Page last updated: 2024-12-04

carbamazepine epoxide

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

Description

carbamazepine epoxide: metabolite of carbamazepine; RN given refers to unlabeled cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

carbamazepine-10,11-epoxide : An epoxide and metabolite of carbamazepine. [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]

Cross-References

ID SourceID
PubMed CID2555
CHEMBL ID1258
CHEBI ID3388
SCHEMBL ID156675
MeSH IDM0059135

Synonyms (46)

Synonym
gp 49-023
brn 1219988
6h-dibenz(b,f)oxiren(d)azepine-6-carboxamide, 1a,10b-dihydro-
carbamazepine 10,11-epoxide
carbamazepine-10,11-trans-dihydrodiol
1a,10b-dihydro-6h-dibenz(b,f)oxiren(d)azepine-6-carboxamide
10,11-epoxycarbamazepine
carbamazepine 10,11-oxide
carbamazepine-10,11-epoxide
C07496
carbamazepine epoxide
36507-30-9
chebi:3388 ,
CHEMBL1258
1a,10b-dihydro-6h-dibenzo[b,f]oxireno[d]azepine-6-carboxamide
qc9505f279 ,
unii-qc9505f279
10,11-dihydro-10,11-epoxycarbamazepine
FT-0639322
bdbm50446047
gp-49-023
6h-dibenz(b,f)oxireno(d)azepine-6-carboxamide, 1a,10b-dihydro-
10,11-dihydro-5h-dibenz(b,f)azepine-5-carboxamide 10,11-epoxide
cbz-e
1ah-dibenzo[b,f]oxireno[2,3-d]azepine-6(10bh)-carboxamide
SCHEMBL156675
1a,10b-dihydro-6h-dibenzo[b,f]oxireno[2,3-d]azepine-6-carboxamide #
6h-dibenz[b,f]oxireno[d]azepine-6-carboxamide, 1a,10b-dihydro-
ZRWWEEVEIOGMMT-UHFFFAOYSA-N
1a,10b-dihydro-6h-dibenz(b,f)oxireno(d)azepine-6-carboxamide
3-oxa-11-azatetracyclo[10.4.0.02,4.05,10]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
carbamazepine 10,11-epoxide, analytical standard
AKOS027327549
1a,10b-dihydro-6h-dibenzo[b,f]oxireno[2,3-d]azepine-6-carboxamide
mfcd00467137
carbamazepine 10,11-epoxide 1.0 mg/ml in acetonitrile
carbamazepine10,11-epoxide
DTXSID60891456
DS-11818
Q27106058
3-(4-bromo-3,5-dimethyl-pyrazol-1-ylmethyl)-benzoicacid
3-oxa-11-azatetracyclo[10.4.0.0^{2,4.0^{5,10]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
HY-W013378
CS-W014094
carbamazepin-10,11-epoxide
carbamazepine 10,11-epoxide 100 microg/ml in acetonitrile

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"We evaluated the efficacy, development of adverse effects, and possible correlation between the plasma concentration of carbamazepine (CBZ) and its major metabolite, carbamazepine-10,11-epoxide (CBZ-E), in a group of epileptic patients in whom selective increases in CBZ doses were made."( Carbamazepine and its epoxide: an open study of efficacy and side effects after carbamazepine dose increment in refractory partial epilepsy.
Baulac, M; Gimenez, F; Laplane, D; Longer, E; Semah, F; Thuillier, A, 1994
)
0.29
"05) change in the serum concentrations of either CBZ or its epoxide metabolite when LTG was added either to the group as a whole or to the nine patients who experienced adverse CNS effects."( Carbamazepine toxicity with lamotrigine: pharmacokinetic or pharmacodynamic interaction?
Berry, DJ; Besag, FM; Newbery, JE; Pool, F; Subel, B, 1998
)
0.3

