code English
TROSPIUM CHLORIDE [EP MONOGRAPH]
Common Name English
SPASMEX
Brand Name English
TROSPIUM CHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
NCI_THESAURUS C29698
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
Code System Code Type Description
INN
3001
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
CHEBI
32270
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL1888176
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
NCI_THESAURUS
C61995
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
USAN
NN-09
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
SMS_ID
100000092335
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
DRUG BANK
DB00209
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
WIKIPEDIA
Trospium chloride
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
MESH
C003330
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
233-875-4
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
RS_ITEM_NUM
1699300
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
RXCUI
38891
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY RxNorm
EVMPD
SUB11349MIG
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
CAS
10405-02-4
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY https://en.wikipedia.org/wiki/Trospium_chloride
FDA UNII
1E6682427E
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
MERCK INDEX
m11236
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY Merck Index
DAILYMED
1E6682427E
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID7023724
Created by admin on Sat Dec 16 16:53:37 UTC 2023 , Edited by admin on Sat Dec 16 16:53:37 UTC 2023
PRIMARY
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Structure of TROSPIUM CHLORIDE
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Structure of TROSPIUM CHLORIDE
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