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C8981

Carbamazepine

Name: Carbamazepine
Brand: SIAL

meets USP testing specifications

Synonym(s):

5H-Dibenz[b,f]azepine-5-carboxamide

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₂N₂O

CAS Number:

298-46-4

Molecular Weight:

236.27

EC Number:

206-062-7

MDL number:

MFCD00005073

UNSPSC Code:

41116107

PubChem Substance ID:

24893120

NACRES:

NA.21

Agency

USP/NF
meets USP testing specifications

Quality Level

200

form

solid

mp

191-192 °C (lit.)

storage temp.

2-8°C

SMILES string

NC(=O)N1c2ccccc2C=Cc3ccccc13

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)

InChI key

FFGPTBGBLSHEPO-UHFFFAOYSA-N

Gene Information

human ... PRNP(5621) , SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)
rat ... Scn2a1(24766) , Scnn1a(25122) , Scnn1g(24768) , Slc6a1(79212)

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Biochem/physiol Actions

Anticonvulsant; ligand for the GABA_A receptor benzodiazepine modulatory site. Sodium channel inhibitor.

Pictograms

GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H317,H334,H336,H360FD

Precautionary Statements

P202 - P261 - P280 - P301 + P312 - P302 + P352 - P308 + P313

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1A - Resp. Sens. 1 - Skin Sens. 1A - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Antiseizure activity of novel gamma-aminobutyric acid (A) receptor subtype-selective benzodiazepine analogues in mice and rat models.

Felix M Rivas et al.

Journal of medicinal chemistry, 52(7), 1795-1798 (2009-03-12)

The antiseizure activity of benzodiazepines (BDZs) 1-5 in mice and rats as animal models is described. These BDZs have selective efficacy for alpha2beta3gamma2 and alpha3beta3gamma2 GABA(A)-receptors. Significant anticonvulsant activity with little or no motor impairment and therapeutic indexes (TI) of

HLA-A 31:01 and HLA-B 15:02 as genetic markers for carbamazepine hypersensitivity in children.

U Amstutz et al.

Clinical pharmacology and therapeutics, 94(1), 142-149 (2013-04-17)

The occurrence of hypersensitivity reactions including rare but life-threatening Stevens-Johnson syndrome (SJS) and drug-induced hypersensitivity syndrome (HSS) limits the use of the anticonvulsant carbamazepine (CBZ). Human leukocyte antigen-B (HLA)-B 15:02 and HLA-A 31:01 have been identified as predictive genetic markers

Recommendations for HLA-B*15:02 and HLA-A*31:01 genetic testing to reduce the risk of carbamazepine-induced hypersensitivity reactions.

Ursula Amstutz et al.

Epilepsia, 55(4), 496-506 (2014-03-07)

To systematically review evidence on genetic risk factors for carbamazepine (CBZ)-induced hypersensitivity reactions (HSRs) and provide practice recommendations addressing the key questions: (1) Should genetic testing for HLA-B*15:02 and HLA-A*31:01 be performed in patients with an indication for CBZ therapy

Intrauterine exposure to carbamazepine and specific congenital malformations: systematic review and case-control study.

Janneke Jentink et al.

BMJ (Clinical research ed.), 341, c6581-c6581 (2010-12-04)

To identify specific major congenital malformations associated with use of carbamazepine in the first trimester of pregnancy. A review of all published cohort studies to identify key indications and a population based case-control study to test these indications. Review of

Network-specific mechanisms may explain the paradoxical effects of carbamazepine and phenytoin.

Evan A Thomas et al.

Epilepsia, 54(7), 1195-1202 (2013-04-10)

A common notion of the mechanism by which the antiepileptic drugs (AEDs) carbamazepine and phenytoin act is that they block sodium channels by binding preferentially to the inactivated state, thereby allowing normal neuronal firing while blocking ictal activity. However, these

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