Pharmacokinetics

ExcerptReferenceRelevance
" The two formulations, therefore, have a similar pharmacokinetic profile and could be used interchangeably in the management of patients with epilepsy."( A comparative pharmacokinetic study of conventional and chewable carbamazepine in epileptic patients.
Patsalos, PN, 1990
)
0.28
" Therefore, the present study was undertaken in order to develop a pharmacokinetic model to predict the behavior of EPO in the body after administration of CBZ."( Pharmacokinetic study of carbamazepine and its epoxide metabolite in humans.
Kaneniwa, N; Sumi, M; Umezawa, O; Watari, N, 1987
)
0.27
" Some other pharmacokinetic aspects which could be useful in extrapolating to the amount and time of ingestion of the overdose are discussed."( Pharmacokinetic aspects of carbamazepine and its two major metabolites in plasma during overdosage.
Aucamp, AK; Hundt, HK; Müller, FO, 1983
)
0.27
"We studied the steady-state pharmacokinetic profile of topiramate (TPM) as a function of dose and the effects of comedication with carbamazepine (CBZ)."( Steady-state pharmacokinetics of topiramate and carbamazepine in patients with epilepsy during monotherapy and concomitant therapy.
Doose, DR; Kramer, LD; Nayak, RK; Sachdeo, RC; Sachdeo, SK; Walker, SA, 1996
)
0.29
" Adjusting the CBZ dose for pharmacokinetic reasons when TPM is administered as adjunctive treatment does not appear to be necessary."( Steady-state pharmacokinetics of topiramate and carbamazepine in patients with epilepsy during monotherapy and concomitant therapy.
Doose, DR; Kramer, LD; Nayak, RK; Sachdeo, RC; Sachdeo, SK; Walker, SA, 1996
)
0.29
" Following multiple dosing, the LSM was developed from a training data set of 10 subjects using the steady state Cmin (plasma concentration obtained 5 min before the last CBZ-SR dose)."( A limited sampling method for the estimation of AUC and Cmax of carbamazepine and carbamazepine epoxide following a single and multiple dose of a sustained-release product.
Chamberlin, N; Mahmood, I, 1998
)
0.53
"The model provided good estimates of AUC and Cmax for CBZ and CBZE."( A limited sampling method for the estimation of AUC and Cmax of carbamazepine and carbamazepine epoxide following a single and multiple dose of a sustained-release product.
Chamberlin, N; Mahmood, I, 1998
)
0.53
"The method described here may be used to estimate AUC and Cmax for CBZ and CBZE without detailed pharmacokinetic studies following single or multiple dose of CBZ."( A limited sampling method for the estimation of AUC and Cmax of carbamazepine and carbamazepine epoxide following a single and multiple dose of a sustained-release product.
Chamberlin, N; Mahmood, I, 1998
)
0.53
"To determine whether the toxicity that occurs in some patients when lamotrigine (LTG) is added to carbamazepine (CBZ) is the result of either a pharmacokinetic or a pharmacodynamic interaction."( Carbamazepine toxicity with lamotrigine: pharmacokinetic or pharmacodynamic interaction?
Berry, DJ; Besag, FM; Newbery, JE; Pool, F; Subel, B, 1998
)
0.3
" This appears to be the result of a pharmacodynamic interaction."( Carbamazepine toxicity with lamotrigine: pharmacokinetic or pharmacodynamic interaction?
Berry, DJ; Besag, FM; Newbery, JE; Pool, F; Subel, B, 1998
)
0.3
" A linear pharmacokinetic model which describes clearances of parent and metabolite is developed."( A partial area difference analysis for estimating elimination rate constants and distribution volumes of metabolites.
Riad, LE; Sawchuk, RJ, 1998
)
0.3
" We compared carbamazepine and carbamazepine-10,11-epoxide noncompartmental pharmacokinetic parameter values before and after St John's Wort with a paired Student t test."( Lack of effect of St John's Wort on carbamazepine pharmacokinetics in healthy volunteers.
Alfaro, RM; Burstein, AH; Dunn, T; Horton, RL; Piscitelli, SC; Theodore, W, 2000
)
0.31
"We found no significant differences before or after the administration of St John's Wort in carbamazepine peak concentration (7."( Lack of effect of St John's Wort on carbamazepine pharmacokinetics in healthy volunteers.
Alfaro, RM; Burstein, AH; Dunn, T; Horton, RL; Piscitelli, SC; Theodore, W, 2000
)
0.31
" Concurrent administration of LTG with CBZ did not have any significant effect on the pharmacokinetic parameters of CBZ."( Effect of lamotrigine on the pharmacokinetics of carbamazepine and its active metabolite in dogs.
Al-Hassan, MI; Al-Khamis, KI; Bawazir, SA; Matar, KM; Nicholls, PJ,
)
0.13
