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Details

Stereochemistry ACHIRAL
Molecular Formula C2H5NO2
Molecular Weight 75.0666
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Acetohydroxamic acid

SMILES

CC(=O)NO

InChI

InChIKey=RRUDCFGSUDOHDG-UHFFFAOYSA-N
InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)

HIDE SMILES / InChI

Description

Acetohydroxamic acid (also known as AHA or by the trade name Lithostat) is 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 is used to lower the level of ammonia in the urine, which may help with some types of urinary infections. 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. In 1983 the US Food and Drug Administration approved acetohydroxamic acid (AHA) as an orphan drug for "prevention of so-called struvite stones" under the newly enacted Orphan Drug Act of 1983.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
27.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
LITHOSTAT

Cmax

ValueDoseCo-administeredAnalytePopulation
9 μg/mL
250 mg single, oral
ACETOHYDROXAMIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
21.9 h
250 mg single, oral
ACETOHYDROXAMIC ACID plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Urinary Tract Infection Starting dose: 12 mg/kg/day administered at 6 to 8 hour intervals at a time when the stomach is empty. Then progress to one tablet orally 3 to 4 times a day in a total daily dose of 10 to 15 mg/kg/day. The maximum daily dose should be no more than 1.5 grams, regardless of body weight.
Route of Administration: Oral