Cefovecin

Last updated
Cefovecin
Cefovecin.svg
Clinical data
Trade names Convenia
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • do not administer to pregnant cat or during breeding or lactation period
Routes of
administration 		dorsoscapular subcutaneous injection
ATCvet code
Legal status
Legal status
Pharmacokinetic data
Protein binding Dogs: 98.5%, Cats: 99.8%
Metabolism none
Elimination half-life Dogs: 133 hours, Cats: 166 hours
Excretion unchanged in urine/bile
Identifiers
  • (7R)-7-([(2Z)- 2-(2-amino- 1,3-thiazol- 4-yl)- 2-methoxyiminoacetyl]amino)- 8-oxo- 3-[(2S)-oxolan- 2-yl]- 5-thia- 1-azabicyclo[4.2.0]oct- 2-ene- 2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H19N5O6S2
Molar mass 453.49 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3nc(sc3)N)[C@H]4OCCC4)C(=O)O
  • InChI=1S/C17H19N5O6S2/c1-27-21-10(8-6-30-17(18)19-8)13(23)20-11-14(24)22-12(16(25)26)7(5-29-15(11)22)9-3-2-4-28-9/h6,9,11,15H,2-5H2,1H3,(H2,18,19)(H,20,23)(H,25,26)/b21-10+/t9-,11+,15+/m0/s1 X mark.svgN
  • Key:ZJGQFXVQDVCVOK-MSUXKOGISA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Cefovecin (INN) is an antibiotic of the cephalosporin class, licensed for the treatment of skin infections in cats and dogs. It is marketed by Zoetis under the trade name Convenia. It is used to treat skin infections caused by Pasteurella multocida in cats, and Staphylococcus intermedius and Streptococcus canis in dogs. The advantage of using a long-acting injectable antibiotic is that, unlike in daily administration, doses cannot be missed. Missed doses may allow partially resistant microbes to recover. The disadvantage is the presence of subtherapeutic concentrations in the weeks after the resolution of infections. This is associated with the development of resistance in microbes. It should not be used in pregnant or lactating animals or in animals with a history of allergies to penicillin or cephalosporin drugs. [1]

Contents

Medical uses

Cefovecin is a broad-spectrum, third-generation cephalosporin antibiotic administered by subcutaneous injection. [2] It is used to treat skin and soft tissue infections in dogs and cats. [2] The antimicrobial effects last for 14 days following administration. [3]

In drug studies, cefovecin administered to dogs was 92.4% effective against skin infections (secondary superficial pyoderma, abscesses, and infected wounds). In cats, it was 96.8% effective against skin infections. [1]

Contraindications

Contraindications include known allergies to cefovecin or antibiotics containing β-lactam rings such as penicillin or cephalosporins. Adverse reactions can include anaphylaxis. It is not for use in humans and should be kept out of reach of children. People with similar known allergies should avoid dermal contact when handling cefovecin.[ citation needed ]

Adverse effects

In dogs, adverse effects may include lethargy, decreased appetite, vomiting, diarrhea, blood in feces, and flatulence. In cats, adverse reactions may include vomiting, diarrhea, decreased appetite, lethargy, odd hyperactive behavior, and inappropriate urination. Mildly increased serum alanine transaminase (ALT) and gamma-glutamyltransferase may also occur. [1]

Other reported events in dogs and cats include death, tremors/ataxia, seizures, anaphylaxis, acute pulmonary edema, facial edema, injection site reactions (alopecia, scabs, necrosis, and erythema), hemolytic anemia, salivation, pruritus, lethargy, vomiting, diarrhea, and inappetence. [4]

Pharmacology

Mechanism of action

Cefovecin interferes with the synthesis of bacterial cell walls, by binding to penicillin binding proteins. Due to high protein-binding, it is not effective against species of Pseudomonas or Enterococcus . The maximum anti-bacterial activity occurs approximately two days after cefovecin has been administered. [5]

Pharmacokinetics

In the dog, the half-life of cefovecin is 5.5 days, and in the cat, it is 6.9 days. [5] In birds and reptiles, the half-life is only a few hours, much shorter than in dogs and cats. [6] In cats, 99% of cefovecin is bound to proteins in the blood plasma. [5]

Society and culture

Cefovecin was first authorized for use in the European Union in June 2006, [7] and was approved for use in the United States in June 2008. [8]

Related Research Articles

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

Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously.

<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">Aztreonam</span> Chemical compound

Aztreonam, sold under the brand name Azactam among others, is an antibiotic used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa. This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis. It is given by intravenous or intramuscular injection or by inhalation.

<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">Ceftriaxone</span> Antibiotic medication

Ceftriaxone, sold under the brand name Rocephin, is a third-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. These include middle ear infections, endocarditis, meningitis, pneumonia, bone and joint infections, intra-abdominal infections, skin infections, urinary tract infections, gonorrhea, and pelvic inflammatory disease. It is also sometimes used before surgery and following a bite wound to try to prevent infection. Ceftriaxone can be given by injection into a vein or into a 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">Cefixime</span> A third generation cephalosporin antibiotic

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required. In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.

<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">Cefprozil</span> Chemical compound

Cefprozil is a second-generation cephalosporin antibiotic. Originally discovered in 1983, and approved in 1992, it was sold under the tradename Cefzil by Bristol Meyers Squibb until 2010 when the brand name version was discontinued. It continues to be available from various companies in its generic form. It is used in the treatment of pharyngitis, tonsillitis, ear infections, acute sinusitis, bacterial exacerbation of chronic bronchitis, and skin and skin structure infections. It is currently available as a tablet and as a liquid suspension.

