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10,11-Dihydrocarbamazepine Sale

(Synonyms: 10,11-二氢卡马西平) 目录号 : GC66057

10,11-二氢卡马西平(10,11-Dihydrocarbamazepine)用作液相色谱法同时测定血浆中卡马西平及其活性代谢物的内标。可用于化学发光法测定卡马西平的含量。

10,11-Dihydrocarbamazepine Chemical Structure

Cas No.:3564-73-6

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Quality Control & SDS

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产品描述

10,11-Dihydrocarbamazepine is the active metabolite of Oxcarbazepine. 10,11-Dihydrocarbamazepine also is an intermediate. Oxcarbazepine is rapidly and almost completely converted to 10,11-Dihydrocarbamazepine with probable Anticonvulsant efficacy[1].

Oxcarbazepine is metabolized in the liver to its active metabolite, 10,11-Dihydrocarbamazepine. Oxcarbazepine is an antiepileptic drug (AED) used to treat partial seizures as a monotherapy or adjunctive therapy[1].
10,11-Dihydrocarbamazepine may be used as a reference standard for the determination of 10,11-dihydrocarbamazepine in pharmaceutical formulations by liquid chromatography (LC)[1].

Chemical Properties

Cas No. 3564-73-6 SDF Download SDF
别名 10,11-二氢卡马西平
分子式 C15H14N2O 分子量 238.28
溶解度 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 4.1967 mL 20.9837 mL 41.9674 mL
5 mM 0.8393 mL 4.1967 mL 8.3935 mL
10 mM 0.4197 mL 2.0984 mL 4.1967 mL
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Research Update

Polymorphic Phase Transitions in Carbamazepine and 10,11-Dihydrocarbamazepine

Chemistry 2018 Sep 12;24(51):13573-13581.PMID:29979477DOI:10.1002/chem.201802368.

Temperature-induced phase transitions in carbamazepine (CBZ) and 10,11-Dihydrocarbamazepine (DHC) were studied by simultaneous differential scanning calorimetry-X-ray diffraction in this work. The transitions generally involve a transitional melt phase which is quickly followed by recrystallisation. The expansions of the unit cell as a function of temperature could be quantified and allow us to determine a directional order of stability in relation to the lattice constants. Dihydrocarbamazepine form II undergoes a conversion to form I by a localised melt phase. Carbamazepine (CBZ) form IV converts to form I at 182 °C, again by a localised intermediate melt phase. CBZ form II converted to form I at 119 °C by a pathway that appears to have included some melting, and form III underwent a part melt-recrystallisation and a part sublimation-recrystallisation to form I.

An orthorhombic polymorph of 10,11-Dihydrocarbamazepine

Acta Crystallogr C 2006 May;62(Pt 5):o240-2.PMID:16679591DOI:10.1107/S0108270106008651.

The title compound (systematic name: 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide), C15H14N2O, is shown to crystallize as an orthorhombic polymorph to complement the known monoclinic form. The molecular conformations of both forms are very similar, involving a bent conformation for the seven-membered azepine ring and an overall ;butterfly' shape. The molecules assemble into chains by way of N-H...O bonds and N-H...pi interactions in both crystal modifications. The two polymorphs appear to form due to different van der Waals interactions between the layer-like sheets of molecules.

Methanesulfonic acid salt forms of carbamazepine and 10,11-Dihydrocarbamazepine

Acta Crystallogr C 2013 Nov;69(Pt 11):1260-6.PMID:24192169DOI:10.1107/S010827011302859X.

New methanesulfonic acid salt forms of the anticonvulsant and analgesic active pharmaceutical ingredient carbamazepine and its closely related structural analogue 10,11-Dihydrocarbamazepine have been prepared and characterized by single-crystal X-ray diffraction at 120 and 100 K, respectively {namely [(5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H13N2O(+)·CH3SO3(-), and [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H15N2O(+)·CH3SO3(-)}. In light of the structural information obtained, the crystal structure of the carbamazepine trifluoroacetic acid monosolvate [dibenzo[b,f]azepine-5-carboxamide-trifluoroacetic acid (1/1), C15H12N2O·CF3COOH] was redetermined at 100 and 270 K, and from this data it was concluded that the protonation state for this solvate species is best described as in an `intermediate state' with the acidic proton located almost at the mid-point between the acid and base.

Liquid chromatographic methods for assay of carbamazepine, 10,11-Dihydrocarbamazepine, and related compounds in carbamazepine drug substance and tablets

J Assoc Off Anal Chem 1987 Sep-Oct;70(5):836-40.PMID:3680120doi

Liquid chromatographic (LC) methods have been developed for the determination of carbamazepine, the impurity 10,11-Dihydrocarbamazepine, and related compounds in carbamazepine drug substance and tablets. The LC methods specify a 5 micron diol column and a mobile phase of acetonitrile-methanol-0.05% aqueous acetic acid (5 + 5 + 90). Iminodibenzyl and iminostilbene, starting materials for some routes of synthesis, elute late in the LC system; therefore, a thin-layer chromatographic method for their detection at the 0.05% level has been developed. Eight tablet and 13 raw material samples from several sources were examined. The impurities most frequently found were 10, 11-dihydrocarbamazepine and a compound identified as 10-bromocarbamazepine at levels up to 1.3 and 0.5%, respectively; minimum detectable amounts were about 0.01 and 0.03%, respectively.

Analysis of carbamazepine and its active metabolite, carbamazepine-10,11-epoxide, in human plasma using high-performance liquid chromatography

Anal Bioanal Chem 2006 Nov;386(6):1931-6.PMID:17019579DOI:10.1007/s00216-006-0724-7.

A sensitive method based on high-performance liquid chromatography (HPLC) with ultraviolet (UV) detection was developed for the determination of carbamazepine (CBZ) and one of its active metabolites, carbamazepine-10,11-epoxide (CBZ-E) in human plasma. CBZ, CBZ-E and the internal standard (IS) 10,11-Dihydrocarbamazepine were extracted from human plasma into methyl tert-butyl ether. CBZ, CBZ-E and the IS were successfully separated on an RP C18 column with a mobile phase of acetonitrile:methanol:water (18:19:63, v/v/v) and monitored via UV detection at 210 nm. The calibration curves were linear over the concentration ranges of 0.01-10 microg/mL for CBZ and 0.005-5 microg/mL for CBZ-E in human plasma, respectively. The method displayed excellent sensitivity, precision and accuracy, and was successfully applied to the quantification of CBZ and CBZ-E in human plasma after oral administration of a single 200 mg CBZ CR tablet. This method is suitable for bioequivalence studies following single doses given to healthy volunteers.