Tìm theo
Carbamazepine
Các tên gọi khác (11 ) :
  • 5-Carbamoyl-5H-dibenz(b,f)azepine
  • 5-Carbamoyl-5H-dibenz[b,F]azepine
  • 5-Carbamoyl-5H-dibenzo(b,F)azepine
  • 5-Carbamyl-5H-dibenzo(b,F)azepine
  • 5H-Dibenz(b,F)azepine-5-carboxamide
  • Carbamazepen
  • Carbamazepin
  • Carbamazepina
  • Carbamazépine
  • Carbamazepinum
  • CBZ
Thuốc điều trị về tâm thần
Thuốc Gốc
Small Molecule
CAS: 298-46-4
ATC: N03AF01
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C15H12N2O
PTK: 236.2686
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. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C15H12N2O
Phân tử khối
236.2686
Monoisotopic mass
236.094963016
InChI
InChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)
InChI Key
InChIKey=FFGPTBGBLSHEPO-UHFFFAOYSA-N
IUPAC Name
2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide
Traditional IUPAC Name
tegretol
SMILES
NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12
Độ tan chảy
204-206
Độ hòa tan
17.7 mg/L
logP
2.45
logS
-3.2
pKa (strongest acidic)
15.96
pKa (Strongest Basic)
-3.8
PSA
46.33 Å2
Refractivity
71.89 m3·mol-1
Polarizability
25 Å3
Rotatable Bond Count
0
H Bond Acceptor Count
1
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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. The response to carbamazepine is variable and may be due to its variable transport, especially across the blood-brain-barrier. The transporter that may confer drug resistance is RALBP1.
Cơ Chế Tác Dụng : 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. [PubChem] 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.
Dược Động Học :
▧ Absorption :
In clinical studies, carbamazepine suspension, conventional tablets, and extended-release tablets delivered equivalent amounts of drug to the systemic circulation. However, it has been observed that the suspension is somewhat faster absorbed. Furthermore, the extended-release tablet is slightly slower than the conventional tablet. The bioavailability of the extended-release tablet is 89%, compared to the suspension. Plasma levels of carbamazepine are variable. The time to peak concentration for the different formulations are as follows: Suspension = 1.5 hours; Conventional tablets = 4-5 hours; Extended-release tablets = 3-12 hours.
▧ Protein binding :
76% bound to plasma proteins.
▧ Metabolism :
Hepatic. CYP3A4 is the primary isoform responsible for the formation of carbamazepine-10,11-epoxide. This metabolite is active and shown to be equipotent to carbamazepine as an anticonvulsant. Carbamazepine is more rapidly metabolized to the aforementioned metabolite in younger patients than in adults. It also undergoes glucuronidation via UGT2B7, however this finding has been disputed.
▧ Route of Elimination :
72% of the dose is in the urine while 28% is in the feces. Hydroxylated and conjugated metabolites are largely what was recovered in the urine. 3% of the dose is recovered as unchanged carbamazepine.
▧ Half Life :
Initial half-life values range from 25-65 hours, decreasing to 12-17 hours on repeated doses.
Độc Tính : Mild ingestions cause vomiting, drowsiness, ataxia, slurred speech, nystagmus, dystonic reactions, and hallucinations. Severe intoxications may produce coma, seizures, respiratory depression, and hypotension
Chỉ Định : For the treatment of epilepsy and pain associated with true trigeminal neuralgia.
Tương Tác Thuốc :
  • Abiraterone Strong CYP3A4 inducers may decrease levels of abiraterone. Monitor concomitant therapy closely.
  • Acenocoumarol Carbamazepine may decrease the anticoagulant effect of acenocoumarol by decreasing its serum concentration.
  • Alprazolam Carbamazepine may decrease the effect of the benzodiazepine, alprazolam.
  • 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.
  • 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.
  • Anisindione Carbamazepine may decrease the anticoagulant effect of anisindione by decreasing its serum concentration.
  • Aprepitant The CYP3A4 inducer, carbamazepine, may decrease the effect of aprepitant.
  • Aripiprazole Carbamazepine, a strong CYP3A4 inducer, may decrease the serum concentration of aripiprazole by increasing its metabolism.
  • Asenapine Carbamazepine is a CYP1A2 inducer that decreases asenapine's exposure by 20%.
