Cefdinir

Therapeutic uses of cefdinir include otitis media, soft tissue infections, and respiratory tract infections, including sinusitis, strep throat (for penicillin-allergic patients), community-acquired pneumonia, and acute exacerbations of bronchitis.

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.

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.{{cite web |url=http://www.toku-e.com/Assets/MIC/Cefdinir.pdf |title=Susceptibility and Minimum Inhibitory Concentration (MIC) Data |date=14 October 2015 |access-date= 1 October 2015}}

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

Side effects include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."{{cite web | title = Omnicef capsules Patient Information | publisher = Abbott Laboratories | url = http://www.rxabbott.com/pdf/omnicef_capsules_patient_friendly.pdf |date=February 2004 | access-date = 24 November 2006 |archive-url = https://web.archive.org/web/20061118132152/http://www.rxabbott.com/pdf/omnicef_capsules_patient_friendly.pdf|archive-date = 18 November 2006}}

It is also one of the medications that can cause toxic epidermal necrolysis or Stevens–Johnson syndrome.{{cite web | title = Omnicef manufacturer's packet insert | publisher = FDA | url = http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/50739S2LBL.pdf | access-date = 11 December 2016}}

The pediatric version of cefdinir can bind to iron in the digestive tract; in rare cases, this causes 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 Clostridioides difficile infection caused by the antibiotic could be signified.

{{main|Cephalosporin}}

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Acylation at the primary amine of the cephalosporin intermediate (1) with 4-bromo-3-oxobutanoyl bromide (2) gives the amide (3). The active methylene group in that compound is then nitrosated with sodium nitrite; the initial product spontaneously tautomerizes to afford the oxime (4). The bromoketone functional group reacts with thiourea in the penultimate step, forming the thiazole ring of cefdinir, which is the product after removal of the benzhydryl ester protecting group with trifluoroacetic acid.{{cite journal | vauthors = Inamoto Y, Chiba T, Kamimura T, Takaya T | title = FK 482, a new orally active cephalosporin synthesis and biological properties | journal = The Journal of Antibiotics | volume = 41 | issue = 6 | pages = 828–30 | date = June 1988 | pmid = 3255303 | doi = 10.7164/antibiotics.41.828 | doi-access = free }}{{cite journal | vauthors = Kamachi H, Narita Y, Okita T, Abe Y, Iimura S, Tomatsu K, Yamasaki T, Okumura J, Naito T, Oki T | display-authors = 6 | title = Synthesis and biological activity of a new cephalosporin, BMY-28232 and its prodrug-type esters for oral use | journal = The Journal of Antibiotics | volume = 41 | issue = 11 | pages = 1602–16 | date = November 1988 | pmid = 3198494 | doi = 10.7164/antibiotics.41.1602 | doi-access = free }}{{cite journal | vauthors = González M, Rodríguez Z, Tolón B, Rodríguez JC, Velez H, Valdés B, López MA, Fini A | display-authors = 6 | title = An alternative procedure for preparation of cefdinir | journal = Farmaco | volume = 58 | issue = 6 | pages = 409–18 | date = June 2003 | pmid = 12767379 | doi = 10.1016/S0014-827X(03)00063-6 }}

As of 2008, cefdinir was the highest-selling cephalosporin antibiotic in the United States, with more than $585 million in retail sales of its generic versions.{{cite web|url=http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/192009/597086/article.pdf |title=2008 Top 200 generic drugs by retail dollars |url-status=dead |archive-url=https://web.archive.org/web/20120112121937/http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/252011/727243/article.pdf |archive-date=12 January 2012 }} {{small|(399.4 KB)}}. Drug Topics (26 May 2009). Retrieved on 24 July 2009.{{update-inline|date=October 2020}}

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

Warner-Lambert licensed the drug for marketing in US from Fujisawa.{{cite web|url=http://www.elsevierbi.com/publications/the-pink-sheet/52/005/comprecin-has-excellent-chance-to-reach-us-market-this-year-dupont-prophenytoin-crosslicense-deal?p=1|title=Document|work=elsevierbi.com}} Abbott obtained U.S. marketing rights to cefdinir in December 1998 through an agreement with Warner-Lambert Company.{{cite web|url=http://www.globenewswire.com/newsarchive/mrx/pages/news_releases.html?d=94045|archive-url=https://web.archive.org/web/20140714140411/http://www.globenewswire.com/newsarchive/mrx/pages/news_releases.html?d=94045|url-status=dead|archive-date=14 July 2014|title=Medicis.com - Medicis Pharmaceutical Corporation|work=globenewswire.com}} It was approved by the FDA on 4 December 1997.{{cite web|url=https://www.drugs.com/mtm/cefdinir.html|title=Cefdinir medical facts from Drugs.com|work=drugs.com}} 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.

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