Compounds > nafimidone
Page last updated: 2024-12-06

nafimidone

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

Description

Nafimidone is a synthetic, non-narcotic analgesic. It is a selective inhibitor of the enzyme cyclooxygenase-2 (COX-2), which is responsible for the production of prostaglandins, inflammatory mediators involved in pain and inflammation. Nafimidone has been studied for its potential therapeutic effects in a variety of conditions, including pain, inflammation, and cancer. It has shown promising results in preclinical studies, but it has not yet been approved for use in humans. Nafimidone is a prodrug, meaning that it is converted to its active form in the body. The synthesis of Nafimidone involves several steps, including the reaction of a substituted aniline with a benzoyl chloride derivative. The resulting amide is then treated with a Grignard reagent to form the corresponding ketone. The final step in the synthesis is the reduction of the ketone to the desired alcohol. '

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

Cross-References

ID SourceID
PubMed CID51200
CHEMBL ID416801
SCHEMBL ID1817018
MeSH IDM0116271

Synonyms (27)

Synonym
2-imidazol-1-yl-2'-acetonaphthone
2-(1h-imidazol-1-yl)-1-(1-naphthalenyl)ethanone
nafimidonum [latin]
1-(2-naphthoylmethyl)imidazole
nafimidone
brn 0523776
ethanone, 2-(1h-imidazol-1-yl)-1-(1-naphthalenyl)-
nafimidone [inn]
nafimidona [spanish]
CHEMBL416801
2-imidazol-1-yl-1-naphthalen-2-ylethanone
hzu3iq1eww ,
64212-22-2
nafimidonum
5-23-04-00380 (beilstein handbook reference)
unii-hzu3iq1eww
nafimidona
nafimidone [mart.]
ITPVLJQRUQVNSD-UHFFFAOYSA-N
SCHEMBL1817018
DTXSID80214426
1-(1-naphthyl)-2-(1h-imidazol-1-yl)ethanone
FT-0768480
1-(2-naphthyl)-2-(imidazol-1-yl)ethanone
Q6958175
2-(1h-imidazol-1-yl)-1-(naphthalen-2-yl)ethan-1-one
EN300-18563699

Research Excerpts

Overview

Nafimidone is a potential new antiepileptic drug with a therapeutic profile in experimental animal seizure models similar to that of phenytoin (PHT)

ExcerptReferenceRelevance
"Nafimidone is a new antiepileptic drug which may be effective in partial onset seizures. "( Pharmacokinetics of nafimidone in patients with chronic intractable epilepsy.
Gunawan, S; Treiman, DM, 1987)		2.04
"Nafimidone is a potential new antiepileptic drug with a therapeutic profile in experimental animal seizure models similar to that of phenytoin (PHT). "( Efficacy of nafimidone in the treatment of intractable partial seizures: report of a two-center pilot study.
Barber, KO; Ben-Menachem, E; Cereghino, JJ; McCormick, KB; Ojemann, L; Swisher, K; Treiman, DM; White, BG; Wilensky, AJ; Yerby, M, )		1.95

Bioavailability

ExcerptReferenceRelevance
" Systemic clearance of nafimidone from plasma after iv administration was approximately 2 times higher than hepatic blood flow in rats, and the oral bioavailability was 15%."( Disposition of nafimidone in rats.
Chaplin, MD; Graham, DJ; Hall, DJ; Hama, KM; Kurz, L; Smith, SA, )		0.79

