Cefuroxime axetil

Cefuroxime axetil, sold under the brand name Ceftin among others, is a second generation oral cephalosporin antibiotic.

Cefuroxime axetil

Clinical data
Trade names	Zinnat, Ceftin, Ceftum
Other names	Cefuroxime 1-acetoxyethyl ester
AHFS/Drugs.com	Monograph
MedlinePlus	a601206
Routes of administration	By mouth, intravenous, intramuscular
ATC code	None
Legal status
Legal status	AU: S4 (Prescription only)[1] US: ℞-only
Pharmacokinetic data
Bioavailability	well absorbed
Metabolism	Cefuroxime is not metabolized and excreted as it is in urine, axetil is metabolized to acetaldehyde and acetic acid[medical citation needed]
Excretion	Urine
Identifiers
IUPAC name 1-Acetoxyethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CAS Number	64544-07-6
PubChem CID	6321416
DrugBank	DBSALT001355
ChemSpider	4882027
UNII	Z49QDT0J8Z
KEGG	D00914
ChEBI	CHEBI:3516
ChEMBL	ChEMBL1095930
CompTox Dashboard (EPA)	DTXSID0022775
ECHA InfoCard	100.166.374
Chemical and physical data
Formula	C20H22N4O10S
Molar mass	510.47 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3occc3)COC(=O)N)C(=O)OC(OC(=O)C)C
InChI InChI=1S/C20H22N4O10S/c1-9(25)33-10(2)34-19(28)15-11(7-32-20(21)29)8-35-18-14(17(27)24(15)18)22-16(26)13(23-30-3)12-5-4-6-31-12/h4-6,10,14,18H,7-8H2,1-3H3,(H2,21,29)(H,22,26)/b23-13-/t10?,14-,18-/m1/s1 Key:KEJCWVGMRLCZQQ-YJBYXUATSA-N

It is an acetoxyethyl ester prodrug of cefuroxime which is effective orally.^[2] The activity depends on in vivo hydrolysis and release of cefuroxime tablets.^{[citation needed]}

It was patented in 1976 and approved for medical use in 1987.^[3]

Medical uses

Second generation cephalosporins are more effective in treating Gram-negative bacilli compared to first generation cephalosporins, which have a greater coverage for Gram-positive cocci. Also, it has been reported that cefuroxime is resistant to hydrolysis by β-lactamases produced by Gram-negative bacteria.^[4]

Some medical uses are:^[5][6]

• Upper respiratory tract infections
• Lower respiratory tract infections
• Urinary tract infections
• Skin and soft tissue infections
• Gonorrhoea
• Early Lyme disease

Bacterial susceptibility

Cefuroxime axetil treats infections against methicillin-, oxacillin- and penicillin-sensitive bacterial strains.^[7] Cefuroxime axetil does not work against enterococci. ^[5]

Gram-positive aerobic microorganisms

• Staphylococcus aureus (Methicillin-sensitive only)
• Staphylococcus epidermidis
• Streptococcus pneumoniae (Penicillin-sensitive only)

Gram-negative aerobic microorganisms

• Haemophilus influenzae
• Moraxella catarrhalis
• Neisseria gonorrhoeae
• Escherichia coli
• Proteus mirabilis
• Klebsiella pneumoniae (variable activity)

Mechanism of action

Cefuroxime axetil is a second generation cephalosporin that, like penicillins antibiotics, contains a β-lactam ring structure. Cephalosporins work as bactericidal antibiotics; that by binding to penicillin-binding proteins (PBPs), inhibit the last step of the bacterial cell wall synthesis. Once the β-lactam ring binds to PBPs, cross-linking between peptidoglycan units is inhibited.^[4]

Pharmacokinetics

Absorption: Once consumed, cefuroxime axetil is converted to the active compound cefuroxime by esterases of mucosal cells in the gastrointestinal tract. Cefuroxime is then released for systematic circulation. If cefuroxime axetil is given with food, absorption values can increase from 37% in fasting patients to 52% in fed patients.^[5]

Distribution: It has been reported that after cefuroxime axetil administration, it can be found in tonsil tissue, sinus tissue, bronchial tissue and middle ear effusion.^[5]

Elimination: After cefuroxime production, the body is unable to metabolize the drug, and is eliminated unchanged in the urine.^[5]

History

It was discovered by Glaxo (now GlaxoSmithKline) and introduced in 1987.^[8] It was approved by FDA on December 28, 1987.^[9] It is available by GSK as Ceftin in the US^[10] and Ceftum in India.^[11]