Pipemidic Acid
palin · 1489rb · rb1489 · pipram · dolcol · xylique · pipemid · pipedac
식별자 및 물리적 특성
| CAS No. | 51940-44-4 |
|---|---|
| 분자식 | C14H17N5O3 |
| 평균 분자량 | 303.32 g/mol |
| 단동위원소 질량 | 303.1331394 g/mol |
| SMILES | CCn1cc(C(=O)O)c(=O)c2cnc(N3CCNCC3)nc21 |
| InChIKey | JOHZPMXAZQZXHR-UHFFFAOYSA-N |
| PubChem CID | 4831 |
| ChEMBL | CHEMBL30116 |
| ChEBI | CHEBI:75250 |
| EC No. | 257-530-2 |
| DTXSID | DTXSID3023479 |
화학 및 물리적 성질
| XLogP | -2.1 |
|---|---|
| 극성 표면적 | 98.7 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 8 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 22 |
| 형식 전하 | 0 |
| 복잡도 | 489 |
| 의약품 | Pharmaceuticals -> Antibiotics |
| LogP(분배 계수) | -2.15 |
| 용해도 | 0.322 mg/mL at 25 °C1M NaOH: 용해성50mg/mL |
| Human Drugs | Pharmaceuticals |
| 녹는점 | 253 - 255 °C251-255℃ |
| Physical Description | Solid |
| Collision Cross Section | 185.6 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]171 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]172.63 Ų [M+H]+ |
| 끓는 점 | 717℃ |
| 밀도 | 1.1931 (rough estimate) |
| 굴절률 | 1.7000 (estimate) |
| 인화점 | >110°(230°F) |
| 저장 조건 | Amber Vial, -20°C Freezer, Under inert atmosphere |
| pKa(산도 계수) | 4.14±0.20(Predicted) |
| 물리적 상태 | 가루 |
| 색상 | White to off-white |
| 용해도 | 1N 수산화나트륨 또는 DMSO에 용해됩니다. 물에 불용성 |
| InChI | InChI=1S/C14H17N5O3/c1-2-18-8-10(13(21)22)11(20)9-7-16-14(17-12(9)18)19-5-3-15-4-6-19/h7-8,15H,2-6H2,1H3,(H,21,22) |
| InChIKey | JOHZPMXAZQZXHR-UHFFFAOYSA-N |
| SMILES | C1(N2CCNCC2)=NC=C2C(=O)C(C(O)=O)=CN(CC)C2=N1 |
화학적 성질
The substance is a light yellow crystalline powder with an odorless, bitter taste. It has a melting point range of 251-255°C, with decomposition. It is soluble in glacial acetic acid, but only slightly soluble in methanol, acetone, and DMF. It is extremely difficult to dissolve in water, ethanol, and chloroform, and is insoluble in benzene. However, it can be dissolved in dilute alkali or acid solutions.
안전 및 규제
| GHS 분류 | DangerH317 (97.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 기타 안전 정보 | IMAP assessments - Pyrido[2,3-d]pyrimidine-6-carboxylic acid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-: Environment tier I assessment |
| Hazard Classes and Categories | Skin Sens. 1 (97.6%) |
| 수질 위해 등급(WGK) | 2 |
| RTECS 번호 | UV1153800 |
| 독성 | LD50 in mice (mg/kg): 4000 orally1000 i.p., 50 i.v. (Ficicchia) |
| 관세 코드 | 29335990 |
| 위험 문구(R) | 42/43 |
| 위험 표시 | Xi |
| 안전 문구(S) | 22-36/37-45 |
| 기존화학 물질 | KE-13607 |
| 위험 등급 | Resp. Sens. 1Skin Sens. 1 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
Pipemidic acid is a quinolone antibacterial drug that is primarily used to treat gram-negative infections of the urinary tract. It is also an antibiotic and cell selection agent. Unlike nalidixic acid, pipemidic acid has a broader spectrum of antibacterial activity and is effective for treating urinary tract and ENT infections.
일반 설명
Chemical structure: quinolone
제조 및 합성 방법
제조 방법
The synthesis of pipemidic acid involves a series of steps. First, ethyl 2,4-dichloropyrimidine-5-carboxylate is condensed and cyclized with ethyl β-ethylaminopropionate to yield 2-chloro-5-hydroxy-7,8-dihydro-8-ethylpyridine[2,3-d]pyrimidine-6-carboxylate. This compound is then brominated and subsequently condensed with piperazine. The resulting product is hydrolyzed and neutralized to obtain pipemidic acid.