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

Piperacillin is a broad-spectrum β-lactam antibiotic of the ureidopenicillin class. The chemical structure of piperacillin and other ureidopenicillins incorporates a polar side chain that enhances penetration into Gram-negative bacteria and reduces susceptibility to cleavage by Gram-negative beta lactamase enzymes. These properties confer activity against the important hospital pathogen Pseudomonas aeruginosa. Thus piperacillin is sometimes referred to as an "anti-pseudomonal penicillin".

<span class="mw-page-title-main">Imipenem/cilastatin</span> Combination antibiotic medication

Imipenem/cilastatin, sold under the brand name Primaxin among others, is an antibiotic useful for the treatment of a number of bacterial infections. It is made from a combination of imipenem and cilastatin. Specifically it is used for pneumonia, sepsis, endocarditis, joint infections, intra-abdominal infections, and urinary tract infections. It is given by injection into a vein or muscle.

<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">Amikacin</span> Antibiotic medication

Amikacin is an antibiotic medication used for a number of bacterial infections. This includes joint infections, intra-abdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections. It is also used for the treatment of multidrug-resistant tuberculosis. It is used by injection into a vein using an IV or into a muscle.

Ampicillin/sulbactam is a fixed-dose combination medication of the common penicillin-derived antibiotic ampicillin and sulbactam, an inhibitor of bacterial beta-lactamase. Two different forms of the drug exist. The first, developed in 1987 and marketed in the United States under the brand name Unasyn, generic only outside the United States, is an intravenous antibiotic. The second, an oral form called sultamicillin, is marketed under the brand name Ampictam outside the United States, and generic only in the United States. Ampicillin/sulbactam is used to treat infections caused by bacteria resistant to beta-lactam antibiotics. Sulbactam blocks the enzyme which breaks down ampicillin and thereby allows ampicillin to attack and kill the bacteria.

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

Marbofloxacin is a carboxylic acid derivative third generation fluoroquinolone antibiotic. It is used in veterinary medicine under the brand names Marbocyl, Forcyl, Marbo vet and Zeniquin. A formulation of marbofloxacin combined with clotrimazole and dexamethasone is available under the name Aurizon.

<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">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.

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

Ceftaroline fosamil (INN), brand name Teflaro in the US and Zinforo in Europe, is a cephalosporin antibiotic with anti-MRSA activity. Ceftaroline fosamil is a prodrug of ceftaroline. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and other Gram-positive bacteria. It retains some activity of later-generation cephalosporins having broad-spectrum activity against Gram-negative bacteria, but its effectiveness is relatively much weaker. It is currently being investigated for community-acquired pneumonia and complicated skin and skin structure infection.

There are many circumstances during dental treatment where antibiotics are prescribed by dentists to prevent further infection. The most common antibiotic prescribed by dental practitioners is penicillin in the form of amoxicillin, however many patients are hypersensitive to this particular antibiotic. Therefore, in the cases of allergies, erythromycin is used instead.

The side effects of penicillin are bodily responses to penicillin and closely related antibiotics that do not relate directly to its effect on bacteria. A side effect is an effect that is not intended with normal dosing. Some of these reactions are visible and some occur in the body's organs or blood. Penicillins are a widely used group of medications that are effective for the treatment of a wide variety of bacterial infections in human adults and children as well as other species. Some side effects are predictable, of which some are common but not serious, some are uncommon and serious and others are rare. The route of administration of penicillin can have an effect on the development of side effects. An example of this is irritation and inflammation that develops at a peripheral infusion site when penicillin is administered intravenously. In addition, penicillin is available in different forms. There are different penicillin medications as well as a number of β-lactam antibiotics derived from penicillin.

References

  1. 1 2 3 Pfizer Animal Health. "Pfizer Convenia" (PDF). Pfizer. Retrieved 29 January 2013.[ permanent dead link ]
  2. 1 2 Pfizer Animal Health. "Convenia". Pfizer. Archived from the original on 11 April 2012. Retrieved 29 January 2013.
  3. ↑ Maddison JE, Page SW, Church DB, eds. (2008). "Chapter 8: Antibacteria drugs. Cephalosporins and cephamycins". Small animal clinical pharmacology (2nd ed.). Edinburgh: Saunders/Elsevier. pp. 164–168. ISBN   9780702028588.
  4. ↑ Convenia Prescribing Information. "Convenia Prescribing Information" (PDF). Pfizer. Retrieved 18 October 2015.
  5. 1 2 3 Boothe DM (2012). "Chapter 7: Antimicrobial drugs". In Boothe DM (ed.). Small animal clinical pharmacology & therapeutics (2nd ed.). St. Louis, Mo.: Elsevier Saunders. ISBN   9781437723571.
  6. ↑ Thuesen LR, Bertelsen MF, Brimer L, Skaanild MT (December 2009). "Selected pharmacokinetic parameters for Cefovecin in hens and green iguanas" (PDF). Journal of Veterinary Pharmacology and Therapeutics. 32 (6): 613–7. doi:10.1111/j.1365-2885.2009.01083.x. PMID   20444017. S2CID   44902923.
  7. ↑ "European Public Assessment Report for Convenia (from the EMEA website)". Archived from the original on 2008-08-04. Retrieved 2008-07-11.
  8. ↑ "FDA Approves First and Only Single-dose Antibiotic for Dogs and Cats" (Press release). Pfizer Inc. 2008-06-30. Retrieved 2008-07-11.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.