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Revision as of 20:39, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 18:56, 27 November 2024 edit undo2601:642:c303:f370:69ec:ece3:9acc:3a04 (talk) ce 
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{{Short description|Chemical compound}}
{{Use dmy dates|date=February 2024}}
{{Drugbox {{Drugbox
| verifiedrevid = 443508701 | verifiedrevid = 460022886
⚫ | IUPAC_name = 8-amino-4-ethenyl-7-oxo-2-thia-6-<br>azabicyclooct-4-ene-5-carboxylic acid
| image = Cefdinir.svg | image = Cefdinir.svg


<!--Clinical data--> <!-- Clinical data -->
| pronounce = SEF-di-nir
| tradename = Omnicef | tradename = Cefzon, Omnicef, others
| Drugs.com = {{drugs.com|monograph|cefdinir}} | Drugs.com = {{drugs.com|monograph|cefdinir}}
| MedlinePlus = a698001 | MedlinePlus = a698001
| DailyMedID = Cefdinir
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = B
| pregnancy_category = | pregnancy_category =
⚫ | routes_of_administration = ]
⚫ | ATC_prefix = J01
⚫ | ATC_suffix = DD15
⚫ | ATC_supplemental =

| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD --> | legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = Rx-only | legal_US = Rx-only
| legal_status = | legal_status =
⚫ | routes_of_administration = Oral


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = 16% to 21% (dose-dependent) | bioavailability = 16% to 21% (dose-dependent)
| protein_bound = 60% to 70% | protein_bound = 60% to 70%
| metabolism = Negligible | metabolism = Negligible
| elimination_half-life = 1.7 ± 0.6 hours | elimination_half-life = 1.7 ± 0.6 hours
| excretion = ] | excretion = ]


<!--Identifiers--> <!-- Identifiers -->
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 91832-40-5 | CAS_number = 91832-40-5
⚫ | ATC_prefix = J01
⚫ | ATC_suffix = DD15
⚫ | ATC_supplemental =
| PubChem = 6915944 | PubChem = 6915944
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
Line 44: Line 47:
| ChEMBL = 927 | ChEMBL = 927


<!--Chemical data--> <!-- Chemical data -->
⚫ | IUPAC_name = 8-amino-4-ethenyl-7-oxo-2-thia-6-<br>azabicyclooct-4-ene-5-carboxylic acid
| C=14 | H=13 | N=5 | O=5 | S=2 | C=14 | H=13 | N=5 | O=5 | S=2
| molecular_weight = 395.416 g/mol
| smiles = O=C2N1/C(=C(/C=C)CS12NC(=O)C(=N\O)/c3nc(sc3)N)C(=O)O | smiles = O=C2N1/C(=C(/C=C)CS12NC(=O)C(=N\O)/c3nc(sc3)N)C(=O)O
| InChI = 1/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
| InChIKey = RTXOFQZKPXMALH-GHXIOONMBC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RTXOFQZKPXMALH-GHXIOONMSA-N | StdInChIKey = RTXOFQZKPXMALH-GHXIOONMSA-N
| melting_point = 170
| melting_notes = (dec.)
}} }}
<!-- Definition and medical uses -->
'''Cefdinir''' (marketed by ] under the ] '''Omnicef''') is a semi-synthetic, ] in the third generation of the ] class, proven effective for common ]l ]s of the ear, sinus, throat, and skin. It was approved by the U.S. ] (FDA) in December 1997.
'''Cefdinir''', sold under the brand name '''Omnicef''' among others, is an ] used to treat ], ], ], and ].<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 ].<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 -->
⚫ As of 2008, cefdinir was the highest-selling ] antibiotic in the United States, with more than US$585 million in retail sales of its generic versions alone.<ref>{{PDFlink||399.4&nbsp;KB}}. ''Drug Topics'' (May 26, 2009). Retrieved on July 24, 2009.</ref>
Common side effects include diarrhea, nausea, and a skin rash.<ref name=AHFS2019/> Serious side effects may include ], ], and ].<ref name=AHFS2019/> Use in ] and ] 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 ] and works by interfering with a bacteria's ability to make a ] 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 ].<ref name=AHFS2019/> In 2022, it was the 168th most commonly prescribed medication in the United States, with more than 3{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Cefdinir Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Cefdinir | access-date = 30 August 2024 }}</ref>

