Page last updated: 2024-12-07

n-desmethylclobazam

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

Description

desmethylclobazam: major pharmacologically active metabolite of clobazam; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID89657
CHEMBL ID2260842
CHEBI ID190616
SCHEMBL ID4531733
MeSH IDM0082972

Synonyms (38)

Synonym
8-chloro-1-phenyl-1h-1,5-benzodiazepine-2,4(3h,5h)-dione
1h-1,5-benzodiazepine-2,4(3h,5h)-dione, 8-chloro-1-phenyl-
norclobazam
7-chloro-5-phenyl-1h-1,5-benzodiazepine-2,4(3h,5h)-dione
einecs 244-909-2
n-demethylclobazam
clofazin
demethylclobazam
desmethylclobazam
n-desmethylclobazam
FT-0666101
FT-0666102
CHEBI:190616
22316-55-8
7-chloro-5-phenyl-1h-1,5-benzodiazepine-2,4-dione
mz4l647o2h ,
unii-mz4l647o2h
nor-clobazam
CHEMBL2260842
n-desmethyl clobazam-d5
clobazam impurity a [ep impurity]
clobazam metabolite m9
7-chloro-5-phenyl-1,5-dihydro-3h-1,5-benzodiazepine-2,4-dione
1-phenyl 8-chloro 1,2,4,5-tetrahydro 2,4-dioxo 3h-1,5-benzodiazepine
5-phenyl-7-chloro-1h-1,5-benzodiazepine-2,4-(3h,5h)-dione
7-chloro-5-phenyl-1,2,3,5-tetrahydro-4h-1,5-benzodiazepin-2,4-dione
1-phenyl 8-chloro 1,2,4,5-tetrahydro 2,4 -dioxo 3h-1,5-benzodiazepine
SCHEMBL4531733
8-chloro-1-phenyl-1h-benzo[b][1,4]diazepine-2,4(3h,5h)-dione
DTXSID40176859
AKOS027381895
clobazam-m nor
n-desmethylclobazam (norclobazam) 0.1 mg/ml in acetonitrile
n-desmethylclobazam (norclobazam)
7-chloro-5-phenyl-1,5-dihydro-3h-1,5-benzodiazepine-2,4-dione (norclobazam)
Q27284309
8-chloro-1-phenyl-2,3,4,5-tetrahydro-1h-1,5-benzodiazepine-2,4-dione
norclobazam, 1mg/ml in acetonitrile

