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セフォニシド

Cefonicid

HCID 43594
ノート反応
基本情報名称と識別子物性化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
61270-58-4
標準SMILES
O=C(O)C1=C(CSc2nnnn2CS(=O)(=O)O)CS[C@@H]2[C@H](NC(=O)[C@H](O)c3ccccc3)C(=O)N12
InChIKey
DYAIAHUQIPBDIP-AXAPSJFSSA-N
分子式
C18H18N6O8S3
平均分子量
542.6 g/mol
単同位体質量
542.03482507

名称と識別子

優先名称
Cefonicid
IUPAC
(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
現地名
セフォニシド
英語名
Cefonicid
分子式
C18H18N6O8S3
分子量
542.57

名称と別名

CEFONICID61270-58-4CefonicidoCefonicidumMonocefCEFONICIDE6532B86WFG(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCHEBI:3491DTXSID7022758SK&F 75073(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-8-oxo-3-({[1-(sulfomethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
名称をさらに表示
(6R,7R)-7α-[[(R)-ヒドロキシフェニルアセチル]アミノ]-8-オキソ-3-[[[1-(スルホメチル)-1H-テトラゾール-5-イル]チオ]メチル]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セホニシドセフォニシド(6R,7R)-7-[(2R)-2-ヒドロキシ-2-フェニルアセトアミド]-8-オキソ-3-({[1-(スルホメチル)-1H-1,2,3,4-テトラゾール-5-イル]スルファニル}メチル)-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MonocidCefodiePratledMonocidurSKF-750737-beta(r*)))-Cefonicid USP/EP/BPCefonicid (free base)amino)-8-oxo-3-(((1-sulfomethyl)-1h-tetrazol-5-yl)thio)methyl)-,(6r-(6-alpha,

物性

構造計算による物性

XLogP
-1.9
極性表面積
264 Ų
水素結合供与体数
4
水素結合受容体数
13
回転可能結合数
9
重原子数
35
形式電荷
0
複雑度
999

実験および物理化学的性質

Solubility8.95e-01 g/L
Physical DescriptionSolid
Collision Cross Section205.05 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

比重(密度)
1.92 · 1.92±0.1 g/cm3(Predicted)
酸解離定数(Pka)
-1.23 · -1.23±0.50(Predicted)

化学と産業

薬理情報

ATC Code · 2 件

J - Antiinfectives for systemic use;J01 - Antibacterials for systemic use;J01D - Other beta-lactam antibacterials;J01DC - Second-generation cephalosporins;J01DC06 - Cefonicid

QJ - Antiinfectives for systemic use;QJ01 - Antibacterials for systemic use;QJ01D - Other beta-lactam antibacterials;QJ01DC - Second-generation cephalosporins;QJ01DC06 - Cefonicid

Protein Binding98% bound to plasma proteins.
Pharmacodynamics · 1 件

Cefonicid is a second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections.

Mechanism of Action · 1 件

Cefonicid, 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.

Biological Half-Life4.5 hours
Metabolism/MetabolitesNot metabolized.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Cellular LocationsExtracellular;Membrane
応用分野 · 2 件

説明Cefonicid has an unesterified D-mandelic acid moiety at C-7 and a methylsulfothiotetrazole group at C-3. The latter is related to the MTT moiety mentioned above under cefamandole nafate; however, the clotting problems and Antabuse-like side effects associated with MTT have not been reported with cefonicid. The extra acid group in the C-3 side chain leads to this molecule being sold as an injectable disodium salt. Pain and discomfort at IM sites is experienced by some patients, as is a burning sensation and phlebitis. Cefonicid has a longer half-life than the other members of its group but achieves this at the price of somewhat lower potency against Gram-positive bacteria and aerobes. The drug is somewhat unstable, needs to be protected from light and heat, and may yellow or darken. If modest, however, this does not necessarily mean that the potency has decreased significantly, but overt precipitation does. Kirby-Bauer disk testing may overestimate the sensitivity of β-lactamase–producing bacteria to this agent, so some extra caution in interpretation of laboratory results is required.

関連反応

1 件
反応記録を作成
HRID 724796 の反応式
HRID 724796反応物としてuspto-grants-1998_01

化合物ノート

読み込み中…

このページの内容基本情報名称と識別子物性化学と産業関連反応化合物ノート
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-8-oxo-3-({[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-(((2R)-2-hydroxy-2-phenylacetyl)amino)-8-oxo-3-(((1-(sulfomethyl)-1H-tetrazol-5-yl)sulfanyl)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-(((2R)-2-hydroxy-2-phenylacetyl)amino)-8-oxo-3-((1-(sulfomethyl)tetrazol-5-yl)sulfanylmethyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-7-((2R)-2-hydroxy-2-phenylacetamido)-8-oxo-3-(((1-(sulfomethyl)-1H-1,2,3,4-tetrazol-5-yl)sulfanyl)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:124234DTXCID302758J01DA17SK&F75073

データベース識別子

CAS
61270-58-4
PubChem CID
43594
DTXSID
DTXSID7022758
ChEMBL
CHEMBL1601
ChEBI
CHEBI:3491
UNII
6532B86WFG
Nikkaji
J18.085H

使用A semi-synthetic cephalosporin antibiotic related to Cefamandole. Antibacterial

上流・下流製品情報

上流原料

2-ヒドロキシ-2-フェニルアセトアミドアジ化ナトリウム2-エチルヘキサン酸ナトリウムカルバミン酸メチル5-メチルテトラゾールMethanol solution of sodium methoxideIon exchange resin column酢酸エチル炭酸水素ナトリウムAlcohol solubleMethyl dithiocarbamateアミノメタンスルホン酸イソプロピルアルコールヨードメタン

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補足説明

定義ChEBI: A cephalosporin bearing {[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl and (R)-2-hydroxy-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton.