Cefuroxime (CED0002019)

Record Information

Version

1.0

Creation Date

2016-05-22 03:38:39 UTC

Update Date

2026-05-14 16:57:55 UTC

Accession Number

CHEM016620

Identification

Common Name

Cefuroxime

Class

Small Molecule

Description

Cefuroxime is an organic compound with the formula C16H16N4O8S and an average molecular weight of 424.38 g/mol. Cefuroxime belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified as an organoheterocyclic compound. In terms of biological activity, it is a recorded inhibitor of the protein target penicillin-binding protein 1A (pbpA). The compound is found in or released from ten recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics, antiinfectives, beta-lactam antibacterials, and combinations of antibacterials. It is also found in household cleaning and consumer products, specifically other smoking requisites and non-electric simulated smoking devices. Additionally, it is linked to electrical and electronic equipment, including video games, antennas, amplifiers, and emergency protective devices. Recorded exposure routes for cefuroxime include oral, intravenous, intramuscular, and inhalation.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6R,7R)-7-{[2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(C-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator
Cefuroxime	MeSH
Zinacef	MeSH
Cephuroxime	MeSH
Ketocef	MeSH

Chemical Formula

C₁₆H₁₆N₄O₈S

Average Molecular Mass

424.380 g/mol

Monoisotopic Mass

424.069 g/mol

CAS Registry Number

55268-75-2

IUPAC Name

(6R,7R)-7-{[2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(C-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

(6R,7R)-7-{[2-(furan-2-yl)-1-hydroxy-2-(methoxyimino)ethylidene]amino}-3-[(C-hydroxycarbonimidoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

SMILES

[H][C@]12SCC(COC(O)=N)=C(N1C(=O)[C@@]2([H])N=C(O)C(=NOC)C1=CC=CO1)C(O)=O

InChI Identifier

InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/t10-,14-/m1/s1

InChI Key

JFPVXVDWJQMJEE-QMTHXVAHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporin 3'-carbamates

Alternative Parents

Substituents

Cephalosporin 3'-carbamate
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Meta-thiazine
Furan
Heteroaromatic compound
Carbamic acid ester
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Carbonic acid derivative
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Dialkylthioether
Hemithioaminal
Thioether
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	0.35	ALOGPS
logP	-2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	-3.5	ChemAxon
pKa (Strongest Basic)	11.08	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	178.24 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	108.89 m³·mol⁻¹	ChemAxon
Polarizability	40.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ar0-2192200000-206265fb15a436edf6ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0avi-4293000000-c8a2cea122e40dacb6e8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0aou-9561000000-9cb40ec2c90933d73f88	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9262100000-c572c9da887b9e4fe33c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9210000000-469bbe70e6e9b2ae098d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9100000000-6a9d50ea1c4e799bc865	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
6441.0	Log mg/kg	[3600:11000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
341	Beta-lactam antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
346	Combinations of antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
395	Antiinfectives	Healthcare, pharmaceuticals & veterinary products	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
520	Emergency Protective Devices	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available

Pathways

1 pathway

Cefuroxime Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	2.72472
Click to view 3D structure	Solute carrier family 22 member 11	Q9NSA0	Humans	Predicted (SEA)	0.856341
Click to view 3D structure	Beta-lactamase	B2ZTR6	Acinetobacter baumannii	Predicted (SEA)	0.389246
Click to view 3D structure	ADC-11	D6NSM8	Acinetobacter baumannii	Predicted (SEA)	0.389246
Click to view 3D structure	Speckle-type POZ protein	O43791	Humans	Predicted (SEA)	0.622794
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	76.1365
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	262.819
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	111.869
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	2232.79
Click to view 3D structure	Probable nicotinate-nucleotide adenylyltransferase	P65502	Staphylococcus aureus (strain N315)	Predicted (SEA)	529.92
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	2102.47
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	2990.89
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	3462.73
Click to view 3D structure	Sodium/iodide cotransporter	Q63008	Rattus norvegicus	Predicted (SEA)	266.711
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	3579.59
Click to view 3D structure	Solute carrier family 12 member 5	Q63633	Rattus norvegicus	Predicted (SEA)	175.083
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	3782.77
Click to view 3D structure	Alpha-1D adrenergic receptor	P23944	Rattus norvegicus	Predicted (SEA)	1421.92
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	4593.49
Click to view 3D structure	26S proteasome non-ATPase regulatory subunit 14	O00487	Humans	Predicted (SEA)	351.256
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	2298.42
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	5110.26
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	1830.62
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	3397.81
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	1.55698