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1093001

USP

Carbamazepine

United States Pharmacopeia (USP) Reference Standard

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
MDL number:
MFCD00005073
UNSPSC Code:
41116107
PubChem Substance ID:
329749228
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

carbamazepine

manufacturer/tradename

USP

mp

191-192 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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 ... SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Carbamazepine USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Carbamazepine Extended-Release Tablets
  • Carbamazepine Oral Suspension
  • Carbamazepine Tablets
  • Oxcarbazepine
  • Oxcarbazepine Oral Suspension
  • Oxcarbazepine Tablets

Biochem/physiol Actions

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

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

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C0450000

Carbamazepine, European Pharmacopoeia (EP) Reference Standard

1093023

Carbamazepine Related Compound B, United States Pharmacopeia (USP) Reference Standard

1093012

Carbamazepine Related Compound A, United States Pharmacopeia (USP) Reference Standard

1424084

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BP974

Carbamazepine, British Pharmacopoeia (BP) Reference Standard

PHR1918

Carbamazepine Related Compound A, Pharmaceutical Secondary Standard; Certified Reference Material

PHR2433

Carbamazepine Impurity F, Pharmaceutical Secondary Standard; Certified Reference Material

PHR2330

Carbamazepine Impurity C, Pharmaceutical Secondary Standard; Certified Reference Material

PHR2237

Carbamazepine Impurity B, pharmaceutical secondary standard, certified reference material

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
V L Yip et al.
Clinical pharmacology and therapeutics, 92(6), 757-765 (2012-11-08)
Carbamazepine (CBZ) therapy is associated with cutaneous adverse reactions in up to 10% of patients. Predisposition to these hypersensitivity reactions has been linked to the human leukocyte antigen (HLA) genotype. This systematic review determines the strength of these associations and
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
Sandeep Grover et al.
Pharmacogenetics and genomics, 24(2), 94-112 (2013-12-18)
A considerable heterogeneity exists in the literature on the role of different HLA alleles in carbamazepine (CBZ)-induced cutaneous adverse drug reactions (cADRs) of varying severity among diverse ethnic groups. The aim of the present study was to understand and summarize
Wimonchat Tangamornsuksan et al.
JAMA dermatology, 149(9), 1025-1032 (2013-07-26)
The US Food and Drug Administration recommends screening for the HLA-B*1502 allele before initiation of carbamazepine therapy in patients of Asian ancestry, but there remains unclear evidence of a relationship between HLA-B*1502 and Stevens-Johnson syndrome (SJS) and toxic epidermal necrolysis
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