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Steady-state pharmacokinetic data are described from four healthy male volunteers and eight epileptic patients taking NDMC."( Pharmacokinetics of N-desmethylclobazam in healthy volunteers and patients with epilepsy.
Feely, MP; Haigh, JR; Peaker, S; Pullar, T, 1987
)
0.6
"The pharmacokinetic interaction between clobazam and cimetidine was studied in 9 healthy male volunteers in an open-labelled study."( Pharmacokinetic aspects of the interaction between clobazam and cimetidine.
Grigoleit, HG; Hajdú, P; Hundt, HK; Koeppen, D; Malerczyk, V; Meyer, BH; Müller, FO; Witte, PU, 1983
)
0.27
" The aim of this study was to evaluate the impact of the CYP2C19 and POR genotypes on the pharmacokinetic parameters of CLB and N-CLB."( Effects of CYP2C19 and P450 oxidoreductase polymorphisms on the population pharmacokinetics of clobazam and N-desmethylclobazam in japanese patients with epilepsy.
Ishitsu, T; Kaneko, S; Nagata, R; Nakagawa, K; Nakashima, H; Nishimura, M; Ogusu, N; Saruwatari, J; Seo, T; Shimomasuda, M; Tanikawa, K; Tsuda, Y; Yasui-Furukori, N, 2014
)
0.62
"To develop a physiologically based pharmacokinetic model in adults and children for clobazam, its active metabolite norclobazam and stiripentol and to account for significant clinical interaction that has been reported when clobazam and stiripentol are co-administered."( A physiologically based pharmacokinetic model for clobazam and stiripentol in adults and children.
Aarons, L; Ogungbenro, K, 2015
)
0.42
"Thirty-five children with epilepsy were included in a prospective population pharmacokinetic study (using NONMEM(®) software)."( Pharmacokinetics of clobazam and N-desmethylclobazam in children with dravet syndrome receiving concomitant stiripentol and valproic Acid.
Chhun, S; Chiron, C; Dulac, O; Jullien, V; Pons, G; Rey, E; Tod, M, 2015
)
0.7
"This is the first simultaneous pharmacokinetic model for clobazam and N-CLB in epileptic children."( Pharmacokinetics of clobazam and N-desmethylclobazam in children with dravet syndrome receiving concomitant stiripentol and valproic Acid.
Chhun, S; Chiron, C; Dulac, O; Jullien, V; Pons, G; Rey, E; Tod, M, 2015
)
0.7
"A metabolic mechanism-based characterization of antiepileptic drug-drug interactions (DDIs) with clobazam in patients with Lennox-Gastaut syndrome (LGS) was performed using a population pharmacokinetic (PPK) approach."( Drug-metabolism mechanism: Knowledge-based population pharmacokinetic approach for characterizing clobazam drug-drug interactions.
Bekersky, I; Chu, HM; Ette, EI; Tolbert, D, 2016
)
0.43
" There is still insufficient data regarding its pharmacokinetic variability in clinical practice."( Therapeutic Drug Monitoring of Clobazam and Its Metabolite-Impact of Age and Comedication on Pharmacokinetic Variability.
Baftiu, A; Burns, ML; Johannessen, SI; Landmark, CJ; Opdal, MS, 2016
)
0.43
"The pharmacokinetic variability of CLB and its metabolite NCLB in clinical practice is extensive, and is influenced by drug-drug interactions, age, and pharmacogenetics."( Therapeutic Drug Monitoring of Clobazam and Its Metabolite-Impact of Age and Comedication on Pharmacokinetic Variability.
Baftiu, A; Burns, ML; Johannessen, SI; Landmark, CJ; Opdal, MS, 2016
)
0.43
" The aim was to use long-term TDM to investigate pharmacokinetic variability of ASMs in these patients."( Pharmacokinetic Variability During Long-Term Therapeutic Drug Monitoring of Valproate, Clobazam, and Levetiracetam in Patients With Dravet Syndrome.
Bjørnvold, M; Burns, ML; Heger, K; Johannessen Landmark, C; Johannessen, SI; Lund, C; Sætre, E, 2020
)
0.56
" Pharmacokinetic variability of the total number of measurements of valproate (n = 417), clobazam and N-desmethylclobazam (n = 328), and levetiracetam (n = 238) was determined."( Pharmacokinetic Variability During Long-Term Therapeutic Drug Monitoring of Valproate, Clobazam, and Levetiracetam in Patients With Dravet Syndrome.
Bjørnvold, M; Burns, ML; Heger, K; Johannessen Landmark, C; Johannessen, SI; Lund, C; Sætre, E, 2020
)
0.77
" Pharmacokinetic variability and interactions can thus be identified and adjusted to facilitate decision making to achieve the optimal treatment outcome."( Pharmacokinetic Variability During Long-Term Therapeutic Drug Monitoring of Valproate, Clobazam, and Levetiracetam in Patients With Dravet Syndrome.
Bjørnvold, M; Burns, ML; Heger, K; Johannessen Landmark, C; Johannessen, SI; Lund, C; Sætre, E, 2020
)
0.56

