10,11-DIHYDRO-10-HYDROXYCARBAZEPINE

Chemical Properties

White Solid

Uses

A metabolite of Oxcarbazepine

Uses

A labelled metabolite of Oxcarbazepine

Uses

10,11-dihydro-10-hydroxy Carbamazepinee is the active metabolite of oxcarbazepine . Oxcarbazepine is rapidly and almost completely converted to 10,11-dihydro-10-hydroxycarbamazepine, which then demonstrates anticonvulsant efficacy by modulating several ion channels and receptors. 10,11-dihydro-10-hydroxy Carbamazepine is reported to inhibit both voltage-gated Na+ and Ca2+ channels, to potentiate voltage-gated K+ channels, to antagonize adenosine A1 receptors, to increase dopaminergic transmission, and to inhibit glutamate release.

Definition

ChEBI: A dibenzoazepine that is 5H-dibenzo[b,f]azepine, reduced across the C-10,11 positions and carrying a carbamoyl substituent at the azepine nitrogen and a hydroxy function at C-10. A voltage-gated sodium channel b ocker with anticonvulsant and mood-stabilizing effects, it is related to oxcarbazepine and is an active metabolite of oxcarbazepine.

Synthesis

36507-30-9

29331-92-8

Step-2: Synthesis of compound 3 1aH-dibenzo[b,f]epoxyvinyl[2,3-d]azepine-6(10bH)-carboxamide (5.03 g, 20 mmol) was dissolved in a solvent mixture of methanol (100 ml), dichloromethane (50 ml) and water (5 ml) at room temperature and protected by nitrogen. Ammonium formate (3.78 g, 60 mmol) and 10% palladium carbon catalyst (540 mg, 0.51 mmol Pd) were subsequently added. The reaction mixture was stirred for 1 h at room temperature and then filtered through diatomaceous earth to recover the catalyst. The filter cake was washed with dichloromethane (20 ml) and the combined filtrates were separated and the organic phase was dried with anhydrous sodium sulfate. After filtration, the solvent was evaporated by rotary evaporator at 40°C and absorber pressure to give the crude product 3. The crude product was purified by crystallization from ethyl acetate (20 ml) to give white crystalline 10-hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide (4.7 g, 93% yield).

in vivo

storage

Store at RT

References

[1] Patent: WO2013/167985, 2013, A1. Location in patent: Paragraph 00102; 00103
[2] Patent: US2016/122332, 2016, A1. Location in patent: Paragraph 0123-0124
[3] Patent: WO2006/75925, 2006, A2. Location in patent: Page/Page column 9-10
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1077 - 1088