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Cimetropium bromide

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
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
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.169.259Edit 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 semisyntheticquaternary ammonium compound derived from reactingscopolamine (an alkaloid isolated frombelladonna) with cyclopropylmethyl bromide. It is used primarily as anantispasmodic agent for the treatment of gastrointestinal disorders such asirritable bowel syndrome (IBS).[1] Acting as a potentmuscarinic receptor antagonist, it inhibitsacetylcholine-mediated contractions in the smooth muscle of the digestive tract, thereby reducing spasms and alleviatingabdominal 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 ofatropine but typically result in fewer or milder central nervous system side effects.[1]

Evidence does not support its use ininfantile colic.[2]

Physicochemical properties

[edit]
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

[edit]
  1. ^abScarpignato 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.
Drugs for
functional
bowel
disorders
Antimuscarinics
Tertiary
amino group
Quaternary
ammonium

compounds
Phosphodiesterase
inhibitors
Acting on
serotonin receptors
Other
Belladonna
and derivatives
(antimuscarinics)
Propulsives
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)
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