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
New developments in the pharmacotherapy of alcohol dependence.
2001
Update on anticonvulsants for the treatment of alcohol withdrawal.
2001
Investigation and medical management of trigeminal neuralgia by consultant oral and maxillofacial surgeons in the British Isles.
2001 Apr
Novel treatments for bipolar disorder.
2001 Apr
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.
2001 Feb 23
Changes in color vision after a single dose of vigabatrin or carbamazepine in healthy volunteers.
2001 Jan-Feb
Taking the sting out of trigeminal neuralgia.
2001 Mar
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
Treatment of bipolar affective disorder in clinical practice.
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
CARBIDOPUM [WHO-IP LATIN]
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
CARBIDOPA [WHO-IP]
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
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
NDF-RT N0000008486
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
NDF-RT N0000175753
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 24.2.2
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
NDF-RT N0000175751
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
WHO-ATC N03AF01
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
LIVERTOX 146
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
WHO-VATC QN03AF01
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
Code System Code Type Description
EVMPD
SUB06113MIG
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
EPA CompTox
298-46-4
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
CAS
298-46-4
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
HSDB
298-46-4
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
ECHA (EC/EINECS)
206-062-7
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
WIKIPEDIA
CARBAMAZEPINE
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
ChEMBL
CHEMBL108
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
NDF-RT
N0000191266
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY Cytochrome P450 1A2 Inducers [MoA]
LactMed
298-46-4
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
PUBCHEM
2554
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY SWITZERF
MERCK INDEX
M3053
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY Merck Index
RXCUI
2002
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY RxNorm
DRUG BANK
DB00564
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
INN
1836
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
NCI_THESAURUS
C341
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
NDF-RT
N0000185607
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY Cytochrome P450 2C19 Inducers [MoA]
MESH
D002220
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CARBAMAZEPINE
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
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 Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
NDF-RT
N0000185507
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY Cytochrome P450 2C9 Inducers [MoA]
IUPHAR
5339
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY
NDF-RT
N0000185506
Created by admin on Tue Mar 06 10:28:44 UTC 2018 , Edited by admin on Tue Mar 06 10:28:44 UTC 2018
PRIMARY Cytochrome P450 3A4 Inducers [MoA]