Compounds > flumezapine
Page last updated: 2024-10-15

flumezapine

Description

flumezapine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135413528
CHEMBL ID273786
CHEBI ID177815
SCHEMBL ID123704
MeSH IDM0133440

Synonyms (33)

Synonym
7-luoro-2-methyl-4-(4-methylpiperazin-1-yl)-10h-thieno[2,3-b][1,5]benzodiazepine
CHEBI:177815
flumezapine
ly-120363
61325-80-2
flumezapine (usan)
D02659
ly 120363
10h-thieno(2,3-b)(1,5)benzodiazepine, 7-fluoro-2-methyl-4-(4-methyl-1-piperazinyl)-
brn 1033583
flumezapina [inn-spanish]
7-fluoro-2-methyl-4-(4-methyl-1-piperazinyl)-10h-thieno(2,3-b)(1,5)benzodiazepine
flumezapinum [inn-latin]
L010290
ly120363
CHEMBL273786 ,
7-fluoro-2-methyl-4-(4-methylpiperazin-1-yl)-5h-thieno[3,2-c][1,5]benzodiazepine
(flumezapine)7-fluoro-2-methyl-10-(4-methyl-piperazin-1-yl)-4h-3-thia-4,9-diaza-benzo[f]azulene
7-fluoro-2-methyl-10-(4-methyl-piperazin-1-yl)-4h-3-thia-4,9-diaza-benzo[f]azulene
bdbm50017536
flumezapine [usan:inn:ban]
flumezapina
flumezapinum
unii-na9gm10x6c
na9gm10x6c ,
o-chloro benzoic acid
SCHEMBL123704
flumezapine [inn]
flumezapine [usan]
7-fluoro-2-methyl-4-(4-methyl-1-piperazinyl)-10h-thieno[2,3-b][1,5]benzodiazepine
DTXSID60976813
Q27284758
7-fluoro-2-methyl-4-(4-methylpiperazin-1-yl)-10h-thieno[2,3-b][1,5]benzodiazepine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzodiazepineA group of heterocyclic compounds with a core structure containing a benzene ring fused to a diazepine ring.
[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]

