基本情報
- CAS
80210-62-4- 標準SMILES
COCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\OC)c3csc(N)n3)[C@H]2SC1- InChIKey
WYUSVOMTXWRGEK-HBWVYFAYSA-N- 分子式
- C15H17N5O6S2
- 平均分子量
- 427.5 g/mol
- 単同位体質量
- 427.06202563
概要
Cefpodoxime is a third-generation cephalosporin antibiotic with methoxymethyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamino substituents at positions 3 and 7, respectively, of the cephem skeleton. Given by mouth as its proxetil ester prodrug, it is used to treat acute otitis media, pharyngitis, and sinusitis. 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
- Cefpodoxime
- IUPAC
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セフポドキシム
- 英語名
- Cefpodoxime
- 分子式
- C15H17N5O6S2
- 分子量
- 427.46
名称と別名
CEFPODOXIME80210-62-4CefpodoximaCefpodoximumEpoxim(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid7R4F94TVGYSodium, CefpodoximeSalt, Cefpodoxime SodiumSodium Salt, CefpodoximeCHEBI:3504DTXSID6022765
名称をさらに表示
(6R,7R)-7α-[[(2-アミノ-4-チアゾリル)[(Z)-メトキシイミノ]アセチル]アミノ]-3-(メトキシメチル)-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(7R)-7-[[(2Z)-2-(2-アミノ-4-チアゾリル)-2-メトキシイミノアセチル]アミノ]-3-メトキシメチルセファム-3-エン-4-カルボン酸(6R,7R)-7α-[[(2-アミノチアゾール-4-イル)[(Z)-メトキシイミノ]アセチル]アミノ]-3-(メトキシメチル)-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セフポドキシムセフポドキシム酸CPDXUnii-7R4F94tvgyCefpodoxime sulfateCefpodoximum [latin]Cefpodoxime (R 3763)Cefpodoxima [spanish]Cefpodoxime USP/EP/BP
RU-5174651746, RU76253A, UU 76,253A(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-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-methoxyiminoacetyl)amino)-3-(methoxymethyl)-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-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:56372
物性
構造計算による物性
- XLogP
- -1.4
- 極性表面積
- 210 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 11
- 回転可能結合数
- 7
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 744
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Metabolite of Cefpodoxime Proxetil
Solubility1.85e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Physical DescriptionSolid
物理化学的性質
- 融点
- 200 · 200-202°C
- 比重(密度)
- 1.78 · 1.78±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- 溶解性
- DMSOに可溶
- 酸解離定数(Pka)
- 2.77 · 2.77±0.50(Predicted)
- 外見
- Solid
- 色
- White to off-white
- BRN
- 6021381 · 6021381
- 安定性
- Hygroscopic
- 主な用途
- 法医学と毒物学獣医
- InChIKey
- WYUSVOMTXWRGEK-HBWVYFAYSA-N
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
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 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 CategoriesSkin Sens. 1 (100%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefpodoxime
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
- wgk
- 3
- risk_code
- 42/43
- hazard_code
- Xn
- safety_code
- 22-36/37-45
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- 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
QJ - Antiinfectives for systemic use
Protein Binding22 to 33% in serum and from 21 to 29% in plasma.
PharmacodynamicsCefpodoxime is shown to be effective against most Gram positive and Gram negative bacteria, except <i>Pseudomonas aeruginosa</i>, <i>Enterococcus</i>, and <i>Bacteroides fragilis</i>.
Mechanism of Action
Cefpodoxime is active against a wide spectrum of Gram-positive and Gram-negative bacteria. Cefpodoxime is stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and cephalosporins, due to their production of beta-lactamase, may be susceptible to cefpodoxime. Cefpodoxime is inactivated by certain extended spectrum beta-lactamases. The bactericidal activity of cefpodoxime results from its inhibition of cell wall synthesis. The active metabolite of cefpodoxime binds preferentially to penicillin binding protein 3, which inhibits production of peptidoglycan, the primary constituent of bacterial cell walls.
Biological Half-Life2.09 to 2.84 hours
FDA Pharmacological Classification
7R4F94TVGY
CEFPODOXIME
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefpodoxime is a Cephalosporin Antibacterial.
MeSH Pharmacological ClassificationBactericidal agents that contain a beta-lactam ring in their chemical structure. They inhibit bacterial cell wall synthesis by binding to PENICILLIN-BINDING PROTEINS, preventing the synthesis of peptidoglycan in bacterial cell walls.
Absorption, Distribution and Excretion
Cefpodoxime proxetil is a prodrug that is absorbed from the gastrointestinal tract and de-esterified to its active metabolite, cefpodoxime. Following oral administration of 100 mg of cefpodoxime proxetil to fasting subjects, approximately 50% of the administered cefpodoxime dose was absorbed systemically.
サプライヤー
読み込み中…
公開中の見積依頼
読み込み中…
関連反応
2 件
化合物ノート
読み込み中…