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
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.
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.
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acid is a member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.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.
