Page last updated: 2024-11-05

metopimazine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Metopimazine is a phenothiazine derivative with antipsychotic and antiemetic properties. It is used to treat psychosis, anxiety, and nausea. It is also used as an antihistamine and antipruritic agent. Metopimazine is a synthetic compound that is structurally related to chlorpromazine. It is believed to exert its therapeutic effects by blocking dopamine receptors in the brain. Metopimazine is not widely studied due to the availability of newer and safer antipsychotic medications. However, it remains an important drug for the treatment of certain conditions, such as severe nausea and vomiting.'

metopimazine: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID26388
CHEMBL ID398615
CHEBI ID135726
SCHEMBL ID49905
MeSH IDM0046673

Synonyms (61)

Synonym
1-(3-(2-(methylsulfonyl)-10h-phenothiazin-10-yl)propyl)-4-piperidinecarboxamide
brn 4278585
phenothiazine, 10-(3-(4'-carbamoylpiperidino)propyl)-2-methylsulfonyl-
10-(3-(4-carbamoylpiperidine)propyl)-2-(methanesulfonyl)phenothiazine
metopimazina [inn-spanish]
1-(3-(2-(methylsulfonyl)phenothiazin-10-yl)propyl)-4-piperidinecarboxamide
4-piperidinecarboxamide, 1-(3-(2-(methanesulfonyl)phenothiazin-10-yl)propyl)-
einecs 237-818-4
4-piperidinecarboxamide, 1-(3-(2-(methylsulfonyl)-10h-phenothiazin-10-yl)propyl)-
nortrip
metopimazinum [inn-latin]
exp 999
isonipecotamide, 1-(3-(2-(methylsulfonyl)phenothiazin-10-yl)propyl)-
vogalene
1-(3-(2-(methylsulfonyl)phenothiazin-10-yl)propyl)isonipecotamide
2-methylsulfonyl-10-(3-(4-carbamoylpiperidino)propyl)phenothiazine
rp 9965
metopimazine
metopimazine (usan/inn)
D05010
14008-44-7
CHEBI:135726
CHEMBL398615
exp-999
AKOS005065914
1-[3-[2-(methylsulfonyl)phenothiazin-10-yl]propyl]isonipecotamide
1-[3-[2-(methylsulfonyl)-10h-phenothiazin-10-yl]propyl]-4-piperidinecarboxamide
1-[3-(2-methylsulfonylphenothiazin-10-yl)propyl]piperidine-4-carboxamide
238s75v9av ,
metopimazina
metopimazinum
metopimazine [usan:inn:ban]
unii-238s75v9av
bdbm82383
nsc_26388
cas_26388
BCP9000921
FT-0672379
SCHEMBL49905
metopimazine [usan]
metopimazine [inn]
metopimazine [who-dd]
metopimazine [mi]
metopimazine [mart.]
rp-9965
BQDBKDMTIJBJLA-UHFFFAOYSA-N
1-(3-[2-(methylsulfonyl)-10h-phenothiazin-10-yl]propyl)-4-piperidinecarboxamide #
4-piperidinecarboxamide, 1-[3-[2-(methylsulfonyl)-10h-phenothiazin-10-yl]propyl]-
bdbm179867
us9132134, metopimazine (ng101)
DTXSID80161224
gtpl11140
ng-101
J-007351
1-[3-[2-(methylsulfonyl)-10h-phenothiazin-10-yl]propyl]piperidin-4-carboxamide
FT-0672380
DB13591
1-(3-(2-(methylsulfonyl)-10h-phenothiazin-10-yl)propyl)piperidin-4-carboxamide
Q194682
CS-0065952
HY-116578

Research Excerpts

Overview

Metopimazine (MPZ) is a peripherally restricted, dopamine D2 receptor antagonist used for four decades to treat acute nausea and vomiting. It is an antiemetic drug already used by oral and rectal administration.

