Cefuroxime axetil

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Cefuroxime axetil
Cefuroxime axetil.svg
Clinical data
Trade names Zinnat, Ceftin, Ceftum
Other namesCefuroxime 1-acetoxyethyl ester
AHFS/Drugs.com Monograph
MedlinePlus a601206
Routes of
administration
By mouth, intravenous, intramuscular
ATC code
  • None
Legal status
Legal status
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
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.166.374 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H22N4O10S
Molar mass 510.47 g·mol−1
3D model (JSmol)
  • 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=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

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

Contents

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]

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

Gram-negative aerobic microorganisms

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 by 52% compared to fasting 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]

Related Research Articles

<span class="mw-page-title-main">Beta-lactam antibiotics</span> Class of broad-spectrum antibiotics

β-lactam antibiotics are antibiotics that contain a beta-lactam ring in their chemical structure. This includes penicillin derivatives (penams), cephalosporins and cephamycins (cephems), monobactams, carbapenems and carbacephems. Most β-lactam antibiotics work by inhibiting cell wall biosynthesis in the bacterial organism and are the most widely used group of antibiotics. Until 2003, when measured by sales, more than half of all commercially available antibiotics in use were β-lactam compounds. The first β-lactam antibiotic discovered, penicillin, was isolated from a strain of Penicillium rubens.

<span class="mw-page-title-main">Ertapenem</span> Antibiotic medication

Ertapenem, sold under the brand name Invanz, is a carbapenem antibiotic medication used for the treatment of infections of the abdomen, the lungs, the upper part of the female reproductive system, and the diabetic foot.

<span class="mw-page-title-main">Methicillin</span> Antibiotic medication

Methicillin (USAN), also known as meticillin (INN), is a narrow-spectrum β-lactam antibiotic of the penicillin class.

<span class="mw-page-title-main">Cephalosporin</span> Class of pharmaceutical drugs

The cephalosporins are a class of β-lactam antibiotics originally derived from the fungus Acremonium, which was previously known as Cephalosporium.

<span class="mw-page-title-main">Cefazolin</span> Antibiotic medication

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

<span class="mw-page-title-main">Cefuroxime</span> Antibiotic medication

Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease. It is used by mouth or by injection into a vein or muscle.

<span class="mw-page-title-main">Cefalexin</span> Beta-lactam antibiotic

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins. It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.

<span class="mw-page-title-main">Ceftazidime</span> Antibiotic medication

Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.

<span class="mw-page-title-main">Cefaclor</span> Chemical compound

Cefaclor, sold under the trade name Ceclor among others, is a second-generation cephalosporin antibiotic used to treat certain bacterial infections such as pneumonia and infections of the ear, lung, skin, throat, and urinary tract. It is also available from other manufacturers as a generic.

<span class="mw-page-title-main">Carbapenem</span> Class of highly effective antibiotic agents

Carbapenems are a class of very effective antibiotic agents most commonly used for treatment of severe bacterial infections. This class of antibiotics is usually reserved for known or suspected multidrug-resistant (MDR) bacterial infections. Similar to penicillins and cephalosporins, carbapenems are members of the beta-lactam antibiotics drug class, which kill bacteria by binding to penicillin-binding proteins, thus inhibiting bacterial cell wall synthesis. However, these agents individually exhibit a broader spectrum of activity compared to most cephalosporins and penicillins. Furthermore, carbapenems are typically unaffected by emerging antibiotic resistance, even to other beta-lactams.

<span class="mw-page-title-main">Cefepime</span> Fourth-generation Cephalosporin Antibiotic

Cefepime is a fourth-generation cephalosporin antibiotic. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in people treated with cefepime compared with other β-lactam antibiotics. In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.

<span class="mw-page-title-main">Cefotaxime</span> Chemical compound

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

<span class="mw-page-title-main">Dicloxacillin</span> Chemical compound

Dicloxacillin is a narrow-spectrum β-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).

<span class="mw-page-title-main">Oxacillin</span> Chemical compound

Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.

<span class="mw-page-title-main">Cefoxitin</span> Chemical compound

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum. It is often grouped with the second-generation cephalosporins. Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.

