N-hydroxyacetamide

• ChemBase ID: 433
• Molecular Formular: C2H5NO2
• Molecular Mass: 75.0666
• Monoisotopic Mass: 75.03202841
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 166438-83-1; 546-88-3
• 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

JChem

• Acid pKa: 8.9435215
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.0336257
• LogD (pH = 7.4): -1.0456617
• Log P: -1.03347
• Molar Refractivity: 16.2305 cm^3
• Polarizability: 6.3648486 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.46
• LOG S: 0.83
• Solubility (Water): 5.09e+02 g/l

PROPERTIES

Physical Property

• Solubility: 1E+006 mg/L; Water
• Apperance: White Crystalline Solid
• Melting Point: 86-90°C; 86-90°C; 88-90 °C; 88-90 °C(lit.); 89-91°C; 89-92°C; 91 - 92°C
• Hydrophobicity(logP): -0.7; -1.594

Safety Information

• Storage Condition: 0°C, Desiccate; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Hygroscopic; IRRITANT; Teratogenic/Hygroscopic/Store under Argon
• RTECS: AK8157000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-20-36-45; 53-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313; P281-P201-P202-P308+P313-P405-P501A
• 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; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

Pharmacology Properties

• Gene Information: human ... CA2(760), MMP3(4314)

Product Information

• Purity: ≥98.0% (NT); 95%; 95+%; 97%; 98%
• Grade: purum
• Linear Formula: CH3CONHOH

DETAILS

MP Biomedicals - 02100018

Urease Inhibitor

DrugBank - DB00551

• 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

A urease inhibitor.

Sigma Aldrich - 159034

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

A urease inhibitor. Used in the synthesis of pyrogallol and catechol derivatives as Helicobacter pylori urease inhibitors.

REFERENCES

• Link
• Xiao, Z.-P., et al.: Eur. J. Med. Chem., 45, 5064 (2010)