ピペミド酸
Pipemidic Acid
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基本情報
- CAS
51940-44-4- 標準SMILES
CCn1cc(C(=O)O)c(=O)c2cnc(N3CCNCC3)nc21- InChIKey
JOHZPMXAZQZXHR-UHFFFAOYSA-N- 分子式
- C14H17N5O3
- 平均分子量
- 303.32 g/mol
- 単同位体質量
- 303.1331394
概要
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.
名称と識別子
- 優先名称
- Pipemidic Acid
- IUPAC
- 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid
- 現地名
- ピペミド酸
- 英語名
- Pipemidic acid
- 分子式
- C14H17N5O3
- 分子量
- 303.32
名称と別名
pipemidic acid51940-44-4PipedacPipemidAcido pipemidicoAcide pipemidiqueAcidum pipemidicumpipeaciduropimidFiltraxPipemidatePipurin
名称をさらに表示
ウロミジンピペミジン酸デブラストンピペミドピプラム8-エチル-5-オキソ-2-(1-ピペラジニル)-5,8-ジヒドロピリド[2,3-d]ピリミジン-6-カルボン酸8-エチル-5,8-ジヒドロ-5-オキソ-2-(1-ピペラジニル)ピリド[2,3-d]ピリミジン-6-カルボン酸ピペミド酸ピペラミン酸ピペダックドルコールパリンピペミド酸標準品8-エチル-5,8-ジヒドロ-5-オキソ-2-ピペラジノピリド[2,3-d]ピリミジン-6-カルボン酸8-エチル-5-オキソ-2-(ピペラジン-1-イル)-5H,8H-ピリド[2,3-d]ピリミジン-6-カルボン酸palin1489rbrb1489pipramdolcolxyliquePB-1489deblaston
TracturUrostenUrovalNurilPi-coli8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acidMemento 400PIPEMIDIC ACID ANHYDROUS
物性
構造計算による物性補完中
- XLogP
- -2.1
- 極性表面積
- 98.7 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 8
- 回転可能結合数
- 3
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 489
実験および物理化学的性質
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]+
物理化学的性質
- 融点
- 251 · 251-255℃
- 沸点
- 717 ℃ · 717℃
- 比重(密度)
- 1.1931 · 1.1931 (rough estimate)
- 屈折率
- 1.7 · 1.7000 (estimate)
- 闪点
- 110 ° · >110°(230°F)
- 貯蔵温度
- -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
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%)
安全データ
- wgk
- 2
- rtecs
- UV1153800
- 毒性
- LD50 in mice (mg/kg): 4000 orally; 1000 i.p., 50 i.v. (Ficicchia)
- hs_code
- 29335990
- risk_code
- 42/43
- hazard_code
- Xi
- safety_code
- 22-36/37-45
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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.
用途と製造
UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
応用分野
使用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.
一般的な説明Chemical structure: quinolone
調製方法
製造方法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.
関連反応
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