Identification
- Summary
Carbamazepine is an anticonvulsant used to treat various types of seizures and pain resulting from trigeminal neuralgia.
- Brand Names
- Carbatrol, Carnexiv, Epitol, Equetro, Tegretol
- Generic Name
- Carbamazepine
- DrugBank Accession Number
- DB00564
- Background
Carbamazepine, also known as Tegretol, is an anticonvulsant drug and analgesic drug used to control seizures and to treat pain resulting from trigeminal neuralgia. It was initially approved by the FDA in 1965.3 Aside from the above uses, this drug is also given to control the symptoms of bipolar 1.16 Interestingly, carbamazepine was the first anticonvulsant used to treat individuals with bipolar disorder.6
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Carbamazepine (DB00564)
- Weight
- Average: 236.2686
Monoisotopic: 236.094963016 - Chemical Formula
- C15H12N2O
- Synonyms
- 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
- Carbamazepine
- Carbamazepinum
- CBZ
- Molecusol-Carbamazepine
- External IDs
- G 32 883
- G-32883
- GEIGY 32883
- NSC-169864
- PR-320
- SPD417
Pharmacology
- Indication
Carbamazepine is indicated for the treatment of epilepsy and pain associated with true trigeminal neuralgia.16 In particular, carbamazepine has shown efficacy in treating mixed seizures, partial seizures with complex symptoms, and generalized tonic-clonic seizures.3,16 Carbamazepine is also indicated for the treatment of manic episodes and mixed manic-depressive episodes caused by bipolar I disorder.16 Some off-label, unapproved uses of carbamazepine include the treatment of alcohol withdrawal syndrome and restless leg syndrome.9,10
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute mania •••••••••••• •••••••• •••••••• ••••••• Treatment of Alcohol withdrawal syndrome(aws) ••• ••••• Treatment of Complex partial seizure disorder •••••••••••• •••• •••••••••• ••• ••••••••• ••••••••• Treatment of Complex partial seizure disorder •••••••••••• •••••••• •••••••• •••••••• ••••••••••• ••••••• ••••••••• ••••••• •••••••• ••••••• Treatment of Generalized tonic-clonic seizures •••••••••••• •••• •••••••••• ••• ••••••••• ••••••••• - Contraindications & Blackbox Warnings
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General effects
Carbamazepine treats seizures and the symptoms of trigeminal neuralgia by inhibiting sodium channels. In bipolar 1 disorder, carbamazepine has been found to decrease mania symptoms in a clinically significant manner according to the Young Mania Rating Scale (YMRS).16 Carbamazepine has a narrow therapeutic index.3
A note on genetic variation and carbamazepine use
In studies of Han Chinese ancestry patients, a pronounced association between the HLA-B*1502 genotype and Steven Johnson syndrome and/or toxic epidermal necrolysis (SJS/TEN) resulting from carbamazepine use was observed.7
- Mechanism of action
Carbamazepine's mechanism of action is not fully elucidated and is widely debated.5,22 One major hypothesis is that carbamazepine inhibits sodium channel firing, treating seizure activity. Animal research studies have demonstrated that carbamazepine exerts its effects by lowering polysynaptic nerve response and inhibiting post-tetanic potentiation. In both cats and rats, carbamazepine was shown to decrease pain caused by infraorbital nerve stimulation. A decrease in the action potential in the nucleus ventralis of the thalamus in the brain and inhibition of the lingual mandibular reflex were observed in other studies after carbamazepine use. Carbamazepine causes the above effects by binding to voltage-dependent sodium channels and preventing action potentials, which normally lead to stimulatory effects on nerves.8,15 In bipolar disorder, carbamazepine is thought to increase dopamine turnover and increase GABA transmission, treating manic and depressive symptoms.19
A common issue that has arisen is resistance to this drug in up to 30% of epileptic patients, which may occur to altered metabolism in patients with variant genotypes.13 A potential therapeutic target to combat carbamazepine resistance has recently been identified as the EPHX1 gene promoter, potentially conferring resistance to carbamazepine through methylation.14
Target Actions Organism AVoltage-gated sodium channel alpha subunit inhibitorHumans UNeuronal acetylcholine receptor subunit alpha-4 Not Available Humans UNuclear receptor subfamily 1 group I member 2 activatorHumans - Absorption
The bioavailability of carbamazepine is in the range of 75-85% of an ingested dose.3 After one 200 mg oral extended-release dose of carbamazepine in a pharmacokinetic study, the Cmax carbamazepine was measured to be 1.9 ± 0.3 mcg/mL. The Tmax was 19 ± 7 hours. After several doses of 800 mg every 12 hours, the peak concentrations of carbamazepine were measured to be 11.0 ± 2.5 mcg/mL. The Tmax was reduced to 5.9 ± 1.8 hours. Extended-release carbamazepine demonstrated linear pharmacokinetics over a range of 200–800 mg.16
Effect of food on absorption
A meal containing high-fat content increased the rate of absorption of one 400 mg dose but not the AUC of carbamazepine.16 The elimination half-life remained unchanged between fed and fasting state. The pharmacokinetics of an extended-release carbamazepine dose was demonstrated to be similar when administered in the fasted state or with food.16 Based on these findings, food intake is unlikely to exert significant effects on carbamazepine absorption.
- Volume of distribution
The volume of distribution of carbamazepine was found to be 1.0 L/kg in one pharmacokinetic study.4 Another study indicates that the volume of distribution of carbamazepine ranges between 0.7 to 1.4 L/kg.11. Carbamazepine crosses the placenta, and higher concentrations of this drug are found in the liver and kidney as opposed to lung and brain tissue.16 Carbamazepine crosses variably through the blood-brain barrier.13
- Protein binding
Carbamazepine is 75%-80% bound to plasma proteins.3,16 One pharmacokinetic study indicates that it is 72% bound to plasma proteins.11
- Metabolism
Carbamazepine is largely metabolized in the liver. CYP3A4 hepatic enzyme is the major enzyme that metabolizes carbamazepine to its active metabolite, carbamazepine-10,11-epoxide12, which is further metabolized to its trans-diol form by the enzyme epoxide hydrolase.16 Other hepatic cytochrome enzymes that contribute to the metabolism of carbamazepine are CYP2C8, CYP3A5, and CYP2B6.17 Carbamazepine also undergoes hepatic glucuronidation by UGT2B7 enzyme and several other metabolic reactions occur, resulting in the formation of minor hydroxy metabolites and quinone metabolites.17 Interestingly, carbamazepine induces its own metabolism.16 This leads to enhanced clearance, reduced half-life, and a reduction in serum levels of carbamazepine.3,16
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- Route of elimination
After an oral dose of radiolabeled carbamazepine, 72% of the administered radioactive dose was detected in the urine and the remainder of the ingested dose was found in the feces. Carbamazepine is mainly excreted as hydroxylated and conjugated metabolites, and minimal amounts of unchanged drug.16
- Half-life
The mean elimination half-life of carbamazepine was 35 to 40 hours after one dose of carbamazepine extended-release formulations. The half-life ranged from 12-17 hours after several doses of carbamazepine.16 One pharmacokinetic study determined the elimination half-life of carbamazepine to range between 27 to 36.8 hours in healthy volunteers.11
- Clearance
In a pharmacokinetic study, the apparent oral clearance of carbamazepine was 25 ± 5 mL/min 11,16 after one dose of carbamazepine and 80 ± 30 mL/min after several doses.16
- Adverse Effects
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Toxicity information Oral LDLO (female): 1920 mg/kg/17W (intermittent); Oral LDLO (male): 54 mg/kg/9D (intermittent)18 Oral LD50 (rat): 1957 mg/kg 18
Overdose information
The initial signs of carbamazepine overdose occur 1-3 hours post ingestion. These signs and symptoms may vary in case of an overdose between carbamazepine and other drugs. Carbamazepine may cause various cardiovascular, neurological, respiratory, urinary symptoms as well as laboratory abnormalities including leukocytosis, reduced leucocytes, acetonuria, and glycosuria.16
Neuromuscular symptoms may occur initially, followed by mild cardiac symptoms such as tachycardia, hypertension, or hypotension. Higher doses of carbamazepine may cause more severed cardiovascular effects. Restlessness, muscular twitching, tremor, dilated pupils, nystagmus, psychomotor disturbances, and other neurological symptoms may occur. Hyperreflexia in the initial stages of overdose may be followed by hyporeflexia. Nausea, vomiting, urinary retention, dizziness or drowsiness may also occur.16 In cases of overdose, contact the local poison control center. Ensure to provide supportive and symptomatic treatment, which may include monitoring and careful supervision by a medical professional. The possibility of overdose with multiple drugs must be considered in the case of carbamazepine overdose. Maintain an adequate airway, oxygen, in addition to ventilation. Vital signs should be monitored.16
- Pathways
Pathway Category Carbamazepine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Heat shock 70 kDa protein 1-like --- (T;T) / (C;T) T allele ADR Directly Studied Patients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine. Details Heat shock 70 kDa protein 1A/1B --- (C;G) / (C;C) / (C;T) C allele / C allele ADR Directly Studied Patients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine. Details HLA class I histocompatibility antigen, B-15 alpha chain --- (T;T) / (G;T) T allele ADR Directly Studied Patients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine. Details HLA class I histocompatibility antigen, A-31 alpha chain --- (G;G) / (C;G) G allele ADR Directly Studied Patients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine. Details Promotilin --- (A;A) / (A;C) A allele ADR Directly Studied Patients with this genotype have increased risk of cutaneous hypersensitivity reactions with carbamazepine. Details Sodium channel protein type 1 subunit alpha --- (A;A) / (A;G) IVS5N + 5 G>A Effect Directly Studied Patients with this genotype have increased resistance to the anti-epileptic effects of carbamazepine. Details Flotillin-1 HLA-B*1502 (G;G) / (C;G) G > C / G > C ADR Directly Studied Taiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine. Details Mucin-21 HLA-B*1502 (G;G) / (A;G) G>A / G>A ADR Directly Studied Taiwanese, Chinese, Indians, and Chinese–American patients with this genotype have increased risk of Stevens-Johnson syndrome or toxic epidermal necrolysis with carbamazepine. Details HLA class I histocompatibility antigen, B-15 alpha chain HLA-B*15:02 Not Available HLA-B*15 ADR Directly Studied Patients who carry this allele may be at an increased risk of Stevens-Johnson Syndrome and toxic epidermal necrolysis when treated with carbamazepine. Details HLA class I histocompatibility antigen, A-3 alpha chain HLA-A*3101 (T;T) / (A;T) A > T ADR Directly Studied Patients who carry this genotype in HLA-A are at a higher risk of experiencing a hypersensitivity reaction to carbamazepine. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The metabolism of 1,2-Benzodiazepine can be increased when combined with Carbamazepine. Abacavir Abacavir may decrease the excretion rate of Carbamazepine which could result in a higher serum level. Abametapir The serum concentration of Carbamazepine can be increased when it is combined with Abametapir. Abatacept The metabolism of Carbamazepine can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Carbamazepine. - Food Interactions
- Avoid alcohol. Ingesting alcohol may increase drowsiness and dizziness.