  • 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.
  • Atracurium Decreases the effect of muscle relaxant
  • Bendamustine Decreases levels of bendamustine by affecting CYP1A2 hepatic enzyme metabolism. May increase concentrations of active metabolites.
  • Boceprevir Strong CYP3A4 inducers will decrease levels of boceprevir. Concomitant therapy is contraindicated.
  • 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.
  • Cabazitaxel Concomitant therapy with a strong CYP3A inducer may decrease concentrations of cabazitaxel. Avoid concomitant therapy.
  • 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.
  • 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.
  • 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.
  • Cyclosporine Carbamazepine may decrease the therapeutic effect of cyclosporine.
  • Dabigatran etexilate P-Glycoprotein inducers such as carbamazepine may decrease the serum concentration of dabigatran etexilate. This combination should be avoided.
  • Dabrafenib Strong CYP3A4 inducers may decrease levels of dabrafenib. Consider alternate therapy.
  • 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.
  • Delavirdine The anticonvulsant, carbamazepine, decreases the effect of delavirdine.
  • 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.
  • Dextropropoxyphene Propoxyphene increases the effect of carbamazepine
  • Dicoumarol Carbamazepine may decrease the anticoagulant effect of dicumarol by decreasing its serum concentration.
  • 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.
  • Doxacurium chloride Decreases the effect of muscle relaxant
  • 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.
  • Doxycycline The anticonvulsant, carbamazepine, may decrease the therapeutic effect of doxycycline.
  • 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.
  • Eltrombopag Affects hepatic CYP1A2 metabolism, will decrease effect/level of eltrombopag. Affects hepatic CYP2C9/10 metabolism, will decrease effect/level of eltrombopag.
  • Erythromycin The macrolide, erythromycin, may increase the effect of carbamazepine.
  • Estradiol valerate/Dienogest Affects CYP3A4 metabolism, decreases or effects levels of Estradiol valerate/Dienogest.
  • Ethinyl Estradiol Carbamazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with carbamazepine.
  • Etravirine Carbamazepine, when used concomitantly with certain NNRTIs (ie. efavirenz), may experience a decrease in serum concentration. Etravirine, and other NNRTIs, when used concomitantly with carbamazepine, may experience an increase in serum concentration. It is recommended to avoid this combination.
  • Ezogabine Ezogabine increases the clearance of carbamazepine (30%). The mechanism of this interaction is unknown.
  • Felbamate Decreased effect of both products
  • 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.
  • Fluconazole Fluconazole may increase the therapeutic and adverse effects of carbamazepine.
  • 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.
  • Fluvoxamine Fluvoxamine increases the effect of carbamazepine
  • Gefitinib The CYP3A4 inducer, carbamazepine, may decrease the serum concentration and therapeutic effects of gefitinib.
  • 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.
  • 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.
  • 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.
  • Indinavir Indinavir increases the effect and toxicity of carbamazepine
  • Isoniazid Carbamazepine effect is increased as is isoniazid toxicity
  • Isotretinoin Isotretinoine decreases the effect of carbamazepine
  • Itraconazole Itraconazole may increase the effect of carbamazepine.
  • Ivacaftor Strong CYP3A4 inducers may decrease levels of ivacaftor. Monitor concomitant therapy closely.
  • Josamycin The macrolide, josamycin, may increase the effect of carbamazepine.
  • Ketoconazole Ketoconazole may increase the effect of carbamazepine.
  • 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.
  • Levetiracetam Concomitant therapy may results in additive adverse CNS effects.
  • Levonorgestrel Carbamazepine may decrease the contraceptive effect of levonorgestrel.
  • Linagliptin CYP3A4 and p-glycoprotein inducers may decreases levels of linagliptin. Monitor concomitant therapy closely.
  • 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.
  • Lurasidone Concomitant therapy with a CYP3A4 inducer will decrease levels of lurasidone. Coadministration with lurasidone is contraindicated.
  • Mestranol This product may cause a slight decrease of contraceptive effect
  • 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.
  • Methylphenidate Carbamazepine may decrease the effect of methylphendiate.
  • Metocurine Decreases the effect of muscle relaxant
  • Metronidazole Metronidazole increases the effect of carbamazepine
  • Midazolam Carbamazepine may decrease the effect of the benzodiazepine, midazolam.
