Cimetropium bromide

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Cimetropium bromide
Cimetropium bromide.png
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)
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Chemical and physical data
Formula C21H28BrNO4
Molar mass 438.362 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

FeatureValue
Number of Hydrogen Acceptors4
The number of hydrogen donors1
Number of Rotational Connections7
Partition coefficient [3] (-{ALogP)}--2,1
Solubility [4] (-{logS, log(mol/L}-))-3,6
Polar surface [5] (-{PSA}-, Å2)102,1

References

  1. 1 2 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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