QuickView for carbamazepine (compound)

Summary
General Info

PubChem

PubChem Compound 158856

Name:	Carbamazepine
PubChem Compound ID:	158856
Description:	An anticonvulsant used to control grand mal and psychomotor or focal seizures. Its mode of action is not fully understood, but some of its actions resemble those of PHENYTOIN; although there is little chemical resemblance between the two compounds, their three-dimensional structure is similar.
Molecular formula:	C₁₅H₁₆N₂O₃
Molecular weight:	272.299 g/mol
Synonyms:	85756-57-6; 5H-Dibenz(b,f)azepine-5-carboxamide, dihydrate; Carbamazepine dihydrate; 298-46-4

DrugBank

Identification

Name:	Carbamazepine
Name (isomeric):	DB00564
Drug Type:	small molecule
Description:	An anticonvulsant used to control grand mal and psychomotor or focal seizures. Its mode of action is not fully understood, but some of its actions resemble those of PHENYTOIN; although there is little chemical resemblance between the two compounds, their three-dimensional structure is similar.
Synonyms:	Carbamezepine
Brand:	Carbazepine, Tegretol-Xr, Carbelan, Calepsin, Finlepsin, Lexin, Carbatrol, Tegretol Cr, Novo-Carbamaz, Nu-Carbamazepine, Neurotol, Apo-Carbamazepine, Carbamazepen, Tegretal, Taro-Carbamazepine, Biston, Equetro, Taro-Carbamazepine Cr, Tegretol, Stazepin, Karbamazepin, Epitol, Teril, Tegretol Chewtabs, Sirtal, Timonil, Telesmin, Stazepine, Atretol
Category:	Analgesics, Non-Narcotic, Analgesics, Antimanic Agents, Anticonvulsants
CAS number:	298-46-4

Pharmacology

Indication:	For the treatment of epilepsy and pain associated with true trigeminal neuralgia.
Pharmacology:	Carbamazepine, an anticonvulsant structurally similar to tricyclic antidepressants, is used to treat partial seizures, tonic-clonic seizures, pain of neurologic origin such as trigeminal neuralgia, and psychiatric disorders including manic-depressive illness and aggression due to dementia.
Mechanism of Action:	Carbamazepine inhibits sustained repetitive firing by blocking use-dependent sodium channels. Pain relief is believed to be associated with blockade of synaptic transmission in the trigeminal nucleus and seizure control with reduction of post-tetanic potentiation of synaptic transmission in the spinal cord. Carbamazepine also possesses anticholiner... show more » Carbamazepine inhibits sustained repetitive firing by blocking use-dependent sodium channels. Pain relief is believed to be associated with blockade of synaptic transmission in the trigeminal nucleus and seizure control with reduction of post-tetanic potentiation of synaptic transmission in the spinal cord. Carbamazepine also possesses anticholinergic, central antidiuretic, antiarrhythmic, muscle relaxant, antidepressant (possibly through blockade of norepinephrine release), sedative, and neuromuscular-blocking properties. show less «
Protein binding:	Carbamazepine in blood is 76% bound to plasma proteins.
Biotransformation:	Hepatic
Half Life:	25-65 hours
Toxicity:	Mild ingestions cause vomiting, drowsiness, ataxia, slurred speech, nystagmus, dystonic reactions, and hallucinations. Severe intoxications may produce coma, seizures, respiratory depression, and hypotension
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol.

Avoid taking grapefruit or grapefruit juice throughout treatment.

Grapefruit can significantly increase serum levels of this product.

Take with food, increases availability and reduces irritation.

Drug interaction:

Midazolam	Carbamazepine may decrease the effect of the benzodiazepine, midazolam.
Metocurine	Decreases the effect of muscle relaxant
Atracurium	Decreases the effect of muscle relaxant
Oxtriphylline	Carbamazepine may decrease the serum concentration of oxtriphylline. Oxtriphylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
Nortriptyline	Carbamazepine may decrease the serum concentration of the tricyclic antidepressant, nortriptyline, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if carbamazepine is initiated, discontinued or dose changed.