- Avoid grapefruit products.
- Exercise caution with St. John's Wort. This herb induces the CYP3A metabolism of carbamazepine and may reduce its serum concentration.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Actebral (Sanofi-Aventis) / Anleptic (Square) / Biston (Zentiva) / Carbamat (AstraZeneca) / Neurotop (Gerot) / TEGretol Chewtabs / TEGretol-CR (Novartis) / TEGretol-XR (Novartis) / Teril (Taro) / Timonil (Desitin) / Versitol (Micro Synapse) / Versizur (Micro Labs)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Carbamazepine Tablet 400 mg/1 Oral Caraco Pharmaceutical Laboratories, Ltd. 2008-01-29 Not applicable US 
Carbamazepine Tablet 100 mg/1 Oral Caraco Pharmaceutical Laboratories, Ltd. 2008-01-29 Not applicable US Carbamazepine Tablet, extended release 200 mg/1 Oral Kaiser Foundations Hospitals 2009-10-28 2012-06-30 US Carbamazepine Tablet 300 mg/1 Oral Caraco Pharmaceutical Laboratories, Ltd. 2008-01-29 Not applicable US Carbamazepine Tablet, chewable 100 mg/1 Oral Caraco Pharmaceutical Laboratories, Ltd. 2008-01-29 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-carbamazepine Tablet 200 mg Oral Apotex Corporation 1980-12-31 Not applicable Canada 
Apo-carbamazepine CR Tablet, extended release 400 mg Oral Apotex Corporation Not applicable Not applicable Canada Apo-carbamazepine CR Tablet, extended release 200 mg Oral Apotex Corporation Not applicable Not applicable Canada Bio-carbamazepine Tablet 200 mg Oral Biomed Pharma 2003-08-20 2010-03-16 Canada Carbamazepin Tablet, extended release 200 mg/1 Oral Upsher-Smith Laboratories, LLC 2021-04-13 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image TEGRETOL CR 200 MG TABLET, 20 ADET Carbamazepine (200 mg) Tablet Oral NOVARTİS ÜRÜNLERİ 2020-08-14 Not applicable Turkey 
TEGRETOL CR 400 MG TABLET, 20 ADET Carbamazepine (400 mg) Tablet Oral NOVARTİS ÜRÜNLERİ 2020-08-14 Not applicable Turkey
Categories
- ATC Codes
- N03AF01 — Carbamazepine
- Drug Categories
- Analgesics
- Analgesics, Non-Narcotic
- Anticonvulsants
- Antimanic Agents
- Carboxamide Derivatives
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Inducers
- Cytochrome P-450 CYP1A2 Inducers (strong)
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strong)
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C19 Inducers (moderate)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inducers
- Cytochrome P-450 CYP2C8 Inducers (strength unknown)
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP2C9 Inducers (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inducers (strong)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strong)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 CYP3A5 Inducers (strong)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Decreased Central Nervous System Disorganized Electrical Activity
- Dibenzazepines
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index
- Enzyme Inducing Antiepileptic Drugs
- Heterocyclic Compounds, Fused-Ring
- Immunosuppressive Agents
- Inducers of Drug Clearance
- Membrane Transport Modulators
- Miscellaneous Anticonvulsants
- Mood Stabilizer
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- P-glycoprotein inducers
- P-glycoprotein substrates
- Peripheral Nervous System Agents
- Psychotropic Drugs
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Sodium Channel Blockers
- Thyroxine-binding globulin substrates
- UGT1A1 Inducers
- UGT1A6 inducer
- UGT2B7 substrates
- UGT2B7 Substrates with a Narrow Therapeutic Index
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzazepines
- Sub Class
- Dibenzazepines
- Direct Parent
- Dibenzazepines
- Alternative Parents
- Azepines / Benzenoids / Ureas / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzenoid / Carbonic acid derivative / Carbonyl group / Dibenzazepine / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- ureas, dibenzoazepine (CHEBI:3387)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 33CM23913M
- CAS number
- 298-46-4
- InChI Key
- FFGPTBGBLSHEPO-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide
- SMILES
- NC(=O)N1C2=CC=CC=C2C=CC2=CC=CC=C12
References
- Synthesis Reference
Ketan Dhansukhlal Vyas, Wajid Sajjad Jafri, Ashok Krishna Kulkarni, "Process for preparing carbamazepine from iminostilbene." U.S. Patent US6245908, issued February, 1998.
