Cefdinir

Last updated
Cefdinir
Cefdinir.svg
Clinical data
PronunciationSEF-di-nir
Trade names Cefzon, Omnicef, others
AHFS/Drugs.com Monograph
MedlinePlus a698001
License data
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 16% to 21% (dose-dependent)
Protein binding 60% to 70%
Metabolism Negligible
Elimination half-life 1.7 ± 0.6 hours
Excretion Kidney
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.171.145 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H13N5O5S2
Molar mass 395.41 g·mol−1
3D model (JSmol)
Melting point 170 °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 Yes check.svgY
  • Key:RTXOFQZKPXMALH-GHXIOONMSA-N Yes check.svgY
   (verify)

Cefdinir, sold under the brand name Omnicef among others, is an antibiotic used to treat pneumonia, otitis media, strep throat, and cellulitis. [1] 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. [1] It is taken by mouth. [1]

Contents

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. [3] It is available as a generic medication. [1] In 2020, it was the 228th 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 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. [6]

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

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.

Warner-Lambert licensed the drug for marketing in US from Fujisawa. [10] Abbott obtained U.S. marketing rights to cefdinir in December 1998 through an agreement with Warner-Lambert Company. [11] It was approved by the FDA on December 4, 1997. [12] 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.

Synthesis

Cefdinir synthesis: Improved prepn: Cefdinir synthesis.svg
Cefdinir synthesis: Improved prepn:

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).

Related Research Articles

<span class="mw-page-title-main">Ampicillin</span> Antibiotic

Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously.

<span class="mw-page-title-main">Amoxicillin</span> Beta-lactam antibiotic

Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections. It is taken by mouth, or less commonly by injection.

<span class="mw-page-title-main">Streptococcal pharyngitis</span> Medical condition

Streptococcal pharyngitis, also known as streptococcal sore throat, is pharyngitis caused by Streptococcus pyogenes, a gram-positive, group A streptococcus. Common symptoms include fever, sore throat, red tonsils, and enlarged lymph nodes in the front of the neck. A headache and nausea or vomiting may also occur. Some develop a sandpaper-like rash which is known as scarlet fever. Symptoms typically begin one to three days after exposure and last seven to ten days.

<span class="mw-page-title-main">Upper respiratory tract infection</span> Medical condition

An upper respiratory tract infection (URTI) is an illness caused by an acute infection, which involves the upper respiratory tract, including the nose, sinuses, pharynx, larynx or trachea. This commonly includes nasal obstruction, sore throat, tonsillitis, pharyngitis, laryngitis, sinusitis, otitis media, and the common cold. Most infections are viral in nature, and in other instances, the cause is bacterial. URTIs can also be fungal or helminthic in origin, but these are less common.

<span class="mw-page-title-main">Aztreonam</span> Chemical compound

Aztreonam, sold under the brand name Azactam among others, is an antibiotic used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa. This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis. It is given by intravenous or intramuscular injection or by inhalation.

<span class="mw-page-title-main">Cefazolin</span> Antibiotic medication

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

<span class="mw-page-title-main">Cefuroxime</span> Antibiotic medication

Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease. It is used by mouth or by injection into a vein or muscle.

<span class="mw-page-title-main">Cefalexin</span> Beta-lactam antibiotic

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins. It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.

<span class="mw-page-title-main">Cefixime</span> A third generation cephalosporin antibiotic

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required. In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.

<span class="mw-page-title-main">Ceftazidime</span> Antibiotic medication

Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.

<span class="mw-page-title-main">Cefaclor</span> Chemical compound

Cefaclor, sold under the trade name Ceclor among others, is a second-generation cephalosporin antibiotic used to treat certain bacterial infections such as pneumonia and infections of the ear, lung, skin, throat, and urinary tract. It is also available from other manufacturers as a generic.

<span class="mw-page-title-main">Cefprozil</span> Chemical compound

Cefprozil is a second-generation cephalosporin antibiotic. Originally discovered in 1983, and approved in 1992, it was sold under the tradename Cefzil by Bristol Meyers Squibb until 2010 when the brand name version was discontinued. It continues to be available from various companies in its generic form. It is used in the treatment of pharyngitis, tonsillitis, ear infections, acute sinusitis, bacterial exacerbation of chronic bronchitis, and skin and skin structure infections. It is currently available as a tablet and as a liquid suspension.

<span class="mw-page-title-main">Cefpodoxime</span> Antibiotic

Cefpodoxime is an oral, third-generation cephalosporin antibiotic available in various generic preparations. It is active against both Gram-positive and Gram-negative organisms with notable exceptions including Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. It is typically used to treat acute otitis media, pharyngitis, sinusitis, and gonorrhea. It also finds use as oral continuation therapy when intravenous cephalosporins are no longer necessary for continued treatment.

<span class="mw-page-title-main">Cefepime</span> Fourth-generation Cephalosporin Antibiotic

Cefepime is a fourth-generation cephalosporin antibiotic. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in people treated with cefepime compared with other β-lactam antibiotics. In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.

<span class="mw-page-title-main">Cefotaxime</span> Chemical compound

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

<span class="mw-page-title-main">Cefadroxil</span> Antibiotic

Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections. It is a bactericidal antibiotic.

<span class="mw-page-title-main">Sultamicillin</span> Chemical compound

Sultamicillin, sold under the brand name Unasyn among others, is an oral form of the penicillin antibiotic combination ampicillin/sulbactam. It is used for the treatment of bacterial infections of the upper and lower respiratory tract, the kidneys and urinary tract, skin and soft tissues, among other organs. It contains esterified ampicillin and sulbactam.

<span class="mw-page-title-main">Ceftibuten</span> Chemical to treat chronic bronchitis

Ceftibuten is a third-generation cephalosporin antibiotic. It is an orally administered agent, with two dosage forms, capsule or oral suspension. It is marketed by Pernix Therapeutics under the trade name Cedax.

<span class="mw-page-title-main">Cefditoren</span> Chemical to treat skin infections

Cefditoren, also known as cefditoren pivoxil is an antibiotic used to treat infections caused by Gram-positive and Gram-negative bacteria that are resistant to other antibiotics. It is mainly used for treatment of community acquired pneumonia. It is taken by mouth and is in the cephalosporin family of antibiotics, which is part of the broader beta-lactam group of antibiotics.

Pneumococcal infection is an infection caused by the bacterium Streptococcus pneumoniae.

References

  1. 1 2 3 4 5 6 7 "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. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 49X. ISBN   9783527607495.
  4. ↑ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  5. ↑ "Cefdinir - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  6. ↑ "Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). October 14, 2015. Retrieved 1 October 2015.
  7. ↑ "Omnicef capsules Patient Information" (PDF). Abbott Laboratories. February 2004. Archived from the original (PDF) on 2006-11-18. Retrieved 2006-11-24.
  8. ↑ "Omnicef manufacturer's packet insert" (PDF). FDA . Retrieved 2016-12-11.
  9. ↑ "2008 Top 200 generic drugs by retail dollars" (PDF). Archived from the original (PDF) on 2012-01-12. (399.4 KB). Drug Topics (May 26, 2009). Retrieved on July 24, 2009.
  10. ↑ "Document". elsevierbi.com.
  11. ↑ "Medicis.com - Medicis Pharmaceutical Corporation". globenewswire.com. Archived from the original on 2014-07-14.
  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. ↑ 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.
  15. ↑ 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.
  16. ↑ 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.