Cimetropium bromide

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Cimetropium bromide
Clinical data
ATC code
Identifiers
  • 9-Cyclopropylmethyl-7-(3-hydroxy-2-phenyl-propionyloxy)-9-methyl-3-oxa-9-azonia-tricyclo[3.3.1.02,4
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.169.259 Edit this at Wikidata
Chemical and physical data
FormulaC21H28BrNO4
Molar mass438.362 g·mol−1
3D model (JSmol)
  • 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=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
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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]

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

Physicochemical properties

[edit]
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

References

[edit]
  1. ^ a b Scarpignato C, Bianchi Porro G (1985). "Cimetropium bromide, a new antispasmodic compound: pharmacology and therapeutic perspectives". International Journal of Clinical Pharmacology Research. 5 (6): 467–77. PMID 3912339.
  2. ^ Hall B, Chesters J, Robinson A (February 2012). "Infantile colic: a systematic review of medical and conventional therapies". Journal of Paediatrics and Child Health. 48 (2): 128–137. doi:10.1111/j.1440-1754.2011.02061.x. PMID 21470331.
  3. ^ Ghose AK, Viswanadhan VN, Wendoloski JJ (1998). "Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods". The Journal of Physical Chemistry A. 102 (21): 3762–3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.
  4. ^ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). "Estimation of aqueous solubility of chemical compounds using E-state indices". Journal of Chemical Information and Computer Sciences. 41 (6): 1488–1493. doi:10.1021/ci000392t. PMID 11749573.
  5. ^ Ertl P, Rohde B, Selzer P (October 2000). "Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties". Journal of Medicinal Chemistry. 43 (20): 3714–3717. doi:10.1021/jm000942e. PMID 11020286.
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