Midazolam	Carbamazepine may decrease the effect of the benzodiazepine, midazolam.
Metocurine	Decreases the effect of muscle relaxant
Atracurium	Decreases the effect of muscle relaxant
Oxtriphylline	Carbamazepine may decrease the serum concentration of oxtriphylline. Oxtriphylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
Nortriptyline	Carbamazepine may decrease the serum concentration of the tricyclic antidepressant, nortriptyline, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if carbamazepine is initiated, discontinued or dose changed.
Fluconazole	Fluconazole may increase the therapeutic and adverse effects of carbamazepine.
Simvastatin	Carbamazepine, a p-glycoprotein inducer, may decrease the effect of simvastatin by increasing its efflux. Monitor for changes in the therapeutic and adverse effects of simvastatin if carbamazepine is initiated, discontinued or dose changed.
Tretinoin	The strong CYP2C8 inducer, Carbamazepine, may increase the metabolism and clearance of oral Tretinoin. Consider alternate therapy to avoid failure of Tretinoin therapy or monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Carbamazepine is initiated, discontinued or dose changed.
Risperidone	Decreases the effect of risperidone
Delavirdine	The anticonvulsant, carbamazepine, decreases the effect of delavirdine.
Praziquantel	Markedly lower praziquantel levels
Lamotrigine	Lamotrigine may increase the adverse effects of carbamazepine by increasing the concentration of its active metabolite, carbamazepine-epoxide. Carbamazepine may decrease the therapeutic effect of lamotrigine by increasing its metabolism. Lamotrigine doses should be adjusted accordingly. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinue or doses are changed.
Verapamil	Verapamil may increase the serum concentration of Carbamazepine by decreasing its metabolism. Monitor for changes in the therapeutic/adverse effects of Carbamazepine if Verapamil is initiated, discontinued or dose changed.
Tubocurarine	Decreases the effect of muscle relaxant
Desipramine	Carbamazepine may decrease the serum concentration of the tricyclic antidepressant, desipramine, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of desipramine if carbamazepine is initiated, discontinued or dose changed.
Propoxyphene	Propoxyphene increases the effect of carbamazepine
Erythromycin	The macrolide, erythromycin, may increase the effect of carbamazepine.
Imipramine	Carbamazepine may decrease the serum concentration of the tricyclic antidepressant, imipramine, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if carbamazepine is initiated, discontinued or dose changed.
Isoniazid	Carbamazepine effect is increased as is isoniazid toxicity
Ticlopidine	Ticlopidine increases the effect of carbamazepine
Tacrolimus	Carbamazepine may decrease the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Carbamazepine therapy is initiated, discontinued or altered.
Anisindione	Carbamazepine may decrease the anticoagulant effect of anisindione by decreasing its serum concentration.
Temsirolimus	Carbamazepine may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
Aprepitant	The CYP3A4 inducer, carbamazepine, may decrease the effect of aprepitant.
Clozapine	Carbamazepine may decrease the serum concentration of clozapine by increasing its metabolism. Concomitant therapy should also be avoided due to increased risk of bone marrow suppression. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of clozapine if carbamazepine is initiated, discontinued or dose changed.
Valproic Acid	Decreases the effect of valproic acid
Itraconazole	Itraconazole may increase the effect of carbamazepine.
Vilazodone	Carbamazepine may increase the metabolism of Selective Serotonin Reuptake Inhibitors (SSRI). Specifically those agents metabolized via CYP1A2, 2C, and/or 3A4 isoenzymes. Selective Serotonin Reuptake Inhibitors may decrease the metabolism of Carbamazepine. Specifically those SSRIs that inhibit CYP3A4 isoenzymes.
Cyclosporine	Carbamazepine may decrease the therapeutic effect of cyclosporine.
Triprolidine	The CNS depressants, Triprolidine and Carbamazepine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Doxycycline	The anticonvulsant, carbamazepine, may decrease the therapeutic effect of doxycycline.
Theophylline	Carbamazepine may decrease the serum concentration of theophylline. Theophylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
Metronidazole	Metronidazole increases the effect of carbamazepine
Ritonavir	Ritonavir increases the effect of carbamazepine
Levonorgestrel	Carbamazepine may decrease the contraceptive effect of levonorgestrel.
Telithromycin	Co-administration may cause decreased Telithromycin and increased Carbemazepine plasma concentrations. Consider alternate therapy.
Quinupristin	This combination presents an increased risk of toxicity
Dicumarol	Carbamazepine may decrease the anticoagulant effect of dicumarol by decreasing its serum concentration.
Ethinyl Estradiol	Carbamazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with carbamazepine.
Isotretinoin	Isotretinoine decreases the effect of carbamazepine
Mestranol	This product may cause a slight decrease of contraceptive effect
Aminophylline	Carbamazepine may decrease the serum concentration of aminophylline. Aminophylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
Pancuronium	Decreases the effect of muscle relaxant
Mivacurium	Decrease the effect of muscle relaxant
Josamycin	The macrolide, josamycin, may increase the effect of carbamazepine.
Clarithromycin	Clarithromycin may decrease the metabolism of carbamazepine. Monitor for changes in the therapeutic or adverse effects of carbamazepine if clarithromycin is initiated, discontinued or dose changed.
Voriconazole	Carbamazepine may reduce serum concentrations and efficacy of voriconazole likely by increasing its metabolism. Concomitant voriconazole and carbamazepine therapy is contraindicated.
