Cefdinir: Difference between revisions

{{Short description|Chemical compound}}

{{Use dmy dates|date=February 2024}}

| verifiedrevid = 460022886

<!-- Clinical data -->

| pronounce = SEF-di-nir

| tradename = Cefzon, Omnicef, others

| DailyMedID = Cefdinir

| routes_of_administration = [[By mouth]]

| ATC_prefix = J01

| ATC_suffix = DD15

| ATC_supplemental =

<!-- Pharmacokinetic data -->

| excretion = [[Kidney]]

<!-- Identifiers -->

| CAS_number_Ref = {{cascite|correct|??}}

<!-- Chemical data -->

| 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

| melting_point = 170

| melting_notes = (dec.)

<!-- Definition and medical uses -->

'''Cefdinir''', sold under the brand name '''Omnicef''' among others, is an [[antibiotic]] used to treat [[pneumonia]], [[otitis media]], [[strep throat]], and [[cellulitis]].<ref name=AHFS2019/> It is a less preferred option for pneumonia, otitis media, and strep throat which may be used in those with a severe [[penicillin allergy|allergy to penicillin]].<ref name=AHFS2019/> 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>

<!-- Side effects and mechanisms -->

Common side effects include diarrhea, nausea, and a skin rash.<ref name=AHFS2019/> Serious side effects may include [[Clostridioides difficile infection|''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 [[Cephalosporin#Classification|third-generation cephalosporin]] and works by interfering with a bacteria's ability to make a [[cell wall]] resulting in its death.<ref name=AHFS2019/>

<!-- Society and culture -->

It was patented in 1979 and approved for medical use in 1991.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=49X |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA49X |language=en}}</ref> It is available as a [[generic medication]].<ref name=AHFS2019/> In 2021, it was the 197th most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Cefdinir - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Cefdinir | access-date = 14 January 2024}}</ref>

==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]].

Cefdinir is a [[bactericide|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

Side effects 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}}</ref>

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 ''[[Clostridioides difficile]]'' infection caused by the antibiotic could be signified.

==Mechanism of action==

{{main|Cephalosporin}}

==Society and culture==

===Economics===

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 }}&nbsp;{{small|(399.4&nbsp;KB)}}. ''Drug Topics'' (26 May 2009). Retrieved on 24 July 2009.</ref>{{update-inline|date=October 2020}}

===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.

[[Warner-Lambert]] licensed the drug for marketing in US from [[Fujisawa Pharmaceutical|Fujisawa]].<ref>{{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}}</ref> Abbott obtained U.S. marketing rights to cefdinir in December 1998 through an agreement with Warner-Lambert Company.<ref>{{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}}</ref> It was approved by the FDA on 4 December 1997.<ref>{{cite web|url=https://www.drugs.com/mtm/cefdinir.html|title=Cefdinir medical facts from Drugs.com|work=drugs.com}}</ref> It is available in US as Omnicef by [[Abbott Laboratories]] and in India as Cednir by Abbott, Kefnir by [[Glenmark Pharmaceuticals|Glenmark]], Cefdair by Xalra Pharma and Cefdiel by [[Ranbaxy]].

===Synthesis===

[[File:Cefdinir synthesis.svg|thumb|center|700px|Cefdinir synthesis:<ref>Takaya T, et al., {{Cite patent|country=BE|number=897864}}; eidem, {{US patent|4559334}} (1984, 1985 both to Fujisawa Pharmaceuticals).</ref><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> Improved prepn:<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>]]

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 [[thiazole]]s. Reaction of '''4''' with [[thiourea]] thus leads to formation of an aminothiazole moiety. Thus there is obtained the antibiotic cefdinir ('''5''').

== References ==

{{Reflist}}

{{Cell wall disruptive antibiotics}}

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[[Category:Wikipedia medicine articles ready to translate]]

[[Category:Thiazoles]]

[[Category:Drugs developed by AbbVie]]

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[[Category:Vinyl compounds]]