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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

Molecular Formula C15H12N2O
Molecular Weight 236.2686
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Anticonvulsant-induced dyskinesias: a comparison with dyskinesias induced by neuroleptics.
1976 Dec
A common mutation in the methylenetetrahydrofolate reductase gene is a determinant of hyperhomocysteinemia in epileptic patients receiving anticonvulsants.
1999 Aug
Effects of the calcium antagonists verapamil and nitrendipine on carbamazepine withdrawal.
1999 Dec
Carbamazepine-associated severe bile duct injury.
1999 Feb
N-acetyl-beta-glucosaminidase and beta-galactosidase activity in children receiving antiepileptic drugs.
1999 Jan
[Carbamazepine induced hyponatremia].
1999 Jan
[Severe intoxication probably from olanzapine (Zyprexa). Beneficial effect of glucagon].
1999 Jun
Lithium-treated mood disorders, paroxysmal rhinorrhea, and mesial temporal lobe epilepsy.
1999 Summer
Carbamazepine-associated severe left ventricular dysfunction.
2000
Worsening of symptoms of multiple sclerosis associated with carbamazepine.
2000 Apr 22
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
Potential interaction between ritonavir and carbamazepine.
2000 Jul
Refractory idiopathic absence status epilepticus: A probable paradoxical effect of phenytoin and carbamazepine.
2000 Jul
Color vision in epilepsy patients treated with vigabatrin or carbamazepine monotherapy.
2000 May
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
Renal tubular function in patients receiving anticonvulsant therapy: a long-term study.
2000 Nov
[Carbamazepine-induced hepatitis].
2000 Oct 10
[Two cases of auditory disturbance caused by carbamazepine].
2000 Sep
New developments in the pharmacotherapy of alcohol dependence.
2001
Update on anticonvulsants for the treatment of alcohol withdrawal.
2001
Mood and behavioural disorders following traumatic brain injury: clinical evaluation and pharmacological management.
2001 Feb
Determination of the antiepileptics vigabatrin and gabapentin in dosage forms and biological fluids using Hantzsch reaction.
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
Recommendations for the management of behavioral and psychological symptoms of dementia.
2001 Feb
Relation between dosage of carbamazepine and concentration in hair and plasma samples from a compliant inpatient epileptic population.
2001 Feb
Pleomorphic xanthoastrocytoma: report of a case diagnosed by intraoperative cytopathological examination.
2001 Feb
Rufinamide: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy.
2001 Feb
A model of atypical absence seizures: EEG, pharmacology, and developmental characterization.
2001 Feb 13
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
Relief of cluster headache and cranial neuralgias. Promising prophylactic and symptomatic treatments.
2001 Jan
Effects of antiepileptic drugs on rat platelet aggregation: ex vivo and in vitro study.
2001 Jan
Interleukin-6 enhances expression of adenosine A(1) receptor mRNA and signaling in cultured rat cortical astrocytes and brain slices.
2001 Jan
Effects of antimanic mood-stabilizing drugs on fetuses, neonates, and nursing infants.
2001 Mar
Influence of retigabine on the anticonvulsant activity of some antiepileptic drugs against audiogenic seizures in DBA/2 mice.
2001 Mar
Suppressive effects of oxcarbazepine on tooth pulp-evoked potentials recorded at the trigeminal spinal tract nucleus in cats.
2001 Mar
Separation of olanzapine, carbamazepine and their main metabolites by capillary electrophoresis with pseudo-stationary phases.
2001 Mar 5
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:54:51 UTC 2019
Edited
by admin
on Mon Oct 21 20:54:51 UTC 2019
Record UNII
33CM23913M
Record Status Validated (UNII)
Record Version
  • Download
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]
Related Record Type Details
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INDUCER
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INDUCER
TARGET -> INHIBITOR
METABOLIC ENZYME -> INDUCER
POTENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
PARENT -> IMPURITY
UNSPECIFIED
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC