CIMETROPIUM BROMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H28NO4.Br
Molecular Weight	438.355
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 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

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 160 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3912339	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Irritable bowel syndrome 60 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2182401	Primary	Approved 8429	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 8429	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 8429	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 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4076532	Diagnostic	Approved 8429	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.

PubMed

Title	Date	PubMed
Longterm treatment of irritable bowel syndrome with cimetropium bromide: a double blind placebo controlled clinical trial.	1990 Mar	2182401
[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 Jul	9282303
Looking for new treatments of Infantile Colic.	2014 Jun 5	24898541
Comparison between the Effectiveness of Oral Phloroglucin and Cimetropium Bromide as Premedication for Diagnostic Esophagogastroduodenoscopy: An Open-Label, Randomized, Comparative Study.	2015 Jan	25674526

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.

Name

Type

Language

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

ALGINOR

Brand 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