Acetohydroxamic Acid
N-HYDROXYACETAMIDE · AHA · Acetylhydroxamic acid · Acetylhydroxylamine · Acetomenadione · N-hydroxyacetimidic acid · T-41B · NSC 5073
Identifiers & Physical Properties
| CAS No. | 546-88-3 |
|---|---|
| Molecular formula | C2H5NO2 |
| Average molar mass | 75.07 g/mol |
| Monoisotopic mass | 75.0320284 g/mol |
| SMILES | CC(=O)NO |
| InChIKey | RRUDCFGSUDOHDG-UHFFFAOYSA-N |
| PubChem CID | 1990 |
| ChEMBL | CHEMBL734 |
| ChEBI | CHEBI:27777 |
| EC No. | 208-913-8 |
| DTXSID | DTXSID7022546 |
Chemical & Physical Properties
| XLogP | -1.6 |
|---|---|
| Topological polar surface area | 49.3 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 42.9 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| pH | 9.39 (aq soln) |
| SpringerMaterials Properties | Chemical shift |
| LogP (partition coefficient) | log Kow= -1.59-0.7 |
| Solubility | 5.09e+02 g/L<0.2 [ug/mL] (The mean of the results at pH 7.4)Methanol (Sparingly), Water (Sparingly)Soluble in water. |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Decomposition | When heated to decomposition it emits toxic fumes of nitroxides. |
| Melting point | 89-92 °C90.5 °C88-90 °C (lit.) |
| Physical Description | Solid |
| Dissociation Constants | 8.7 (at 25 °C)pKa= 8.70 |
| Boiling point | 133.7°C (rough estimate) |
| Density | 1.2269 (rough estimate) |
| Refractive index | 1.4264 (estimate) |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| Physical state | Crystalline Solid |
| pKa (acidity coefficient) | 8.70(at 25℃) |
| Color | White to pale yellow |
| Sensitivity | Hygroscopic |
| Merck | 14,63 |
| BRN | 1739019 |
| Stability | Moisture and Temperature Sensitive |
| InChI | 1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) |
| InChIKey | RRUDCFGSUDOHDG-UHFFFAOYSA-N |
| SMILES | CC(NO)=O |
| CAS DataBase Reference | 546-88-3(CAS DataBase Reference) |
| EWG's Food Scores | 2 |
| NCI Dictionary of Cancer Terms | AHA |
| FDA UNII | 4RZ82L2GY5 |
| ATC code | G04BX03 |
| Proposition 65 List | Acetohydroxamic Acid |
| NIST Chemistry Reference | Acetamide,N-hydroxy(546-88-3) |
| EPA Substance Registry System | Acetohydroxamic acid (546-88-3) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS08 |
| Signal word | Danger |
| GHS hazard statements | H360 |
| GHS precautionary statements | P201-P280-P308+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type P2 (EN 143) respirator cartridges |
| Hazard symbols | T |
| Risk statements (R) | 61-40 |
| Safety statements (S) | 53-45-36/37/39-22 |
| UN transport number | 3263 |
| Water hazard class (WGK) | 3 |
| RTECS number | AK8157000 |
| Hazard Note | Toxic |
| Packing group | II |
| Customs code | 29225090 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazard class | Repr. 1B |
| Hazardous substances data | 546-88-3(Hazardous Substances Data) |
| Toxicity | mmo-sat 160 mmol/plate JOPHDQ 3,557,80 |
Safety & Regulations
| GHS classification | DangerH360 (96.1%): May damage fertility or the unborn child [Danger Reproductive toxicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 9 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Hazard Traits - Developmental Toxicity |
| FDA requirements | Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392). |
| Hazard Classes and Categories | Repr. 1B (96.1%) |
| Disposal methods | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Interactions | Concurrent use of alcoholic beverages with acetohydroxamic acid has resulted in a nonpruritic, reddish, macular skin rash about 30 to 45 minutes after ingestion. The rash may be associated with a general feeling of warmth and tingling, and usually disappears spontaneously in 30 to 60 minutes.Acetohydroxamic acid chelates iron and possibly other heavy metals with concurrent oral administrationthis may result in reduced intestinal absorption of bothif iron therapy is indicated, parenteral administration of iron is recommended.In vitro studies indicate that acetohydroxamic acid and methenamine have a synergistic effect in inhibiting increases in pH caused by urease-producing Proteus spp. and that acetohydroxamic acid potentiates the antibacterial effect of methenamine against these bacteria... |
| Human Toxicity Excerpts | Acetohydroxamic acid was positive for mutagenicity in the Ames test.Acetohydroxamic acid overdose has not been reported. However, if it should occur, concomitant reduction in platelets and/or white blood cells should be anticipated |
Applications & Uses
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.
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.
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.
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.