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546-88-3 molecular structure
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N-hydroxyacetamide

ChemBase ID: 433
Molecular Formular: C2H5NO2
Molecular Mass: 75.0666
Monoisotopic Mass: 75.03202841
SMILES and InChIs

SMILES:
ONC(=O)C
Canonical SMILES:
CC(=O)NO
InChI:
InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)
InChIKey:
RRUDCFGSUDOHDG-UHFFFAOYSA-N

Cite this record

CBID:433 http://www.chembase.cn/molecule-433.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-hydroxyacetamide
IUPAC Traditional name
acetohydroxamic acid
Brand Name
Lithostat
Synonyms
Acetohydroxamic acid
Acetohydroxamic acid
N-Acetylhydroxylamine
N-Hydroxyacetamide
AHA
Cetohyroxamic acid
Methylhydroxamic acid
N-Hydroxyacetamide
Acetylhydroxamic acid
Acetyl hydroxyamino
Acetohydroximic acid
Acetic acid, oxime
Acethydroxamsaure
Acetohydroxamate
Acetohydroxamic Acid
Acetic Acid Oxime
Acetylhydroxylamine
NSC 176136
NSC 408425
NSC 5073
乙酰氧肟酸
乙酰羟肟酸
CAS Number
546-88-3
166438-83-1
EC Number
208-913-8
MDL Number
MFCD00009994
Beilstein Number
1739019
Merck Index
1463
PubChem SID
160963896
24845057
24849786
46508546
PubChem CID
1990

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.9435215  H Acceptors
H Donor LogD (pH = 5.5) -1.0336257 
LogD (pH = 7.4) -1.0456617  Log P -1.03347 
Molar Refractivity 16.2305 cm3 Polarizability 6.3648486 Å3
Polar Surface Area 49.33 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.46  LOG S 0.83 
Solubility (Water) 5.09e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1E+006 mg/L expand Show data source
Water expand Show data source
Apperance
White Crystalline Solid expand Show data source
Melting Point
86-90°C expand Show data source
86-90°C expand Show data source
88-90 °C expand Show data source
88-90 °C(lit.) expand Show data source
89-91°C expand Show data source
89-92°C expand Show data source
91 - 92°C expand Show data source
Hydrophobicity(logP)
-0.7 expand Show data source
-1.594 expand Show data source
Storage Condition
0°C, Desiccate expand Show data source
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
Storage Warning
Hygroscopic expand Show data source
IRRITANT expand Show data source
Teratogenic/Hygroscopic/Store under Argon expand Show data source
RTECS
AK8157000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
61 expand Show data source
Safety Statements
53-20-36-45 expand Show data source
53-45 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H360 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
P281-P201-P202-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
Gene Information
human ... CA2(760), MMP3(4314) expand Show data source
Purity
≥98.0% (NT) expand Show data source
95% expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Linear Formula
CH3CONHOH expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Apollo Scientific Apollo Scientific Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02100018 external link
Urease Inhibitor
DrugBank - DB00551 external link
Item Information
Drug Groups approved
Description Acetohydroxamic Acid, a synthetic drug derived from hydroxylamine and ethyl acetate, is similar in structure to urea. In the urine, it acts as an antagonist of the bacterial enzyme urease. Acetohydroxamic Acid has no direct antimicrobial action and does not acidify urine directly. It is used, in addition to antibiotics or medical procedures, to treat chronic urea-splitting urinary infections.
Indication Used, in addition to antibiotics or medical procedures, to treat chronic urea-splitting urinary infections.
Pharmacology Acetohydroxamic Acid, a synthetic drug derived from hydroxylamine and ethyl acetate, is similar in structure to urea. In the urine, it acts as an antagonist of the bacterial enzyme urease. Acetohydroxamic Acid has no direct antimicrobial action and does not acidify urine directly.
Toxicity Oral, rat: LD50 = 4.8gm/kg. Symptoms of overdose include anorexia, malaise, lethargy, diminished sense of wellbeing, tremor, anxiety, nausea, and vomiting.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation 35-65% of oral dose excreted unchanged in urine (which provides the drug's therapeutic effect).
Absorption Well absorbed from the GI tract following oral administration.
Half Life 5-10 hours in patients with normal renal function
Protein Binding No known binding
References
[Link]
External Links
Wikipedia
Drugs.com
Apollo Scientific Ltd - OR6375T external link
A urease inhibitor.
Sigma Aldrich - 159034 external link
Packaging
5, 10, 50 g in glass bottle
Application
Used in urease inhibition studies1,2 and for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile.3
Toronto Research Chemicals - A163750 external link
A urease inhibitor. Used in the synthesis of pyrogallol and catechol derivatives as Helicobacter pylori urease inhibitors.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  Link
  • • Xiao, Z.-P., et al.: Eur. J. Med. Chem., 45, 5064 (2010)
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PATENTS

PATENTS

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INTERNET

INTERNET

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