" The fitted pharmacokinetic parameters of CBZ and CBZ-E were generally consistent with published values from previous studies."( Reanalysis of carbamazepine and carbamazepine-epoxide pharmacokinetics after multiple dosing of extended release formulation.
Dechasathian, S; Konsil, J; Mason, DH; Stevens, RE,
)
0.13
" The aim of the present work was to study the pharmacokinetic behavior of this group of women during steady state."( Pharmacokinetic study of carbamazepine and its carbamazepine 10,11-epoxide metabolite in a group of female epileptic patients under chronic treatment.
Amancio, O; Belmont, A; Campos, MG; Heinze, G; Jaimes, O; López, G; Moreno, J; Pérez, P; Santos, JA,
)
0.13
" Pharmacokinetic parameters were calculated by statistical moment method after obtaining serum concentrations."( Pharmacokinetic study of carbamazepine and its carbamazepine 10,11-epoxide metabolite in a group of female epileptic patients under chronic treatment.
Amancio, O; Belmont, A; Campos, MG; Heinze, G; Jaimes, O; López, G; Moreno, J; Pérez, P; Santos, JA,
)
0.13
"The schedule we suggest for therapeutic monitoring of serum concentrations of CBZ in chronic treatments is 3 h for maximum peak concentration of C(max) after dose administration and for minimum peak concentration, C(min) prior to subsequent administration of the dose."( Pharmacokinetic study of carbamazepine and its carbamazepine 10,11-epoxide metabolite in a group of female epileptic patients under chronic treatment.
Amancio, O; Belmont, A; Campos, MG; Heinze, G; Jaimes, O; López, G; Moreno, J; Pérez, P; Santos, JA,
)
0.13
"To develop a population pharmacokinetic model to evaluate the effects of variety of covariates on clearance of carbamazepine (CBZ) and its main metabolite carbamazepine-10,11-epoxide (CBZE) in Chinese population."( Population pharmacokinetic modeling of steady state clearance of carbamazepine and its epoxide metabolite from sparse routine clinical data.
Jiao, Z; Shi, XJ; Zhao, ZG; Zhong, MK, 2004
)
0.32
" Two hundred and thirty-four patients, and 1254 and 1251 plasma concentrations for delavirdine and N-delavirdine, respectively, were available for population pharmacokinetic analysis."( Population pharmacokinetics of delavirdine and N-delavirdine in HIV-infected individuals.
Dicenzo, R; DiFrancesco, R; Fischl, M; Forrest, A; Friedland, G; Morse, GD; Para, M; Pollard, R; Shelton, M; Smith, PF, 2005
)
0.33
" Mean (%CV) population pharmacokinetic parameter estimates for delavirdine were: volume of distribution at steady state 67."( Population pharmacokinetics of delavirdine and N-delavirdine in HIV-infected individuals.
Dicenzo, R; DiFrancesco, R; Fischl, M; Forrest, A; Friedland, G; Morse, GD; Para, M; Pollard, R; Shelton, M; Smith, PF, 2005
)
0.33
"Delavirdine disposition exhibits nonlinear pharmacokinetics and large interpatient variability, and is significantly altered by time of day (impacting potential therapeutic drug monitoring and future pharmacokinetic study designs)."( Population pharmacokinetics of delavirdine and N-delavirdine in HIV-infected individuals.
Dicenzo, R; DiFrancesco, R; Fischl, M; Forrest, A; Friedland, G; Morse, GD; Para, M; Pollard, R; Shelton, M; Smith, PF, 2005
)
0.33
" In summary, a 2-way pharmacokinetic interaction between efavirenz and carbamazepine was demonstrated in this study."( Pharmacokinetic interaction between efavirenz and carbamazepine after multiple-dose administration in healthy subjects.
Damle, B; Grasela, DM; Ji, P; Kaul, S; Unger, SE; Xie, J, 2008
)
0.35
"CBZ and CBZE time-concentration profiles in various scenarios were generated based on a population pharmacokinetic study in Chinese epilepsy patients using Monte Carlo simulation."( The effect of poor compliance on the pharmacokinetics of carbamazepine and its epoxide metabolite using Monte Carlo simulation.
Ding, JJ; Jiao, Z; Wang, Y; Zhang, YJ, 2012
)
0.38
" Our methodology allowed for a precise pharmacokinetic assessment of clearance based on total quantity of parent drug and active metabolite removed."( Carbamazepine and carbamazepine-10,11-epoxide clearance measurements during continuous venovenous hemofiltration in a massive overdose.
Kearney, T; Petrie, MS; Smollin, CG, 2016
)
0.43
" Plasma samples had been collected and analyzed for CBZ and CBZE, then their noncompartmental pharmacokinetic parameters before and after CBD administration were determined."( The effect of cannabidiol on the pharmacokinetics of carbamazepine in rats.
Darweesh, RS; El-Elimat, T; Khamis, TN, 2020
)
0.56

