Cefdinir

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Cefdinir
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Clinical data
PronunciationSEF-di-nir
Trade namesCefzon, Omnicef, others
AHFS/Drugs.comMonograph
MedlinePlusa698001
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Routes of
administration		By mouth
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Legal status
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Pharmacokinetic data
Bioavailability16% to 21% (dose-dependent)
Protein binding60% to 70%
MetabolismNegligible
Elimination half-life1.7 ± 0.6 hours
ExcretionKidney
Identifiers
  • 8-[2-(2-amino-1,3-thiazol-4-yl)-1-hydroxy-2-nitroso-
    ethenyl]amino-4-ethenyl-7-oxo-2-thia-6-
    azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
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Chemical and physical data
FormulaC14H13N5O5S2
Molar mass395.41 g·mol−1
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Melting point170 °C (338 °F) (dec.)
  • O=C2N1/C(=C(/C=C)CS[C@@H]1[C@@H]2NC(=O)C(=N\O)/c3nc(sc3)N)C(=O)O
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  • Key:RTXOFQZKPXMALH-GHXIOONMSA-N checkY
Data page
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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.[1][2][3]

Common side effects include diarrhea, nausea, and a skin rash.[1] Serious side effects may include Clostridioides difficile infection, anaphylaxis, and Stevens–Johnson syndrome.[1] Use in pregnancy and breastfeeding is believed to be safe but has not been well studied.[4]

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.[1]

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.[5]

  • 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.[6]

Side effects

Side effects of cefdinir include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."[7]

It is also one of the medications that can cause toxic epidermal necrolysis or Stevens–Johnson syndrome.[8]

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

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Synthesis

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.[9][10][11]

Society and culture

Economics

Cefdinir was patented in 1979 and first approved for medical use in 1991.[12]

Warner-Lambert licensed the drug for marketing in the US from Fujisawa.[13] Abbott later obtained U.S. marketing rights to cefdinir in December 1998 through an agreement with Warner-Lambert Company.[14] It was approved by the US FDA on 4 December 1997.[15] 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.[16][needs update]Template:DMCA

In 2023, it was the 165th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[17][18]

References

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  1. ^ a b c d Page Module:Citation/CS1/styles.css has no content."Cefdinir Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 23 March 2019.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Cefdinir (oral route)". Mayo Clinic. Retrieved 26 May 2025.
  3. ^ Page Module:Citation/CS1/styles.css has no content."Cefdinir: MedlinePlus Drug Information". medlineplus.gov. Retrieved 26 May 2025.
  4. ^ Page Module:Citation/CS1/styles.css has no content."Cefdinir Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  5. ^ Page Module:Citation/CS1/styles.css has no content."Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). 14 October 2015. Retrieved 1 October 2015.
  6. ^ Page Module:Citation/CS1/styles.css has no content."Cefdinir Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 23 March 2019.
  7. ^ Page Module:Citation/CS1/styles.css has no content."Omnicef capsules Patient Information" (PDF). Abbott Laboratories. February 2004. Archived from the original (PDF) on 18 November 2006. Retrieved 24 November 2006.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Omnicef manufacturer's packet insert" (PDF). FDA. Retrieved 11 December 2016.[dead link]
  9. ^ Page Module:Citation/CS1/styles.css has no content.Inamoto Y, Chiba T, Kamimura T, Takaya T (June 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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Kamachi H, Narita Y, Okita T, Abe Y, Iimura S, Tomatsu K, et al. (November 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.
  11. ^ Page Module:Citation/CS1/styles.css has no content.González M, Rodríguez Z, Tolón B, Rodríguez JC, Velez H, Valdés B, et al. (June 2003). "An alternative procedure for preparation of cefdinir". Farmaco. 58 (6): 409–18. doi:10.1016/S0014-827X(03)00063-6. PMID 12767379.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 49X. ISBN 9783527607495.
  13. ^ Page Module:Citation/CS1/styles.css has no content."Document". elsevierbi.com.
  14. ^ Page Module:Citation/CS1/styles.css has no content."Medicis.com - Medicis Pharmaceutical Corporation". globenewswire.com. Archived from the original on 14 July 2014.
  15. ^ Page Module:Citation/CS1/styles.css has no content."Cefdinir medical facts from Drugs.com". drugs.com.
  16. ^ Page Module:Citation/CS1/styles.css has no content."2008 Top 200 generic drugs by retail dollars" (PDF). Archived from the original (PDF) on 12 January 2012. (399.4 KB). Drug Topics (26 May 2009). Retrieved on 24 July 2009.
  17. ^ Page Module:Citation/CS1/styles.css has no content."Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.
  18. ^ Page Module:Citation/CS1/styles.css has no content."Cefdinir Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 19 August 2025.

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