Cefdinir

Cefdinir
Clinical data
Trade names Cefzon, Omnicef
AHFS/Drugs.com Monograph
MedlinePlus a698001
Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    administration    		 Oral
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    Bioavailability 16% to 21% (dose-dependent)
    Protein binding 60% to 70%
    Metabolism Negligible
    Elimination half-life 1.7 ± 0.6 hours
    Excretion Renal
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    ECHA InfoCard 100.171.145 Edit this at Wikidata
    Chemical and physical data
    Formula C14H13N5O5S2
    Molar mass 395.416 g/mol
    3D model (JSmol)
      (verify)

    Cefdinir (SEF-di-nir) is a third-generation oral cephalosporin antibiotic sold under the brand names Cefzon and Omnicef.

    As of 2008, cefdinir, as Omnicef, was the highest-selling cephalosporin antibiotic in the United States, with more than US$585 million in retail sales of its generic versions alone.[1] Cefdinir is structurally similar to cefixime.

    It was discovered by Fujisawa Pharmaceutical Co., Ltd. (now Astellas) and introduced in 1991 under the brand name Cefzon.[2][3] Warner-Lambert licensed this cephalosporin for marketing in US from Fujisawa.[4] Abbott obtained U.S. marketing rights to Omnicef (cefdinir) in December 1998 through an agreement with Warner-Lambert Company.[5] It was approved by FDA on Dec 4, 1997.[6] It is available in US as Omnicef by Abbott Laboratories and in India as Cednir by Abbott, Kefnir by Glenmark, Cefdair by Xalra Pharma and Cefdiel by Ranbaxy.

    Medical uses

    Therapeutic uses of cefdinir include otitis media, soft tissue infections, and respiratory tract infections, including sinusitis, strep throat (note: no documented resistance of Group A Streptococcus to penicillin has ever been reported, and penicillin or amoxicillin is preferred except in penicillin allergic patients), community-acquired pneumonia, and acute exacerbations of bronchitis.

    Susceptible organisms

    Cefdinir is a bactericidal antibiotic of the cephalosporin class of antibiotics. It can be used to treat infections caused by several Gram-negative and Gram-positive bacteria.

    Spectrum of bacterial susceptibility and resistance

    Cefdinir is a broad-spectrum antibiotic and has been used to treat infections of the respiratory tract including pneumonia, sinusitis, and bronchitis. The following represents MIC susceptibility data for a few medically significant microorganisms.[7]

    • Haemophilus influenzae: 0.05 - 4 μg/ml
    • Streptococcus pneumoniae: 0.006 - 64 μg/ml
    • Streptococcus pyogenes: ≤0.004 - 2 μg/ml

    Side effects

    Side effects include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."[8]

    It is also one of the medications that can cause toxic epidermal necrolysis or Stevens-Johnson Syndrome.[9]

    Mechanism of action

    Available forms

    Cefdinir is administered orally. It is available as capsules and a suspension. Dosage, schedule, and duration of therapy varies according to the type of infection.

    "Blood" in the stool

    The pediatric version of cefdinir can bind to iron in the digestive tract; in rare cases, this causes a rust or red discoloration of the stool. Blood typically appears dark brown or black in stool, and testing may confirm which is present. If the reddish stool is accompanied by abdominal pain, weight loss, diarrhea, etc., a Clostridium difficile infection caused by the antibiotic could be signified.

    Synthesis

    Cefdinir synthesis:[10][11][12] Improved prepn:[13]

    Acylation of the primary amine 1 with 4-bromo-3-oxobutanoyl bromide (2) leads to the amide (3). The active methylene group in that product is then nitrosated with sodium nitrite; the initial product spontaneously tautomerizes to afford the oxime (4). The bromoketone array in that intermediate constitutes a classical starting function for construction of thiazoles. Reaction of 4 with thiourea thus leads to formation of an aminothiazole moiety. Thus there is obtained the antibiotic cefdinir (5).

    References

    1. ↑ ""2008 Top 200 generic drugs by retail dollars"" (PDF). Archived from the original (PDF) on 2012-01-12.  (399.4 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009.
    2. ↑ "2005 News Releases - Astellas Pharma Inc". astellas.com.
    3. ↑ Cabri, Walter; Ghetti, Paolo; Pozzi, Giovanni; Alpegiani, Marco (2007). "Polymorphisms and Patent, Market, and Legal Battles: Cefdinir Case Study". Organic Process Research & Development. 11: 64. doi:10.1021/op0601060.
    4. ↑ "Document". elsevierbi.com.
    5. ↑ "Medicis.com - Medicis Pharmaceutical Corporation". globenewswire.com.
    6. ↑ "Cefdinir medical facts from Drugs.com". drugs.com.
    7. ↑ "Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). October 14, 2015. Retrieved 1 October 2015.
    8. ↑ "Omnicef capsules Patient Information" (PDF). Abbott Laboratories. February 2004. Archived from the original (PDF) on 2006-11-18. Retrieved 2006-11-24.
    9. ↑ "Omnicef manufacturer's packet insert" (PDF). FDA. Retrieved 2016-12-11.
    10. ↑ T. Takaya et al., BE 897864; eidem, U.S. Patent 4,559,334 (1984, 1985 both to Fujisawa Pharmaceuticals).
    11. ↑ Inamoto, Y; Chiba, T; Kamimura, T; Takaya, T (1988). "FK 482, a new orally active cephalosporin synthesis and biological properties". The Journal of Antibiotics. 41 (6): 828–30. doi:10.7164/antibiotics.41.828. PMID 3255303.
    12. ↑ Kamachi, H; Narita, Y; Okita, T; Abe, Y; Iimura, S; Tomatsu, K; Yamasaki, T; Okumura, J; Naito, T; Oki, T (1988). "Synthesis and biological activity of a new cephalosporin, BMY-28232 and its prodrug-type esters for oral use". The Journal of Antibiotics. 41 (11): 1602–16. doi:10.7164/antibiotics.41.1602. PMID 3198494.
    13. ↑ González, M; Rodríguez, Z; Tolón, B; Rodríguez, J. C.; Velez, H; Valdés, B; López, M. A.; Fini, A (2003). "An alternative procedure for preparation of cefdinir". Il Farmaco. 58 (6): 409–18. doi:10.1016/S0014-827X(03)00063-6. PMID 12767379.
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