Compound-Compound Interactions

ExcerptReferenceRelevance
"Steady state carbamazepine (CBZ) plasma concentrations were similar in 15 epileptics receiving monotherapy and in 24 patients taking CBZ in combination with one other anticonvulsant."( Carbamazepine 10, 11 epoxide concentrations in epileptics on carbamazepine alone and in combination with other anticonvulsants.
Brodie, MJ; Forrest, G; Rapeport, WG, 1983
)
0.27
" In addition, carbamazepine and carbamazepine 10, 11-epoxide concentrations were determined using a reference liquid chromatography combined with a tandem mass spectrometry (LC/MS/MS) reference method in another 15 specimens."( Effect of Carbamazepine 10, 11-Epoxide on Serum Carbamazepine Measurement Using a New CMIA Assay: Comparison of Values Obtained by Using PETINIA, CEDIA and Liquid Chromatography Combined with Tandem Mass Spectrometry.
Dasgupta, A; Davis, B; Johnson-Davis, KL; Slawson, MH, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
"The in-vitro dissolution profiles of two carbamazepine formulations (Tegretol and a generic carbamazepine) have been assessed and the bioavailability of carbamazepine compared in 12 epileptic children at steady-state."( Dissolution and relative bioavailability of two carbamazepine preparations for children with epilepsy.
Aleksandrowicz, J; Bowmer, CJ; Cawood, A; Forsythe, WI; Hartley, R, 1991
)
0.28
" No significant changes were determined for fraction of absorbed dose, volume of distribution, absorption rate constant, and elimination rate constant."( Increased carbamazepine plasma concentrations after fluoxetine coadministration.
Carter, JG; D'Mello, AP; D'Souza, MJ; Grimsley, SR; Jann, MW, 1991
)
0.28
" The bioavailability of CBZ from the two preparations was similar."( Treatment of epilepsy in mentally retarded patients with a slow-release carbamazepine preparation.
Anttila, M; Heinonen, E; Kaski, M; Sivenius, J; Tuominen, J, 1991
)
0.28
" Mean concentration values also differed significantly, which is explained by a somewhat reduced bioavailability (22% less) of the slow-release formulation."( Diurnal variation of carbamazepine and carbamazepine-10,11-epoxide in plasma and saliva in children with epilepsy: a comparison between conventional and slow-release formulations.
Arvidsson, J; Eeg-Olofsson, O; Grahn, PA; Gylje, H; Larsson, C; Nilsson, HL; Norén, L; Tonnby, B, 1990
)
0.28
"The relative bioavailability of carbamazepine mixture was studied after oral and rectal administration to healthy subjects."( Bioavailability of rectally administered carbamazepine mixture.
Neuvonen, PJ; Tokola, O, 1987
)
0.27
" Most oral formulations of carbamazepine are well absorbed with high bioavailability."( Clinical pharmacokinetics and pharmacological effects of carbamazepine and carbamazepine-10,11-epoxide. An update.
Bertilsson, L; Tomson, T,
)
0.13
"A comparative bioavailability study of carbamazepine (CBZ) in tablets and a syrup preparation was carried out in six volunteers, using a crossover design."( Simultaneous plasma carbamazepine and carbamazepine-epoxide concentrations in pharmacokinetic and bioavailability studies.
Dickinson, RG; Eadie, MJ; Hooper, WD; King, AR; Patterson, M, 1985
)
0.27
" An antacid did not affect the bioavailability of single CBZ doses given to three subjects and was therefore used to neutralize gastric juice when administering CBZ-E."( Single-dose kinetics and metabolism of carbamazepine-10,11-epoxide.
Bertilsson, L; Tomson, T; Tybring, G, 1983
)
0.27
" Accordingly, carbamazepine had a more rapid absorption rate from F-CBZ, DAK than from Tegretol in a comparative absorption test involving single-dose administration of 200 mg to 8 healthy volunteers."( Carbamazepine: a clinical biopharmaceutical study.
Christiansen, J; Dam, M; Helles, A; Jaegerskou, A; Kristensen, CB; Schmiegelow, M, 1981
)
0.26
" In rectal-resected rabbits, the bioavailability of CBZ and the plasma level of CBZ-E after rectal administration were significantly lower than those in normal rabbits, and furthermore these values after intracolostomal administration to colostoma-constructed rabbits tended to be lower than those in rectal-resected ones."( Decreased bioavailability of carbamazepine suppository after its intrarectal and intracolostomal administration to rectal-resected or colostoma-constructed rabbits.
Fujimoto, S; Kintsuji, S; Nagasawa, K; Nakanishi, H; Yamamoto, R, 2002
)
0.31
" In conclusion, berberine produced a dose-dependent increased bioavailability of digoxin and cyclosporine A by inhibition of intestinal P-gp."( Effect of berberine on the pharmacokinetics of substrates of CYP3A and P-gp.
Jiang, XH; Jin, JX; Ju, Y; Liu, CX; Qiu, W, 2009
)
0.35
" Moreover, the impact of body weight, absorption rate and co-therapy with other antiepileptic drugs (phenytoin, phenobarbital and valproic acid) on the dosage recommendation was investigated in the event of poor compliance."( The effect of poor compliance on the pharmacokinetics of carbamazepine and its epoxide metabolite using Monte Carlo simulation.
Ding, JJ; Jiao, Z; Wang, Y; Zhang, YJ, 2012
)
0.38
" Patient body weight, absorption rate and co-therapy with phenytoin, phenobarbital and valproic acid had no significant impact on the dose recommendation."( The effect of poor compliance on the pharmacokinetics of carbamazepine and its epoxide metabolite using Monte Carlo simulation.
Ding, JJ; Jiao, Z; Wang, Y; Zhang, YJ, 2012
)
0.38

Dosage Studied

ExcerptRelevanceReference
"01) in serum CBZ concentration were substantially less with CBZ-CR and were similar to those calculated during a 6 or 8 hourly dosage interval with conventional CBZ (fluctuation 33 +/- 3%, variation 42 +/- 5%)."( Monotherapy with conventional and controlled-release carbamazepine: a double-blind, double-dummy comparison in epileptic patients.
Blacklaw, J; Brodie, MJ; Butler, E; Gillham, RA; McKee, PJ, 1991
)
0.28
"The inhibitory effect of stiripentol (STP) on disposition of carbamazepine (CBZ) and carbamazepine-10,11-epoxide (CBZE) was quantitated to establish CBZ dosage reduction guidelines for future clinical add-on efficacy trials of STP."( Carbamazepine dose requirements during stiripentol therapy: influence of cytochrome P-450 inhibition by stiripentol.
Eddy, AC; Kerr, BM; Levy, RH; Martinez-Lage, JM; Tor, J; Viteri, C,
)
0.13
" During a dosing interval, no significant differences were observed with respect to trough or peak serum concentrations of CBZ and CBZ-10,11-epoxide (CBZ-E), the active metabolite."( A comparative pharmacokinetic study of conventional and chewable carbamazepine in epileptic patients.
Patsalos, PN, 1990
)
0.28
" Dosing was single blind."( Carbamazepine-10,11-epoxide in epilepsy. A pilot study.
Almkvist, O; Bertilsson, L; Nilsson, BY; Svensson, JO; Tomson, T, 1990
)
0.28
" One group (n = 6) received sodium valproate (1,100 mg/day) for 2 weeks, while the other group (n = 6) was given, for the same period, a dosage of VPM (1,200 mg/day) expected to produce VPA levels equivalent to those achieved with valproate."( Sodium valproate and valpromide: differential interactions with carbamazepine in epileptic patients.
Fazio, A; Gitto, C; Oteri, G; Perucca, E; Pisani, F; Ruello, C; Russo, F,
)
0.13
" These results suggest that flurithromycin can inhibit the conversion of CBZ to CBZ-E, although, at the dosage tested, the magnitude of this effect was significantly smaller than that observed after administration of erythromycin in the same subjects."( Effect of flurithromycin, a new macrolide antibiotic, on carbamazepine disposition in normal subjects.
Amione, C; Barzaghi, N; Crema, F; Faja, A; Gatti, G; Leone, L; Monteleone, M; Perucca, E, 1988
)
0.27
" In some patients, with pronounced fluctuation of plasma concentrations during the dosage interval, side effects may be avoided by more frequent dosing."( Clinical pharmacokinetics and pharmacological effects of carbamazepine and carbamazepine-10,11-epoxide. An update.
Bertilsson, L; Tomson, T,
)
0.13
" Differences in CBZ and CBZ-E disposition between day and night dosing were minor."( Intradose and circadian variation in circulating carbamazepine and its epoxide in epileptic patients: a consequence of autoinduction of metabolism.
Brodie, MJ; Butler, E; Macphee, GJ,
)
0.13
" The results demonstrate the bioequivalence of the dosage forms with respect to the extent of absorption, and similar steady-state concentrations of carbamazepine in plasma can be expected."( Bioequivalence of carbamazepine chewable and conventional tablets: single-dose and steady-state studies.
Chan, KK; Gerardin, A; Hall, NR; LeSher, AR; Redalieu, E; Sawchuk, RJ; Thompson, TA; Wagner, WE; Weeks, BJ, 1985
)
0.27
" dosing schedule, total plasma levels of CBZ and CBZ-E fluctuated to a similar extent (average 34% and 29%, respectively)."( Free and total plasma concentrations of carbamazepine and carbamazepine-10,11-epoxide in epileptic patients: diurnal fluctuations and relationship with side effects.
Albani, F; Ambrosetto, G; Baruzzi, A; Contin, M; Cortelli, P; Gobbi, G; Perucca, E; Procaccianti, G; Riva, R, 1984
)
0.27
" Relatively large fluctuations were observed for both CBZ (mean, 57%; range, 32-100%) and EP (mean, 97%; range, 19-189%) during a dosage interval."( Fluctuations in salivary carbamazepine and carbamazepine-10,11-epoxide concentrations during the day in epileptic children.
Aman, MG; Paxton, JW; Werry, JS, 1983
)
0.27
"Levels of carbamazepine and its -10,11-epoxide metabolite were measured in plasma and CSF of affectively ill patients treated only with carbamazepine for an average of 33 days at an average dosage of 1,055 mg/day."( Carbamazepine and its -10,11-epoxide metabolite in plasma and CSF. Relationship to antidepressant response.
Ballenger, JC; Bunney, WE; Chatterji, DC; Greene, RF; Post, RM; Uhde, TW, 1983
)
0.27
" After dosing with CBZ-E, peak plasma concentrations of the parent compound were reached within 2 hr."( Single-dose kinetics and metabolism of carbamazepine-10,11-epoxide.
