Date published: 2025-9-22

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Metopimazine (CAS 14008-44-7)

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Alternate Names:
1-[3-[2-(Methylsulfonyl)-10H-phenothiazin-10-yl]propyl]-4-piperidinecarboxamide
Application:
Metopimazine is a dopamine receptor antagonist
CAS Number:
14008-44-7
Molecular Weight:
445.60
Molecular Formula:
C22H27N3O3S2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Metopimazine is a chemical compound that functions as a dopamine antagonist. It acts by blocking dopamine receptors in the chemoreceptor trigger zone of the brain, thereby inhibiting the stimulation of the vomiting center. This mechanism of action prevents the transmission of signals that induce nausea and vomiting. By interfering with the dopamine signaling pathway, metopimazine disrupts the communication between the vestibular system and the vomiting center, ultimately reducing the urge to vomit. This chemical′s function as a dopamine antagonist may be useful for studying the role of dopamine in the regulation of nausea and vomiting in experimental models. Its mode of action at the molecular level provides insights into the neurochemical basis of emesis, contributing to a better understanding of the physiological process.


Metopimazine (CAS 14008-44-7) References

  1. Differential pulse cathodic voltammetric determination of floctafenine and metopimazine.  |  Gazy, AA., et al. 2007. J Pharm Biomed Anal. 43: 1535-9. PMID: 17161576
  2. Evidence of lowest brain penetration of an antiemetic drug, metopimazine, compared to domperidone, metoclopramide and chlorpromazine, using an in vitro model of the blood-brain barrier.  |  Jolliet, P., et al. 2007. Pharmacol Res. 56: 11-7. PMID: 17572097
  3. Percutaneous absorption of metopimazine and effect of cyclodextrins.  |  Frédéric, B., et al. 2008. Drug Dev Ind Pharm. 34: 478-84. PMID: 18473229
  4. Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine.  |  Bounoure, F., et al. 2008. J Dermatol Sci. 52: 170-7. PMID: 18678472
  5. Development and validation of stability indicating HPLC and HPTLC methods for determination of sulpiride and mebeverine hydrochloride in combination.  |  Naguib, IA. and Abdelkawy, M. 2010. Eur J Med Chem. 45: 3719-25. PMID: 20538381
  6. Fragmentation pathways of metopimazine and its metabolite using ESI-MS(n), HR-MS and H/D exchange.  |  Hubert-Roux, M., et al. 2010. J Mass Spectrom. 45: 1121-9. PMID: 20690157
  7. Estimating the excess of inappropriate prescriptions of anti-dopaminergic anti-emetics during acute gastroenteritis epidemics in France.  |  Roussel, V., et al. 2013. Pharmacoepidemiol Drug Saf. 22: 1080-5. PMID: 23935001
  8. Initial data on the safety of metopimazine during pregnancy and the risk of major birth defects and pregnancy loss - An observational study using the EFEMERIS database.  |  Vabre, C., et al. 2022. Therapie. 77: 405-412. PMID: 34756562
  9. Risk of first ischaemic stroke and use of antidopaminergic antiemetics: nationwide case-time-control study.  |  Bénard-Laribière, A., et al. 2022. BMJ. 376: e066192. PMID: 35321876
  10. A data-driven pipeline to extract potential adverse drug reactions through prescription, procedures and medical diagnoses analysis: application to a cohort study of 2,010 patients taking hydroxychloroquine with an 11-year follow-up.  |  Sabatier, P., et al. 2022. BMC Med Res Methodol. 22: 166. PMID: 35676635
  11. Antiemetic specificity of dopamine antagonists.  |  Niemegeers, CJ. 1982. Psychopharmacology (Berl). 78: 210-3. PMID: 6130555
  12. Effects of metopimazine on gastro-intestinal and biliary tract smooth muscle in vitro.  |  Tonini, M., et al. 1980. Arch Int Pharmacodyn Ther. 243: 139-48. PMID: 7387256
  13. A comparative in vitro study of transdermal absorption of antiemetics.  |  Calpena, AC., et al. 1994. J Pharm Sci. 83: 29-33. PMID: 8138905
  14. Interaction of the antiemetic metopimazine and anticancer agents with brain dopamine D2, 5-hydroxytryptamine3, histamine H1, muscarine cholinergic and alpha 1-adrenergic receptors.  |  Herrstedt, J., et al. 1993. Cancer Chemother Pharmacol. 33: 53-6. PMID: 8269589

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Metopimazine, 5 mg

sc-211901
5 mg
$444.00