Pipemidic Acid
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기본 정보
- CAS
51940-44-4- 표준 SMILES
CCn1cc(C(=O)O)c(=O)c2cnc(N3CCNCC3)nc21- InChIKey
JOHZPMXAZQZXHR-UHFFFAOYSA-N- 분자식
- C14H17N5O3
- 평균 분자량
- 303.32 g/mol
- 단동위원소 질량
- 303.1331394
개요
Pipemidic acid is a pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid substituted at position 2 by a piperazin-1-yl group and at position 8 by an ethyl group. A synthetic broad-spectrum antibacterial, it is used for treatment of gastrointestinal, biliary, and urinary infections. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a monocarboxylic acid, an amino acid, a pyridopyrimidine, a N-arylpiperazine and a quinolone antibiotic.
이름 및 식별자
- 우선 이름
- Pipemidic Acid
- IUPAC
- 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid
- 영어명
- Pipemidic acid
- 분자식
- C14H17N5O3
- 분자량
- 303.32
이름 및 동의어
pipemidic acid51940-44-4PipedacPipemidAcido pipemidicoAcide pipemidiqueAcidum pipemidicumpipeaciduropimidFiltraxPipemidatePipurin
이름 더 보기
palin1489rbrb1489pipramdolcolxyliquePB-1489deblaston
TracturUrostenUrovalNurilPi-coli8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acidMemento 400PIPEMIDIC ACID ANHYDROUS
데이터베이스 식별자
- CAS
51940-44-4- PubChem CID
- 4831
- DTXSID
DTXSID3023479- ChEMBL
CHEMBL30116- ChEBI
CHEBI:75250- UNII
- LT12J5HVR8
- EC Number
- 257-530-2
- Nikkaji
- J10.405A
물성
구조 계산 물성보충 중
- XLogP
- -2.1
- 극성 표면적
- 98.7 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 8
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 22
- 형식 전하
- 0
- 복잡도
- 489
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Antibiotics
LogP-2.15
Solubility0.322 mg/mL at 25 °C
Human DrugsPharmaceuticals
Melting Point253 - 255 °C
Physical DescriptionSolid
Collision Cross Section
185.6 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
171 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
172.63 Ų [M+H]+
물리화학적 성질
- 녹는점
- 251 · 251-255℃
- 끓는 점
- 717 ℃ · 717℃
- 밀도
- 1.1931 · 1.1931 (rough estimate)
- 굴절률
- 1.7 · 1.7000 (estimate)
- 인화점
- 110 ° · >110°(230°F)
- 저장 조건
- -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H317 (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.
유해성 정보
Other Safety InformationIMAP 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 CategoriesSkin Sens. 1 (97.6%)
안전 데이터
- wgk
- 2
- rtecs
- UV1153800
- 독성
- LD50 in mice (mg/kg): 4000 orally; 1000 i.p., 50 i.v. (Ficicchia)
- HS 번호
- 29335990
- risk_code
- 42/43
- hazard_code
- Xi
- safety_code
- 22-36/37-45
- 기존화학 물질
- KE-13607
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of ActionPipemidic acid is a quinolone antibacterial, which acts by inhibiting the bacterial DNA gyrase DNA topoisomerase IV.
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
용도 및 제조
UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
응용 분야
용도Pipemidic 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 설명Chemical structure: quinolone
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.
관련 반응
33건
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