Oxcarbazepine, an antiepileptic agent

Kalis, Michelle M.

doi:10.1016/s0149-2918(01)80019-9

Cited by 90 publications

(64 citation statements)

References 51 publications

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“…antiepileptic drug (AED) in several years to be FDA-approved in 2000 as a monotherapy for the treatment of partial seizures in adults [3,4].…”

Section: Open Accessmentioning

confidence: 99%

“…Accordingly, 11a was obtained by reaction of 11 with methyl propiolate catalysed by TEA in MeCN-DMF (4:1) at r.t. for 1 hour. The transient O-vinyl oxime derivative underwent a tandem [3,3]-sigmatropic rearrangement-cyclocondensation to 11a (57% isolated yield). This reaction is usually reported [21] to require more drastic conditions (DMSO, >90 °C) than those reported here.…”

Section: Scheme 2 [3+2] Fischer Indolization Like Strategymentioning

confidence: 99%

“…Yield = 94%. [1,3]oxazolo [4,5- (10). 9 (100 mg, 0.37 mmol), pyridine (30 μL, 0.37 mmol) and benzoyl chloride (108 μL, 0.93 mmol) were added to chlorobenzene (5 mL).…”

Section: -(2-pyridinylhydrazono)-1011-dihydro-5h-dibenzo[bf]azepimentioning

confidence: 99%

“…8H- [1,2,3]Thiadiazolo [4,5- (13). Thionyl chloride (5 mL) was cooled to −10 °C with an ice/NaCl bath, 12 (496 mg, 1.60 mmol) was slowly added and the reaction mixture was left rise to r.t. under stirring.…”

Section: -(Carbamoylhydrazono)-1011-dihydro-5h-dibenzo[bf]azepinementioning

confidence: 99%

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A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

et al. 2013

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A library of new heterocyclic systems was synthesized starting from oxcarbazepine (OXC, Trileptal ® , 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide). The key for these transformations is the α-enolizable ketone present on the [d]-side of our starting material OXC, thus, an in depth investigation of the literature to find heteroannulation reactions for substrates carrying an α-enolizable ketone gave us a boost to discover an excellent derivatization strategy and [3+2], [4+2] and [4+1] approaches were successfully developed. Almost always a pre-functionalization was needed, but also the direct one-pot heterocycle construction was also explored.

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“…antiepileptic drug (AED) in several years to be FDA-approved in 2000 as a monotherapy for the treatment of partial seizures in adults [3,4].…”

Section: Open Accessmentioning

confidence: 99%

Section: Scheme 2 [3+2] Fischer Indolization Like Strategymentioning

confidence: 99%

“…Yield = 94%. [1,3]oxazolo [4,5- (10). 9 (100 mg, 0.37 mmol), pyridine (30 μL, 0.37 mmol) and benzoyl chloride (108 μL, 0.93 mmol) were added to chlorobenzene (5 mL).…”

Section: -(2-pyridinylhydrazono)-1011-dihydro-5h-dibenzo[bf]azepimentioning

confidence: 99%

Section: -(Carbamoylhydrazono)-1011-dihydro-5h-dibenzo[bf]azepinementioning

confidence: 99%

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A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

et al. 2013

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“…Oxcarbazepine (OXC) is a keto-analogue of carbamazepine (CBZ) and approved as a monotherapy or adjunctive therapy to treat partial seizures in adults and children (1). It has less severe cutaneous adverse drug reactions (cADRs) and thus a safer choice for CBZ-intolerant patients (2).…”

Section: Introductionmentioning

confidence: 99%

Association Between HLA genotypes and Oxcarbazepine-induced Cutaneous Adverse Drug Reactions: A Systematic Review and Meta-Analysis

2018

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-PURPOSE:To systematically review and quantitatively synthesize associations between HLA genotypes and oxcarbazepine-induced cutaneous adverse drug reactions (OXC-cADRs), including StevensJohnson syndrome (SJS) and maculopapular rash. METHODS: Studies investigating associations between HLA genotypes and OXC-cADRs were systematically searched irrespective of language, in PubMed, HuGENet (Human Genome Epidemiology Network), and the Cochrane Library from their inception until January, 2017. Inclusion criteria were studies investigating associations between HLA genotypes and OXCcADRs that reported sufficient data for calculating the frequency of HLA genotype carriers among cases and controls. Overall odds ratios (ORs) with corresponding 95%CIs were calculated using a random-effects model to determine the association between HLA genotypes and OXC-cADRs. RESULTS: The initial searches identified 91 articles, of which 6 studies met the selection criteria. . CONCLUSIONS: Strong associations between the HLA-B*1502 and OXC-cADRs (SJS and maculopapular rash) were found in both controls from general population and OXC-tolerant groups. There was also an association between HLA-B*3101 and OXCinduced maculopapular rash. For patient safety, genetic screening especially for HLA-B*1502 prior to OXC therapy at least in these closely related ethnicities is warranted. Further studies need to better define other ethnicities at risk and a wider range of MHC gene subtypes.

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