Cefoxitin
Grundinformationen
- CAS
51014-44-9- Standard-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- Summenformel
- C16H17N3O7S2
- Durchschnittliche Molmasse
- 427,5 g/mol
Überblick
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-).
Namen und Bezeichner
- Bevorzugter Name
- 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
- Englischer Name
- 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]-, cis-(+-)-
- Summenformel
- C16H17N3O7S2
- Molmasse
- 427.45
Namen und Synonyme
cefoxitin35607-66-0CefoxitinaCefoxitineCEPHOXITINCefoxitinumRephoxitinMefoxitinCenomycinceftoxitinDTXSID10227646OEV9DX57Y
Weitere Namen anzeigen
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]-, cis-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]-, cis-(+-)-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-, (6R,7S)-rel-
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 acidDTXCID002764MK306(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(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 acid5-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,7S)-
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0
- Polarare Oberfläche (TPSA)
- 202 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 744
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
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 Section186.93 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Siedepunkt
- 843.371 · 843.371±65.00 °C(Press: 760.00 Torr)(predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Regulatory InformationStatus: Active Update: 26-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27779
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%)
Toxikologische Informationen
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
Chemie und Industrie
Pharmakologische Informationen
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
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