基本情報
- CAS
35607-66-0- 標準SMILES
CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@@H]21- InChIKey
WZOZEZRFJCJXNZ-ZBFHGGJFSA-N- 分子式
- C16H17N3O7S2
- 平均分子量
- 427.5 g/mol
- 単同位体質量
- 427.05079224
概要
Cefoxitin is a semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase. It has a role as an antibacterial drug. It is a cephalosporin, a cephamycin, a semisynthetic derivative and a beta-lactam antibiotic allergen. It is a conjugate acid of a cefoxitin(1-).
名称と識別子
- 優先名称
- Cefoxitin
- IUPAC
- (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 現地名
- セフォキシチン
- 英語名
- Cefoxitin
- 分子式
- C16H17N3O7S2
- 分子量
- 427.45
名称と別名
cefoxitin35607-66-0CefoxitinaCefoxitineCEPHOXITINCefoxitinumRephoxitinMefoxitinCenomycinceftoxitinDTXSID10227646OEV9DX57Y
名称をさらに表示
(7S)-7-[(2-テニルカルボニル)アミノ]-7-メトキシ-3-[(カルバモイルオキシ)メチル]セファム-3-エン-4-カルボン酸(6R,7S)-3-(カルバモイルオキシメチル)-7β-メトキシ-8-オキソ-7-[(2-チエニル)アセチルアミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸セフォキシチンセホキシチン(6R,7S)-3-[(カルバモイルオキシ)メチル]-7-メトキシ-8-オキソ-7-[2-(チオフェン-2-イル)アセトアミド]-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cfxCEFOXITIN ACIDC06887MefoxinCefotaxidineCefoxitinic acid
J01DC01CHEBI:209807(6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidDTXCID002764(6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidMK306MK 306(6R,7S)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
データベース識別子
物性
構造計算による物性
- XLogP
- 0
- 極性表面積
- 202 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 9
- 回転可能結合数
- 8
- 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 -> Antibiotics
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP
-0.02
-0.02
Solubility1.95e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
Melting Point
165-167
149.5 °C
Physical DescriptionSolid
Collision Cross Section180.82 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 149 · 149-150℃
- 沸点
- 843 ℃ · 843℃
- 比重(密度)
- 1.4441 · 1.4441 (rough estimate)
- 屈折率
- 1.639 · 1.6390 (estimate)
- 闪点
- 110 ° · >110°(230°F)
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
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
Danger
H317 (33.3%): 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 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationREACH registered substance: Cefoxitin (EC: 252-641-2)
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6R-cis)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (33.3%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefoxitin
DILI Negative
Intravenous
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- ridadr
- 3077
- hs_code
- 30032013
- hazard_class
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Pharmacodynamics
Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. It is active against a broad range of gram-negative bacteria including anaerobes. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria.
Mechanism of ActionThe bactericidal action of cefoxitin results from inhibition of cell wall synthesis.
Biological Half-LifeThe half-life after an intravenous dose is 41 to 59 minutes.
Metabolism/MetabolitesMinimal (approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period).
FDA Pharmacological Classification
6OEV9DX57Y
CEFOXITIN
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefoxitin is a Cephalosporin Antibacterial.
CEFOXITIN
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period, resulting in high urinary concentrations. Cefoxitin passes into pleural and joint fluids and is detectable in antibacterial concentrations in bile.
Cellular LocationsExtracellular
関連反応
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化合物ノート
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