基本情報
- CAS
104145-95-1- 標準SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(/C=C\c3scnc3C)CS[C@H]12)c1csc(N)n1- InChIKey
KMIPKYQIOVAHOP-YLGJWRNMSA-N- 分子式
- C19H18N6O5S3
- 平均分子量
- 506.6 g/mol
- 単同位体質量
- 506.05008122
概要
Cefditoren is a broad spectrum, third-generation cephalosporin antibiotic with (Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. Generally administered as its orally absorbed pivaloyloxymethyl ester prodrug, it is used for the treatment of mild to moderate infections caused by susceptible strains of microorganisms in acute bacterial exacerbation of chronic bronchitis, community-acquired pneumonia, pharyngitis/tonsillitis, and uncomplicated skin and skin-structure infections. It has a role as an antibacterial drug. It is a cephalosporin and a carboxylic acid.
名称と識別子
- 優先名称
- Cefditoren
- IUPAC
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セフジトレン
- 英語名
- Cefditoren
- 分子式
- C19H18N6O5S3
- 分子量
- 506.58
名称と別名
Cefditoren104145-95-1cefditoreneCefditoreno81QS09V3YWCHEBI:593435-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-, (6R-(3(Z),6alpha,7beta(Z)))-cefditorenum(6R,7R)-7-((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido)-3-((Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidRefChem:56293J01DD16
名称をさらに表示
セフジトレン(6R,7R)-7-[(2Z)-2-(2-アミノ-1,3-チアゾール-4-イル)-2-(メトキシイミノ)アセトアミド]-3-[(1Z)-2-(4-メチル-1,3-チアゾール-5-イル)エテニル]-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-[[(Z)-2-(2-アミノチアゾール-4-イル)-2-(メトキシイミノ)アセチル]アミノ]-3-[(Z)-2-(4-メチルチアゾール-5-イル)エテニル]-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CefotoloneCeftopolam
物性
構造計算による物性
- XLogP
- 0.7
- 極性表面積
- 242 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 12
- 回転可能結合数
- 7
- 重原子数
- 33
- 形式電荷
- 0
- 複雑度
- 928
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Solubility
Soluble at levels equal to < 0.1 mg/mL.
4.41e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Melting Point
127-129 °C
127 - 129 °C
Physical DescriptionSolid
物理化学的性質
- 比重(密度)
- 1.75 · 1.75
- 酸解離定数(Pka)
- 2.43 · 2.43±0.50(Predicted)
- 外見
- Solid
- 色
- Light yellow to yellow
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。
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefditoren
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingBinding of cefditoren to plasma proteins averages 88% from <i>in vitro</i> determinations, and is concentration-independent at cefditoren concentrations ranging from 0.05 to 10 mg/mL.
Pharmacodynamics
Cefditoren pivoxil is a prodrug which is hydrolyzed by esterases during absorption, and the drug is distributed in the circulating blood as active cefditoren. Cefditoren is a cephalosporin with antibacterial activity against gram-positive and gram-negative pathogens. Cefditoren is effective against <i>Staphylococcus aureus</i> (methicillin-susceptible strains, including b-lactamase-producing strains), penicillin-susceptible strains of <i>Staphylococcus aureus</i> and <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>, <i>Haemophilus influenzae</i> (including b-lactamase-producing strains), <i>Haemophilus parainfluenzae</i> (including b-lactamase-producing strains), <i>Moraxella catarrhalis</i> (including b-lactamase-producing strains), <i>Streptococcus agalactiae</i>, <i>Streptococcus</i> Groups C and G, and <i>Streptococcus</i>, viridans group (penicillin-susceptible and -intermediate strains).
Mechanism of Action
The bactericidal activity of cefditoren results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefditoren is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.
Biological Half-LifeMean terminal elimination half-life is 1.6 ± 0.4 hours in young healthy adults.
Metabolism/MetabolitesHydrolysis of cefditoren pivoxil to its active component, cefditoren, results in the formation of pivalate. Cefditoren is not appreciably metabolized.
FDA Pharmacological Classification
81QS09V3YW
CEFDITOREN
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
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