METOPIMAZINE

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

Structure Search

SMILES

CS(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN4CCC(CC4)C(N)=O)C=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)

HIDE SMILES / InChI

Molecular Formula	C22H27N3O3S2
Molecular Weight	445.598
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://link.springer.com/article/10.2165/00024669-200605020-00006 | https://www.ncbi.nlm.nih.gov/pubmed/6130555

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
Fragmentation pathways of metopimazine and its metabolite using ESI-MS(n), HR-MS and H/D exchange.	2010-10	20690157
Development and validation of stability indicating HPLC and HPTLC methods for determination of sulpiride and mebeverine hydrochloride in combination.	2010-09	20538381
Investigational use of metomidate hydrochloride as a shipping additive for two ornamental fishes.	2009-09	20043397
Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine.	2008-12	18678472
Percutaneous absorption of metopimazine and effect of cyclodextrins.	2008-05	18473229
Optimizing antiemetic therapy in multiple-day and multiple cycles of chemotherapy.	2008-03	18685391
[Tolerance and efficacy of mefloquine as the first line treatment of uncomplicated P. falciparum malaria in children].	2008-02	18178023
Efficacy and safety of artesunate plus amodiaquine in routine use for the treatment of uncomplicated malaria in Casamance, southern Sénégal.	2007-11-15	18005408
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.	2007-07	17572097
Randomized, double-blind trial comparing the antiemetic effect of tropisetron plus metopimazine with tropisetron plus placebo in patients receiving multiple cycles of multiple-day cisplatin-based chemotherapy.	2007-04	17093916
Aprepitant: the evidence for its place in the prevention of chemotherapy-induced nausea and vomiting.	2007-03-31	21221195
Differential pulse cathodic voltammetric determination of floctafenine and metopimazine.	2007-03-12	17161576
A pilot study of ondansetron plus metopimazine vs. ondansetron monotherapy in children receiving highly emetogenic chemotherapy: a Bayesian randomized serial N-of-1 trials design.	2006-03	16052316
A randomized, double-blind trial assessing the efficacy and safety of sublingual metopimazine and ondansetron in the prophylaxis of chemotherapy-induced delayed emesis.	2006-02	16428941
Comparison of the efficacy and safety of combinations of metopimazine or ondansetron with methylprednisolone in the prevention of delayed emesis in patients receiving chemotherapy.	2005-11	16307696
Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy.	2003-09-17	14521717
Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children.	2003	12956617
Ondansetron plus metopimazine compared with ondansetron plus metopimazine plus prednisolone as antiemetic prophylaxis in patients receiving multiple cycles of moderately emetogenic chemotherapy.	2001-04-01	11283143

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:57 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:57 GMT 2025`
Record UNII	238S75V9AV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EXP 999

Preferred Name

English

METOPIMAZINE

Official Name

English

METOPIMAZINE [MI]

Common Name

English

Metopimazine [WHO-DD]

Common Name

English

1-[3-[2-(Methylsulfonyl)phenothiazin-10-yl]propyl]isonipecotamide

Systematic Name

English

4-PIPERIDINECARBOXAMIDE, 1-(3-(2-(METHYLSULFONYL)-10H-PHENOTHIAZIN-10-YL)PROPYL)-

Systematic Name

English

metopimazine [INN]

Common Name

English

METOPIMAZINE [MART.]

Common Name

English

METOPIMAZINE [USAN]

Common Name

English

EXP-999

Code

English

Classification Tree Code System Code

WHO-VATC

QA04AD05