==Medical uses==
⚫ Therapeutic uses of cefdinir include ], ] infections, and ] infections, including sinusitis, strep throat (note: no documented resistance of Group A Streptococcus to penicillin has ever been reported, and penicillin or ] is preferred except in penicillin-allergic patients), ], and acute exacerbations of ].


==Mechanism of action==
⚫ {{main|Cephalosporin}}
==Indications==
⚫ Therapeutic uses of cefdinir include ], ] infections, and ] infections, including sinusitis, strep throat, ] and acute exacerbations of ].
===Susceptible organisms=== ===Susceptible organisms===
Cefdinir is a ] antibiotic. It can be used to treat infections caused by several ] and ] bacteria. Cefdinir is a ] antibiotic of the cephalosporin class of antibiotics. It can be used to treat infections caused by several ] and ] bacteria.

===Bacterial susceptibility and resistance===
Cefdinir is a ] 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== ==Side effects==
According to the Omnicef website, side effects include "(...) diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."<ref>{{cite web | title = Omnicef capsules Patient Information | publisher = ] | url = http://www.rxabbott.com/pdf/omnicef_capsules_patient_friendly.pdf | month = February | year = 2004 | accessdate = 2006-11-24 |archiveurl = http://web.archive.org/web/20061118132152/http://www.rxabbott.com/pdf/omnicef_capsules_patient_friendly.pdf <!-- Bot retrieved archive --> |archivedate = 2006-11-18}}</ref> Side effects include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."<ref>{{cite web | title = Omnicef capsules Patient Information | publisher = ] | 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 ] or ].<ref>{{cite web | title = Omnicef manufacturer's packet insert | publisher = ] | url = http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/50739S2LBL.pdf | access-date = 11 December 2016}}</ref>
==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.


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 '']'' infection caused by the antibiotic could be signified.
Cefdinir is available as a ].


=="Blood" in the Stool== ==Mechanism of action==
⚫ {{main|Cephalosporin}}
The pediatric version of Omnicef can bind to iron in the digestive tract. In rare cases, this creates a discoloration of the stool to a rust or red color. Some patients may interpret this as blood in the stool, although in reality blood appears dark brown or black in the stool. A doctor's office can perform a simple test on the stool to confirm that it does not have blood. If you simply wait one hour, the red color will remain red, (while real blood will turn black).


==Synthesis==
On the other hand, if the reddish stool is accompanied by abdominal pain, weight loss, diarrhea, etc., it could be a C. difficile (]) infection caused by the antibiotic. This infection can occur as a result of taking an antibiotic. Talk to your pediatrician immediately to see if you should stop using the antibiotic.
:]
] at the primary amine of the cephalosporin intermediate (1) with 4-bromo-3-oxobutanoyl bromide (2) gives the amide (3). The active ] in that compound is then nitrosated with ]; the initial product spontaneously ]s to afford the ] (4). The bromoketone ] reacts with ] in the penultimate step, forming the ] ring of cefdinir, which is the product after removal of the ] ester ] with ].<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==
⚫ ==References==
===Economics===
⚫ {{Reflist}}
⚫ 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}}
U.S. Prescribing Information from Omnicef.com


==Outside Links== ===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.


] licensed the drug for marketing in US from ].<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 ] and in India as Cednir by Abbott, Kefnir by ], Cefdair by Xalra Pharma and Cefdiel by ].
]
⚫ ]


⚫ == References ==
{{CephalosporinAntiBiotics}}
⚫ {{Reflist}}


{{Cell wall disruptive antibiotics}}
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