基本情報
- CAS
51762-05-1- 標準SMILES
COC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CCC=CC3)[C@H]2SC1- InChIKey
RDMOROXKXONCAL-UEKVPHQBSA-N- 分子式
- C16H19N3O5S
- 平均分子量
- 365.4 g/mol
- 単同位体質量
- 365.10454189
概要
Cefroxadine is a first-generation cephalosporin antibiotic having methoxy and [(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetyl]amino side groups located at positions 3 and 7 respectively.
名称と識別子
- 優先名称
- Cefroxadine
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セフロキサジン
- 英語名
- Cefroxadine
- 分子式
- C16H19N3O5S
- 分子量
- 365.4
名称と別名
cefroxadine51762-05-1OrasporCefroxadinCgp 9000CefroxadinumCefroxadinoCefthan-DSCGP-9000cefroxadinaDTXSID1022768B908C4MV2R
名称をさらに表示
オラスポア(6R,7R)-7-[[(R)-アミノ(1,4-シクロヘキサジエン-1-イル)アセチル]アミノ]-3-メトキシ-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セフロキサジンセフサンセフサン-DS抗生物質CGP-9000オラスポル(6R,7R)-7-[(2R)-2-アミノ-2-(シクロヘキサ-1,4-ジエン-1-イル)アセトアミド]-3-メトキシ-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-[[(R)-Amino(1,4-cyclohexadien-1-yl)acetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidcxdC12979cgp9000BRN 0587499antibioticcgp9000Cefroxadine. Oraspor
DTXCID602768CHEBI:313797-(D-2-amino-2-(1,4-cyclohexadienyl)acetamido)-3-methoxy-3-cephem-4-carboxylic acid(6R,7R)-7-(((2R)-2-amino-2-cyclohexa-1,4-dien-1-yl-acetyl)amino)-3-methoxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-[[(2R)-2-amino-2-cyclohexa-1,4-dien-1-yl-acetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidRefChem:124252J01DA35257-391-8
物性
構造計算による物性
- XLogP
- -2.3
- 極性表面積
- 147 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 7
- 回転可能結合数
- 5
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 715
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
物理化学的性質
- 融点
- 170 ° · 170° (dec)
- 比旋光度
- 20 · D20 +87° (c = 1.093 in 0.1N HCl)
- 沸点
- 251 °C · 251°C (rough estimate)
- 比重(密度)
- 1.3163 · 1.3163 (rough estimate)
- 屈折率
- 1.639 · 1.6390 (estimate)
- 酸解離定数(Pka)
- 3.3 · pKa 3.30±0.02(H2O t=35.0 I=0.00)(Approximate)
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)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesSkin Sens. 1 (100%)
安全データ
- 毒性
- LD50 in mice (mg/kg): >6000 orally; 7090 i.p. (Scartazzini, Bickel, 1978)
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingCefrixadine is 10% bound to human plasma proteins.
PharmacodynamicsCefroxadine is a cephalosporin antibiotic which produces a bactericidal effect on susceptible bacteria.
Mechanism of Action
Cefrixadine is a cephalosporin antibiotic, a class of β-lactam antibiotics similar to penicillins, which binds to and inhibits penicillin binding proteins (PBPs). PBPs are responsible for catalyzing the transpeptidase reaction which cross-links the peptide side chains on the sugar residues of a peptidoglycan unit, adding the unit to the peptidoglycan layer. This disrupts the balance between the hydrolysis of peptidoglycan, in order to insert new peptidoglycan units, by murein hydrolase and the attachment of the new units which leads to overall destruction of the peptidoglycan layer. With the loss of its peptidoglycan layer the cell also loses its resistance to the high osmotic pressure inside its membrane and lyses.
Biological Half-LifeThe serum half life is 0.9-1.1 h.
Absorption, Distribution and Excretion
Oral bioavailability of 90%.
Primarily eliminated in the urine (80-96%).
Volume of distrubution of 15 L.
The total body clearance is 340 mL/min and the renal clearance is 250 mL/min.
応用分野
説明Cefroxadine was synthesized by Ciba-Geigy in 1972. A methoxyl group replaced the methyl group of cephradine at the 3 position of the cephem nucleus. Cefroxadine shows stronger activities than cephalexin, especially bactericidal and bacteriolytic activities, and it has better oral absorption that is less affected by a recent meal. Cefroxadine shows less renal toxicity than cephalexin in toxicological studies using animals.
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