US6245908- General References
- Staines AG, Coughtrie MW, Burchell B: N-glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther. 2004 Dec;311(3):1131-7. Epub 2004 Aug 3. [Article]
- Sisodiya SM, Goldstein DB: Drug resistance in epilepsy: more twists in the tale. Epilepsia. 2007 Dec;48(12):2369-70. [Article]
- Tolou-Ghamari Z, Zare M, Habibabadi JM, Najafi MR: A quick review of carbamazepine pharmacokinetics in epilepsy from 1953 to 2012. J Res Med Sci. 2013 Mar;18(Suppl 1):S81-5. [Article]
- Marino SE, Birnbaum AK, Leppik IE, Conway JM, Musib LC, Brundage RC, Ramsay RE, Pennell PB, White JR, Gross CR, Rarick JO, Mishra U, Cloyd JC: Steady-state carbamazepine pharmacokinetics following oral and stable-labeled intravenous administration in epilepsy patients: effects of race and sex. Clin Pharmacol Ther. 2012 Mar;91(3):483-8. doi: 10.1038/clpt.2011.251. Epub 2012 Jan 25. [Article]
- Ambrosio AF, Soares-Da-Silva P, Carvalho CM, Carvalho AP: Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024. Neurochem Res. 2002 Feb;27(1-2):121-30. [Article]
- Chen CH, Lin SK: Carbamazepine treatment of bipolar disorder: a retrospective evaluation of naturalistic long-term outcomes. BMC Psychiatry. 2012 May 23;12:47. doi: 10.1186/1471-244X-12-47. [Article]
- Johnson DL, Gellman H, Waters RL, Tognella M: Brachioradialis transfer for wrist extension in tetraplegic patients who have fifth-cervical-level neurological function. J Bone Joint Surg Am. 1996 Jul;78(7):1063-7. doi: 10.2106/00004623-199607000-00011. [Article]
- Kuo CC, Chen RS, Lu L, Chen RC: Carbamazepine inhibition of neuronal Na+ currents: quantitative distinction from phenytoin and possible therapeutic implications. Mol Pharmacol. 1997 Jun;51(6):1077-83. doi: 10.1124/mol.51.6.1077. [Article]
- Barrons R, Roberts N: The role of carbamazepine and oxcarbazepine in alcohol withdrawal syndrome. J Clin Pharm Ther. 2010 Apr;35(2):153-67. doi: 10.1111/j.1365-2710.2009.01098.x. [Article]
- Aurora RN, Kristo DA, Bista SR, Rowley JA, Zak RS, Casey KR, Lamm CI, Tracy SL, Rosenberg RS: The treatment of restless legs syndrome and periodic limb movement disorder in adults--an update for 2012: practice parameters with an evidence-based systematic review and meta-analyses: an American Academy of Sleep Medicine Clinical Practice Guideline. Sleep. 2012 Aug 1;35(8):1039-62. doi: 10.5665/sleep.1988. [Article]
- Rawlins MD, Collste P, Bertilsson L, Palmer L: Distribution and elimination kinetics of carbamazepine in man. Eur J Clin Pharmacol. 1975 Feb 28;8(2):91-6. [Article]
- Yoshimura R, Yanagihara N, Terao T, Minami K, Toyohira Y, Ueno S, Uezono Y, Abe K, Izumi F: An active metabolite of carbamazepine, carbamazepine-10,11-epoxide, inhibits ion channel-mediated catecholamine secretion in cultured bovine adrenal medullary cells. Psychopharmacology (Berl). 1998 Feb;135(4):368-73. [Article]
- Thorn CF, Leckband SG, Kelsoe J, Leeder JS, Muller DJ, Klein TE, Altman RB: PharmGKB summary: carbamazepine pathway. Pharmacogenet Genomics. 2011 Dec;21(12):906-10. doi: 10.1097/FPC.0b013e328348c6f2. [Article]
- Lv Y, Zheng X, Shi M, Wang Z, Cui L: Different EPHX1 methylation levels in promoter area between carbamazepine-resistant epilepsy group and carbamazepine-sensitive epilepsy group in Chinese population. BMC Neurol. 2019 Jun 4;19(1):114. doi: 10.1186/s12883-019-1308-4. [Article]
- Jasdave S. Maan; Abdolreza Saadabadi (2019). Carbamazepine. Stat Pearls Publishing.
- FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules [Link]
- Pharm KGB, carbamazepine pathway, pharmacokinetics [Link]
- Carbamazepine MSDS [Link]
- ipolar Disorders and Carbamazepine: Pharmacokinetics,Pharmacodynamics, Therapeutic Effects and Indications of Carbamazepine: Review of Articles [Link]
- FDA Approved Drug Products: Tegretol (carbamazepine) [Link]
- FDA Approved Drug Products: CARNEXIV (carbamazepine) injection [Link]
- FDA Approved Drug Products: Carbatrol (carbamazepine) extended-release capsules for oral use [Link]
- FDA Approved Drug Products: Carbatrol (carbamazepine) extended-release capsules for oral use (April 2023) [Link]
- External Links
- Human Metabolome Database
- HMDB0014704
- KEGG Drug
- D00252
- KEGG Compound
- C06868
- PubChem Compound
- 2554
- PubChem Substance
- 46507583
- ChemSpider
- 2457
- BindingDB
- 50003659
- 2002
- ChEBI
- 3387
- ChEMBL
- CHEMBL108
- ZINC
- ZINC000000004785
- Therapeutic Targets Database
- DAP000129
- PharmGKB
- PA448785
- PDBe Ligand
- N6W
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Carbamazepine
- PDB Entries
- 6tfb / 8s9c
- FDA label
- Download (55.9 KB)
- MSDS
- Download (71.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Alcohol Dependency 1 4 Completed Treatment Bipolar 1 Disorder 2 4 Completed Treatment Bipolar Disorder (BD) 2 4 Completed Treatment Bipolar Disorder (BD) / Mania 1 4 Completed Treatment Bronchial Asthma 2
Pharmacoeconomics
- Manufacturers
- Shire development inc
- Validus pharmaceuticals inc
- Taro pharmaceutical industries ltd
- Wockhardt eu operations (swiss) ag
- Novartis pharmaceuticals corp
- Taro pharmaceuticals usa inc
- Cadista pharmaceuticals inc
- Torrent pharmaceuticals ltd
- Teva pharmaceuticals usa inc
- Actavis elizabeth llc
- Apotex inc etobicoke site
- Inwood laboratories inc sub forest laboratories inc
- Pliva inc
- Usl pharma inc
- Warner chilcott div warner lambert co
- Packagers
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apotex Inc.
- A-S Medication Solutions LLC
- Caraco Pharmaceutical Labs
- Cardinal Health
- Ciba Geigy Ltd.
- Coupler Enterprises Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DSM Corp.
- Goldline Laboratories Inc.
- Hawkins Inc.
- Heartland Repack Services LLC
- Innoviant Pharmacy Inc.
- Inwood Labs
- Kaiser Foundation Hospital
- Lake Erie Medical and Surgical Supply
- Major Pharmaceuticals
- Mckesson Corp.
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Neuman Distributors Inc.
- Novartis AG
- Nucare Pharmaceuticals Inc.
- Patheon Inc.
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Packaging Center
- Pharmacy Service Center
- Physicians Total Care Inc.
- Precision Dose Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Qualitest
- Redpharm Drug
- Remedy Repack
- Resource Optimization and Innovation LLC
- Sandhills Packaging Inc.
- Sandoz
- Shire Inc.
- Southwood Pharmaceuticals
- Stat Rx Usa
- Taro Pharmaceuticals USA
- Teva Pharmaceutical Industries Ltd.
- Torpharm Inc.
- Torrent Pharmaceuticals
- Tya Pharmaceuticals
- UDL Laboratories
- Validus Pharmaceuticals
- Vangard Labs Inc.
- Vistapharm Inc.
- Wellspring Pharmaceutical
- Wockhardt Ltd.
- Xactdose Inc.
- Dosage Forms
Form Route Strength Tablet Oral Suspension Oral 2.0000 g Tablet, extended release Oral 300 MG Tablet, extended release Oral 600 MG Tablet Oral 400 MG Tablet, extended release Oral 300 mg/1 Tablet, extended release Oral 600 mg/1 Suspension Oral 2 g Suspension Oral 2 % Suspension Oral Capsule, extended release Oral 200 mg Powder Not applicable 1 g/1g Suspension Oral 100 mg/5mL Suspension Oral 200 mg/10mL Tablet Oral 100 mg/1 Tablet Oral 200 mg/1 Tablet Oral 300 mg/1 Tablet Oral 400 mg/1 Tablet, chewable Oral 100 mg/1 Tablet, chewable Oral 200 mg/1 Tablet, film coated Oral Tablet Oral 200 mg / tab Tablet, extended release Oral 400 mg/1 Tablet Oral 400.000 mg Injection, powder, for solution Intravenous 10 mg/1mL Suspension Oral 2.00 g Tablet Oral 200.00 mg Tablet, extended release Oral 200 mg / srt Tablet, extended release Oral 400 mg / srt Tablet Oral 400.00 mg Capsule, extended release Oral 100 mg/1 Capsule, extended release Oral 200 mg/1 Capsule, extended release Oral 300 mg/1 Tablet Oral 200 mg Tablet Oral 100.000 mg Suspension Oral 2.000 g Tablet Oral 300 mg Tablet Oral 600 mg Tablet, chewable Oral 100 mg Tablet, chewable Oral 200 mg Syrup Oral 2 % Suppository 125 MG Suppository 250 MG Syrup Oral 20 MG/ML Suspension Oral 20 mg/ml Syrup Oral Syrup Oral 100 mg/5mL Tablet, extended release Oral Tablet, film coated Oral 200 mg Tablet, film coated Oral 400 mg Syrup Oral 2 g/100ml Suspension Oral 100 mg / 5 mL Tablet, extended release Oral 100 mg/1 Tablet, extended release Oral 200 mg/1 Tablet, extended release Oral 150 mg Tablet Oral 200.000 mg Tablet, extended release Oral 200 mg Tablet, extended release Oral 400 mg Tablet, delayed release 200 mg Tablet, delayed release 400 mg - Prices
