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159034

Sigma-Aldrich

Acetohydroxamic acid

98%

Synonym(s):

AHA

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About This Item

Linear Formula:
CH3CONHOH
CAS Number:
546-88-3
Molecular Weight:
75.07
Beilstein/REAXYS Number:
1739019
EC Number:
208-913-8
MDL number:
MFCD00009994
UNSPSC Code:
12352100
PubChem Substance ID:
24849786
NACRES:
NA.22

assay

98%

mp

88-90 °C (lit.)

SMILES string

CC(NO)=O

InChI

1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)

InChI key

RRUDCFGSUDOHDG-UHFFFAOYSA-N

Gene Information

human ... CA2(760) , MMP3(4314)

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General description

Acetohydroxamic acid is a potent inhibitor of bacterial urease activity and reduces urinary ammonia levels. 2-Acetohydroxamic acid loaded floating microspheres forms an efficient drug delivery system for the treatment of Helicobacter pylori.

Application

Acetohydroxamic acid was used:
  • to study the mechanism of complexation of iron (III) with acetohydroxamic acid
  • to study the inhibitory mechanism of lansoprazole and omeprazole on Helicobacter pyloni
  • in urease inhibition studies
  • for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile
Used in urease inhibition studies and for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Journal of the Chemical Society. Perkin Transactions 1, 1001-1001 (1991)
K Nagata et al.
Antimicrobial agents and chemotherapy, 37(4), 769-774 (1993-04-01)
The gastric proton pump inhibitor lansoprazole, its active analog AG-2000, and omeprazole dose dependently inhibited urease activity extracted with distilled water from Helicobacter pylori cells; the 50% inhibitory concentrations were between 3.6 and 9.5 microM, which were more potent than
Chem. Abstr., 116, 124530f-124530f (1992)
Mechanism of iron (III) complex formation. Activation volumes for the complexation of the iron (III) ion with thiocyanate ion and acetohydroxamic acid.
Funahashi S, et al.
Inorganic Chemistry, 22(14), 2070-2073 (1983)
R B Umamaheshwari et al.
The Journal of pharmacy and pharmacology, 55(12), 1607-1613 (2004-01-24)
This investigation is part of our ongoing effort to develop effective drug delivery systems for the treatment of Helicobacter pylori infection using polycarbonate (PC) floating microspheres as drug carriers. In an effort to augment the anti-H. pylori effect of acetohydroxamic
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