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Acetohydroxamic acid

Product Name
Acetohydroxamic acid
CAS No.
546-88-3
Chemical Name
Acetohydroxamic acid
Synonyms
AHA;N-HYDROXYACETAMIDE;Acetylhydroxamic acid;Acetomenadione;Acetylhydroxylamine;T-41B;NSC 5073;Lithostat;yangwosuan;NSC 176136
CBNumber
CB6395344
Molecular Formula
C2H5NO2
Formula Weight
75.07
MOL File
546-88-3.mol
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Acetohydroxamic acid Property

Melting point:
88-90 °C (lit.)
Boiling point:
133.7°C (rough estimate)
Density 
1.2269 (rough estimate)
refractive index 
1.4264 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Methanol (Sparingly), Water (Sparingly)
form 
Crystalline Solid
pka
8.70(at 25℃)
color 
White to pale yellow
Water Solubility 
Soluble in water.
Sensitive 
Hygroscopic
Merck 
14,63
BRN 
1739019
Stability:
Moisture and Temperature Sensitive
InChIKey
RRUDCFGSUDOHDG-UHFFFAOYSA-N
CAS DataBase Reference
546-88-3(CAS DataBase Reference)
NIST Chemistry Reference
Acetamide,N-hydroxy(546-88-3)
EPA Substance Registry System
Acetohydroxamic acid (546-88-3)
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Safety

Hazard Codes 
T
Risk Statements 
61-40
Safety Statements 
53-45-36/37/39-22
RIDADR 
3263
WGK Germany 
3
RTECS 
AK8157000
Hazard Note 
Toxic
PackingGroup 
II
HS Code 
29225090
Hazardous Substances Data
546-88-3(Hazardous Substances Data)
Toxicity
mmo-sat 160 mmol/plate JOPHDQ 3,557,80
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
159034
Product name
Acetohydroxamic acid
Purity
98%
Packaging
5g
Price
$66.3
Updated
2024/03/01
Sigma-Aldrich
Product number
1006506
Product name
Acetohydroxamic acid
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$412
Updated
2024/03/01
TCI Chemical
Product number
A0051
Product name
Acetohydroxamic Acid
Purity
>98.0%(T)
Packaging
10g
Price
$50
Updated
2024/03/01
TCI Chemical
Product number
A0051
Product name
Acetohydroxamic Acid
Purity
>98.0%(T)
Packaging
25g
Price
$145
Updated
2024/03/01
Cayman Chemical
Product number
23979
Product name
Acetohydroxamic Acid
Purity
≥98%
Packaging
5g
Price
$32
Updated
2024/03/01
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Acetohydroxamic acid Chemical Properties,Usage,Production

Description

Acetohydroxamic acid is a potent, non-competitive and irreversible inhibitor of bacterial urease (Ki≈lO-7M). This enzyme, which is widely distributed in plants and bacteria, but not in mammalian cells, catalyzes the decomposition of urea to ammonia. Elevated urinary ammonia levels can reduce the antibacterial effectiveness of a number of agents. Thus, acetohydroxamic acid is useful as adjunctive therapy to decrease urinary ammonia and alkalinity in patients with chronic urea-splitting urinary infection. Such infections are a leading cause of recurring complications and death in paraplegics.

Chemical Properties

White Crystalline Solid

Originator

Research Organics; Baylor Unk. (USA)

Uses

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.
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.

Uses

A urease inhibitor. Used in the synthesis

Uses

Urease inhibitorAcetohydroxamic acid acts as a drug, as an inhibitor of bacterial and plant urease, which is used for urinary tract infections. It is also used in organic synthesis. It acts as an antiurolithic and antibacterial agent. It is involved in the study of complexation of iron(III) with acetohydroxamic acid as well as in the inhibition study of lansoprazole and omeprazole on Helicobacter pyloni. It plays an important role in the insitu generation of nitrosocarbonylmethane as a Diels-Alder dienophile. In addition to this, it is used in the treatment of kidney stones and urinary tract infections.

Definition

ChEBI: Acetohydroxamic acid is a member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group. It has a role as an EC 3.5.1.5 (urease) inhibitor and an algal metabolite. It is functionally related to an acetamide. It is a tautomer of a N-hydroxyacetimidic acid.

Manufacturing Process

3 Methods of producing of acetohydroxamic acid:
1. Ethyl acetic acid ether was treated with hydroxylamine and acetohydroxamic acid was obtained.
2. Acetohydroxamic acid was obtained in the result of reaction of acetamide with hydroxylamine.
3. Acetohydroxamic acid was obtained by treatment of acetaldehyde with nitrohydroxylamine.

brand name

Lithostat (Mission).