Unit description Cost Unit Equetro 300 mg capsule 2.65USD capsule TEGretol XR 400 mg 12 Hour tablet 2.42USD tablet Carbamazepine powder 2.26USD g Tegretol xr 400 mg tablet 2.19USD tablet Carbatrol 100 mg 12 Hour Capsule 2.18USD capsule Equetro 200 mg capsule 2.15USD capsule CarBAMazepine 400 mg 12 Hour tablet 2.05USD tablet Carbatrol 300 mg 12 Hour Capsule 1.95USD capsule Carbatrol 200 mg 12 Hour Capsule 1.92USD capsule Carbatrol er 100 mg capsule 1.84USD capsule Carbatrol er 200 mg capsule 1.84USD capsule Carbatrol er 300 mg capsule 1.84USD capsule Equetro 100 mg capsule 1.74USD capsule TEGretol XR 200 mg 12 Hour tablet 1.45USD tablet Tegretol xr 200 mg tablet 1.1USD tablet CarBAMazepine 200 mg 12 Hour tablet 1.03USD tablet TEGretol XR 100 mg 12 Hour tablet 0.97USD tablet Tegretol Cr 400 mg Sustained-Release Tablet 0.84USD tablet Tegretol 200 mg tablet 0.75USD tablet Tegretol xr 100 mg tablet 0.55USD tablet Tegretol Cr 200 mg Sustained-Release Tablet 0.42USD tablet Mylan-Carbamazepine Cr 400 mg Sustained-Release Tablet 0.4USD tablet Pms-Carbamazepine-Cr 400 mg Sustained-Release Tablet 0.4USD tablet Sandoz Carbamazepine Cr 400 mg Sustained-Release Tablet 0.4USD tablet Tegretol 200 mg Chewable Tablet 0.34USD tablet Carbamazepine 200 mg tablet 0.31USD tablet Epitol 200 mg tablet 0.3USD tablet CarBAMazepine 100 mg Chew Tabs 0.25USD tab Mylan-Carbamazepine Cr 200 mg Sustained-Release Tablet 0.2USD tablet Pms-Carbamazepine-Cr 200 mg Sustained-Release Tablet 0.2USD tablet Sandoz Carbamazepine Cr 200 mg Sustained-Release Tablet 0.2USD tablet Tegretol 100 mg Chewable Tablet 0.17USD tablet CarBAMazepine 100 mg/5ml Suspension 0.16USD ml Pms-Carbamazepine 200 mg Chewable Tablet 0.16USD tablet Sandoz Carbamazepine 200 mg Chewable Tablet 0.16USD tablet Taro-Carbamazepine 200 mg Chewable Tablet 0.16USD tablet Apo-Carbamazepine 200 mg Tablet 0.08USD tablet Novo-Carbamaz 200 mg Tablet 0.08USD tablet Nu-Carbamazepine 200 mg Tablet 0.08USD tablet Pms-Carbamazepine 100 mg Chewable Tablet 0.08USD tablet Sandoz Carbamazepine 100 mg Chewable Tablet 0.08USD tablet Taro-Carbamazepine 100 mg Chewable Tablet 0.08USD tablet Tegretol 20 mg/ml Suspension 0.08USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5284662 No 1994-02-08 2011-02-08 US US5912013 No 1999-06-15 2016-06-15 US US6977253 No 2005-12-20 2024-05-19 US US7635773 No 2009-12-22 2029-03-13 US US8410077 No 2013-04-02 2029-03-13 US US9493582 No 2016-11-15 2033-02-27 US US9629797 No 2017-04-25 2028-11-10 US US9770407 No 2017-09-26 2028-11-10 US US9750822 No 2017-09-05 2029-03-13 US US11529357 No 2020-01-31 2040-01-31 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 189-192 https://www.lookchem.com/Carbamazepine/ boiling point (°C) 399.6±45.0 https://www.lookchem.com/Carbamazepine/ logP 2.77 http://www.t3db.ca/toxins/T3D2826 logS -3.2 http://www.t3db.ca/toxins/T3D2826 pKa 15.96, -3.8 http://www.t3db.ca/toxins/T3D2826 - Predicted Properties
Property Value Source Water Solubility 0.152 mg/mL ALOGPS logP 2.1 ALOGPS logP 2.77 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 15.96 Chemaxon pKa (Strongest Basic) -3.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.33 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 71.89 m3·mol-1 Chemaxon Polarizability 25 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9962 Blood Brain Barrier + 0.9958 Caco-2 permeable + 0.6538 P-glycoprotein substrate Non-substrate 0.6466 P-glycoprotein inhibitor I Non-inhibitor 0.8748 P-glycoprotein inhibitor II Non-inhibitor 0.8381 Renal organic cation transporter Non-inhibitor 0.8177 CYP450 2C9 substrate Non-substrate 0.7466 CYP450 2D6 substrate Substrate 0.884 CYP450 3A4 substrate Non-substrate 0.6204 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8222 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7358 Ames test Non AMES toxic 0.5554 Carcinogenicity Non-carcinogens 0.8848 Biodegradation Not ready biodegradable 0.978 Rat acute toxicity 2.1131 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9653 hERG inhibition (predictor II) Non-inhibitor 0.8734
Spectra
- Mass Spec (NIST)
- Download (7.72 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 158.7182099 predictedDarkChem Lite v0.1.0 [M-H]- 158.7037099 predictedDarkChem Lite v0.1.0 [M-H]- 158.5649099 predictedDarkChem Lite v0.1.0 [M-H]- 146.49779 predictedDeepCCS 1.0 (2019) [M+H]+ 159.0095099 predictedDarkChem Lite v0.1.0 [M+H]+ 159.2038099 predictedDarkChem Lite v0.1.0 [M+H]+ 158.9806099 predictedDarkChem Lite v0.1.0 [M+H]+ 148.89336 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.8605099 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.6311099 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.9874099 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.80588 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
