Cefuroxime

HCID 5479529CAS 55268-75-2

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

cefuroximeCephuroximeCefuroxim55268-75-2CefuroximoCefuroximumSharoxZinacef DanmarkCefuroximaCefuroxime AcidO1R9FJ93EDCHEBI:3515
Show more names
CEFUROXIME AXETILCefuroxime VETRANALCefuroxime Axetil EP Impurity D-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCXMKetocef-7-((Z)
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-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-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))-DTXSID5022774(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(6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-((carbamoyloxy)methyl)-7-(((2Z)-2-furan-2-yl-2-(methoxyimino)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-3-((carbamoyloxy)methyl)-7-((2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(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

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

Experimental & physicochemical properties

Drugs · 5 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Cefuroxime axetil

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

LogP · 2 items

-0.8

-0.17

Solubility · 2 items

Freely soluble as sodium salt (145 mg/L)

2.84e-01 g/L

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins

FDA approved drugs -> Active ingredient

Watch group antibiotics

Melting Point · 2 items

218-225 °C

218 - 225 °C

Physical DescriptionSolid

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)

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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.

Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6.alpha.,7.beta.(Z)]]-: Human health tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (31%)

Toxicology

Adverse Effects · 1 item

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.

Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefuroxime

DILI Positive

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
XI0329000
risk_code
42/43
Signal word
Danger
Symbol(GHS)
GHS08

Chemistry & industry

Pharmacology

ATC Code · 6 items

J - Antiinfectives for systemic use

S - Sensory organs

QJ - Antiinfectives for systemic use

QS - Sensory organs

QJ - Antiinfectives for systemic use

J01DC02

Protein Binding50% to serum protein
Pharmacodynamics · 1 item

Cefuroxime is a &beta;-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 · 1 item

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.

Biological Half-LifeApproximately 80 minutes following intramuscular or intravenous injection.
Metabolism/MetabolitesThe axetil moiety is metabolized to acetaldehyde and acetic acid.

Uses & manufacturing

UsesUse (kg) in Switzerland (2009): >100
Use ClassificationVeterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Applications · 3 items

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.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
天津始加生物医药科技有限公司15022261580 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Additional notes

DefinitionChEBI: A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.

Related reactions

20 records

Linked notes

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