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Merck

76307

Pefabloc® SC

Synonym(s):

4-(2-Aminoethyl)benzenesulfonyl fluoride hydrochloride, AEBSF

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About This Item

Empirical Formula (Hill Notation):
C8H10FNO2S · HCl
CAS Number:
Molecular Weight:
239.69
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
7604627

InChI

1S/C8H10FNO2S.ClH/c9-13(11,12)8-3-1-7(2-4-8)5-6-10;/h1-4H,5-6,10H2;1H

SMILES string

FS(C1=CC=C(CCN)C=C1)(=O)=O.[H]Cl

InChI key

WRDABNWSWOHGMS-UHFFFAOYSA-N

assay

≥95.0% (HPLC)

form

powder or crystals

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

storage temp.

2-8°C

Quality Level

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Application

Pefabloc® SC may be used as an analytical standard in determining the native oligomeric state and substrate specificity of rat NTPDase1 and NTPDase2 after heterologous expression in Xenopus oocytes. It may also be used as an esterase inhibitor, which is added to the whole blood to improve the stability of ciclesonide for the determination of ciclesonide (CIC) and its active metabolite, desisobutyryl-ciclesonide (des-CIC), in human plasma using liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometric (LC-APCI-MS/MS) method.
Recommended concentrations for use are 0.1-1 mM.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

4-(2-Aminoethyl)benzenesulfonyl fluoride hydrochloride (AEBSF) is an irreversible serine protease inhibitor. Inhibition constants are similar to those of phenylmethanesulfonyl fluoride (PMSF) and diisopropylfluorophosphate (DFP). AEBSF has been shown to inhibit trypsin, chymotrypsin, plasmin kallikrein, and thrombin. As an alternative to PMSF and DFP, AEBSF offers lower toxicity, improved solubility in water, and improved stability in aqueous solutions. AEBSF can be used in cell culture in concentrations of up to 0.25 mM.

General description

Pefabloc® SC is a potent, nontoxic and relatively easy to use, irreversible serine proteinase inhibitor. It is reported to efficiently inhibit the platelet activating factor (PAF)-degrading acetylhydrolase (acetylhydrolase) in both humans and rats.
Pefabloc® SC is a trypsin inhibitor, which can be used in the synthesis of its arginine-like analogue, 4-(2-guanidinoethyl)benzenesulfonyl fluoride.

Other Notes

Potent and irreversible inhibitor of serine proteases; in contrast to PMSF, it is water soluble and non-toxic; Unaffected by albumin

Legal Information

Pefabloc is a registered trademark of Pentapharm

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1A

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Pefabloc, 4-[2-aminoethyl] benzenesulfonyl fluoride, is a new, potent nontoxic and irreversible inhibitor of PAF-degrading acetylhydrolase
Dentan C, et al.
Biochimica et Biophysica Acta, 1299(3), 353-357 (1996)
Determination of native oligomeric state and substrate specificity of rat NTPDase1 and NTPDase2 after heterologous expression in Xenopus oocytes
Failer UB, et al.
European Journal of Biochemistry, 270(8), 1802-1809 (2003)
A trypsin-based bistable switch
Postma.J.GS, et al.
Tetrahedron (2017)
Simultaneous determination of ciclesonide and its active metabolite desisobutyryl-ciclesonide in human plasma by LC?APCI-MS/MS: Application to pharmacokinetic study in healthy Chinese volunteer
Su X-M, et al.
Journal of Pharmaceutical and Biomedical Analysis, 55(1), 230-235 (2011)
V Michael Holers et al.
Frontiers in immunology, 11, 201-201 (2020-03-11)
The complement system plays an important role in the pathogenesis of rheumatoid arthritis (RA). Besides driving lectin pathway (LP) activation, the mannan-binding lectin (MBL)-associated serine proteases (MASPs) also play a key role in regulating the alternative pathway (AP). We evaluated

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