Components:
References
- Yang YC, Huang CS, Kuo CC: Lidocaine, carbamazepine, and imipramine have partially overlapping binding sites and additive inhibitory effect on neuronal Na+ channels. Anesthesiology. 2010 Jul;113(1):160-74. doi: 10.1097/ALN.0b013e3181dc1dd6. [Article]
- Yang YC, Kuo CC: Inhibition of Na(+) current by imipramine and related compounds: different binding kinetics as an inactivation stabilizer and as an open channel blocker. Mol Pharmacol. 2002 Nov;62(5):1228-37. [Article]
- Lipkind GM, Fozzard HA: Molecular model of anticonvulsant drug binding to the voltage-gated sodium channel inner pore. Mol Pharmacol. 2010 Oct;78(4):631-8. doi: 10.1124/mol.110.064683. Epub 2010 Jul 19. [Article]
- Rogawski MA, Loscher W: The neurobiology of antiepileptic drugs. Nat Rev Neurosci. 2004 Jul;5(7):553-64. doi: 10.1038/nrn1430. [Article]
- FDA Approved Drug Products: EQUETRO (carbamazepine) extended-release capsules [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
- Gene Name
- CHRNA4
- Uniprot ID
- P43681
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-4
- Molecular Weight
- 69956.47 Da
References
- Ortells MO, Barrantes GE: Molecular modelling of the interactions of carbamazepine and a nicotinic receptor involved in the autosomal dominant nocturnal frontal lobe epilepsy. Br J Pharmacol. 2002 Jul;136(6):883-95. doi: 10.1038/sj.bjp.0704786. [Article]
- Di Resta C, Ambrosi P, Curia G, Becchetti A: Effect of carbamazepine and oxcarbazepine on wild-type and mutant neuronal nicotinic acetylcholine receptors linked to nocturnal frontal lobe epilepsy. Eur J Pharmacol. 2010 Sep 15;643(1):13-20. doi: 10.1016/j.ejphar.2010.05.063. Epub 2010 Jun 16. [Article]
- Bertrand D: Neuronal Nicotinic Acetylcholine Receptors and Epilepsy. Epilepsy Curr. 2002 Nov;2(6):191-193. doi: 10.1046/j.1535-7597.2002.00072.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- Curator comments
- weak activator based on results of one in vitro study
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [Article]
- Levy RH: Cytochrome P450 isozymes and antiepileptic drug interactions. Epilepsia. 1995;36 Suppl 5:S8-13. [Article]
- Cazali N, Tran A, Treluyer JM, Rey E, d'Athis P, Vincent J, Pons G: Inhibitory effect of stiripentol on carbamazepine and saquinavir metabolism in human. Br J Clin Pharmacol. 2003 Nov;56(5):526-36. [Article]
- Chen L, Boinpally R, Gad N, Greenberg WM, Wangsa J, Periclou A, Ghahramani P: Evaluation of Cytochrome P450 (CYP) 3A4-Based Interactions of Levomilnacipran with Ketoconazole, Carbamazepine or Alprazolam in Healthy Subjects. Clin Drug Investig. 2015 Oct;35(10):601-12. doi: 10.1007/s40261-015-0318-2. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA interactions table [Link]
- Tegretol FDA label [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Cazali N, Tran A, Treluyer JM, Rey E, d'Athis P, Vincent J, Pons G: Inhibitory effect of stiripentol on carbamazepine and saquinavir metabolism in human. Br J Clin Pharmacol. 2003 Nov;56(5):526-36. [Article]
- Kato Y, Fujii T, Mizoguchi N, Takata N, Ueda K, Feldman MD, Kayser SR: Potential interaction between ritonavir and carbamazepine. Pharmacotherapy. 2000 Jul;20(7):851-4. [Article]
- Mesdjian E, Seree E, Charvet B, Mirrione A, Bourgarel-Rey V, Desobry A, Barra Y: Metabolism of carbamazepine by CYP3A6: a model for in vitro drug interactions studies. Life Sci. 1999;64(10):827-35. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Liu A, Wang C, Hehir M, Zhou T, Yang J: In vivo induction of CYP in mice by carbamazepine is independent on PXR. Pharmacol Rep. 2015 Apr;67(2):299-304. doi: 10.1016/j.pharep.2014.10.002. Epub 2014 Oct 18. [Article]
- de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [Article]
- de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [Article]
- Masubuchi Y, Nakano T, Ose A, Horie T: Differential selectivity in carbamazepine-induced inactivation of cytochrome P450 enzymes in rat and human liver. Arch Toxicol. 2001 Nov;75(9):538-43. [Article]
- Jerling M, Lindstrom L, Bondesson U, Bertilsson L: Fluvoxamine inhibition and carbamazepine induction of the metabolism of clozapine: evidence from a therapeutic drug monitoring service. Ther Drug Monit. 1994 Aug;16(4):368-74. [Article]
- CYP table [Link]
- CP450 drug interactions [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [Article]
- Tegretol FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Lakehal F, Wurden CJ, Kalhorn TF, Levy RH: Carbamazepine and oxcarbazepine decrease phenytoin metabolism through inhibition of CYP2C19. Epilepsy Res. 2002 Dec;52(2):79-83. [Article]