Bertilsson, L; Tomson, T; Tybring, G, 1983
)
0.27
"Plasma carbamazepine (CBZ) and carbamazepine-10,11-epoxide (CBZ-E) concentrations were measured in 160 epileptic patients in order to determine the effect of factors such as age, daily dosing schedule, formulation, and combination with other antiepileptic drugs on these concentrations in relation to the daily dose."( Factors influencing plasma concentrations of carbamazepine and carbamazepine-10,11-epoxide in epileptic children and adults.
Bonato, PS; Campos, GM; Lanchote, VL; Rodrigues, I, 1995
)
0.29
" Fifty-two children between the age of 2 weeks and 15 years were treated with CBZ (mean dosage 17 mg/kg body weight) either as mono- (n = 36) or in polytherapy (n = 16)."( The metabolization of carbamazepine to CBZ-10,11-epoxide in children from the newborn age to adolescence.
Hannak, D; Haug, C; Korinthenberg, R, 1994
)
0.29
" No dosage adjustment is necessary when GBP and CBZ or VPA are coadministered."( Lack of interaction of gabapentin with carbamazepine or valproate.
Bockbrader, HN; Chang, T; Erdman, GR; Leppik, IE; Posvar, EL; Radulovic, LL; Sedman, AJ; Uthman, BM; Wilder, BJ,
)
0.13
" Phenobarbital cotreatment (45 mg/kg/day) with OXC (1100 mg/kg/day) did not lead to changes in the incidence of malformation when compared with OXC (1100 mg/kg/day) dosed alone."( Teratogenicity of carbamazepine-10, 11-epoxide and oxcarbazepine in the SWV mouse.
Amore, BM; Bennett, GD; Finnell, RH; Kalhorn, TF; Nelson, SD; Skiles, GL; Slattery, JT; Wlodarczyk, B, 1996
)
0.29
" Sectional hair analysis of a patient on a constant dosage of CBZ demonstrates an exponential decrease in hair concentrations of CBZ and CBZ-diol with increasing distance from the root, probably caused by shampooing."( High-performance liquid chromatographic determination of carbamazepine and metabolites in human hair.
Brekelmans, GJ; Edelbroek, PM; Rademaker, RV; Saris, LA; van der Linden, GJ, 1997
)
0.3
" The LTG dosage was increased step by step until clinical response or side effects were observed."( No increase in carbamazepine-10,11-epoxide during addition of lamotrigine treatment in children.
Boreus, LO; Eriksson, AS, 1997
)
0.3
" dosing with either Carbatrol (extended-release beads) or Tegretol-XR (an osmotic pump tablet, an Oros tablet) using compartmental method."( Reanalysis of carbamazepine and carbamazepine-epoxide pharmacokinetics after multiple dosing of extended release formulation.
Dechasathian, S; Konsil, J; Mason, DH; Stevens, RE,
)
0.13
" When compared to published literature of single dose data, the investigation of CBZ and CBZ-E pharmacokinetics from this study suggested that autoinduction might occur by the fifth day of dosing and might partly contribute to the sigmoidal shape of CBZ-E profiles."( Reanalysis of carbamazepine and carbamazepine-epoxide pharmacokinetics after multiple dosing of extended release formulation.
Dechasathian, S; Konsil, J; Mason, DH; Stevens, RE,
)
0.13
" Although race and sex appear to influence delavirdine pharmacokinetics, men and women and patients of different races should receive similar mg/kg dosage regimens."( Population pharmacokinetics of delavirdine and N-delavirdine in HIV-infected individuals.
Dicenzo, R; DiFrancesco, R; Fischl, M; Forrest, A; Friedland, G; Morse, GD; Para, M; Pollard, R; Shelton, M; Smith, PF, 2005
)
0.33
" Daily fluctuations in serum levels of carbamazepine and carbamazepine-10,11-epoxide did not appear to be related to the dosage schedule, but some patients tended to have lower fluctuations when the carbamazepine was given more frequently."( CSF concentrations and serum protein binding of carbamazepine and carbamazepine-10,11-epoxide in epileptic patients.
Bakke, J; Gerna, M; Johannessen, SI; Morselli, PL; Strandjord, RE, 1976
)
0.26
" Moreover, the impact of body weight, absorption rate and co-therapy with other antiepileptic drugs (phenytoin, phenobarbital and valproic acid) on the dosage recommendation was investigated in the event of poor compliance."( The effect of poor compliance on the pharmacokinetics of carbamazepine and its epoxide metabolite using Monte Carlo simulation.
Ding, JJ; Jiao, Z; Wang, Y; Zhang, YJ, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
marine xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
drug metabolitenull
allergenA chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
[role 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]

