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Cefuroxime

HCID 5479529
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Basic information

CAS
55268-75-2
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
424.06888465

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

cefuroxime55268-75-2CephuroximeCefuroximoCefuroximumCefuroximZinacef DanmarkSharoxCefuroximaCefuroxime 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 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 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-[(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

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 · 5 items

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Cefuroxime axetil

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)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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

REACH registered substance: Cefuroxime (EC: 259-560-1)

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.

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.
FDA Pharmacological Classification · 6 items

Related reactions

20 records
New reaction record
HRID 377529 reaction equation
HRID 377529As reactantuspto-grants-2000_02
HRID 543529 reaction equation
HRID 543529As reactantuspto-grants-1984_05
HRID 543530 reaction equation
HRID 543530As reactantuspto-grants-1984_05
HRID 745968 reaction equation
HRID 745968As reactantuspto-grants-1986_07
HRID 745969 reaction equation
HRID 745969As reactantuspto-grants-1986_07
HRID 894826 reaction equation
HRID 894826As productuspto-grants-1981_08
HRID 894832 reaction equation
HRID 894832As productuspto-grants-1981_08
HRID 894833 reaction equation
HRID 894833As productuspto-grants-1981_08
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Compound notes

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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
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
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
EPA Human Health Benchmarks for Pharmaceuticals · 6 items

Cefuroxime

11.7

49.3

For pharyngitis/tonsillitis (mild to moderate), dosage is 250 mg every 12 hours.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 500 mg/day, Lowest Therapeutic Dose (LTD): 6.3 mg/kg-day, and Screening Dose: 0.002 mg/kg-day.

21-Oct-21

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

O1R9FJ93ED

CEFUROXIME

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Cefuroxime is a Cephalosporin Antibacterial.

CEFUROXIME

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionAbsorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Cellular LocationsCytoplasm

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.

Upstream & downstream products

Upstream raw materials

Trichloroacetyl isocyanateCefuroxime sodium4-carboxylic acidSodium 2-ethylhexanoateTriethylamineMethoxyiminoacetic acidPhosphorus pentachlorideCephalothin sodiumAzoxymethaneFuranHydrochloric acid(Z)-2-Methoxyimino-2-(furyl-2-yl) acetic acid ammonium saltPhosphoroisocyanatidic dichlorideDesethyl Acetate (E)-CefuroxiMe Axetil[6R-[6alpha,7beta(Z)]]-7-[2-furyl(methoxyimino)acetamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidcefuracetime7-Aminocephalosporanic acid

Downstream products

Cefuroxime 1-acetoxyethyl esterDiisopropyl ether

Additional notes

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