Page last updated: 2024-12-06

metapramine

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

Description

Metapramine is a tricyclic antidepressant (TCA) with a chemical structure similar to imipramine. It was synthesized in the 1960s and was initially marketed as an antidepressant. It is believed to exert its antidepressant effects by inhibiting the reuptake of serotonin and norepinephrine in the brain. However, metapramine has been found to have significant side effects, including anticholinergic effects, sedation, and cardiovascular problems. Consequently, its use as an antidepressant has largely been discontinued. Some studies have investigated its potential use in treating other conditions, such as chronic pain and anxiety disorders, but further research is needed. Metapramine continues to be studied due to its unique chemical structure and its potential for therapeutic applications in specific patient populations. It is also used in the synthesis of other tricyclic antidepressants.'

metapramine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65700
CHEMBL ID2106919
CHEBI ID134971
SCHEMBL ID49125
MeSH IDM0061475

Synonyms (25)

Synonym
metapramine
19560 rp
10,11-dihydro-5-methyl-10-(methylamino)-5h-dibenz(b,f)azepin
metapramina [inn-spanish]
metapramina [spanish]
10,11-dihydro-5-methyl-10-(methylamino)-5h-dibenz(b,f)azepine
metapraminum [inn-latin]
metapraminum [latin]
metapramine [inn]
CHEBI:134971
n,11-dimethyl-5,6-dihydrobenzo[b][1]benzazepin-5-amine
metapraminum
metapramina
unii-303954m7yf
21730-16-5
303954m7yf ,
FT-0671037
CHEMBL2106919
SCHEMBL49125
metapramine [who-dd]
metapramine [mi]
Q15409392
DTXSID60865011
CS-0027176
HY-107031

Research Excerpts

Pharmacokinetics

Metapramine is a tricyclic antidepressant without anticholinergic or cardiotoxic effects. The plasma level of metapramsine decreased tri-exponentially, with a terminal half-life of about 7.

ExcerptReferenceRelevance
"The antinociceptive effect of acutely and chronically (every brain elimination half-life time) administered metapramine, a tricyclic antidepressant without anticholinergic or cardiotoxic effects, was studied in three different pain tests."( Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties.
Aumaitre, O; Berger, JA; Bougerolle, AM; Dordain, G; Eschalier, A; Fialip, J; Marty, H, 1992
)
0.79
"Previous studies on pharmacokinetic parameters of tricyclic antidepressants (TCAs) in rodents have shown different results from those obtained for the same drugs in man."( Pharmacokinetics of metapramine and its demethylated metabolites in plasma and brain of mice.
Aumaitre, O; Berger, JA; Bougerolle, AM; Chabard, JL; Dordain, G; Eschalier, A; Fialip, J; Petit, J, 1989
)
0.6
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dibenzooxazepineAn organic heterotricyclic compound consisting of two benzene rings fused to a seven-membered ring containing one oxygen and one nitrogen atom.
[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 (19)

Assay IDTitleYearJournalArticle
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
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]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' 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
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]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' 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]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079945Animal toxicity known. [column 'TOXIC' 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]
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]
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]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (85.00)18.7374
1990's3 (15.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.53

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.53 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.57%)5.53%
Reviews0 (0.00%)6.00%
Case Studies7 (25.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (71.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]