Acetohydroxamic acid

{{Short description|Enzyme inhibitor that inhibits urease}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 477239146

| IUPAC_name = N-Hydroxyacetamide

| image = Acetohydroxamic acid.svg

| width = 125

| image2 = Acetohydroxamic-acid-3D-balls.png

| width2 = 125

| tradename = Lithostat

| Drugs.com = {{drugs.com|CDI|acetohydroxamic_acid}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 546-88-3

| ATC_prefix = G04

| ATC_suffix = BX03

| ATC_supplemental =

| PubChem = 1990

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00551

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 1913

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4RZ82L2GY5

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00220

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 49029

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 734

| C=2 | H=5 | N=1 | O=2

| smiles = O=C(NO)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RRUDCFGSUDOHDG-UHFFFAOYSA-N

}}

Acetohydroxamic acid (also known as AHA or by the trade name Lithostat) is a drug that is a potent and irreversible enzyme inhibitor of the urease enzyme in various bacteria and plants; it is usually used for urinary tract infections. The molecule is similar to urea but is not hydrolyzable by urease;{{cite journal | vauthors = Fishbein WN, Carbone PP | title = Urease Catalysis. Ii. Inhibition of the Enzyme by Hydroxyurea, Hydroxylamine, and Acetohydroxamic Acid | journal = The Journal of Biological Chemistry | volume = 240 | pages = 2407–14 | date = June 1965 | doi = 10.1016/S0021-9258(18)97338-2 | pmid = 14304845 | doi-access = free }} it thus disrupts the bacteria's metabolism through competitive inhibition.