Acetohydroxamic acid

Acetohydroxamic acid Basic information
Product Name:Acetohydroxamic acid
Synonyms:yangwosuan;Acetylhydroxylamine;AHA;cetohyroxamic acid;Hydroxylamine, N-Acetyl-;Hydroxylamine,N-acetyl-;Lithostat;Methylhydroxamic acid
CAS:546-88-3
MF:C2H5NO2
MW:75.07
EINECS:208-913-8
Product Categories:LITHOSTAT;inhibitor;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;All Inhibitors;Hydroxylamines (N-Substituted);Amines;Hydroxylamines;Inhibitors;Nitrogen Compounds;Organic Building Blocks;546-88-3
Mol File:546-88-3.mol
Acetohydroxamic acid Structure
Acetohydroxamic acid Chemical Properties
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)
pka8.70(at 25℃)
form Crystalline Solid
color White to pale yellow
Water Solubility Soluble in water.
Sensitive Hygroscopic
Merck 14,63
BRN 1739019
Stability:Moisture and Temperature Sensitive
InChIKeyRRUDCFGSUDOHDG-UHFFFAOYSA-N
CAS DataBase Reference546-88-3(CAS DataBase Reference)
NIST Chemistry ReferenceAcetamide,N-hydroxy(546-88-3)
EPA Substance Registry SystemAcetohydroxamic acid (546-88-3)
Safety Information
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 Data546-88-3(Hazardous Substances Data)
Toxicitymmo-sat 160 mmol/plate JOPHDQ 3,557,80
MSDS Information
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Acetohydroxamic acid English
SigmaAldrich English
ACROS English
ALFA English
Acetohydroxamic acid Usage And Synthesis
DescriptionAcetohydroxamic 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 PropertiesWhite Crystalline Solid
OriginatorResearch Organics; Baylor Unk. (USA)
UsesAcetohydroxamic 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.
UsesA urease inhibitor. Used in the synthesis
UsesUrease 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.
DefinitionChEBI: 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 Process3 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 nameLithostat (Mission).
Therapeutic FunctionUrease inhibitor
General DescriptionAcetohydroxamic 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 effectsGet 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 ProfileModerately toxic by intraperitonealroute. An experimental teratogen. Other experimentalreproductive effects. Mutation data reported. When heatedto decomposition it emits toxic fumes of NOx.
Veterinary Drugs and TreatmentsAcetohydroxamic 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 materialsHYDROXYLAMINE
Preparation ProductsAcetaldoxime-->Caracemide-->5-(trifluoromethyl)benzo[d]isoxazol-3-amine
Triethyl acetyl citrate N-Hydroxymaleimide Vanadyl acetylacetonate Hyaluronic acid Acetaminophen Ethyl 2-(Chlorosulfonyl)acetate (2-NAPHTHOXY)ACETIC ACID N-HYDROXYSUCCINIMIDE ESTER 2,3-Butanedione monoxime DIACETAMIDE Benzohydroxamic acid Salicylhydroxamic acid Chloroacetamide Acetohydroxamic acid FLUOROACETAMIDE Thioacetamide 2-Cyanoacetamide N-Phenylbenzohydroxamic acid D-Cycloserine

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