- de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [Article]
- Indiana University - Department of Medicine Clinical Pharmacology [Link]
- Drug Interactions & Labeling - FDA [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Pearce RE, Vakkalagadda GR, Leeder JS: Pathways of carbamazepine bioactivation in vitro I. Characterization of human cytochromes P450 responsible for the formation of 2- and 3-hydroxylated metabolites. Drug Metab Dispos. 2002 Nov;30(11):1170-9. [Article]
- de Leon J, Santoro V, D'Arrigo C, Spina E: Interactions between antiepileptics and second-generation antipsychotics. Expert Opin Drug Metab Toxicol. 2012 Mar;8(3):311-34. doi: 10.1517/17425255.2012.660918. Epub 2012 Feb 15. [Article]
- Pharm KGB, carbamazepine pathway, pharmacokinetics [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Hidaka M, Okumura M, Fujita K, Ogikubo T, Yamasaki K, Iwakiri T, Setoguchi N, Arimori K: Effects of pomegranate juice on human cytochrome p450 3A (CYP3A) and carbamazepine pharmacokinetics in rats. Drug Metab Dispos. 2005 May;33(5):644-8. doi: 10.1124/dmd.104.002824. Epub 2005 Jan 26. [Article]
- Henshall J, Galetin A, Harrison A, Houston JB: Comparative analysis of CYP3A heteroactivation by steroid hormones and flavonoids in different in vitro systems and potential in vivo implications. Drug Metab Dispos. 2008 Jul;36(7):1332-40. doi: 10.1124/dmd.108.021279. Epub 2008 Apr 17. [Article]
- Park PW, Seo YH, Ahn JY, Kim KA, Park JY: Effect of CYP3A5*3 genotype on serum carbamazepine concentrations at steady-state in Korean epileptic patients. J Clin Pharm Ther. 2009 Oct;34(5):569-74. doi: 10.1111/j.1365-2710.2009.01057.x. [Article]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Staines AG, Coughtrie MW, Burchell B: N-glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther. 2004 Dec;311(3):1131-7. Epub 2004 Aug 3. [Article]
- Puranik YG, Birnbaum AK, Marino SE, Ahmed G, Cloyd JC, Remmel RP, Leppik IE, Lamba JK: Association of carbamazepine major metabolism and transport pathway gene polymorphisms and pharmacokinetics in patients with epilepsy. Pharmacogenomics. 2013 Jan;14(1):35-45. doi: 10.2217/pgs.12.180. [Article]
- Pharm KGB, carbamazepine pathway, pharmacokinetics [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inducer
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Protein homodimerization activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
- Gene Name
- UGT1A6
- Uniprot ID
- P19224
- Uniprot Name
- UDP-glucuronosyltransferase 1-6
- Molecular Weight
- 60750.215 Da
References
- Asai Y, Sakakibara Y, Nadai M, Katoh M: Effect of carbamazepine on expression of UDP-glucuronosyltransferase 1A6 and 1A7 in rat brain. Drug Metab Pharmacokinet. 2017 Dec;32(6):286-292. doi: 10.1016/j.dmpk.2017.09.002. Epub 2017 Oct 5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A7
- Uniprot ID
- Q9HAW7
- Uniprot Name
- UDP-glucuronosyltransferase 1-7
- Molecular Weight
- 59818.315 Da
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. [Article]
- Owen A, Pirmohamed M, Tettey JN, Morgan P, Chadwick D, Park BK: Carbamazepine is not a substrate for P-glycoprotein. Br J Clin Pharmacol. 2001 Apr;51(4):345-9. [Article]
- Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [Article]
- Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein. Neuropharmacology. 2007 Feb;52(2):333-46. Epub 2006 Oct 10. [Article]
- Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transmembrane transporter activity
- Specific Function
- Can activate specifically hydrolysis of GTP bound to RAC1 and CDC42, but not RALA. Mediates ATP-dependent transport of S-(2,4-dinitrophenyl)-glutathione (DNP-SG) and doxorubicin (DOX) and is the ma...
- Gene Name
- RALBP1
- Uniprot ID
- Q15311
- Uniprot Name
- RalA-binding protein 1
- Molecular Weight
- 76062.86 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Organic anion transmembrane transporter activity
- Specific Function
- Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- Canalicular multispecific organic anion transporter 1
- Molecular Weight
- 174205.64 Da
References
- Ufer M, Mosyagin I, Muhle H, Jacobsen T, Haenisch S, Hasler R, Faltraco F, Remmler C, von Spiczak S, Kroemer HK, Runge U, Boor R, Stephani U, Cascorbi I: Non-response to antiepileptic pharmacotherapy is associated with the ABCC2 -24C>T polymorphism in young and adult patients with epilepsy. Pharmacogenet Genomics. 2009 May;19(5):353-62. [Article]
- Potschka H, Fedrowitz M, Loscher W: Brain access and anticonvulsant efficacy of carbamazepine, lamotrigine, and felbamate in ABCC2/MRP2-deficient TR- rats. Epilepsia. 2003 Dec;44(12):1479-86. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55