Iminostilbene Carbamazepine

Iminostilbenes Carbamazepine (Tegretol) Oxcarbazepine (Trileptal) Similar to hydantoins... 

The useful antiepileptic agents belong to several chemical classes. Most of the drugs introduced before 1965 are closely related in structure to phenobarbital, the oldest member of this therapeutic class. These include the hydantoins, phenytoin, mephenytoin, and ethotoin the deoxybarbiturate, primidone the oxazolidine-diones, trimethadione, and paramethadione and the succinimides, ethosuximide, methsuximide, and phensuximide. The agents introduced after 1965 include the benzodiazepines clonazepan and clorazepate, an iminostilbene, carbamazepine, and a branched-chain carboxylic acid, valproic acid. 

Carbamazepine is a tricyclic iminostilbene derivative and structurally related to the tricyclic antidepressants. It is used as a first-line agent for the management of generalized tonic-clonic epilepsy. It is also highly effective for partial seizures but has no efficacy in patients with absence seizures or atonic seizures. In epilepsy it supposedly has the same mechanism of action as phenytoin. An other well... 

Carbamazepine is an iminostilbene derivative used as an anticonvulsant and for the relief of pain associated... 

Ju C, Uetreeht JP. Detection of-2-hydroxy iminostilbene in the urine of patients taking carbamazepine and its oxidation to a reactive iminoquinone intermediate. J Pharmacol Exp Ther 1999 288 51-56. 

Gas Chromatography. System GA—carbamazepine RI 2290, carbamazepine-10,11-epoxide RI 2030, iminostilbene RI 1930 system GE—carbamazepine retention time 0.83 relative to phenytoin system GF—carbamazepine RI 2610, carbamazepine-10,11-epoxide RI 2560, iminostilbene RI 2620. 

Chemical/Pharmaceutical/Other Class Synthetic iminostilbene derivative structurally similar to imipramine, a tricyclic antidepressant. While unrelated structurally, carbamazepine shares a similar therapeutic action with phenytoin Chemical Formula C15H12N2O Chemical Structure ... 

Nonetheless, even if only 5% of the ingested carbamazepine were excreted as iminostilbene, it would dominate the TPmixture due to its high potency relative to the parent compound. Thus, carbamazepine is clearly an example of a human pharmaceutical where the metabolite formation and metabolite ecotoxicity should be further investigated and where the environmental persistence and presence of iminostilbene should be explored experimentally. 

Carbamazepine, an iminostilbene compound, was introduced in the United States in 1974 for the treatment of trigeminal neuralgia. It has become a first-line drug for the treatment of generalized and partial complex seizure disorders, and has found expanded use for pain syndromes, psychiatric illnesses, and drug withdrawal reactions. 

Labeling of carbamazepine, an anti-epileptic, is carried out by conjugating the alkyne dicobalt hexacarbonyl entity to an amino derivative of the analyte 31 via peptide coupling with (N-succinimidyl-4-pentynoate) hexacarbonyl dicobalt 32 (Scheme 8.15) [45]. The amino derivative of carbamazepine 31 is prepared in one step from iminostilbene. (N-succinimidyl-4-pentynoate) hexacarbonyl dicobalt 32 is synthesized in two steps by esterification of pentynoic acid in the presence of NHS and DCC, followed by complexation of the triple bond by Co2(CO)g to give the tracer 33 [46]. 

This degradation takes place only when carbamazepine is injected onto the column as a methanol solution injection as an ethanol or acetone solution does not give any degradation reaction. The methanol present in the system, increases the acidity of the column, which produces the hydrolysis reaction to form iminostilbene and the extensive rearrangement to give 9-methylacridine. Carbamazepine-10,11-epoxide also decomposes when injected onto an... 

Mass chromatograms of selected ions together with TIC-curve indicating presence in a serum sample from an intoxication case of hexapropymate and -metabolite and carbamazepine. 1. Hexapropymate 2. Hexapropymate metabolite 3. Hexapropymate metabolite 4. Iminostilbene (pyrolysis product of carbamazepine) 5. Tri-2--butozyethyl phosphate (plasticizer in vacutainer) 6. Carbamazepine ... 

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