Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H27N3O3S2.CH4O3S |
| Molecular Weight | 541.704 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CS(=O)(=O)C1=CC2=C(SC3=CC=CC=C3N2CCCN4CCC(CC4)C(N)=O)C=C1
InChI
InChIKey=QJTAWVPBCFAKBU-UHFFFAOYSA-N
InChI=1S/C22H27N3O3S2.CH4O3S/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;1-5(2,3)4/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26);1H3,(H,2,3,4)
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 |
|
| Development and validation of stability indicating HPLC and HPTLC methods for determination of sulpiride and mebeverine hydrochloride in combination. | 2010-09 |
|
| Investigational use of metomidate hydrochloride as a shipping additive for two ornamental fishes. | 2009-09 |
|
| Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine. | 2008-12 |
|
| Percutaneous absorption of metopimazine and effect of cyclodextrins. | 2008-05 |
|
| Optimizing antiemetic therapy in multiple-day and multiple cycles of chemotherapy. | 2008-03 |
|
| [Tolerance and efficacy of mefloquine as the first line treatment of uncomplicated P. falciparum malaria in children]. | 2008-02 |
|
| Efficacy and safety of artesunate plus amodiaquine in routine use for the treatment of uncomplicated malaria in Casamance, southern Sénégal. | 2007-11-15 |
|
| 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 |
|
| 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 |
|
| Aprepitant: the evidence for its place in the prevention of chemotherapy-induced nausea and vomiting. | 2007-03-31 |
|
| Differential pulse cathodic voltammetric determination of floctafenine and metopimazine. | 2007-03-12 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy. | 2003-09-17 |
|
| Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children. | 2003 |
|
| 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 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 04:55:11 GMT 2025
by
admin
on
Wed Apr 02 04:55:11 GMT 2025
|
| Record UNII |
JH694X5YFY
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
2555328-34-0
Created by
admin on Wed Apr 02 04:55:11 GMT 2025 , Edited by admin on Wed Apr 02 04:55:11 GMT 2025
|
PRIMARY | |||
|
155277864
Created by
admin on Wed Apr 02 04:55:11 GMT 2025 , Edited by admin on Wed Apr 02 04:55:11 GMT 2025
|
PRIMARY | |||
|
JH694X5YFY
Created by
admin on Wed Apr 02 04:55:11 GMT 2025 , Edited by admin on Wed Apr 02 04:55:11 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
|