Cimetropium bromide

Cimetropium bromide is a semisynthetic quaternary ammonium compound derived from reacting scopolamine (an alkaloid isolated from belladonna) with cyclopropylmethyl bromide. It is used primarily as an antispasmodic agent for the treatment of gastrointestinal disorders such as irritable bowel syndrome (IBS).^[1] Acting as a potent muscarinic receptor antagonist, it inhibits acetylcholine-mediated contractions in the smooth muscle of the digestive tract, thereby reducing spasms and alleviating abdominal pain. Cimetropium bromide demonstrates efficacy in long-term management of IBS symptoms with a favorable tolerability profile and is generally administered orally. Its peripheral antimuscarinic effects are similar to those of atropine but typically result in fewer or milder central nervous system side effects.^[1]

Cimetropium bromide

Clinical data
ATC code	A03BB05 (WHO)
Identifiers
IUPAC name 9-Cyclopropylmethyl-7-(3-hydroxy-2-phenyl-propionyloxy)-9-methyl-3-oxa-9-azonia-tricyclo[3.3.1.02,4
CAS Number	51598-60-8 Y
PubChem CID	6917944
ChemSpider	16735742
UNII	0C7M5WE60Q
KEGG	D07099 Y
ChEMBL	ChEMBL2105977 N
CompTox Dashboard (EPA)	DTXSID10965919
ECHA InfoCard	100.169.259
Chemical and physical data
Formula	C21H28BrNO4
Molar mass	438.362 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)[C@@H](CO)C4=CC=CC=C4)CC5CC5.[Br-]
InChI 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?;/m0./s1 Key:WDURTRGFUGAJHA-MMQBYREUSA-M
NY (what is this?)  (verify)

Evidence does not support its use in infantile colic.^[2]

Physicochemical properties

Feature	Value
Number of Hydrogen Acceptors	4
The number of hydrogen donors	1
Number of Rotational Connections	7
Partition coefficient[3] (-{ALogP)}-	-2,1
Solubility[4] (-{logS, log(mol/L}-))	-3,6
Polar surface[5] (-{PSA}-, Å2)	102,1