Lovastatin	Carbamazepine, a p-glycoprotein inducer and strong CYP3A4 inducer, may decrease the effect of lovastatin by increasing its efflux and metabolism. Monitor for changes in the therapeutic and adverse effects of lovastatin if carbamazepine is initiated, discontinued or dose changed.
Methadone	Carbamazepine may decrease the serum level of methadone. Monitor for changes in the therapeutic and adverse effects of methadone if carbamazepine is initiated, discontinued or dose changed.
Troleandomycin	The macrolide, troleandomycin, may increase the effect of carbamazepine.
Diltiazem	Carbamazepine may decrease the serum concentration of diltiazem by increasing its metabolism. Diltiazem may increase the serum concentration of carbamazepine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if dosages are changed.
Nefazodone	Nefazodone increases the effect of carbamazepine
Sertraline	Sertraline increases the effect of carbamazepine
Fluvoxamine	Fluvoxamine increases the effect of carbamazepine
Trazodone	The CYP3A4 inducer, Carbamazepine, may decrease Trazodone efficacy by increasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Carbamazepine is initiated, discontinued or dose changed.
Topiramate	Carbamazepine may decrease the effectiveness of Topiramate by increase its clearance. Monitor for changes in the therapeutic and adverse effects of Topiramate if Carbamazepine is initiated, discontinued or dose changed. Adverse effects related to CNS depression have also been observed during concomitant therapy.
Felodipine	Carbamazepine may increase the metabolism of felodipine. Monitor for changes in the therapeutic and adverse effects of felodipine if carbamazepine is initiated, discontinued or dose changed.
Alprazolam	Carbamazepine may decrease the effect of the benzodiazepine, alprazolam.
Gefitinib	The CYP3A4 inducer, carbamazepine, may decrease the serum concentration and therapeutic effects of gefitinib.
Doxacurium chloride	Decreases the effect of muscle relaxant
Cimetidine	Cimetidine may increase the serum concentration of carbamazepine during the first few days of concomitant therapy. Monitor for changes in the therapeutic and adverse effects of carbamazepine if cimetidine is initiated, discontinued or dose changed.
Felbamate	Decreased effect of both products
Dabigatran etexilate	P-Glycoprotein inducers such as carbamazepine may decrease the serum concentration of dabigatran etexilate. This combination should be avoided.
Tipranavir	Concomitant use may result in decreased Tipranavir and increased Carbamazepine concentrations.
Atorvastatin	Carbamazepine, a p-glycoprotein inducer and strong CYP3A4 inducer, may decrease the effect of atorvastatin by increasing its efflux and metabolism. Monitor for changes in the therapeutic and adverse effects of atorvastatin if carbamazepine is initiated, discontinued or dose changed.
Ziprasidone	Increases the effect and toxicity of ziprasidone
Warfarin	Carbamazepine may decrease the anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if carbamazepine is initiated, discontinued or dose changed.
Doxepin	Carbamazepine may decrease the serum concentration of the tricyclic antidepressant, doxepin, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if carbamazepine is initiated, discontinued or dose changed.
Divalproex sodium	Carbamazepine may decrease the effect of divalproex by increasing it metabolism. Divalproex may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or altered (i.e. dosages adjusted).
Imatinib	Carbamazepine, a strong CYP3A4 inducer, may increase the metabolism of imatinib. Imatinib, a strong CYP3A4 inhibitor, may increase the metabolism of carbamazepine. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose changed.
Aripiprazole	Carbamazepine, a strong CYP3A4 inducer, may decrease the serum concentration of aripiprazole by increasing its metabolism.
Levetiracetam	Concomitant therapy may results in additive adverse CNS effects.
Danazol	Danazol may decrease the metabolism of carbamazepine. Monitor for changes in the therapeutic and adverse effects of carbamazepine if danazol is initiated, discontinued or dose changed.
Acenocoumarol	Carbamazepine may decrease the anticoagulant effect of acenocoumarol by decreasing its serum concentration.
Bupropion	Carbamazepine, a strong CYP2B6 inducer, may increase the metabolism of bupropion. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bupropion if carbamazepine is initiated, discontinued or dose changed.
Sunitinib	Possible decrease in sunitinib levels
Haloperidol	Carbamazepine may decrease the serum concentration of haloperidol by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of haloperidol if carbamazepine is initiated, discontinued or dose changed.
Oxybutynin	Oxybutynin may cause carbamazepine toxicity
Norethindrone	This product may cause a slight decrease of contraceptive effect
Dyphylline	Carbamazepine may decrease the serum concentration of diphylline. Diphylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
Fluoxetine	Carbamazepine may decrease the serum concentration of fluoxetine by increasing its metabolism. Fluoxetine may increase the serum concentration of carbamazepine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or doses are changed.
Ketoconazole	Ketoconazole may increase the effect of carbamazepine.
Methylphenidate	Carbamazepine may decrease the effect of methylphendiate.
Amitriptyline	Carbamazepine may decrease the serum concentration of the tricyclic antidepressant, amitriptyline, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amitriptyline if carbamazepine is initiated, discontinued or dose changed.
Indinavir	Indinavir increases the effect and toxicity of carbamazepine
Tramadol	Carbamazepine may decrease the effect of tramadol by increasing Tramadol metabolism and clearance.
Vecuronium	Decreases the effect of muscle relaxant

show less «

Targets

Sodium channel protein type 5 subunit alpha

Enzymes

Transporters

Multidrug resistance protein 1