Compound-Compound Interactions

ExcerptReferenceRelevance
" Because CLB and CBD are both metabolized in the cytochrome P450 (CYP) pathway, we predicted a drug-drug interaction, which we evaluate in this article."( Drug-drug interaction between clobazam and cannabidiol in children with refractory epilepsy.
Bruno, PL; Geffrey, AL; Pollack, SF; Thiele, EA, 2015
)
0.42
"A metabolic mechanism-based characterization of antiepileptic drug-drug interactions (DDIs) with clobazam in patients with Lennox-Gastaut syndrome (LGS) was performed using a population pharmacokinetic (PPK) approach."( Drug-metabolism mechanism: Knowledge-based population pharmacokinetic approach for characterizing clobazam drug-drug interactions.
Bekersky, I; Chu, HM; Ette, EI; Tolbert, D, 2016
)
0.43
"Pharmacokinetic variability of CLB in pediatric patients is extensive, and it is influenced by drug-drug interactions and age."( Impact of Drug Interactions on Clobazam and N-Desmethylclobazam Concentrations in Pediatric Patients With Epilepsy.
Phelps, SJ; Russell, GR; Shelton, CM; Wheless, JW, 2018
)
0.74

Bioavailability

ExcerptReferenceRelevance
" This would suggest that cimetidine either increases the bioavailability of clobazam or reduces that of NDMC."( The effect of cimetidine on the single dose pharmacokinetics of oral clobazam and N-desmethylclobazam.
Edwards, D; Feely, MP; Haigh, JR; Peaker, S; Pullar, T, 1987
)
0.5
" To characterize potential DDIs with clobazam, pharmacokinetic (PK) data from 153 patients with LGS in study OV-1012 (NCT00518713) and 18 healthy participants in bioavailability study OV-1017 were pooled."( Drug-metabolism mechanism: Knowledge-based population pharmacokinetic approach for characterizing clobazam drug-drug interactions.
Bekersky, I; Chu, HM; Ette, EI; Tolbert, D, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" Plasma levels of the active metabolite N-desmethylclobazam were linearly related to dosage and appeared to correlate with both therapeutic and toxic responses."( Add-on trial of clobazam in intractable adult epilepsy with plasma level correlations.
Blaschuk, K; Couture, M; Guberman, A; Sherwin, A, 1990
)
0.55
" Next, training was suspended and the mice received a maintenance dosing regimen in which they were injected twice daily with 10 mg/kg N-desmethylclozapine for 10 days."( The metabolites N-desmethylclozapine and N-desmethylolanzapine produce cross-tolerance to the discriminative stimulus of the atypical antipsychotic clozapine in C57BL/6 mice.
Meltzer, HY; Porter, JH; Webster, KA; Wiebelhaus, JM, 2011
)
0.37
" Because concomitant use of AEDs that are either CYP450 inhibitors or inducers with clobazam in the treatment of LGS patients had negligible to no effect on clobazam PK in this study, dosage adjustments may not be required for clobazam in the presence of the AEDs investigated here."( Drug-metabolism mechanism: Knowledge-based population pharmacokinetic approach for characterizing clobazam drug-drug interactions.
Bekersky, I; Chu, HM; Ette, EI; Tolbert, D, 2016
)
0.43
[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]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1660982Inhibition of Escherichia coli Stx2 in human HeLa cells assessed as stimulation of protein synthesis by measuring increase in [14C]-leucine incorporation at 30 uM incubated with cells for 4 hrs prior to Stx2 addition and further incubated for 20 hrs and s2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (63)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (34.92)18.7374
1990's9 (14.29)18.2507
2000's9 (14.29)29.6817
2010's20 (31.75)24.3611
2020's3 (4.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.32

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

MetricThis Compound (vs All)
Research Demand Index35.32 (24.57)
Research Supply Index4.32 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index45.37 (26.88)
Search Engine Supply Index1.94 (0.95)

This Compound (35.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (12.12%)5.53%
Reviews1 (1.52%)6.00%
Case Studies7 (10.61%)4.05%
Observational0 (0.00%)0.25%
Other50 (75.76%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]