Drug Classes (3)

ClassDescription
epoxideAny cyclic ether in which the oxygen atom forms part of a 3-membered ring.
ureas
dibenzoazepine
[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]

Pathways (1)

PathwayProteinsCompounds
Carbamazepine Metabolism Pathway718

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
P2X purinoceptor 4Homo sapiens (human)IC50 (µMol)10.00000.15602.93526.1000AID1064727
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (36)

Processvia Protein(s)Taxonomy
regulation of ruffle assemblyP2X purinoceptor 4Homo sapiens (human)
tissue homeostasisP2X purinoceptor 4Homo sapiens (human)
regulation of sodium ion transportP2X purinoceptor 4Homo sapiens (human)
response to ischemiaP2X purinoceptor 4Homo sapiens (human)
signal transductionP2X purinoceptor 4Homo sapiens (human)
regulation of blood pressureP2X purinoceptor 4Homo sapiens (human)
positive regulation of calcium ion transport into cytosolP2X purinoceptor 4Homo sapiens (human)
negative regulation of cardiac muscle hypertrophyP2X purinoceptor 4Homo sapiens (human)
neuronal action potentialP2X purinoceptor 4Homo sapiens (human)
sensory perception of painP2X purinoceptor 4Homo sapiens (human)
calcium-mediated signalingP2X purinoceptor 4Homo sapiens (human)
positive regulation of prostaglandin secretionP2X purinoceptor 4Homo sapiens (human)
response to ATPP2X purinoceptor 4Homo sapiens (human)
monoatomic ion transmembrane transportP2X purinoceptor 4Homo sapiens (human)
response to fluid shear stressP2X purinoceptor 4Homo sapiens (human)
purinergic nucleotide receptor signaling pathwayP2X purinoceptor 4Homo sapiens (human)
endothelial cell activationP2X purinoceptor 4Homo sapiens (human)
positive regulation of blood vessel endothelial cell migrationP2X purinoceptor 4Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processP2X purinoceptor 4Homo sapiens (human)
behavioral response to painP2X purinoceptor 4Homo sapiens (human)
response to axon injuryP2X purinoceptor 4Homo sapiens (human)
positive regulation of calcium-mediated signalingP2X purinoceptor 4Homo sapiens (human)
regulation of chemotaxisP2X purinoceptor 4Homo sapiens (human)
sensory perception of touchP2X purinoceptor 4Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionP2X purinoceptor 4Homo sapiens (human)
membrane depolarizationP2X purinoceptor 4Homo sapiens (human)
positive regulation of calcium ion transportP2X purinoceptor 4Homo sapiens (human)
regulation of cardiac muscle contractionP2X purinoceptor 4Homo sapiens (human)
relaxation of cardiac muscleP2X purinoceptor 4Homo sapiens (human)
excitatory postsynaptic potentialP2X purinoceptor 4Homo sapiens (human)
calcium ion transmembrane transportP2X purinoceptor 4Homo sapiens (human)
cellular response to zinc ionP2X purinoceptor 4Homo sapiens (human)
cellular response to ATPP2X purinoceptor 4Homo sapiens (human)
apoptotic signaling pathwayP2X purinoceptor 4Homo sapiens (human)
positive regulation of microglial cell migrationP2X purinoceptor 4Homo sapiens (human)
positive regulation of endothelial cell chemotaxisP2X purinoceptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
purinergic nucleotide receptor activityP2X purinoceptor 4Homo sapiens (human)
