{{Short description|Enzyme inhibitor that inhibits urease}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Watchedfields = changed | verifiedrevid = 477239146 | IUPAC_name = ''N''-Hydroxyacetamide | image = Acetohydroxamic acid.svg | image_class = skin-invert-image | width = 125 | image2 = Acetohydroxamic-acid-3D-balls.png | image_class2 = bg-transparent | width2 = 125 <!--Clinical data--> | tradename = Lithostat | Drugs.com = {{drugs.com|CDI|acetohydroxamic_acid}} | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = X | legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_UK = <!-- GSL / P / POM / CD --> | legal_US = | legal_status = Rx-only | routes_of_administration = <!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = <!--Identifiers--> | 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 <!--Chemical data--> | 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 and urinary stone disease. The molecule is similar to urea but is not hydrolyzable by urease;<ref name="pmid_14304845">{{cite journal | vauthors = Fishbein WN, Carbone PP | date = June 1965 | title = Urease Catalysis. Ii. Inhibition of the Enzyme by Hydroxyurea, Hydroxylamine, and Acetohydroxamic Acid | journal = The Journal of Biological Chemistry | volume = 240 | pages = 2407–2414 | doi = 10.1016/S0021-9258(18)97338-2 | pmid = 14304845 | doi-access = free }}</ref> it thus disrupts the bacteria's metabolism through competitive inhibition. It is particularly effective for the prevention and treatment of infection stones (struvite stones).<ref name="j504">{{cite book | vauthors = Karki N, Leslie SW | date = 2026 | chapter = Struvite and Triple Phosphate Renal Calculi | title = StatPearls | publisher = StatPearls Publishing | pmid = 33760542 | chapter-url = http://www.ncbi.nlm.nih.gov/books/NBK568783/ | access-date = 2026-03-17 | publication-place = Treasure Island (FL) }}</ref>
==Orphan drug==
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.<ref name="JAMA_1983">{{cite journal | vauthors = Marwick C | date = July 1983 | title = New drugs selectively inhibit kidney stone formation | journal = JAMA | volume = 250 | issue = 3 | pages = 321–322 | doi = 10.1001/jama.1983.03340030003001 | pmid = 6854890 }}</ref> AHA cannot be patented because it is a standard chemical compound.<ref name="JAMA_1983" />
== See also == * Salicylhydroxamic acid
== References == {{reflist}}
{{Urologicals}}
Category:Orphan drugs Category:Hydroxamic acids