Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H27N3O3S2 |
Molecular Weight | 445.598 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(=O)(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN4CCC(CC4)C(N)=O)C2=C1
InChI
InChIKey=BQDBKDMTIJBJLA-UHFFFAOYSA-N
InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26)
Metopimazine, a phenothiazine derivative, is a dopamine D2 receptor antagonist. It exerts its antiemetic effects via the chemoreceptor trigger zone. Metopimazine showed potent alpha-adrenergic blocking activity, showed histamine H1 antagonism, and induced palpebral ptosis. Metopimazine can occasionally be associated with orthostatic hypotension, which probably relates to its affinity for the α1-adrenoceptor. Therapeutic doses of metopimazine are likely to produce sedation and side-effects related to autonomic blockade. Metopimazine (Vogalene®) is indicated for the prevention and treatment of nausea and vomiting.
Approval Year
PubMed
Title | Date | PubMed |
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Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy. | 2003 Sep 17 |
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Comparison of the efficacy and safety of combinations of metopimazine or ondansetron with methylprednisolone in the prevention of delayed emesis in patients receiving chemotherapy. | 2005 Nov |
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A randomized, double-blind trial assessing the efficacy and safety of sublingual metopimazine and ondansetron in the prophylaxis of chemotherapy-induced delayed emesis. | 2006 Feb |
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Aprepitant: the evidence for its place in the prevention of chemotherapy-induced nausea and vomiting. | 2007 Mar 31 |
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Investigational use of metomidate hydrochloride as a shipping additive for two ornamental fishes. | 2009 Sep |
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Fragmentation pathways of metopimazine and its metabolite using ESI-MS(n), HR-MS and H/D exchange. | 2010 Oct |
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Development and validation of stability indicating HPLC and HPTLC methods for determination of sulpiride and mebeverine hydrochloride in combination. | 2010 Sep |
Sample Use Guides
Adults:Take 1 orodispersible tablet at the onset of symptoms. If symptoms persist or return, treatment may be continued to a maximum of 4 tablets (= 30 mg of metopimazine) per day.
Children over 6 years:Take 1 orodispersible tablet at the onset of symptoms. If symptoms persist or return, treatment may be continued to a maximum of 2 tablets (= 15 mg of metopimazine) per day.
Route of Administration:
Oral
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WHO-VATC |
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C267
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m7496
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C005260
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METOPIMAZINE
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DB13591
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ACTIVE MOIETY