Carbamazepine

Details

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

SHOW SMILES / InChI

SMILES

NC(=O)N1C2=C(C=CC=C2)C=CC3=C1C=CC=C3

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)

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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

Targets

Primary Target	Pharmacology	Potency
Sodium channel protein type 5 subunit alpha 9	Blocker 555	152.0 µM [IC50]
Sodium channel protein type 2 subunit alpha 2	Blocker 555	25.0 µM [Ki]
Sodium channel protein type 3 subunit alpha 2	Blocker 555	16.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121	Primary		Approved 8,583	TEGRETOL
Trigeminal neuralgia 9	Primary		Approved 8,583	TEGRETOL

C_max

Value	Dose	Analyte	Population
1.9 μg/mL	200 mg single, oral	CARBAMAZEPINE plasma	Homo sapiens
0.11 μg/mL	200 mg single, oral	CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens
1.5 μg/mL	800 mg 1 times / day multiple, oral	CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens
11 μg/mL	800 mg 2 times / day multiple, oral	CARBAMAZEPINE plasma	Homo sapiens
4.3 μg/mL	400 mg single, oral	CARBAMAZEPINE plasma	Homo sapiens
2.2 μg/mL	800 mg 2 times / day multiple, oral	CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens
3.2 μg/mL	1600 mg 1 times / day multiple, oral	CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens
3.2 μg/mL	400 mg single, oral	CARBAMAZEPINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
15.7 μg × h/mL	800 mg 1 times / day multiple, oral		CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens
32.6 μg × h/mL	1600 mg 1 times / day multiple, oral		CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
37.5 h	200 mg single, oral	CARBAMAZEPINE plasma	Homo sapiens
34 h	200 mg single, oral	CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens
14.5 h	800 mg 2 times / day multiple, oral	CARBAMAZEPINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
24%	200 mg single, oral		CARBAMAZEPINE plasma	Homo sapiens
50%	200 mg single, oral		CARBAMAZEPINE-10,11-EPOXIDE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
1000 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 73.1 ± 5.5	Disc. AE: Skin and subcutaneous conditions NEC, Fatigue...

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AEs

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AE	Significance	Dose	Population
Skin and subcutaneous conditions NEC	8.8% Disc. AE	1000 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 73.1 ± 5.5
Fatigue	Disc. AE	1000 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 73.1 ± 5.5
Somnolence	Disc. AE	1000 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 73.1 ± 5.5

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inducer 1,087			inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 UGT2B7 456 UGT1A1 479 UGT1A3 470 UGT1A6 343 UGT1A9 423 UGT2B4 278 UGT1A4 399	CYP1A2 832 CYP2B6 669 UGT1A6 34 UGT1A7 2

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP3A4 2,633	inducer 1,966	strong	yes (co-administration study)
CYP1A2 2,333	inducer 1,966	yes
CYP2B6 1,160	inducer 1,966	yes
UGT1A6 171	inducer 1,966	yes
UGT1A7 25	inducer 1,966	yes

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Drug as victim

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Target	Modality	Activity
UGT1A1 479	substrate 4,014	no
UGT1A3 470	substrate 4,014	no
UGT1A4 399	substrate 4,014	no
UGT1A6 343	substrate 4,014	no
UGT1A9 423	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3387	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3387
ChemicalBook	CB1143564	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1143564
eMolecules	27677745	https://www.emolecules.com/cgi-bin/more?vid=27677745
eMolecules	535714	https://www.emolecules.com/cgi-bin/more?vid=535714
MolPort	MolPort-000-710-574	https://www.molport.com/shop/molecule-link/MolPort-000-710-574

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PubMed

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Title	Date	PubMed
Carbamazepine-associated severe bile duct injury.	1999 Feb	10022661
[Carbamazepine induced hyponatremia].	1999 Jan	10024990
Elimination of oxcarbazepine-induced oculogyric crisis following vagus nerve stimulation.	1999 Jun 10	10371552
Carbamazepine-associated severe left ventricular dysfunction.	2000	10866337
Refractory idiopathic absence status epilepticus: A probable paradoxical effect of phenytoin and carbamazepine.	2000 Jul	10897162

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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: Other

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.

Show entries

Name

Type

Language

CARBAMAZEPINE [WHO-IP]

Preferred Name

English

Carbamazepine

Official Name

English

EQUETRO

Brand Name

English

TERIL

Brand Name

English

NEUROTOP

Common Name

English

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Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C264

Decreased Disorganized Electrical Activity

NDF-RT

N0000008486

Established Pharmacologic Class

NDF-RT

N0000175753

Medicines used in mood disorders

WHO-ESSENTIAL MEDICINES LIST

24.2.2

Established Pharmacologic Class

NDF-RT

N0000175751

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Code System

Code

Type

Description

EVMPD

SUB06113MIG

PRIMARY

LACTMED

Carbamazepine

PRIMARY

NSC

169864

PRIMARY

EPA CompTox

DTXSID4022731

PRIMARY

CAS

298-46-4

PRIMARY

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ACTIVE MOIETY


					33CM23913M

Carbamazepine

METABOLITE (PARENT)


					1UT0PR32AJ

HYDROXYCARBAMAZEPINE, 2-

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator