基本情報
- CAS
34444-01-4- 標準SMILES
Cn1nnnc1SCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](O)c3ccccc3)[C@H]2SC1- InChIKey
OLVCFLKTBJRLHI-AXAPSJFSSA-N- 分子式
- C18H18N6O5S2
- 平均分子量
- 462.5 g/mol
- 単同位体質量
- 462.07801004
概要
Cefamandole is a cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups. It has a role as an antibacterial drug. It is a cephalosporin and a semisynthetic derivative. It is a conjugate acid of a cefamandole(1-).
名称と識別子
- 優先名称
- Cefamandole
- IUPAC
- (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セファマンドール
- 英語名
- Cefamandole
- 分子式
- C18H18N6O5S2
- 分子量
- 462.5
名称と別名
cefamandole34444-01-4CefadoleCEPHAMANDOLECefamandolCephadoleCefamandolumL-CefamandoleCompound 83405COMPOUND-83405cefamandolo5CKP8C2LLI
名称をさらに表示
セファマンドール(6R,7R)-7α-[(R)-ヒドロキシ(フェニル)アセチルアミノ]-3-[[(1-メチル-1H-テトラゾール-5-イル)チオ]メチル]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸(6R,7R)-7-[(R)-ヒドロキシフェニルアセチルアミノ]-3-[[(1-メチル-1H-テトラゾール-5-イル)チオ]メチル]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸化合物83405(6R,7R)-7-[(2R)-2-ヒドロキシ-2-フェニルアセトアミド]-3-{[(1-メチル-1H-1,2,3,4-テトラゾール-5-イル)スルファニル]メチル}-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸Florfenicol-d3 AMine(r*)))-CefoxinolideR hidalgoense
(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCHEBI:3480(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acidDTXSID7022750J01DC03(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6alpha,7beta(R*)))-
物性
構造計算による物性
- XLogP
- -0.9
- 極性表面積
- 201 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 10
- 回転可能結合数
- 7
- 重原子数
- 31
- 形式電荷
- 0
- 複雑度
- 777
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
0.50
0.25
Solubility5.81e-01 g/L
Melting Point182-184
Physical DescriptionSolid
Dissociation Constants3.4
Collision Cross Section
195.97 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
197.9 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
物理化学的性質
- 融点
- 107 · 107-109oC
- 比重(密度)
- 1.3806 · 1.3806 (rough estimate)
- 屈折率
- 1.7 · 1.7000 (estimate)
- 貯蔵温度
- Refrigerator
- 溶解性
- クロロホルム（少量）、メタノール（少量）
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。
危険有害性情報
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Human health tier I assessment
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefamandole
DILI Positive
Intramuscular; Intravenous
DOI:10.1016/j.drudis.2019.09.022
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding75%
Pharmacodynamics
The parenteral prodrug formate ester cefamandole nafate is a broad-spectrum cephalosporin antibiotic. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.
Mechanism of Action
Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor.
Biological Half-LifeThe half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Cellular LocationsMembrane
応用分野
説明Cefamandole is also known as cephamandole. It is a parenterally administered broad-spectrum cephalosporin antibiotic. The pharmacological action and indications for use of cefamandole is analogous to that of cefuroxime and cefamandole. Synonyms of this drug are mandoxef, kefandol, kefadol, and many others.
使用Cefamandole is a second-generation cephalosporin antibiotic with antibacterial activity. It is a labelled metabolite of Deprenyl (D288641) (Selegiline).
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