基本情報
- CAS
50370-12-2- 標準SMILES
CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- InChIKey
BOEGTKLJZSQCCD-UEKVPHQBSA-N- 分子式
- C16H17N3O5S
- 平均分子量
- 363.4 g/mol
- 単同位体質量
- 363.08889182
概要
Cefadroxil is a cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug. It is a conjugate acid of a cefadroxil(1-).
名称と識別子
- 優先名称
- Cefadroxil
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セファドロキシル
- 英語名
- CEFADROXIL
- 分子式
- C16H17N3O5S
- 分子量
- 363.39
名称と別名
cefadroxil50370-12-2CephadroxilCefadroxil anhydrousCefadroxiloCefadroxilumD-CefadroxilDuricefUltracefAnhydrous cefadroxilCefadropsDuracef
名称をさらに表示
(6R,7R)-7-[(R)-2-アミノ-2-(p-ヒドロキシフェニル)アセチルアミノ]-3-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3-メチル-7β-[[(R)-アミノ(4-ヒドロキシフェニル)アセチル]アミノ]セファム-3-エン-4-カルボン酸セファドロキシルオラセファール(6R,7R)-7-[[(R)-アミノ(p-ヒドロキシフェニル)アセチル]アミノ]-3-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-カルボン酸サリスロンサマセフ(6R,7R)-7-[[(R)-アミノ(4-ヒドロキシフェニル)アセチル]アミノ]-3-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-カルボン酸ドルセファンビドセフ(6R,7R)-7-[[(2R)-2-アミノ-2-(p-ヒドロキシフェニル)アセチル]アミノ]-3-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(6R)-7α-[[(R)-アミノ(4-ヒドロキシフェニル)アセチル]アミノ]-3-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(6R,7α)-7-[(R)-4-ヒドロキシフェニル(アミノ)アセチルアミノ]-3-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
- -2.1
- 極性表面積
- 158 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 7
- 回転可能結合数
- 4
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 629
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics (Cefalosporins)
LogP-0.4
Solubility3.99e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
Melting Point197 °C
Physical DescriptionSolid
Collision Cross Section
182.13 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
183.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
187.7 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
183.31 Ų [M-H]-
物理化学的性質
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 (100%): 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 65 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationCefadroxil anhydrous: 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.
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[amino(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Human health tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefadroxil
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Cefadroxil
23.3
化学と産業
薬理情報
ATC Code
J01DB05
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingBinding rates of cefadroxil were 28.1% by U.F. method
PharmacodynamicsCefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.
Mechanism of Action
Like all beta-lactam antibiotics, cefadroxil binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of 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 cefadroxil interferes with an autolysin inhibitor.
Biological Half-Life1.5 hours
FDA Pharmacological Classification
Q525PA8JJB
CEFADROXIL ANHYDROUS
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefadroxil anhydrous is a Cephalosporin Antibacterial.
CEFADROXIL
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.
Over 90% of the drug is excreted unchanged in the urine within 24 hours. Cefadroxil was detected in the placenta and breast milk.
Cellular LocationsMembrane
関連反応
17 件
化合物ノート
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