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Details

Stereochemistry ACHIRAL
Molecular Formula C22H27N3O3S2
Molecular Weight 445.6011
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOPIMAZINE

SMILES

CS(=O)(=O)c1ccc2c(c1)N(CCCN3CCC(CC3)C(=N)O)c4ccccc4S2

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 445.6011
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

PubMed

TitleDatePubMed
Ondansetron plus metopimazine compared with ondansetron plus metopimazine plus prednisolone as antiemetic prophylaxis in patients receiving multiple cycles of moderately emetogenic chemotherapy.
2001 Apr 1
Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children.
2003
Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy.
2003 Sep 17
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
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
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 Mar
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 Apr
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 Jul
Differential pulse cathodic voltammetric determination of floctafenine and metopimazine.
2007 Mar 12
Aprepitant: the evidence for its place in the prevention of chemotherapy-induced nausea and vomiting.
2007 Mar 31
Efficacy and safety of artesunate plus amodiaquine in routine use for the treatment of uncomplicated malaria in Casamance, southern Sénégal.
2007 Nov 15
Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine.
2008 Dec
[Tolerance and efficacy of mefloquine as the first line treatment of uncomplicated P. falciparum malaria in children].
2008 Feb
Optimizing antiemetic therapy in multiple-day and multiple cycles of chemotherapy.
2008 Mar
Percutaneous absorption of metopimazine and effect of cyclodextrins.
2008 May
Investigational use of metomidate hydrochloride as a shipping additive for two ornamental fishes.
2009 Sep
Fragmentation pathways of metopimazine and its metabolite using ESI-MS(n), HR-MS and H/D exchange.
2010 Oct
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:29:43 UTC 2021
Edited
by admin
on Sat Jun 26 15:29:43 UTC 2021
Record UNII
238S75V9AV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METOPIMAZINE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
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
EXP 999
Code 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
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
WHO-ATC A04AD05
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
NCI_THESAURUS C267
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
Code System Code Type Description
MERCK INDEX
M7496
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY Merck Index
MESH
C005260
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
RXCUI
29954
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY RxNorm
FDA UNII
238S75V9AV
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
WIKIPEDIA
METOPIMAZINE
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
NCI_THESAURUS
C81497
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
PUBCHEM
26388
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
CAS
14008-44-7
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
DRUG CENTRAL
1784
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
EPA CompTox
14008-44-7
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
INN
2178
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
EVMPD
SUB08908MIG
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
237-818-4
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL398615
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
DRUG BANK
DB13591
Created by admin on Sat Jun 26 15:29:43 UTC 2021 , Edited by admin on Sat Jun 26 15:29:43 UTC 2021
PRIMARY
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TARGET -> INHIBITOR
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ACTIVE MOIETY