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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

Key Documents

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Product Name

Carbamazepine 10,11-epoxide, analytical standard

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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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

General description

Carbamazepine 10,11-epoxide is a metabolite of the drug 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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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
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
Paul Houeto et al.
Regulatory toxicology and pharmacology : RTP, 62(1), 41-48 (2011-12-20)
Pharmaceutical residues have been detected at low (usually ng/L) concentrations in drinking water sources. The detection of drugs in water intended for human consumption (WIHC) has raised questions of safety. In the absence of regulatory or other official guidance, water
Regina Helena Costa Queiroz et al.
Journal of pharmaceutical and biomedical analysis, 48(2), 428-434 (2008-05-20)
A sensitive and reproducible stir bar-sorptive extraction and high-performance liquid chromatography-UV detection (SBSE/HPLC-UV) method for therapeutic drug monitoring of carbamazepine, carbamazepine-10,11-epoxide, phenytoin and phenobarbital in plasma samples is described and compared with a liquid:liquid extraction (LLE/HPLC-UV) method. Important factors in
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