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Merck
CN

C4206

Carbamazepine 10,11-epoxide

analytical standard

Synonym(s):

1a,10b-Dihydro-6H-dibenzo(b,f)oxireno[d]azepine-6-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C15H12N2O2
CAS Number:
36507-30-9
Molecular Weight:
252.27
NACRES:
NA.24
PubChem Substance ID:
329775057
UNSPSC Code:
41116107
MDL number:
MFCD00467137

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InChI

1S/C15H12N2O2/c16-15(18)17-11-7-3-1-5-9(11)13-14(19-13)10-6-2-4-8-12(10)17/h1-8,13-14H,(H2,16,18)

SMILES string

NC(=O)N1c2ccccc2C3OC3c4ccccc14

InChI key

ZRWWEEVEIOGMMT-UHFFFAOYSA-N

grade

analytical standard

assay

≥98% (HPLC)

technique(s)

gas chromatography (GC): suitable, liquid chromatography (LC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

storage temp.

−20°C

Quality Level

200

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General description

Carbamazepine 10,11-epoxide is a metabolite of the drug carbamazepine.

Application

Carbamazepine 10,11-epoxide may be used as a test material in the quantification of histone deacetylases(HDAC) inhibition using fluorescent HDAC activity assay.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

First metabolite of carbamazepine

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000453562
0000453562
0000450515
0000450516
0000450516

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Ping Ji et al.
Journal of clinical pharmacology, 48(8), 948-956 (2008-06-04)
The effect of efavirenz on the pharmacokinetics of carbamazepine and vice versa was investigated in adult healthy subjects in a randomized, open-label, 2-period crossover, multiple-dose study. Subjects were randomized to receive either efavirenz 600 mg qd for 14 days or
Ying-Chang Chi et al.
Toxicology and applied pharmacology, 263(3), 315-322 (2012-07-21)
Carbamazepine (CBZ), an antiepileptic with narrow therapeutic window, is a substrate of CYP 3A which metabolizes CBZ to carbamazepine-10,11-epoxide (CBZE), an active metabolite. This study investigated the acute and chronic effects of Polygonum cuspidatum (PC), a resveratrol-rich nutraceutical, on the
Luciana Vera-Candioti et al.
Electrophoresis, 29(22), 4527-4537 (2008-11-28)
Drug monitoring in serum samples was performed using second-order data generated by CE-DAD, processed with a suitable chemometric strategy. Carbamazepine could be accurately quantitated in the presence of its main metabolite (carbamazepine epoxide), other therapeutic drugs (lamotrigine, phenobarbital, phenytoin, phenylephrine
G Bellucci et al.
Journal of medicinal chemistry, 30(5), 768-773 (1987-05-01)
Carbamazepine 10,11-oxide (1a,10b-dihydro-6H-dibenzo[b,f]oxireno[d]azepine-6-carboxamide), a key intermediate in carbamazepine metabolism, was found to be unusually resistant to enzymatic hydrolysis when incubated with microsomal and cytosolic fractions from rabbit, rat, and guinea pig livers. However, its hydrolysis product, trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzo[b,f]azepine-5-carboxamide , was excreted
L Bertilsson et al.
Clinical pharmacokinetics, 11(3), 177-198 (1986-05-01)
Carbamazepine is a first-line drug in the treatment of most forms of epilepsy and also the drug of first choice in trigeminal neuralgia. Furthermore, it is now frequently used in bipolar depression. Most oral formulations of carbamazepine are well absorbed
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