Cefdinir

Source: Wikipedia, the free encyclopedia.

Cefdinir
Clinical data
PronunciationSEF-di-nir
Trade namesCefzon, Omnicef, others
AHFS/Drugs.comMonograph
MedlinePlusa698001
License data
By mouth
ATC code
Legal status
Legal status
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
JSmol)
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
  • InChI=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 checkY
  • Key:RTXOFQZKPXMALH-GHXIOONMSA-N checkY
  (verify)

Cefdinir, sold under the brand name Omnicef among others, is an

allergy to penicillin.[1] It is taken by mouth.[1]

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.[2] It is a third-generation cephalosporin and works by interfering with a bacteria's ability to make a cell wall resulting in its death.[1]

It was patented in 1979 and approved for medical use in 1991.

generic medication.[1] In 2021, it was the 197th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[4][5]

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.

Susceptible organisms

Cefdinir is a

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.[6]

  • 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 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 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 article: 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.[9][needs update]

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.

Ranbaxy
.

Synthesis

Cefdinir synthesis:[13][14][15] Improved prepn:[16]

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 thiazoles. Reaction of 4 with thiourea thus leads to formation of an aminothiazole moiety. Thus there is obtained the antibiotic cefdinir (5).

References

  1. ^ a b c d e f g "Cefdinir Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 23 March 2019.
  2. ^ "Cefdinir Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  3. ISBN 9783527607495
    .
  4. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  5. ^ "Cefdinir - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  6. ^ "Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). 14 October 2015. Retrieved 1 October 2015.
  7. ^ "Omnicef capsules Patient Information" (PDF). Abbott Laboratories. February 2004. Archived from the original (PDF) on 18 November 2006. Retrieved 24 November 2006.
  8. FDA
    . Retrieved 11 December 2016.
  9. ^ "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.
  10. ^ "Document". elsevierbi.com.
  11. ^ "Medicis.com - Medicis Pharmaceutical Corporation". globenewswire.com. Archived from the original on 14 July 2014.
  12. ^ "Cefdinir medical facts from Drugs.com". drugs.com.
  13. ^ Takaya T, et al., BE 897864 ; eidem, U.S. patent 4,559,334 (1984, 1985 both to Fujisawa Pharmaceuticals).
  14. PMID 3255303
    .
  15. PMID 3198494
    .
  16. PMID 12767379
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Cefdinir&oldid=1210754617"