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Dequalinium chloride

Pharmaceutical Secondary Standard; Certified Reference Material

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Synonym(s):
1,1′-Decamethylenebis(4-aminoquinaldinium) dichloride
Empirical Formula (Hill Notation):
C30H40Cl2N4
CAS Number:
522-51-0
Molecular Weight:
527.57
EC Number:
208-330-9
MDL number:
MFCD00063502
UNSPSC Code:
41116107
PubChem Substance ID:
329823288
NACRES:
NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

Agency

traceable to Ph. Eur. D0430000

API family

dequalinium

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

≥300 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

[Cl-].[Cl-].Cc1cc(N)c2ccccc2[n+]1CCCCCCCCCC[n+]3c(C)cc(N)c4ccccc34

InChI

1S/C30H38N4.2ClH/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34;;/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H

InChI key

LTNZEXKYNRNOGT-UHFFFAOYSA-N

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General description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Dequalinium chloride (DECA) is a cationic, lipophilic mitochondrial toxin which can act as a cyctotoxic agent on the mitochondrial membrane of specific epithelial carcinoma cells, by inhibiting the cellular energy production. It can have useful applications in cancer therapy.

Application

Dequalinium chloride may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by high performance liquid chromatography (HPLC).
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAC3331 in the slot below. This is an example certificate only and may not be the lot that you receive.

related product

Product No.
Description
Pricing

WGK

WGK 3

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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Toxicity of the mitochondrial poison dequalinium chloride in a murine model system
Gamboa-Vujicic G, et al.
Journal of Pharmaceutical Sciences, 82(3), 231-235 (1993)
Xiao-Xing Wang et al.
Biomaterials, 32(24), 5673-5687 (2011-05-10)
Intrinsic multidrug resistance (MDR) of cancers remains a major obstacle to successful chemotherapy. A dequalinium polyethylene glycol-distearoylphosphatidylethanolamine (DQA-PEG(2000)-DSPE) conjugate was synthesized as a mitochondriotropic molecule, and mitochondrial targeting resveratrol liposomes were developed by modifying DQA-PEG(2000)-DSPE on the surface of liposomes
Ernst Rainer Weissenbacher et al.
Gynecologic and obstetric investigation, 73(1), 8-15 (2011-12-30)
To investigate if vaginal application of dequalinium chloride (DQC, Fluomizin®) is as effective as vaginal clindamycin (CLM) in the treatment of bacterial vaginosis (BV). This was a multinational, multicenter, single-blind, randomized trial in 15 centers, including 321 women. They were
Mar Orzáez et al.
Apoptosis : an international journal on programmed cell death, 16(5), 460-467 (2011-02-23)
Inhibitor of apoptosis proteins (IAPs) regulate the activity of caspases in apoptosis. The human X chromosome-encoded IAP (XIAP) is one of the more potent members of the IAP family and it has been described as a central regulator of apoptosis.
Diana Lyrawati et al.
Pharmaceutical research, 28(11), 2848-2862 (2011-08-13)
We describe a novel strategy for expression of GFP in mammalian mitochondria. The key components of the strategy were an artificially created mitochondrial genome pmtGFP and a DQAsome transfection system. Using immunofluorescence and a combination of immunohistochemical and molecular based
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