ビアペネム
6-[[(4R,5S,6S)-2-カルボキシラト-6β-[(R)-1-ヒドロキシエチル]-4α-メチル-7-オキソ-1-アザビシクロ[3.2.0]ヘプタ-2-エン-3-イル]チオ]-6,7-ジヒドロ-5H-ピラゾロ[1,2-a][1,2,4]トリアゾール-4-イウム · 6-[[(4R,5S,6S)-2-カルボキシラト-6β-[(1R)-1-ヒドロキシエチル]-4α-メチル-7-オキソ-1-アザビシクロ[3.2.0]ヘプタ-2-エン-3-イル]チオ]-6,7-ジヒドロ-5H-ピラゾロ[1,2-a]-s-トリアゾール-4-イウム · 6-[[(4R,5β)-2-カルボキシラト-4α-メチル-6β-[(R)-1-ヒドロキシエチル]-7-オキソ-1-アザビシクロ[3.2.0]ヘプタ-2-エン-3-イル]チオ]-6,7-ジヒドロ-5H-ピラゾロ[1,2-a][1,2,4]トリアゾール-4-イウム · (4R,5S,6S)-3-(6,7-ジヒドロ-5H-ピラゾロ[1,2-a][1,2,4]トリアゾール-4-イウム-6-イルチオ)-6-[(1R)-1-ヒドロキシエチル]-4-メチル-7-オキソ-1-アザビシクロ[3.2.0]ヘプタ-2-エン-2-カルボキシラート · ビアペネム · オメガシン · ビアペネム (JAN) · 6-{[(4R,5S,6S)-2-カルボキシラト-6-[(1R)-1-ヒドロキシエチル]-4-メチル-7-オキソ-1-アザビシクロ[3.2.0]ヘプタ-2-エン-3-イル]スルファニル}-5H,6H,7H-4λ5-ピラゾロ[1,2-a][1,2,4]トリアゾール-4-イリウム
識別子と物理属性
| CAS No. | 120410-24-4 |
|---|---|
| 分子式 | C15H20N4O4S |
| 平均分子量 | 352.4 g/mol |
| 単同位体質量 | 352.12052631 g/mol |
| SMILES | CC(O)[C@H]1C(=O)N2C(C([O-])O)=C(SC3Cn4cnc[n+]4C3)[C@H](C)[C@H]12 |
| InChIKey | ZWULSZNGKIOAFD-XAGUZIBRSA-N |
| PubChem CID | 457413 |
| 現地名 | ビアペネム |
化学・物理的性質
| XLogP | 0.7 |
|---|---|
| 極性表面積 | 131 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 4 |
| 重原子数 | 24 |
| 形式電荷 | 0 |
| 複雑度 | 576 |
| 融点 | 265-271°C (dec.) |
| 比旋光度 | D20 -32.9° (c = 0.5) |
| 貯蔵条件 | -20°C |
| 溶解度 | H2O: ≥5mg/mL (加温)H2O: ≥5mg/mL (warmed) |
| 外観・状態 | 粉 |
| 色 | 白からベージュ |
| InChI | InChI=1/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/s3 |
| InChIKey | MRMBZHPJVKCOMA-YJFSRANCSA-N |
| SMILES | C(C1=C([C@H](C)[C@]2([H])[C@@]([H])([C@H](O)C)C(=O)N12)SC1C[N+]2=CN=CN2C1)(=O)[O-] |&1:3,5,7,9,r| |
| CAS データベース | 120410-24-4(CAS DataBase Reference) |
化学的特性
Off-White Solid
安全性と法規制
| 水環境危害等級（WGK） | 3 |
|---|---|
| 税関コード | 2941.90.5000 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
Biapenem was introduced in Japan as a parenteral treatment for bacterial infections. This new 1-β-methylcarbapenem can be prepared by reaction of commercially available 4-nitrobenzyl protected β-methylcarbapenem enolphosphate with mercapto bicyclotriazolium chloride, obtained in 11 steps starting from hydrazine, followed by deprotection of the carboxylic acid function. Biapenem is a bacterial cell wall synthesis inhibitor with a broad spectrum in vitro antibacterial activity encompassing many Gramnegative and Gram-positive aerobic and anaerobic bacteria, including species producing β-lactamases. Like imipenem, biapenem is moderately active against fnferococcus faecalis and E. faecuirn and is inactive against methicillin-resistant Staphylococcus aureus. Biapenem is stable to hydrolysis by human renal dihydropeptidase I (DHP-I) and therefore does not require the coadministration of a DHP-I inhibitor. In clinical trials, biapenem showed good clinical and microbiological efficacy in the treatment of patients with intraabdominal, lower respiratory tract and complicated urinary tract infections. After intravenous administration, the drug is widely distributed, has linear pharmacokinetics and is mainly excreted in the urine with an elimination half-life of approximately 1 h. Biapenem is generally well tolerated, the most common adverse events being skin eruptions/rashes, nausea and diarrhea.
使用
Biapenem is a carbapenem antibiotic. It has in vitro activity against anaerobes. Biapenem is a new parenteral carbapenem antibacterial agent with a broad spectrum of in vitro antibacterial activity encompassing many Gram-negative and Gram-positive aerobic