U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H12N2O
Molecular Weight 236.2686
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBAMAZEPINE

SMILES

NC(=O)N1C2=CC=CC=C2C=CC3=CC=CC=C13

InChI

InChIKey=FFGPTBGBLSHEPO-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Carbamazepine is an analgesic, anti-epileptic agent that is FDA approved for the treatment of epilepsy, trigeminal neuralgia. It appears to act by reducing polysynaptic responses and blocking the post-tetanic potentiation. It depresses thalamic potential and bulbar and polysynaptic reflexes, including the linguomandibular reflex in cats. Commonly reported side effects of carbamazepine include: dizziness, drowsiness, nausea, ataxia, and vomiting. Carbamazepine is a potent inducer of hepatic CYP1A2, 2B6, 2C9/19, and 3A4 and may reduce plasma concentrations of concomitant medications mainly metabolized by CYP1A2, 2B6, 2C9/19, and 3A4 through induction of their metabolism, like Boceprevir, Cyclophosphamide, Aripiprazole, Tacrolimus, Temsirolimus and others.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Carbamazepine-induced hepatitis. A case report].
1999
Assessment of colour vision in epileptic patients exposed to single-drug therapy.
1999
Multiple hepatocellular adenomas associated with long-term carbamazepine.
1999 Jul
Potential fluconazole-induced carbamazepine toxicity.
1999 Jul-Aug
[Severe intoxication probably from olanzapine (Zyprexa). Beneficial effect of glucagon].
1999 Jun
Elimination of oxcarbazepine-induced oculogyric crisis following vagus nerve stimulation.
1999 Jun 10
A reporter gene assay to assess the molecular mechanisms of xenobiotic-dependent induction of the human CYP3A4 gene in vitro.
1999 Mar
Risperidone-induced mania.
1999 Mar
Severe multisystemic hypersensitivity reaction to carbamazepine including dyserythropoietic anemia.
1999 May
Carbamazepine-induced hepatorenal failure in a child.
1999 May
Carbamazepine in agitation and aggressive behaviour following severe closed-head injury: results of an open trial.
1999 Oct
Epileptic negative myoclonus induced by carbamazepine in a child with BECTS. Benign childhood epilepsy with centrotemporal spikes.
1999 Sep
Carbamazepine-induced thrombocytopenia defined by a challenge test.
1999 Sep
Worsening of symptoms of multiple sclerosis associated with carbamazepine.
2000 Apr 22
Carbamazepine induced bradycardia.
2000 Dec
Increased seizures after discontinuing carbamazepine: results from the gabapentin monotherapy trial.
2000 Dec
Effects of anticonvulsants on local anaesthetic-induced neurotoxicity in rats.
2000 Feb
A multicenter randomized controlled trial on the clinical impact of therapeutic drug monitoring in patients with newly diagnosed epilepsy. The Italian TDM Study Group in Epilepsy.
2000 Feb
Carbamazepine-induced systemic lupus erythematosus presenting as cardiac tamponade.
2000 Feb
Sodium valproate inhibits production of TNF-alpha and IL-6 and activation of NF-kappaB.
2000 Feb 28
Phenytoin poisoning after using Chinese proprietary medicines.
2000 Jul
Potential interaction between ritonavir and carbamazepine.
2000 Jul
Refractory idiopathic absence status epilepticus: A probable paradoxical effect of phenytoin and carbamazepine.
2000 Jul
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.
2000 Jul 28
[A case of superior sagittal sinus thrombosis following long-term medication with carbamazepine].
2000 Jun
Carbamazepine-induced combined phonic and motor tic in a boy with Down's syndrome.
2000 Mar
Carbamazepine suppresses methamphetamine-induced Fos expression in a regionally specific manner in the rat brain. Possible neural substrates responsible for antimanic effects of mood stabilizers.
2000 May
Antiepileptic drug-induced visual hallucinations in a child.
2000 Nov
Investigation and medical management of trigeminal neuralgia by consultant oral and maxillofacial surgeons in the British Isles.
2001 Apr
Population pharmacokinetic modeling of steady state carbamazepine clearance in children, adolescents, and adults.
2001 Feb
Cardiac arrest after fast intravenous infusion of phenytoin mistaken for fosphenytoin.
2001 Feb
Antiepileptic drug withdrawal in patients with temporal lobe epilepsy undergoing presurgical video-EEG monitoring.
2001 Feb
Interactions between carbamazepine and polyethylene glycol (PEG) 6000: characterisations of the physical, solid dispersed and eutectic mixtures.
2001 Feb
Prolonged epileptic blindness in an infant associated with cortical dysplasia.
2001 Feb
Anticonvulsant and sodium channel blocking activity of higher doses of clenbuterol.
2001 Feb
Adverse drug interaction between risperidone and carbamazepine in a patient with chronic schizophrenia and deficient CYP2D6 activity.
2001 Feb
Pleomorphic xanthoastrocytoma: report of a case diagnosed by intraoperative cytopathological examination.
2001 Feb
Significance of atypical presentation of symptomatic SUNCT: a case report.
2001 Feb
Independent short-term variability of spike-like (600 Hz) and postsynaptic (N20) cerebral SEP components.
2001 Feb 12
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.
2001 Feb 23
Seizures in multiple sclerosis.
2001 Jan
Carbamazepine hypersensitivity syndrome mimicking mycosis fungoides.
2001 Jan
Acute intermittent porphyria, seizures, and antiepileptic drugs: a report on a 3-year-old Nigerian boy.
2001 Jan
Additional educational needs in children born to mothers with epilepsy.
2001 Jan
[Klüver-Bucy syndrome in herpetic meningoencephalitis].
2001 Jan 27
Influence of retigabine on the anticonvulsant activity of some antiepileptic drugs against audiogenic seizures in DBA/2 mice.
2001 Mar
Treatment of bipolar affective disorder in clinical practice.
2001 Mar
Suppressive effects of oxcarbazepine on tooth pulp-evoked potentials recorded at the trigeminal spinal tract nucleus in cats.
2001 Mar
Carbamazepine prevents imipramine-induced behavioural sensitization to the dopamine D(2)-like receptor agonist quinpirole.
2001 Mar 23
Patents