ExcerptReferenceRelevance
"Metopimazine is an anti-emetic drug used to treat nausea and vomiting of pregnancy. "( 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.
Araujo, M; Damase-Michel, C; Hurault-Delarue, C; Lacroix, I; Vabre, C,
)
1.86
"Metopimazine (MPZ) is a peripherally restricted, dopamine D2 receptor antagonist used for four decades to treat acute nausea and vomiting. "( Metopimazine is primarily metabolized by a liver amidase in humans.
Busby, RW; Cai, X; De Colle, C; Ramos, L; Sadeque, AJM; Shen, H; Venkatarangan, L; Wax, S; Yang, S, 2022
)
3.61
"Metopimazine is an antiemetic drug already used by oral and rectal administration. "( Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine.
Arnaud, P; Besnard, M; Bounoure, F; Lahiani Skiba, M; Mallet, E; Skiba, M, 2008
)
2.02
"Metopimazine (MPZ) is a phenothiazine derivative used to prevent emesis during chemotherapy where few structural analysis of the aforementioned compound have been described in the literature. "( Fragmentation pathways of metopimazine and its metabolite using ESI-MS(n), HR-MS and H/D exchange.
Bounoure, F; Bozec, P; Churlaud, F; Hubert-Roux, M; Lange, CM; Skiba, M, 2010
)
2.1

Toxicity

ExcerptReferenceRelevance
" Adverse events were also evaluated."( Comparison of the efficacy and safety of combinations of metopimazine or ondansetron with methylprednisolone in the prevention of delayed emesis in patients receiving chemotherapy.
Bloch, J; Delgado, A; Khayat, D; Meric, JB; Rixe, O, 2005
)
0.57

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of MPZ given orally and as enemas was 22."( Bioavailability of the antiemetic metopimazine given as a microenema.
Angelo, HR; Dombernowsky, P; Herrstedt, J; Jørgensen, M; Møller-Sonnergaard, J; Rassing, MR, 1996
)
0.57
" Human oral bioavailability is an important pharmacokinetic property, which is directly related to the amount of drug available in the systemic circulation to exert pharmacological and therapeutic effects."( Hologram QSAR model for the prediction of human oral bioavailability.
Andricopulo, AD; Moda, TL; Montanari, CA, 2007
)
0.34
" Cyclodextrin complexes increased MPZ bioavailability at the skin surface and PMbetaCD was also able to extract cutaneous fatty acids."( Percutaneous absorption of metopimazine and effect of cyclodextrins.
Eric, M; Frédéric, B; Malika, LS; Marie, H; Mohamed, S; Philippe, A, 2008
)
0.64

Dosage Studied

ExcerptRelevanceReference
"A few studies indicate a dose-response effect of the antiemetic metopimazine."( Dose-finding study of oral metopimazine.
Angelo, HR; Hansen, M; Herrstedt, J; Kampmann, JP; Sigsgaard, T, 1997
)
0.83
" Analysis of plasma samples from subjects dosed 60 mg of MPZ verified that these oxidative pathways are very minor and that CYP enzyme involvement was negligible compared to microsomal amidase/hydrolase in overall MPZ metabolism in humans."( Metopimazine is primarily metabolized by a liver amidase in humans.
Busby, RW; Cai, X; De Colle, C; Ramos, L; Sadeque, AJM; Shen, H; Venkatarangan, L; Wax, S; Yang, S, 2022
)
2.16
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenothiazines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID311524Oral bioavailability in human2007Bioorganic & medicinal chemistry, Dec-15, Volume: 15, Issue:24
Hologram QSAR model for the prediction of human oral bioavailability.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (29.27)18.7374
1990's13 (31.71)18.2507
2000's14 (34.15)29.6817
2010's1 (2.44)24.3611
2020's1 (2.44)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 79.80

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index79.80 (24.57)
Research Supply Index4.20 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index139.23 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (79.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials20 (43.48%)5.53%
Reviews2 (4.35%)6.00%
Case Studies1 (2.17%)4.05%
Observational1 (2.17%)0.25%
Other22 (47.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
A Phase 2 Randomized, Double-blind, Placebo-Controlled, Parallel-Group Study, of the Safety and Efficacy of NG101 Administered Orally to Patients With Gastroparesis [NCT04303195]Phase 2162 participants (Actual)Interventional2020-08-01Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]