Cefovecin
{{short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444399954
| image = Cefovecin.svg
| alt =
| tradename = Convenia
| Drugs.com = {{drugs.com|international|cefovecin}}
| pregnancy_AU =
| pregnancy_category = do not administer to pregnant cat or during breeding or lactation period
| routes_of_administration = dorsoscapular subcutaneous injection
| ATCvet = yes
| ATC_prefix = J01
| ATC_suffix = DD91
| ATC_supplemental =
| legal_AU =
| legal_CA = Rx-only
| legal_CA_comment =
| legal_UK =
| legal_US =
| legal_EU = Rx-only
| legal_EU_comment = {{cite web | title=Convenia EPAR | website=European Medicines Agency (EMA) | date=5 September 2007 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/convenia | access-date=26 December 2024}}{{cite web | title=Convenia PI | website=Union Register of medicinal products | date=21 June 2006 | url=https://ec.europa.eu/health/documents/community-register/html/v059.htm | access-date=26 December 2024}}
| legal_status = Rx-only
| bioavailability =
| protein_bound = Dogs: 98.5%, Cats: 99.8%
| metabolism = none
| elimination_half-life = Dogs: 133 hours, Cats: 166 hours
| excretion = unchanged in urine/bile
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 234096-34-5
| PubChem = 9578573
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104475
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0D1OL46ZIE
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7851662
| IUPAC_name = (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
| C = 17
| H = 19
| N = 5
| O = 6
| S = 2
| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3nc(sc3)N)[C@H]4OCCC4)C(=O)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ZJGQFXVQDVCVOK-MSUXKOGISA-N
}}
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.
Medical uses
Cefovecin is a broad-spectrum, third-generation cephalosporin antibiotic administered by subcutaneous injection. It is used to treat skin and soft tissue infections in dogs and cats.{{cite web|last=Pfizer Animal Health|title=Convenia|url=http://www.pfizeranimalhealth.co.nz/sites/pfizeranimalhealth/Pages/Convenia.aspx?Species=Cats|publisher=Pfizer|access-date=29 January 2013|url-status=dead|archive-url=https://web.archive.org/web/20120411102024/http://www.pfizeranimalhealth.co.nz/sites/pfizeranimalhealth/Pages/Convenia.aspx?Species=Cats|archive-date=11 April 2012}} The antimicrobial effects last for 14 days following administration.{{cite book| veditors = Maddison JE, Page SW, Church DB |title=Small animal clinical pharmacology |date=2008 |publisher=Saunders/Elsevier |location=Edinburgh |isbn=9780702028588 |pages=164–168 |edition=2nd |chapter=Chapter 8: Antibacteria drugs. Cephalosporins and cephamycins }}
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.{{cite web|last=Pfizer Animal Health|title=Pfizer Convenia|url=https://animalhealth.pfizer.com/sites/pahweb/us/en/products/pdf/Convenia%20PI.pdf|publisher=Pfizer|access-date=29 January 2013}}{{dead link|date=August 2017 |bot=InternetArchiveBot |fix-attempted=yes }}
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.{{cn|date=March 2023}}
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.
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.{{cite web|last=Convenia Prescribing Information|title=Convenia Prescribing Information|url=https://www.zoetisus.com/products/dogs/convenia/documents/Convenia_PI.pdf|publisher=Pfizer|access-date=18 October 2015}}
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.{{cite book|last1=Boothe|first1=Dawn Merton|editor1-last=Boothe|editor1-first=Dawn Merton | name-list-style = vanc |title=Small animal clinical pharmacology & therapeutics|date=2012|publisher=Elsevier Saunders|location=St. Louis, Mo.|isbn=9781437723571|edition=2nd|chapter=Chapter 7: Antimicrobial drugs}}
=Pharmacokinetics=
In the dog, the half-life of cefovecin is 5.5 days, and in the cat, it is 6.9 days. In birds and reptiles, the half-life is only a few hours, much shorter than in dogs and cats.{{cite journal | vauthors = Thuesen LR, Bertelsen MF, Brimer L, Skaanild MT | title = Selected pharmacokinetic parameters for Cefovecin in hens and green iguanas | journal = Journal of Veterinary Pharmacology and Therapeutics | volume = 32 | issue = 6 | pages = 613–7 | date = December 2009 | pmid = 20444017 | doi = 10.1111/j.1365-2885.2009.01083.x | s2cid = 44902923 | url = https://curis.ku.dk/ws/files/20876580/Poster_cefovecin.pdf }} In cats, 99% of cefovecin is bound to proteins in the blood plasma.
Society and culture
Cefovecin was first authorized for use in the European Union in June 2006,{{cite web |url=http://www.emea.europa.eu/vetdocs/vets/Epar/convenia/convenia.htm |title=European Public Assessment Report for Convenia (from the EMEA website) |access-date=2008-07-11 |archive-url=https://web.archive.org/web/20080804164501/http://www.emea.europa.eu/vetdocs/vets/Epar/convenia/convenia.htm |archive-date=2008-08-04 |url-status=dead }} and was approved for use in the United States in June 2008.{{cite press release
| title = FDA Approves First and Only Single-dose Antibiotic for Dogs and Cats
| publisher = Pfizer Inc.
| date = 2008-06-30
| url = http://www.businesswire.com/portal/site/google/?ndmViewId=news_view&newsId=20080630005686&newsLang=en
| access-date = 2008-07-11
}}
References
{{Reflist}}
External links
- {{PubChem|23670874}} - Cefovecin sodium