  • Mivacurium Decrease the effect of muscle relaxant
  • Nefazodone Nefazodone increases the effect of carbamazepine
  • Norethindrone This product may cause a slight decrease of contraceptive effect
  • 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.
  • 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.
  • Oxybutynin Oxybutynin may cause carbamazepine toxicity
  • Pancuronium Decreases the effect of muscle relaxant
  • Pazopanib Affects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib. Consider alternate therapy.
  • Ponatinib Strong CYP3A4 inducers may decrease levels of ponatinib. Monitor concomitant therapy closely.
  • Ponatinib Strong CYP3A4 inducers may decrease levels of ponatinib. Monitor concomitant therapy closely.
  • Praziquantel Markedly lower praziquantel levels
  • Quinupristin This combination presents an increased risk of toxicity
  • Regorafenib Strong CYP3A4 inducers may decrease levels of regorafenib.
  • Rilpivirine Strong inducers of CYP3A4 decrease the exposure of rilpivirine thus decreasing efficacy.
  • Risperidone Decreases the effect of risperidone
  • Ritonavir Ritonavir increases the effect of carbamazepine
  • Roflumilast Affects CYP3A4 metabolism, decreases level or effect of roflumilast. Also decreases the level or effect of roflumilast by affecting CYP1A2 metabolism.
  • Rufinamide Decrease concentration of rufinamide thus monitor therapy
  • Sertraline Sertraline increases the effect 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.
  • Sunitinib Possible decrease in sunitinib levels
  • 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.
  • Telithromycin Co-administration may cause decreased Telithromycin and increased Carbemazepine plasma concentrations. Consider alternate therapy.
  • Temsirolimus Carbamazepine may increase the metabolism of Temsirolimus decreasing its efficacy. Concomitant therapy should be avoided.
  • 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.
  • Ticlopidine Ticlopidine increases the effect of carbamazepine
  • Tipranavir Concomitant use may result in decreased Tipranavir and increased Carbamazepine concentrations.
  • Tolvaptan Carbamazepine is a CYP3A4 inducer and will decrease serum concentrations of tolvaptan and ultimately, its clinical effects.
  • 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.
  • Tramadol Carbamazepine may decrease the effect of tramadol by increasing Tramadol metabolism and clearance.
  • 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.
  • 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.
  • Triprolidine The CNS depressants, Triprolidine and Carbamazepine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
  • Troleandomycin The macrolide, troleandomycin, may increase the effect of carbamazepine.
  • Tubocurarine Decreases the effect of muscle relaxant
  • Ulipristal Concomitant therapy with strong CYP3A4 inducers may decrease plasma concentrations of ulipristal and ultimately its effectiveness. Avoid combination therapy.
  • Valproic Acid Decreases the effect of valproic acid
  • Vandetanib Decreases levels of vandetanib by affecting CYP3A4 metabolism. Contraindicated.
  • Vecuronium Decreases the effect of muscle relaxant
  • Vemurafenib Strong CYP3A4 inducers may decrease levels of vemurafenib. Monitor concomitant therapy closely.
  • 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.
  • 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.
  • Voriconazole Carbamazepine may reduce serum concentrations and efficacy of voriconazole likely by increasing its metabolism. Concomitant voriconazole and carbamazepine therapy is contraindicated.
  • 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.
  • Ziprasidone Increases the effect and toxicity of ziprasidone
Liều Lượng & Cách Dùng : Capsule, extended release - Oral - 100 mg, 200 mg, 300 mg
Suspension - Oral - 100 mg/5 mL
Tablet - Oral - 200 mg
Tablet, chewable - Oral - 100 mg
Tablet, extended release - Irrigation - 100 mg, 200 mg, 400 mg
Dữ Kiện Thương Mại
Giá thị trường
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Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00564
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2554
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507583
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06868
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00252
ChemSpider
http://www.chemspider.com/Chemical-Structure.2457.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0228-2143-10
PharmGKB
http://www.pharmgkb.org/drug/PA448785
Wikipedia
http://en.wikipedia.org/wiki/Carbamazepine
RxList
http://www.rxlist.com/cgi/generic/carbam.htm
Drugs.com
http://www.drugs.com/carbamazepine.html
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