Therapeutic Function

Urease inhibitor

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.

Side effects

Get emergency medical help if you have any of these signs of an allergic reaction: hives; difficulty breathing; swelling of your face, lips, tongue, or throat.
Call your doctor at once if you have:
pounding heartbeats or fluttering in your chest;
signs of a blood clot in your leg --pain, swelling, warmth, or redness in one or both legs;
signs of a red blood cell disorder --pale or yellowed skin, dark colored urine, fever, confusion or weakness.
Common side effects may include:
headache during the first 2 days of treatment;
skin rash, warmth, tingling or redness (especially if you drink alcohol while taking acetohydroxamic acid);
upset stomach, nausea, loss of appetite;
depressed mood;
anxiety, tremors, nervousness;
hair loss.

Safety Profile

Moderately toxic by intraperitonealroute. An experimental teratogen. Other experimentalreproductive effects. Mutation data reported. When heatedto decomposition it emits toxic fumes of NOx.

Veterinary Drugs and Treatments

Acetohydroxamic acid can be used in dogs as adjunctive therapy in some cases of recurrent urolithiasis or in the treatment of persistent urinary tract infections caused by the following bacteria: E. coli, Klebsiella, Morganella morganii, Staphylococci spp., and Pseudomonas aeruginosa. Adverse effects limit its usefulness.

Acetohydroxamic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Acetohydroxamic acid manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Acetohydroxamic Acid 546-88-3
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-07
Hebei Weibang Biotechnology Co., Ltd
Product
Acetohydroxamic acid 546-88-3
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-31
Hebei Yanxi Chemical Co., Ltd.
Product
Acetohydroxamic acid 546-88-3
Price
US $20.00-1.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-11-07

546-88-3, Acetohydroxamic acidRelated Search:

Phenoxyacetyl chloride 2-Phenylacetamide Citric acid 2-HYDROXYACETAMIDE HYDROXYLAMINE Folic acid N,N-Dimethylacetamide Thioacetamide 2-Cyanoacetamide 2,3-Butanedione monoxime Benzohydroxamic acid DIACETAMIDE Ethyl 2-(Chlorosulfonyl)acetate Vanadyl acetylacetonate Hyaluronic acid Acetaminophen Chloroacetamide Triethyl acetyl citrate

  • yangwosuan
  • Acetylhydroxylamine
  • AHA
  • cetohyroxamic acid
  • Hydroxylamine, N-Acetyl-
  • Hydroxylamine,N-acetyl-
  • Lithostat
  • Methylhydroxamic acid
  • methylhydroxamicacid
  • n-acetyl-hydroxylamin
  • n-hydroxy-acetamid
  • N-ACETYLHYDROXYLAMINE
  • N-HYDROXYACETAMIDE
  • AcetohydroxaMic acid 98%
  • AcetohydroxaMic acid, 95+%
  • Acetomenadione
  • ALA-HIS-ALA
  • Acetohydroxamic acid, N-Acetylhydroxylamine
  • Acetohydroxamic Acid (200 mg)
  • AcetohydroxaMic acid, 98+% 5GR
  • NSC 176136
  • NSC 408425
  • NSC 5073
  • ACETYL HYDROXYAMINE
  • ACETOHYDROXAMIC ACID
  • AcetohydroxamicAcid[Aha]Urostat/LithostatC2H5No2
  • Acetohydroxamicacid,98%
  • Acetohydroxamic
  • Acetamide,N-hydroxy-
  • acethydroxamsaeure
  • Acethydroxamsaure
  • Acetic acid, oxime
  • aceticacid,oxime
  • acetohydroxamicacid(INN)
  • Acetohydroxamsαure
  • Acetohydroximic acid
  • acetohydroximicacid
  • Acetyl hydroxyamino
  • Acetylhydroxamic acid
  • acetylhydroxamicacid
  • N-hydroxyacetimidic acid
  • Acetohydroxamic Acid &gt
  • Acetamide, N-hydroxy- (9CI)
  • acetohydroxmic acid
  • Acetohydroxamic acid USP/EP/BP
  • Acetohydroxamic Acid (1006506)
  • Vinegar acid hydroxylamine
  • Acetoxyoxime acid
  • Acetohydroxamic Acid，Acetomenadione
  • Acetohydroxamic acid (6CI, 8CI)
  • Acetoxoxime acid
  • N-hydroxyacetamide / Acetohydroxamic acid
  • Acetoxyxamic acid
  • Acetohydroxamic Acid, ≥ 95.0%
  • T-41B
  • 546-88-3
  • Organic Building Blocks
  • Nitrogen Compounds