アセトヒドロキサム酸
アセトヒドロキサム酸 · N-ヒドロキシアセトアミド · アセトヒドロキシム酸 · アセチルヒドロキサム酸 · N-アセチルヒドロキシルアミン · エタンヒドロキサム酸 · エタンヒドロキシム酸 · N-HYDROXYACETAMIDE
識別子と物理属性
| CAS No. | 546-88-3 |
|---|---|
| 分子式 | C2H5NO2 |
| 平均分子量 | 75.07 g/mol |
| 単同位体質量 | 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 |
| 現地名 | アセトヒドロキサム酸 |
化学・物理的性質
| XLogP | -1.6 |
|---|---|
| 極性表面積 | 49.3 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 42.9 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| pH | 9.39 (aq soln) |
| SpringerMaterials Properties | Chemical shift |
| LogP（分配係数） | log Kow= -1.59-0.7 |
| 溶解度 | 5.09e+02 g/L<0.2 [ug/mL] (The mean of the results at pH 7.4)メタノール（適量）、水（適量）水に溶ける。 |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Decomposition | When heated to decomposition it emits toxic fumes of nitroxides. |
| 融点 | 89-92 °C90.5 °C88-90 °C (lit.) |
| Physical Description | Solid |
| Dissociation Constants | 8.7 (at 25 °C)pKa= 8.70 |
| 沸点 | 133.7°C (rough estimate) |
| 密度 | 1.2269 (rough estimate) |
| 屈折率 | 1.4264 (estimate) |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Room temperature |
| 外観・状態 | 結晶性固体 |
| pKa（酸解離定数） | 8.70(at 25℃) |
| 色 | 白色～淡黄色 |
| Merck | 14,63 |
| BRN | 1739019 |
| 安定性 | 湿気と温度に敏感 |
| InChI | 1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) |
| InChIKey | RRUDCFGSUDOHDG-UHFFFAOYSA-N |
| SMILES | CC(NO)=O |
| CAS データベース | 546-88-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Acetamide,N-hydroxy(546-88-3) |
| EPAの化学物質情報 | Acetohydroxamic acid (546-88-3) |
化学的特性
White Crystalline Solid
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | Hazard Traits - Developmental Toxicity |
| FDA 要件 | 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%) |
| 処分方法 | 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. |
| 相互作用 | 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 anticipatedreticulocyte count is likely to be elevated, and severe hemolysis may occur. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Acetohydroxamic acidAmbiguous-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Non-Human Toxicity Excerpts | Acetamide, a metabolite or acetohydroxamic acid, has been shown to cause hepatocellular carcinoma in rats when used in very high doses....in long-term studies in rats, large oral dosages (e.g., 4 g/kg daily) of acetamide, a metabolite of acetohydroxamic acid, have been shown to cause hepatocellular carcinoma.Evidence of toxicity did not occur when the drug was administered subcutaneously in mice at a dosage of 500 mg/kg daily for 60-100 dayshowever, evidence of cumulative toxicity, with death occurring at a mean of 21 days, occurred when the drug was administered subcutaneously at a dosage of 1 g/kg daily. |
| Antidote and Emergency Treatment | Treatment of overdose: Administration should be stopped. There is no known specific antidote for acetohydroxamic acid overdose. Recommended treatment consists of the following: Monitoring - Close monitoring of hematologic statusSpecific Treatment - Symptomatic treatment as necessary. Blood transfusions if required. Dialysis (considered possible but not yet proven). |
| Non-Human Toxicity Values | LD50 Mouse ip 2.5 g/kgLD50 Mouse oral 5 g/kgLD50 Rat oral 4.8 g/kg |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | AK8157000 |
| 輸送番号（UN） | 3263 |
| 毒性 | mmo-sat 160 mmol/plate JOPHDQ 3,557,80 |
| 税関コード | 29225090 |
| 危険文句（R） | 61-40 |
| 危険表示 | T |
| hazard_note | Toxic |
| 安全措置（S） | 53-45-36/37/39-22 |
| 包装等級 | II |
| 危険等級 | Repr. 1B |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 有害物質データ | 546-88-3(Hazardous Substances Data) |
用途
用途
有機合成原料、ウレアーゼ阻害剤。
説明
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.
使用
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.
一般的な説明
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.