基本情報
- CAS
89786-04-9- 標準SMILES
C[C@]1(Cn2ccnn2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O- InChIKey
LPQZKKCYTLCDGQ-WEDXCCLWSA-N- 分子式
- C10H12N4O5S
- 平均分子量
- 300.29 g/mol
- 単同位体質量
- 300.05284067
概要
Tazobactam is a member of the class of penicillanic acids that is sulbactam in which one of the exocyclic methyl hydrogens is replaced by a 1,2,3-triazol-1-yl group; used (in the form of its sodium salt) in combination with ceftolozane sulfate for treatment of complicated intra-abdominal infections and complicated urinary tract infections. It has a role as an antimicrobial agent, an antiinfective agent and an EC 3.5.2.6 (beta-lactamase) inhibitor. It is a member of penicillanic acids and a member of triazoles. It is functionally related to a sulbactam. It is a conjugate acid of a tazobactam(1-).
名称と識別子
- 優先名称
- Tazobactam
- IUPAC
- (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- 現地名
- タゾバクタム
- 英語名
- Tazobactam acid
- 分子式
- C10H12N4O5S
- 分子量
- 300.29
名称と別名
Tazobactam89786-04-9TazobactamumYTR-830HCL 298,741CHEBI:9421SE10G96M8WNSC-759887CXA201YTR830DTXSID8023634(2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 4,4-dioxide
名称をさらに表示
タゾバクタム(2S,3S,5R)-2-カルボキシ-3-メチル-3-[(1H-1,2,3-トリアゾール-1-イル)メチル]-7-オキソ-4-チア-1-アザビシクロ[3.2.0]ヘプタン4,4-ジオキシドタゾバクタムTAZOBACTAN ACIDタゾバクタム (JP17)Tarobactam acidytr83ohcl2987417-Methyl-2H-1Tazobactam RSHe (the templeTAZOBACTAM USP
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-, 4,4-dioxide, (2S,3S,5R)-(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4$l^(6)-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-, 4,4-dioxide, (2S,3S,5R)-RefChem:891206DTXCID003634J01CG02YTR-830
物性
構造計算による物性
- XLogP
- -2
- 極性表面積
- 131 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 7
- 回転可能結合数
- 3
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 573
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Used in Switzerland
Solubility9.59e+00 g/L
Melting Point140-147
Physical DescriptionSolid
Dissociation Constants2.1
Collision Cross Section157.7 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8046030]
物理化学的性質
- 融点
- 115 · 115-145℃
- 沸点
- 77 ℃ · 77℃
- 比重(密度)
- 1.92 · 1.92±0.1 g/cm3(Predicted)
- 闪点
- 110 ° · >110°(230°F)
- 貯蔵温度
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- 溶解性
- DMSO（わずかに、加熱）、メタノール（わずかに、加熱、超音波処理）
- 外見
- Solid
- 酸解離定数(Pka)
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 (14.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P273, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, P391, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationREACH registered substance: (2S,3S,5R)-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide (EC: 618-303-7)
Hazard Classes and CategoriesSkin Sens. 1 (14.3%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Tazobactam
DILI Negative
Intravenous; Parenteral
DOI:10.1016/j.drudis.2019.09.022
安全データ
- wgk
- 3
- hs_code
- 2941106000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingTazobactam is bout 30% bound to plasma proteins.
Pharmacodynamics
Tazobactam inhibits the action of bacterial beta-lactamase producing organisms, which are normally resistant to beta-lactam antibiotics. This augments the effects of antibiotics which would otherwise not be effective in treating certain infections. These antibiotics contain a beta-lactam ring in their chemical structure, which is destroyed by beta-lactam resistant organisms. When combined with other antibiotics, a variety of infections, including serious and life-threatening infections may be treated.
Mechanism of Action
Tazobactam broadens the spectrum of piperacillin and ceftolozane by making them effective against organisms that express beta-lactamase and would normally degrade them. This occurs through the irreversible inhibition of beta-lactamase enzymes. In addition, tazobactam may bind covalently to plasmid-mediated and chromosome-mediated beta-lactamase enzymes. Tazobactam is predominantly effective against the OHIO-1, SHV-1, and TEM groups of beta-lactamases, but may also inhibit other beta-lactamases. Tazobactam shows little antibacterial activity by itself, and for this reason, is generally not administered alone.
Biological Half-LifePiperacillin-tazobactam After a single dose in healthy volunteers, the plasma half-life of piperacillin and tazobactam was in the range of 0.7 to 1.2 hours. Ceftolozane-tazobactam 0.91-1.03 hours
Metabolism/MetabolitesTazobactam is mainly metabolized to M1, an inactive metabolite. Hydrolysis occurs on the beta-lactam ring to form M1 (the inactive metabolite).
FDA Pharmacological Classification
SE10G96M8W
TAZOBACTAM
Established Pharmacologic Class [EPC] - beta Lactamase Inhibitor
Mechanisms of Action [MoA] - beta Lactamase Inhibitors
関連反応
17 件
化合物ノート
読み込み中…