CIMETROPIUM BROMIDE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H28NO4.Br
Molecular Weight	438.355
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].C[N@+]2(CC1CC1)[C@H]3C[C@@H](C[C@@H]2[C@H]4O[C@@H]34)OC(=O)[C@H](CO)C5=CC=CC=C5

InChI

InChIKey=WDURTRGFUGAJHA-GSWUYBTGSA-M

InChI=1S/C21H28NO4.BrH/c1-22(11-13-7-8-13)17-9-15(10-18(22)20-19(17)26-20)25-21(24)16(12-23)14-5-3-2-4-6-14;/h2-6,13,15-20,23H,7-12H2,1H3;1H/q+1;/p-1/t15-,16-,17-,18+,19-,20+,22?;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C21H27NO4
Molecular Weight	357.4434
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	6 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3912339

Cimetropium bromide (cimetropium) is a semi-synthetic belladonna alkaliod, a quaternary derivatives of scopolamine. Cimetropium was used in Italy under the name Alginor for the treatment of painful gastrointestinal conditions, such as irritant bowel syndrome or infant colics as well as in preparation for diagnostic procedures. The drug exerts its action by binding to muscarinic receptors and inhibiting their activity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3912339	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Irritable bowel syndrome 61 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2182401	Primary	Approved 8583	ALGINOR Approved Use Irritable colon, spastic-painful manifestations of the gastrointestinal tract. Premedication in diagnostic and operative gastrointestinal endoscopy. In pediatrics: abdominal colic, pylori spasm, spastic gastrointestinal conditions.
Spastic gastrointestinal disorders 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9282303	Primary	Approved 8583	ALGINOR Approved Use Irritable colon, spastic-painful manifestations of the gastrointestinal tract. Premedication in diagnostic and operative gastrointestinal endoscopy. In pediatrics: abdominal colic, pylori spasm, spastic gastrointestinal conditions.
Abdominal colic 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11930101	Primary	Approved 8583	ALGINOR Approved Use Irritable colon, spastic-painful manifestations of the gastrointestinal tract. Premedication in diagnostic and operative gastrointestinal endoscopy. In pediatrics: abdominal colic, pylori spasm, spastic gastrointestinal conditions.
Gastrointestinal disorders 94 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4076532	Diagnostic	Approved 8583	ALGINOR Approved Use Irritable colon, spastic-painful manifestations of the gastrointestinal tract. Premedication in diagnostic and operative gastrointestinal endoscopy. In pediatrics: abdominal colic, pylori spasm, spastic gastrointestinal conditions.

C_max

Value	Dose	Co-administered	Analyte	Population
23.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3761170/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		CIMETROPIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.39 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16810649/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		CIMETROPIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
22.68 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16810649/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		CIMETROPIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
50 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3761170/	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CIMETROPIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
119 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3761170/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CIMETROPIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16810649/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	CIMETROPIUM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2182401/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2182401/	Other AEs: dry mouth... Other AEs: dry mouth (6 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/2182401/

AEs

AE	Significance	Dose	Population
dry mouth	6 patients	50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2182401/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2182401/

PubMed

Title	Date	PubMed
Comparison between the Effectiveness of Oral Phloroglucin and Cimetropium Bromide as Premedication for Diagnostic Esophagogastroduodenoscopy: An Open-Label, Randomized, Comparative Study.	2015-01	25674526
Looking for new treatments of Infantile Colic.	2014-06-05	24898541
[Clinical phase III study of cimetropium bromide (DA3177) on the pain with upper urinary calculus: a double-blind study in comparison with scopolamine butylbromide. DA3177 Study Group].	1997-07	9282303
Longterm treatment of irritable bowel syndrome with cimetropium bromide: a double blind placebo controlled clinical trial.	1990-03	2182401

Patents

Sample Use Guides

In Vivo Use Guide

Solution for injection: 1 vial (equivalent to 5 mg of cimetropium bromide) given intravenously or intramuscularly in the onset of painful spastic crisis. The injection can be repeated in the event of pain relapse even 3-4 times a day (spastic-painful manifestations of the gastrointestinal tract); 2 ampoules (equivalent to 10 mg of cimetropium bromide) given intravenously (preparation for instrumental investigations). Tablets: 1 tablet (equivalent to 50 mg of cimetropium bromide) 2-3 times daily in adults. Oral solution: 20 drops (equivalent to 50 mg of cimetropium bromide) 3 times per day in adults and 3-5 drops (equivalent to 1.2-2 mg of cimetropium bromide) per kg of weight 4-6 times per day in children.

Route of Administration: Other

In Vitro Use Guide

Longitudinal muscle preparations with myenteric plexus of guinea-pig ileum were treated with 0.1, 1, 10 uM cimetropium. The drug caused inhibition of contraction of the preparations, induced by exogenous ACh or electrical field stimulation. pA2 value was determined to be 7.96.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:43:23 GMT 2025` Edited by `admin` on `Wed Apr 02 09:43:23 GMT 2025`
Record UNII	0C7M5WE60Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALGINOR

Preferred Name

English

CIMETROPIUM BROMIDE

Official Name

English

(7(S)-(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.))-9-(CYCLOPROPYLMETHYL)-7-(3-HYDROXY-1-OXO-2-PHENYLPROPOXY)-9-METHYL-3-OXA-9-AZONIATRICYCLO(3.3.1.0(SUP 2,4))NONANE BROMIDE

Common Name

English

cimetropium bromide [INN]

Common Name

English

CIMETROPIUM BROMIDE [MART.]

Common Name

English

CIMETROPIUM BROMIDE [JAN]

Common Name

English

Cimetropium bromide [WHO-DD]

Common Name

English

DA-3177

Code

English

N-CYCLOPROPYLMETHYLSCOPOLAMINE BROMIDE

Common Name

English

3-OXA-9-AZONIATRICYCLO(3.3.1.02,4)NONANE, 9-(CYCLOPROPYLMETHYL)-7-((2S)-3-HYDROXY-1-OXO-2-PHENYLPROPOXY)-9-METHYL-, BROMIDE (1:1), (1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.)-

Common Name

English

CIMETROPIUM BROMIDE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66880