Sample Use Guides

In Vivo Use Guide
Initial Dose: 400 mg per day. Subsequent Dose: add up to 200 mg per day at weekly intervals. Maximum daily dose is 1600 mg
Route of Administration: Oral; Intravenous
In Vitro Use Guide
Human liver microsomes (HLMs) converted carbamazepine (30-300 microM) to 3-hydroxycarbamazepine at rates >25 times those of 2-hydroxycarbamazepine. Rates of carbamazepine 2- and 3-hydroxylation correlated strongly with CYP2B6 activity (r >or= 0.757) in a panel of HLMs (n = 8). Carbamazepine 3-hydroxylation also correlated significantly with CYP2C8 activity at a carbamazepine concentration of 30 microM.
Name Type Language
CARBAMAZEPINE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RC   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
CARBAMAZEPINE [USP-RC]
Common Name English
EQUETRO
Brand Name English
TERIL
Brand Name English
NEUROTOP
Common Name English
KARBAMAZEPIN
Common Name English
CARBAMAZEPINE [INN]
Common Name English
CARBAMAZEPINE [JAN]
Common Name English
CARBAMAZEPINE [WHO-DD]
Common Name English
CARBAMAZEPINE [EP]
Common Name English
OXCARBAZEPINE IMPURITY A [EP]
Common Name English
G-32883
Code English
5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE
Systematic Name English
CARBAMAZEPINE [WHO-IP]
Common Name English
TEGRETOL
Brand Name English
NEUROTOL
Common Name English
CARBAMAZEPINE [VANDF]
Common Name English
NSC-169864
Code English
SIRTAL
Brand Name English
FINLEPSIN
Brand Name English
CARBAMAZEPINE [ORANGE BOOK]
Common Name English
EPITOL
Brand Name English
STAZEPINE
Brand Name English
CARBAMAZEPINE [USAN]
Common Name English
CARBAMAZEPINE [MART.]
Common Name English
CARBAMAZEPINE EXTENDED RELEASE
Common Name English
BISTON
Brand Name English
TELESMIN
Brand Name English
GEIGY 32883
Code English
CARBAMAZEPINE [MI]
Common Name English
CARBATROL
Brand Name English
CARBAMAZEPINE [HSDB]
Common Name English
TIMONIL
Brand Name English
CARBAMAZEPINE ANHYDROUS
Common Name English
KARBELEX
Common Name English
TEGRETAL
Brand Name English
CARBAMAZEPINE [USP-RS]
Common Name English
CARBAMAZEPINUM [WHO-IP LATIN]
Common Name English
CARBAMAZEPINE [USP]
Common Name English
CARNEXIV
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
NDF-RT N0000008486
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
NDF-RT N0000175753
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 24.2.2
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
NDF-RT N0000175751
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
FDA ORPHAN DRUG 43590
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
FDA ORPHAN DRUG 265508
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
WHO-ATC N03AF01
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
LIVERTOX 146
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
WHO-VATC QN03AF01
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
EU-Orphan Drug EU/3/16/1746
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
Code System Code Type Description
EVMPD
SUB06113MIG
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
EPA CompTox
298-46-4
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
CAS
298-46-4
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
HSDB
298-46-4
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
ECHA (EC/EINECS)
206-062-7
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
WIKIPEDIA
CARBAMAZEPINE
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
ChEMBL
CHEMBL108
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
NDF-RT
N0000191266
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY Cytochrome P450 1A2 Inducers [MoA]
LactMed
298-46-4
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
PUBCHEM
2554
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
MERCK INDEX
M3053
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY Merck Index
RXCUI
2002
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB00564
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
INN
1836
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
NCI_THESAURUS
C341
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
NDF-RT
N0000185607
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY Cytochrome P450 2C19 Inducers [MoA]
MESH
D002220
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CARBAMAZEPINE
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY Description: A white to yellowish white, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water and ether R; soluble in ethanol (~750 g/l) TS. Category: Antiepileptic drug. Storage: Carbamazepine should be kept in a tightly closed container. Definition: Carbamazepine contains not less than 98.0% and not more than 102.0% of C15H12N2O, calculated with reference to the dried substance.
NDF-RT
N0000187064
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
NDF-RT
N0000185507
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY Cytochrome P450 2C9 Inducers [MoA]
IUPHAR
5339
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY
NDF-RT
N0000185506
Created by admin on Mon Oct 21 20:54:52 UTC 2019 , Edited by admin on Mon Oct 21 20:54:52 UTC 2019
PRIMARY Cytochrome P450 3A4 Inducers [MoA]