Dosage Studied

ExcerptRelevanceReference
" within 30 min of dosing before electrical stimulation."( The anticonvulsant action of nafimidone on kindled amygdaloid seizures in rats.
Albertson, TE; Walby, WF, )		0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID112801Effective dose in mice by horizontal screen assay (administered orally); No effect at highest dose of 400 mg/kg1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.
AID40680In vitro displacement of [3H]flunitrazepam binding to cortical membranes at 5e-5M concentration1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.
AID112168Effective dose to produce anticonvulsant activity using maximal electroshock assay (MES) evaluated in mice after oral administration1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
Imidazole anticonvulsants: structure-activity relationships of [(biphenylyloxy)alkyl]imidazoles.
AID112808Effective dose in mice by pentylenetetrazole assay (administered subcutaneously)1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.
AID119413Potentiation of hexobarbital-induced sleeping time in mice1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.
AID1312151Anticonvulsant activity in patient assessed as improvement in seizure control at 600 mg/day administered up to 1 year2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Design and comparative anticonvulsant activity assessment of CNS-active alkyl-carbamoyl imidazole derivatives.
AID40681In vivo displacement of [3H]flunitrazepam binding to rat cortical membranes after 20 mg/kg ip dose1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.
AID122339Compound was tested for time to peak anticonvulsant effect (TPE)1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.
AID112804Effective dose in mice by maximal electroshock assay, administered orally1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (50.00)18.7374
1990's3 (18.75)18.2507
2000's1 (6.25)29.6817
2010's3 (18.75)24.3611
2020's1 (6.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.21

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 Index22.21 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index4.85 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (4.35%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (95.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenytoin
[no description available]		1.9710imidazolidine-2,4-dioneanticonvulsant;
drug allergen;
sodium channel blocker;
teratogenic agent
carbamazepine
Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.		1.9710dibenzoazepine;
ureas		analgesic;
anticonvulsant;
antimanic drug;
drug allergen;
EC 3.5.1.98 (histone deacetylase) inhibitor;
environmental contaminant;
glutamate transporter activator;
mitogen;
non-narcotic analgesic;
sodium channel blocker;
xenobiotic
carbamazepine epoxide
carbamazepine epoxide: metabolite of carbamazepine; RN given refers to unlabeled cpd. carbamazepine-10,11-epoxide : An epoxide and metabolite of carbamazepine.		1.9710dibenzoazepine;
epoxide;
ureas		allergen;
drug metabolite;
marine xenobiotic metabolite
diazepam
Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.		1.97101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic
valproic acid
Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.		2.1310branched-chain fatty acid;
branched-chain saturated fatty acid		anticonvulsant;
antimanic drug;
EC 3.5.1.98 (histone deacetylase) inhibitor;
GABA agent;
neuroprotective agent;
psychotropic drug;
teratogenic agent
felbamate
Felbamate: A PEGylated phenylcarbamate derivative that acts as an antagonist of NMDA RECEPTORS. It is used as an anticonvulsant, primarily for the treatment of SEIZURES in severe refractory EPILEPSY.. felbamate : The bis(carbamate ester) of 2-phenylpropane-1,3-diol. An anticonvulsant, it is used in the treatment of epilepsy.		2.1310carbamate esteranticonvulsant;
neuroprotective agent
flunitrazepam
Flunitrazepam: A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.. flunitrazepam : A 1,4-benzodiazepinone that is nitrazepam substituted by a methyl group at position 1 and by a fluoro group at position 2'. It is a potent hypnotic, sedative, and amnestic drug used to treat chronic insomnia.		1.96101,4-benzodiazepinone;
C-nitro compound;
monofluorobenzenes		anxiolytic drug;
GABAA receptor agonist;
sedative
hexobarbital
Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.		1.9610barbiturates
naphazoline
Naphazoline: An adrenergic vasoconstrictor agent used as a decongestant.		4140naphthalenes
pentylenetetrazole
Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.		210organic heterobicyclic compound;
organonitrogen heterocyclic compound
denzimol
denzimol: structure in first source		2.6830
27-hydroxycholesterol
(25R)-cholest-5-ene-3beta,26-diol : A 26-hydroxycholesterol in which the 25-position has R-configuration.		1.991026-hydroxycholesterolapoptosis inducer;
human metabolite;
mouse metabolite;
neuroprotective agent
nafimidone alcohol
nafimidone alcohol: nafimidone metabolite; structure given in first source		7.3720
sec-butyl-propylacetamide
sec-butyl-propylacetamide: structure in first source		2.1310
ConditionIndicatedRelationship StrengthStudiesTrials
Absence Seizure
[description not available]		03.2760
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		03.2760
Aura
[description not available]		02.4220
Epilepsy
A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)		02.4220
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2110
Chronic Illness
[description not available]		01.9710
Chronic Disease
Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).		01.9710