extracellularly ATP-gated monoatomic cation channel activityP2X purinoceptor 4Homo sapiens (human)
signaling receptor bindingP2X purinoceptor 4Homo sapiens (human)
copper ion bindingP2X purinoceptor 4Homo sapiens (human)
protein bindingP2X purinoceptor 4Homo sapiens (human)
ATP bindingP2X purinoceptor 4Homo sapiens (human)
zinc ion bindingP2X purinoceptor 4Homo sapiens (human)
identical protein bindingP2X purinoceptor 4Homo sapiens (human)
cadherin bindingP2X purinoceptor 4Homo sapiens (human)
ligand-gated calcium channel activityP2X purinoceptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
lysosomal membraneP2X purinoceptor 4Homo sapiens (human)
plasma membraneP2X purinoceptor 4Homo sapiens (human)
membraneP2X purinoceptor 4Homo sapiens (human)
cell junctionP2X purinoceptor 4Homo sapiens (human)
neuronal cell bodyP2X purinoceptor 4Homo sapiens (human)
terminal boutonP2X purinoceptor 4Homo sapiens (human)
dendritic spineP2X purinoceptor 4Homo sapiens (human)
cell bodyP2X purinoceptor 4Homo sapiens (human)
perinuclear region of cytoplasmP2X purinoceptor 4Homo sapiens (human)
extracellular exosomeP2X purinoceptor 4Homo sapiens (human)
plasma membraneP2X purinoceptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID20163The ratio of brain-blood partitioning, (C brain / C blood).1996Journal of medicinal chemistry, Nov-22, Volume: 39, Issue:24
Computation of brain-blood partitioning of organic solutes via free energy calculations.
AID1064726Antagonist activity at human P2X4 receptor expressed in human 1321N1 cells assessed as inhibition of ATP-induced cytosolic calcium influx at 10 uM preincubated for 30 mins followed by ATP addition by Fluo-4 AM dye-based fluorescence assay2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Carbamazepine derivatives with P2X4 receptor-blocking activity.
AID409600Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes at 20 uM2009Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1
Inhibition of aquaporin 4 by antiepileptic drugs.
AID26047logBB, log(C brain / C blood)1996Journal of medicinal chemistry, Nov-22, Volume: 39, Issue:24
Computation of brain-blood partitioning of organic solutes via free energy calculations.
AID1064727Antagonist activity at human P2X4 receptor expressed in human 1321N1 cells assessed as inhibition of ATP-induced cytosolic calcium influx preincubated for 30 mins followed by ATP addition by Fluo-4 AM dye-based fluorescence assay2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Carbamazepine derivatives with P2X4 receptor-blocking activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (288)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990105 (36.46)18.7374
1990's109 (37.85)18.2507
2000's37 (12.85)29.6817
2010's33 (11.46)24.3611
2020's4 (1.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.29

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 Index24.29 (24.57)
Research Supply Index5.89 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials36 (11.08%)5.53%
Reviews6 (1.85%)6.00%
Case Studies15 (4.62%)4.05%
Observational0 (0.00%)0.25%
Other268 (82.46%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]