基本情報
- 標準SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1- InChIKey
JFPVXVDWJQMJEE-IZRZKJBUSA-N- 分子式
- C16H16N4O8S
- 平均分子量
- 424.4 g/mol
- 単同位体質量
- 424.06888447
概要
Cefuroxime is a 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain. It has a role as a drug allergen. It is a member of furans, a 3-(carbamoyloxymethyl)cephalosporin and an oxime O-ether.
名称と識別子
- 優先名称
- Cefuroxime
- IUPAC
- (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セフロキシム
- 英語名
- Cefuroxime
- 分子式
- C16H16N4O8S
- 分子量
- 424.39
名称と別名
名称をさらに表示
データベース識別子
- CAS
55268-75-2- PubChem CID
- 5479529
- DTXSID
DTXSID5022774- ChEMBL
CHEMBL1436- ChEBI
CHEBI:3515- UNII
- O1R9FJ93ED
- EC Number
- 259-560-1
- Nikkaji
- J13.093A
物性
構造計算による物性
- XLogP
- -0.2
- 極性表面積
- 199 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
- 8
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 798
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Metabolite of Cefuroxime axetil
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Antibiotics
LogP
-0.8
-0.17
Solubility
Freely soluble as sodium salt (145 mg/L)
2.84e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
Watch group antibiotics
Melting Point
218-225 °C
218 - 225 °C
物理化学的性質
- 融点
- 171.5 · 171.5-173°C
- 比旋光度
- 20 · D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer)
- 比重(密度)
- 1.76 · 1.76
- 屈折率
- 1.6 · 1.6000 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMSO(微量)、メタノール(微量)
- 酸解離定数(Pka)
- 2.5 · pKa 2.5(H2O) (Uncertain)
- 外見
- Solid
- 色
- ホワイトからオフホワイト
- 水溶解度
- 145 mg/L · 145mg/L at 25℃
- BCS Class
- 4 · 4
- 主な用途
- 臨床検査
- InChIKey
- JFPVXVDWJQMJEE-IZRZKJBUSA-N
- SMILES
- N12[C@@]([H])([C@H](NC(/C(/C3=CC=CO3)=N\OC)=O)C1=O)SCC(COC(N)=O)=C2C(O)=O
- CAS データベース
- 55268 · 55268-75-2(CAS DataBase Reference)
- EPAの化学物質情報
- 5 · 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)- (55268-75-2)
化学的性質
化学的特性white crystalline solid
安全と法規制
GHS分類
GHS Classification
Danger
H317 (31%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, 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 Information
Status: Active Update: 08-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21969
Cefuroxime: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
毒性情報
Adverse Effects
Similar to penicillins and most β-lactam antibiotics, cefuroxime is generally well-tolerated. However, cefuroxime may potentially lead to adverse drug reactions in some patients, as seen with other medications. The most commonly reported adverse drug reactions are gastrointestinal disturbances, including nausea, vomiting, and diarrhea. Additional gastrointestinal adverse drug reactions include anorexia, abdominal pain, dizziness, and headache. In cases of parenteral administration, local reactions at the injection site, including thrombophlebitis, can occur.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefuroxime
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
安全データ
- wgk
- 3
- rtecs
- XI0329000
- risk_code
- 42/43
- hazard_code
- Xn
- safety_code
- 22-24-37-45
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
S - Sensory organs
QJ - Antiinfectives for systemic use
QS - Sensory organs
QJ - Antiinfectives for systemic use
J01DC02
Pharmacodynamics
Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: <i>Staphylococcus aureus</i>, <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>. Aerobic Gram-negative Microorganisms: <i>Escherichia coli</i>, <i>Haemophilus influenzae</i> (including beta-lactamase-producing strains), <i>Haemophilus parainfluenzae</i>, <i>Klebsiella pneumoniae</i>, <i>Moraxella catarrhalis</i> (including beta-lactamase-producing strains), <i>Neisseria gonorrhoeae</i> (including beta-lactamase-producing strains). Spirochetes: <i>Borrelia burgdorferi</i>. Cefuroxime axetil is the prodrug
Mechanism of Action
Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits 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 cefuroxime interferes with an autolysin inhibitor.
FDA Pharmacological Classification
O1R9FJ93ED
CEFUROXIME
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefuroxime is a Cephalosporin Antibacterial.
CEFUROXIME
用途と製造
応用分野
説明Cefuroxime axetil is the acetoxyethyl ester and oral prodrug of cefuroxime, a second-generation cephalosporin. It has a broad spectrum of action and is resistant to most P-lactamases. Cefuroxime axed is indicated for serious bacterial infections, especially where no identification of organism(s) has been made.
使用Cefuroxime is a second-generation cephalosporin antibiotic.
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.
関連反応
関連ノート
読み込み中…