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metopimazine
Sign in to saveMetopimazine (, , ), sold under the brand names Vogalen and Vogalene, is an antiemetic of the phenothiazine group which is used to treat nausea and vomiting. It is marketed in Europe, Canada, and South America. As of August 2020, metopimazine has been repurposed and is additionally under development for use in the United States for the treatment of gastroparesis.
Chemical data
- Formula
- C22H27N3O3S2
- Molecular weight
- 445.6 g/mol
- IUPAC name
- 1-[3-(2-methylsulfonylphenothiazin-10-yl)propyl]piperidine-4-carboxamide
- SMILES
- CS(=O)(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN4CCC(CC4)C(=O)N
- InChIKey
- BQDBKDMTIJBJLA-UHFFFAOYSA-N
- XLogP
- 3.1
- Polar surface area
- 117 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- Nausea
via ChEMBL · EBI
Research
77 papers- Metopimazine is primarily metabolized by a liver amidase in humans.Pharmacology research & perspectives · 2022
- 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.Therapie · 2022
- From domperidone to metopimazine: Anticipating the media impact of pharmacovigilance announcements.Therapie · 2021
- Metrological Evaluation of Metopimazine HPLC Assay: ISO-GUM and Monte Carlo Simulation Approaches.Pharmaceutics · 2025
- Granisetron compared with prednisolone plus metopimazine as anti-emetic prophylaxis during multiple cycles of moderately emetogenic chemotherapy.British journal of cancer · 1999
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- carbon
- Mass
- 445.149
Show 5 more facts
- chemical formula
- C₂₂H₂₇N₃O₃S₂
- canonical SMILES
- CS(=O)(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN4CCC(CC4)C(=O)N
- subject has role
- antiemetic
- Commons category
- Metopimazine
- defined daily dose
- 15
Sources (3)
via Wikidata · CC0
~7 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Adverse effects
- Mechanism of action
- Pharmacokinetics
- Research
- Synthesis
- References
- External links
Metopimazine (, , ), sold under the brand names Vogalen and Vogalene, is an antiemetic of the phenothiazine group which is used to treat nausea and vomiting. It is marketed in Europe, Canada, and South America. As of August 2020, metopimazine has been repurposed and is additionally under development for use in the United States for the treatment of gastroparesis.
Metopimazine has antidopaminergic, antihistamine, and anticholinergic activity. However, it has also been described as a highly potent and selective dopamine D2 and D3 receptor antagonist. The D2 receptor antagonism of metopimazine is thought to underlie its antiemetic and gastroprokinetic effects. It is said to not readily cross the blood–brain barrier and hence to have peripheral selectivity, in contrast to metoclopramide but similarly to domperidone. Unlike domperidone however, metopimazine shows no hERG inhibition and hence is expected to have a more favorable cardiovascular profile. In contrast to metoclopramide, metopimazine does not interact with serotonin 5-HT3 and 5-HT4 receptors.
Excerpted from Wikipedia’s “metopimazine” article, available under the CC BY-SA 4.0 licence.