Basic information
- Standard SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1- InChIKey
JFPVXVDWJQMJEE-IZRZKJBUSA-N- Molecular formula
- C16H16N4O8S
- Average molar mass
- 424.4 g/mol
- Monoisotopic mass
- 424.06888447
Overview
Cefuroxime is a 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain. It has a role as a drug allergen. It is a member of furans, a 3-(carbamoyloxymethyl)cephalosporin and an oxime O-ether.
Names & identifiers
- Preferred name
- Cefuroxime
- IUPAC
- (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefuroxime
- Molecular formula
- C16H16N4O8S
- Molecular weight
- 424.39
Names & synonyms
Show more names
Database identifiers
- CAS
55268-75-2- PubChem CID
- 5479529
- DTXSID
DTXSID5022774- ChEMBL
CHEMBL1436- ChEBI
CHEBI:3515- UNII
- O1R9FJ93ED
- EC Number
- 259-560-1
- Nikkaji
- J13.093A
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 199 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 8
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 798
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Metabolite of Cefuroxime axetil
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Antibiotics
LogP
-0.8
-0.17
Solubility
Freely soluble as sodium salt (145 mg/L)
2.84e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
Watch group antibiotics
Melting Point
218-225 °C
218 - 225 °C
Physicochemical properties
- Melting point
- 171.5 · 171.5-173°C
- alpha
- 20 · D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer)
- Density
- 1.76 · 1.76
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 2.5 · pKa 2.5(H2O) (Uncertain)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- 145 mg/L · 145mg/L at 25℃
- BCS Class
- 4 · 4
- Major Application
- clinical testing
- InChIKey
- JFPVXVDWJQMJEE-IZRZKJBUSA-N
- SMILES
- N12[C@@]([H])([C@H](NC(/C(/C3=CC=CO3)=N\OC)=O)C1=O)SCC(COC(N)=O)=C2C(O)=O
- CAS DataBase Reference
- 55268 · 55268-75-2(CAS DataBase Reference)
- FDA UNII
- 1 R9FJ93ED · O1R9FJ93ED
- ATC code
- 1 DC02,S01AA27 · J01DC02,S01AA27
- EPA Substance Registry System
- 5 · 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)- (55268-75-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 334 · H334-H317
- Precautionary statements
- 261 · P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xn
- Risk Statements
- 42 · 42/43
- Safety Statements
- 22 · 22-24-37-45
- WGK Germany
- 3 · 3
- RTECS
- 329000 · XI0329000
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H317 (31%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 08-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21969
Cefuroxime: 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.
Toxicology
Adverse Effects
Similar to penicillins and most β-lactam antibiotics, cefuroxime is generally well-tolerated. However, cefuroxime may potentially lead to adverse drug reactions in some patients, as seen with other medications. The most commonly reported adverse drug reactions are gastrointestinal disturbances, including nausea, vomiting, and diarrhea. Additional gastrointestinal adverse drug reactions include anorexia, abdominal pain, dizziness, and headache. In cases of parenteral administration, local reactions at the injection site, including thrombophlebitis, can occur.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefuroxime
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- XI0329000
- risk_code
- 42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 22-24-37-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H334-H317
- REACH Registrations
- Active
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
S - Sensory organs
QJ - Antiinfectives for systemic use
QS - Sensory organs
QJ - Antiinfectives for systemic use
J01DC02
Pharmacodynamics
Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: <i>Staphylococcus aureus</i>, <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>. Aerobic Gram-negative Microorganisms: <i>Escherichia coli</i>, <i>Haemophilus influenzae</i> (including beta-lactamase-producing strains), <i>Haemophilus parainfluenzae</i>, <i>Klebsiella pneumoniae</i>, <i>Moraxella catarrhalis</i> (including beta-lactamase-producing strains), <i>Neisseria gonorrhoeae</i> (including beta-lactamase-producing strains). Spirochetes: <i>Borrelia burgdorferi</i>. Cefuroxime axetil is the prodrug
Mechanism of Action
Cefuroxime, 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; it is possible that cefuroxime interferes with an autolysin inhibitor.
FDA Pharmacological Classification
O1R9FJ93ED
CEFUROXIME
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefuroxime is a Cephalosporin Antibacterial.
CEFUROXIME
Uses & manufacturing
Applications
DescriptionCefuroxime axetil is the acetoxyethyl ester and oral prodrug of cefuroxime, a second-generation cephalosporin. It has a broad spectrum of action and is resistant to most P-lactamases. Cefuroxime axed is indicated for serious bacterial infections, especially where no identification of organism(s) has been made.
UsesCefuroxime is a second-generation cephalosporin antibiotic.
UsesAntibacterial.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.
Related reactions
Linked notes
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