Protein Targets (11)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)IC50 (µMol)0.07800.00052.773925.1700AID141673; AID141681; AID142510
Muscarinic acetylcholine receptor M3Rattus norvegicus (Norway rat)IC50 (µMol)0.07800.00052.891925.1700AID141673; AID141681; AID142510
Muscarinic acetylcholine receptor M4Rattus norvegicus (Norway rat)IC50 (µMol)0.07800.00052.747825.1700AID141673; AID141681; AID142510
Muscarinic acetylcholine receptor M5Rattus norvegicus (Norway rat)IC50 (µMol)0.07800.00052.780225.1700AID141673; AID141681; AID142510
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)IC50 (µMol)0.07800.00053.314249.5000AID141673; AID141681; AID142510
DRattus norvegicus (Norway rat)IC50 (µMol)0.02000.00030.50267.7625AID62884
D(3) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.02000.00030.39075.4000AID62884
D(2) dopamine receptorBos taurus (cattle)IC50 (µMol)0.02000.00100.79948.0000AID62175
D(1B) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.02000.00030.35635.4000AID62884
D(4) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.02000.00030.38715.4000AID62884
D(2) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.02000.00010.54948.4000AID62884
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicD(2) dopamine receptorBos taurus (cattle)
negative regulation of prolactin secretionD(2) dopamine receptorBos taurus (cattle)
negative regulation of lactationD(2) dopamine receptorBos taurus (cattle)
positive regulation of mammary gland involutionD(2) dopamine receptorBos taurus (cattle)
hyaloid vascular plexus regressionD(2) dopamine receptorBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
Golgi membraneD(2) dopamine receptorBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID62175Inhibitory activity against dopamine receptor D2 in calf caudate tissue using [3H]spiperone1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.
AID141681Displacement of [3H]QNB from Muscarinic acetylcholine receptor of rat brain membrane1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems.
AID141673Inhibitory activity against muscarinic cholinergic receptors in male olac rat brain, using [3H]QNB as the radioligand1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.
AID133182Tested for physostigmine lethality at a dose of 10 mg/kg after oral administration in mice1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems.
AID130393Effective dose required to evoke catalepsy in mouse when administered perorally1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.
AID62884Displacement of [3H]spiroperidol from Dopamine receptor of rat striatum membrane1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems.
AID181436Inhibition of conditioned avoidance response in rats, peroral dose1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.
AID181429Effective dose against muscular incoordination in rats determined by rotarod test when administered peroral1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.
AID130264Dose below which no catalepsy was observed at any time period (following p.o. dosing)1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Synthesis and pharmacological evaluation of a series of 4-piperazinylpyrazolo[3,4-b]- and -[4,3-b][1,5]benzodiazepines as potential anxiolytics.
AID171950compound behavior in rat1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Synthesis and pharmacological evaluation of a series of 4-piperazinylpyrazolo[3,4-b]- and -[4,3-b][1,5]benzodiazepines as potential anxiolytics.
AID142510Inhibition of [3H]QNB binding to muscarinic cholinergic receptor from male Olac rat brain.1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Synthesis and pharmacological evaluation of a series of 4-piperazinylpyrazolo[3,4-b]- and -[4,3-b][1,5]benzodiazepines as potential anxiolytics.
AID130395Effective dose required to produce hypothermia in mouse when administered peroral1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.
AID169969Compound was assessed for its ability to produce catalepsy in rats; Dose administered perorally is 8 mg/kg; Group score is 4-71980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
4-Piperazinyl-10H-thieno[2,3-b][1,5]benzodiazepines as potential neuroleptics.
AID130391Hypothermia in mice after peroral administration1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
4-Piperazinyl-10H-thieno[2,3-b][1,5]benzodiazepines as potential neuroleptics.
AID133186Tested for physostigmine lethality at a dose of 2.5 mg/kg after oral administration in mice1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems.
AID169952Compound was assessed for its ability to block a conditioned avoidance response; Dose administered perorally is 8 mg/kg; 76-99%block1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
4-Piperazinyl-10H-thieno[2,3-b][1,5]benzodiazepines as potential neuroleptics.
AID173417Compound administered perorally was evaluated for the conditioned avoidance response in rats1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Synthesis and pharmacological evaluation of a series of 4-piperazinylpyrazolo[3,4-b]- and -[4,3-b][1,5]benzodiazepines as potential anxiolytics.
AID173415Rotarod response in rat to assess muscular incoordination (following p.o. dosing)1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Synthesis and pharmacological evaluation of a series of 4-piperazinylpyrazolo[3,4-b]- and -[4,3-b][1,5]benzodiazepines as potential anxiolytics.
AID130266Compound administered perorally was evaluated for the hypothermia (rectal temperature) in mice1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Synthesis and pharmacological evaluation of a series of 4-piperazinylpyrazolo[3,4-b]- and -[4,3-b][1,5]benzodiazepines as potential anxiolytics.
AID133191Tested for physostigmine lethality at a dose of 5 mg/kg after oral administration in mice1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems.
AID61555Inhibition of [3H]spiperone binding to dopamine receptor D2 from rat brain striatum1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Synthesis and pharmacological evaluation of a series of 4-piperazinylpyrazolo[3,4-b]- and -[4,3-b][1,5]benzodiazepines as potential anxiolytics.
AID134417Lethal dose in mice after perorla administration1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
4-Piperazinyl-10H-thieno[2,3-b][1,5]benzodiazepines as potential neuroleptics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (100.00)18.7374
1990's0 (0.00)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]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
3,4-dihydroxyphenylacetic acid
3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.		1.9610catechols;
dihydroxyphenylacetic acid		human metabolite
amfonelic acid
amfonelic acid: CNS-stimulant		6.9610
chlordiazepoxide
Chlordiazepoxide: An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal.. chlordiazepoxide : A benzodiazepine that is 3H-1,4-benzodiazepine 4-oxide substituted by a chloro group at position 7, a phenyl group at position 5 and a methylamino group at position 2.		1.9710benzodiazepine
chlorpromazine
Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.		1.9510organochlorine compound;
phenothiazines;
tertiary amine		anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
phenothiazine antipsychotic drug
clonazepam
Clonazepam: An anticonvulsant used for several types of seizures, including myotonic or atonic seizures, photosensitive epilepsy, and absence seizures, although tolerance may develop. It is seldom effective in generalized tonic-clonic or partial seizures. The mechanism of action appears to involve the enhancement of GAMMA-AMINOBUTYRIC ACID receptor responses.. clonazepam : 1,3-Dihydro-2H-1,4-benzodiazepin-2-one in which the hydrogens at positions 5 and 7 are substituted by 2-chlorophenyl and nitro groups, respectively. It is used in the treatment of all types of epilepsy and seizures, as well as myoclonus and associated abnormal movements, and panic disorders. However, its use can be limited by the development of tolerance and by sedation.		1.97101,4-benzodiazepinone;
monochlorobenzenes		anticonvulsant;
anxiolytic drug;
GABA modulator
haloperidol
Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.		2.3620aromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol		antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist
nalidixic acid
[no description available]		1.96101,8-naphthyridine derivative;
monocarboxylic acid;
quinolone antibiotic		antibacterial drug;
antimicrobial agent;
DNA synthesis inhibitor
quipazine
Quipazine: A pharmacologic congener of serotonin that contracts smooth muscle and has actions similar to those of tricyclic antidepressants. It has been proposed as an oxytocic.		1.9610piperazines;
pyridines
thioridazine
Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.		1.9510phenothiazines;
piperidines		alpha-adrenergic antagonist;
dopaminergic antagonist;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
first generation antipsychotic;
H1-receptor antagonist;
serotonergic antagonist
zopiclone
zopiclone: S(+)-enantiomer of racemic zopiclone; azabicyclo(4.3.0)nonane; a nonbenzodiazepine; one of the so-called of Z drugs (zopiclone, eszopiclone, zolpidem, and zaleplon) for which there is some correlation with tumors; was term of zopiclone 2004-2007. zopiclone : A pyrrolo[3,4-b]pyrazine compound having a 4-methylpiperazine-1-carboxyl group at the 5-position, a 5-chloropyridin-2-yl group at the 6-position and an oxo-substituent at the 7-position.		1.9710monochloropyridine;
pyrrolopyrazine		central nervous system depressant;
sedative
zotepine
zotepine: structure		6.9610dibenzothiepine;
tertiary amino compound		alpha-adrenergic drug;
second generation antipsychotic;
serotonergic drug
corticosterone
[no description available]		1.961011beta-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite
pergolide
Pergolide: A long-acting dopamine agonist which has been used to treat PARKINSON DISEASE and HYPERPROLACTINEMIA but withdrawn from some markets due to potential for HEART VALVE DISEASES.. pergolide : A diamine that is ergoline in which the beta-hydrogen at position 8 is replaced by a (methylthio)methyl group and the hydrogen attached to the piperidine nitrogen (position 6) is replaced by a propyl group. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it is used as the mesylate salt in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction.		1.9610diamine;
methyl sulfide;
organic heterotetracyclic compound		antiparkinson drug;
dopamine agonist
2-phenylpyrazolo(4,3-c)quinolin-3(5h)-one
2-phenylpyrazolo(4,3-c)quinolin-3(5H)-one: a mixed agonist/antagonist of the benzodiazepine receptor		1.9710
bremazocine
bremazocine: potent, log-acting opiate kappa-agonist & centrally acting analgesic; RN given refers to (2R)-isomer; structure given in first source		1.9610
flupenthixol
cis-flupenthixol : A flupenthixol in which the double bond adopts a cis-configuration.		1.9510flupenthixoldopaminergic antagonist
scopolamine hydrobromide
[no description available]		1.9610
clozapine
Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.		2.8840benzodiazepine;
N-arylpiperazine;
N-methylpiperazine;
organochlorine compound		adrenergic antagonist;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
environmental contaminant;
GABA antagonist;
histamine antagonist;
muscarinic antagonist;
second generation antipsychotic;
serotonergic antagonist;
xenobiotic
ConditionIndicatedRelationship StrengthStudiesTrials
Anochlesia
[description not available]		02.3720