Cefdinir

{{Short description|Chemical compound}} {{Use dmy dates|date=February 2024}} {{Drugbox | verifiedrevid = 460022886 | image = Cefdinir.svg | image_class = skin-invert-image

| pronounce = SEF-di-nir | tradename = Cefzon, Omnicef, others | Drugs.com = {{drugs.com|monograph|cefdinir}} | MedlinePlus = a698001 | DailyMedID = Cefdinir | pregnancy_AU =  | pregnancy_category = | routes_of_administration = By mouth | ATC_prefix = J01 | ATC_suffix = DD15 | ATC_supplemental =

| legal_AU =  | legal_UK =  | legal_US = Rx-only | legal_status =

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 91832-40-5 | PubChem = 6915944 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00535 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 5291705 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = CI0FAO63WC | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D00917 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 3485 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 927

| IUPAC_name = 8-[2-(2-amino-1,3-thiazol-4-yl)-1-hydroxy-2-nitroso-<br>ethenyl]amino-4-ethenyl-7-oxo-2-thia-6-<br>azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid | C=14 | H=13 | N=5 | O=5 | S=2 | smiles = O=C2N1/C(=C(/C=C)CS[C@@H]1[C@@H]2NC(=O)C(=N\O)/c3nc(sc3)N)C(=O)O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RTXOFQZKPXMALH-GHXIOONMSA-N | melting_point = 170 | melting_notes = (dec.) }}  '''Cefdinir''', sold under the brand name '''Omnicef''' among others, is an antibiotic used to treat bacterial infections including bacterial pneumonia, other respiratory tract infections, otitis media, strep throat, and cellulitis. It may also be used as an alternative antibiotic for those with a severe penicillin allergy. It is taken by mouth.<ref name=AHFS2019>{{cite web |title=Cefdinir Monograph for Professionals |url=https://www.drugs.com/monograph/cefdinir.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=23 March 2019 |language=en}}</ref><ref>{{Cite web |title=Cefdinir (oral route) |url=https://www.mayoclinic.org/drugs-supplements/cefdinir-oral-route/description/drg-20073288 |access-date=2025-05-26 |website=Mayo Clinic |language=en}}</ref><ref>{{Cite web |title=Cefdinir: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a698001.html |access-date=2025-05-26 |website=medlineplus.gov |language=en}}</ref>

Common side effects include diarrhea, nausea, and a skin rash.<ref name=AHFS2019/> Serious side effects may include ''Clostridioides difficile'' infection, anaphylaxis, and Stevens–Johnson syndrome.<ref name=AHFS2019/> Use in pregnancy and breastfeeding is believed to be safe but has not been well studied.<ref name=Preg2019>{{cite web |title=Cefdinir Use During Pregnancy |url=https://www.drugs.com/pregnancy/cefdinir.html |website=Drugs.com |access-date=3 March 2019 |language=en}}</ref>

It is a third-generation cephalosporin antibiotic and works by interfering with a bacteria's ability to make a cell wall, resulting in its death.<ref name="AHFS2019" />

==Medical uses== 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.

===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.

===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.<ref>{{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}}</ref> * ''Haemophilus influenzae'': 0.05 - 4 μg/ml * ''Streptococcus pneumoniae'': 0.006 - 64 μg/ml * ''Streptococcus pyogenes'': ≤0.004 - 2 μg/ml

=== Available forms === 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.

It is available under several brand names and as a generic medication.<ref name="AHFS2019222">{{cite web |title=Cefdinir Monograph for Professionals |url=https://www.drugs.com/monograph/cefdinir.html |access-date=23 March 2019 |website=Drugs.com |publisher=American Society of Health-System Pharmacists |language=en}}</ref>

==Side effects== Side effects of cefdinir include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."<ref>{{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}}</ref>

It is also one of the medications that can cause toxic epidermal necrolysis or Stevens–Johnson syndrome.<ref>{{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}}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}</ref>

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.

==Mechanism of action== {{main|Cephalosporin}} {{needs expansion|date=February 2026}}

==Synthesis== :upright=2 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.<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref>

==Society and culture== ===Economics=== Cefdinir was patented in 1979 and first approved for medical use in 1991.<ref name="Fis20062">{{cite book |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA49X |title=Analogue-based Drug Discovery |vauthors=Fischer J, Ganellin CR |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=49X |language=en}}</ref>

Warner-Lambert licensed the drug for marketing in the US from Fujisawa.<ref>{{cite web |title=Document |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 |work=elsevierbi.com}}</ref> Abbott later obtained U.S. marketing rights to cefdinir in December 1998 through an agreement with Warner-Lambert Company.<ref>{{cite web |title=Medicis.com - Medicis Pharmaceutical Corporation |url=http://www.globenewswire.com/newsarchive/mrx/pages/news_releases.html?d=94045 |url-status=dead |archive-url=https://web.archive.org/web/20140714140411/http://www.globenewswire.com/newsarchive/mrx/pages/news_releases.html?d=94045 |archive-date=14 July 2014 |work=globenewswire.com}}</ref> It was approved by the US FDA on 4 December 1997.<ref>{{cite web |title=Cefdinir medical facts from Drugs.com |url=https://www.drugs.com/mtm/cefdinir.html |work=drugs.com}}</ref> 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.

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.<ref>{{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.</ref>{{update-inline|date=October 2020}}

In 2023, it was the 165th most commonly prescribed medication in the United States, with more than 3{{nbsp}}million prescriptions.<ref name="Top 300">{{cite web | title=Top 300 of 2023 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=12 August 2025 | archive-date=12 August 2025 | archive-url=https://web.archive.org/web/20250812130026/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web |title=Cefdinir Drug Usage Statistics, United States, 2014 - 2023 |url=https://clincalc.com/DrugStats/Drugs/Cefdinir |access-date=19 August 2025 |website=ClinCalc}}</ref>

== References == {{Reflist}}

Category:Wikipedia medicine articles ready to translate Category:Thiazoles Category:Drugs developed by AbbVie Category:Astellas Pharma Category:Vinyl compounds Category:Methylglyoxalmonoxim derivatives