基本情報
- CAS
97519-39-6- 標準SMILES
Nc1nc(/C(=C/CC(=O)O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=CCS[C@H]23)cs1- InChIKey
UNJFKXSSGBWRBZ-BJCIPQKHSA-N- 分子式
- C15H14N4O6S2
- 平均分子量
- 410.4 g/mol
- 単同位体質量
- 410.03547653
概要
Ceftibuten is a third-generation cephalosporin antibiotic with a [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino substituent at the 7 position of the cephem skeleton. An orally-administered agent, ceftibuten is used as the dihydrate to treat urinary-tract and respiratory-tract infections. It has a role as an antibacterial drug. It is a cephalosporin and a dicarboxylic acid.
名称と識別子
- 優先名称
- Ceftibuten
- IUPAC
- (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セフチブテン
- 英語名
- Ceftibuten
- 分子式
- C15H14N4O6S2
- 分子量
- 410.42
名称と別名
ceftibuten97519-39-6CeftibutenoCeftibuteneCeftibutenumSch 39720cis-ceftibutenSch-397207432-SDTXSID4045925CeftibutinACHN383
名称をさらに表示
(6R,7R)-7-[[(Z)-2-(2-アミノ-4-チアゾリル)-4-カルボキシ-2-ブテノイル]アミノ]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸抗生物質7432Sセフチブテン(6R,7R)-7α-[[(Z)-2-(2-アミノ-4-チアゾリル)-4-カルボキシ-1-オキソ-2-ブテニル]アミノ]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セフテムcis-セフチブテンセダックス(6R,7R)-7-[(2Z)-2-(2-アミノ-1,3-チアゾール-4-イル)-4-カルボキシブタ-2-エンアミド]-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cephems74327432SCS-1355Cedax：Isocefcis-ceftibutinantibiotic7432s
NSC-758925ACHN-383CHEBI:3510IW71N46B4Y(+)-(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidDTXCID2025925PF-06264006(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
物性
構造計算による物性
- XLogP
- -0.3
- 極性表面積
- 216 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 10
- 回転可能結合数
- 6
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 755
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Solubility7.05e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Physical DescriptionSolid
Collision Cross Section
191.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
188.81 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 沸点
- 966 ℃ · 966℃
- 比重(密度)
- 1.75 · 1.75±0.1 g/cm3(Predicted)
- 闪点
- 110 ° · >110°(230°F)
- 貯蔵温度
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 溶解性
- 水溶液に可溶。 DMSOにも可溶
- 外見
- 粉
- 酸解離定数(Pka)
- 2.99 · 2.99±0.50(Predicted)
- 色
- 白からベージュ
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
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P233, P260, P261, P271, P284, P304+P340, P317, P342+P316, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 35 reports by companies from 1 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 CategoriesAcute Tox. 4 (100%)
毒性情報
Exposure RoutesRapidly absorbed following oral administration.
Toxicity SummaryCeftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Signs and SymptomsOverdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
ceftibuten
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingCeftibuten is 65% bound to plasma proteins. The protein binding is independent of plasma ceftibuten concentration.
PharmacodynamicsCeftibuten is an antibiotic with bactericidal actions.
Mechanism of ActionCeftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Metabolism/Metabolites
A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer.
A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer. Route of Elimination: Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
FDA Pharmacological Classification
IW71N46B4Y
CEFTIBUTEN
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Ceftibuten is a Cephalosporin Antibacterial.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Rapidly absorbed following oral administration.
Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…