基本情報
- CAS
56796-20-4- 標準SMILES
CO[C@@]1(NC(=O)CSCC#N)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@@H]21- InChIKey
SNBUBQHDYVFSQF-HIFRSBDPSA-N- 分子式
- C15H17N7O5S3
- 平均分子量
- 471.5 g/mol
- 単同位体質量
- 471.04533019
概要
Cefmetazole is a second-generation cephalosporin antibiotic having N1-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7beta and 7alpha respectively of the parent cephem bicyclic structure. It has a role as an antibacterial drug. It is a conjugate acid of a cefmetazole(1-).
名称と識別子
- 優先名称
- Cefmetazole
- IUPAC
- (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セフメタゾール
- 英語名
- Cefmetazole
- 分子式
- C15H17N7O5S3
- 分子量
- 471.53
名称と別名
cefmetazole56796-20-4CefmetazoloCefmetazolum(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCefmetazol3J962UJT8HCHEBI:3489U-72791DTXSID7022756(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-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-((((cyanomethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-cis)-
名称をさらに表示
(6R)-7-[[[(シアノメチル)チオ]アセチル]アミノ]-7β-メトキシ-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-カルボン酸セフメタゾール(6R,7S)-7-[2-[(シアノメチル)チオ]アセチルアミノ]-7-メトキシ-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]オクタン-2-エン-2-カルボン酸(6R,7S)-7-[[[(シアノメチル)チオ]アセチル]アミノ]-7-メトキシ-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
物性
構造計算による物性
- XLogP
- -0.6
- 極性表面積
- 239 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 12
- 回転可能結合数
- 9
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 818
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
-2.2
-0.6
Solubility2.16e+00 g/L
Physical DescriptionSolid
Collision Cross Section192.97 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 163 · 163-165C
- 比重(密度)
- 1.438 · 1.4380 (rough estimate)
- 屈折率
- 1.74 · 1.7400 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- メタノール（わずかに加熱）
- 外見
- 個体
- 酸解離定数(Pka)
- 2.65 · 2.65±0.50(Predicted)
- 色
- 白い
- 水溶解度
- 水に溶ける
- InChIKey
- SNBUBQHDYVFSQF-HIFRSBDPSA-N
- SMILES
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
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 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
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Cefmetazole
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
安全データ
- wgk
- 2
- rtecs
- XI0372200
- hs_code
- 2941906000
- risk_code
- 36/37/38-42/43
- 化審法
- 新規公示化学物質（2011年3月31日以前届出）
- hazard_code
- Xn
- 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
Pharmacodynamics
Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive <i>Proteus</i>, <i>Serratia</i>, anaerobic gram-negative bacilli (including <i>B. fragilis</i>), and some <i>E. coli</i>, <i>Klebsiella</i>, and <i>P. mirabilis</i>, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.
Mechanism of ActionThe bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Biological Half-Life1.50 ±0.14 hours
Metabolism/MetabolitesNo appreciable metabolism.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionBioavailability is approximately 100% following intramuscular injection.
Cellular LocationsExtracellular
応用分野
説明Cefmetazole is a cephamycin with a nonaromatic side chain at C-7. In addition to a fairly characteristic second-generation cephalosporin antimicrobial spectrum, it possess fairly significant anti-antiaerobic activity. The ejection of its C-3 side chain leads to alcohol intolerance of the disulfuram type and prolonged clotting times.
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