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

antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

used to treat pneumonia,

otitis media Otitis media is a group of inflammatory diseases of the middle ear. One of the two main types is acute otitis media (AOM), an infection of rapid onset that usually presents with ear pain. In young children this may result in pulling at the ear, ...

, strep throat, and cellulitis. It is a less preferred option for pneumonia, otitis media, and strep throat which may be used in those with a severe allergy to penicillin. It is taken by mouth. Common side effects include diarrhea, nausea, and a skin rash. Serious side effects may include ''Clostridioides difficile'' infection, anaphylaxis, and Stevens–Johnson syndrome. Use in pregnancy and breastfeeding is believed to be safe but has not been well studied. It is a third-generation cephalosporin and works by interfering with a bacteria's ability to make a

cell wall A cell wall is a structural layer surrounding some types of cells, just outside the cell membrane. It can be tough, flexible, and sometimes rigid. It provides the cell with both structural support and protection, and also acts as a filtering mech ...

resulting in its death. It was patented in 1979 and approved for medical use in 1991. It is available as a

generic medication A generic drug is a pharmaceutical drug that contains the same chemical substance as a drug that was originally protected by chemical patents. Generic drugs are allowed for sale after the patents on the original drugs expire. Because the active ch ...

. In 2021, it was the 197th most commonly prescribed medication in the United States, with more than 2million prescriptions.

Medical uses

Therapeutic uses of cefdinir include

, soft tissue infections, and

respiratory tract The respiratory tract is the subdivision of the respiratory system involved with the process of respiration in mammals. The respiratory tract is lined with respiratory epithelium as respiratory mucosa. Air is breathed in through the nose to th ...

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

bactericidal A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their ...

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. * ''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." It is also one of the medications that can cause toxic epidermal necrolysis or Stevens–Johnson syndrome. 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

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.

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. Abbott obtained U.S. marketing rights to cefdinir in December 1998 through an agreement with Warner-Lambert Company. It was approved by the FDA on 4 December 1997. It is available in US as Omnicef by

Abbott Laboratories Abbott Laboratories is an American multinational medical devices and health care company with headquarters in Abbott Park, Illinois, United States. The company was founded by Chicago physician Wallace Calvin Abbott in 1888 to formulate known dr ...

and in India as Cednir by Abbott, Kefnir by Glenmark, Cefdair by Xalra Pharma and Cefdiel by Ranbaxy.

Synthesis

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

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