<span class="mw-page-title-main">Cefditoren</span> Chemical to treat skin infections

Cefditoren, also known as cefditoren pivoxil is an antibiotic used to treat infections caused by Gram-positive and Gram-negative bacteria that are resistant to other antibiotics. It is mainly used for treatment of community acquired pneumonia. It is taken by mouth and is in the cephalosporin family of antibiotics, which is part of the broader beta-lactam group of antibiotics.

β-Lactamase inhibitor Drugs that inhibit β-Lactamase enzymes

Beta-lactamases are a family of enzymes involved in bacterial resistance to beta-lactam antibiotics. In bacterial resistance to beta-lactam antibiotics, the bacteria have beta-lactamase which degrade the beta-lactam rings, rendering the antibiotic ineffective. However, with beta-lactamase inhibitors, these enzymes on the bacteria are inhibited, thus allowing the antibiotic to take effect. Strategies for combating this form of resistance have included the development of new beta-lactam antibiotics that are more resistant to cleavage and the development of the class of enzyme inhibitors called beta-lactamase inhibitors. Although β-lactamase inhibitors have little antibiotic activity of their own, they prevent bacterial degradation of beta-lactam antibiotics and thus extend the range of bacteria the drugs are effective against.

<span class="mw-page-title-main">Cefodizime</span> Chemical compound

Cefodizime is a 3rd generation cephalosporin antibiotic with broad spectrum activity against aerobic gram positive and gram negative bacteria. Clinically, it has been shown to be effective against upper and lower respiratory tract infections, urinary tract infections, and gonorrhea. Cefodizime is a bactericidal antibiotic that targets penicillin-binding proteins (PBPs) 1A/B, 2, and 3 resulting in the eventual death of the bacterial cell. In vivo experimental models of infection showed that bacterial clearance by this drug is at least as effective compared with other 3rd generation cephalosporins. It has similar adverse effect profile to other 3rd generation cephalosporins as well, mainly being limited to gastrointestinal or dermatological side effects.

Cephalosporins are a broad class of bactericidal antibiotics that include the β-lactam ring and share a structural similarity and mechanism of action with other β-lactam antibiotics. The cephalosporins have the ability to kill bacteria by inhibiting essential steps in the bacterial cell wall synthesis which in the end results in osmotic lysis and death of the bacterial cell. Cephalosporins are widely used antibiotics because of their clinical efficiency and desirable safety profile.

<span class="mw-page-title-main">Ceftolozane/tazobactam</span> Antibiotic

Ceftolozane/tazobactam, sold under the brand name Zerbaxa, is a fixed-dose combination antibiotic medication used for the treatment of complicated urinary tract infections and complicated intra-abdominal infections in adults. Ceftolozane is a cephalosporin antibiotic, developed for the treatment of infections with gram-negative bacteria that are resistant to conventional antibiotics. It was studied for urinary tract infections, intra-abdominal infections and ventilator-associated bacterial pneumonia.

References

  1. "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  2. Sneader W (23 June 2005). Drug Discovery: A History. John Wiley, Chichester, UK. ISBN   0-471-89979-8.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN   9783527607495.
  4. 1 2 Bui T, Preuss CV (2020). "Cephalosporins". StatPearls. StatPearls Publishing. PMID   31855361 . Retrieved 23 April 2020.
  5. 1 2 3 4 5 Perry CM, Brogden RN (July 1996). "Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy". Drugs. 52 (1): 125–158. doi:10.2165/00003495-199652010-00009. PMID   8799689. S2CID   46985101.
  6. "Ceftin (cefuroxime axetil)" (PDF). GlaxoSmithKline. U.S. Food and Drug Administration. 2015. Retrieved 22 April 2020.
  7. "Zinnat SUMMARY OF PRODUCT CHARACTERISTICS - GSKPro for Healthcare Professionals" (PDF).
  8. "Our history - About GSK". GlaxoSmithKline. Archived from the original on 14 May 2011.
  9. "Cefuroxime Axetil Monograph for Professionals". Drugs.com. Retrieved 22 April 2018.
  10. "Brands". Gsksource.com. 22 March 2018. Archived from the original on 20 March 2016. Retrieved 22 April 2018.
  11. "Our products". GlaxoSmithKline. Archived from the original on 22 March 2016. Retrieved 12 March 2012.

"Cefuroxime Injection: MedlinePlus Drug Information". MedlinePlus.