아세토히드록삼 산
아세토하이드록사믹산 · 아세토히드록삼산 · 아세토히드록삼산(ACETOHYDROXAMICACID) · N-HYDROXYACETAMIDE · AHA · Acetylhydroxamic acid · Acetylhydroxylamine · Acetomenadione
식별자 및 물리적 특성
| CAS No. | 546-88-3 |
|---|---|
| 분자식 | C2H5NO2 |
| 평균 분자량 | 75.07 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 아세토히드록삼 산 |
화학 및 물리적 성질
| XLogP | -1.6 |
|---|---|
| 극성 표면적 | 49.3 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 5 |
| 형식 전하 | 0 |
| 복잡도 | 42.9 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| pH | 9.39 (aq soln) |
| SpringerMaterials Properties | Chemical shift |
| LogP(분배 계수) | log Kow= -1.59-0.7 |
| 용해도 | 5.09e+02 g/L<0.2 [ug/mL] (The mean of the results at pH 7.4)메탄올(약간 용해됨), 물(약간 용해됨) |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Decomposition | When heated to decomposition it emits toxic fumes of nitroxides. |
| 녹는점 | 89-92 °C90.5 °C88-90 °C (lit.) |
| Physical Description | Solid |
| Dissociation Constants | 8.7 (at 25 °C)pKa= 8.70 |
| 끓는 점 | 133.7°C (rough estimate) |
| 밀도 | 1.2269 (rough estimate) |
| 굴절률 | 1.4264 (estimate) |
| 저장 조건 | Keep in dark place,Inert atmosphere,Room temperature |
| 물리적 상태 | 결정질 고체 |
| pKa(산도 계수) | 8.70(at 25℃) |
| 색상 | 흰색에서 연한 노란색 |
| 용해도 | 물에 용해됩니다. |
| Merck | 14,63 |
| BRN | 1739019 |
| 안정성 | 수분 및 온도에 민감함 |
| InChI | 1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) |
| InChIKey | RRUDCFGSUDOHDG-UHFFFAOYSA-N |
| SMILES | CC(NO)=O |
| NIST | Acetamide,N-hydroxy(546-88-3) |
| EPA | Acetohydroxamic acid (546-88-3) |
화학적 성질
White Crystalline Solid
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | Hazard Traits - Developmental Toxicity |
| FDA 요건 | 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%) |
| 처리 방법 | 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. |
| 상호 작용 | 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 |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | AK8157000 |
| 운송 번호(UN) | 3263 |
| 독성 | mmo-sat 160 mmol/plate JOPHDQ 3,557,80 |
| 관세 코드 | 29225090 |
| 위험 문구(R) | 61-40 |
| 위험 표시 | T |
| 안전 문구(S) | 53-45-36/37/39-22 |
| 포장분류 | II |
| 기존화학 물질 | KE-00066 |
| 위험 참고 사항 | Toxic |
| 위험 등급 | Repr. 1B |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 유해 물질 데이터 | 546-88-3(Hazardous Substances Data) |
용도
개요
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.
용도
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.
일반 설명
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.