All Photos(2)

C8981

Sigma-Aldrich

Carbamazepine

meets USP testing specifications

Synonym(s):
5H-Dibenz[b,f]azepine-5-carboxamide
Empirical Formula (Hill Notation):
C15H12N2O
CAS Number:
Molecular Weight:
236.27
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

Agency/Method

USP/NF
meets USP testing specifications

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

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Packaging

5, 25 g in glass bottle

Biochem/physiol Actions

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

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1A - 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 Germany

WGK 2

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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...
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...
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...
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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