Cefdinir

Cefdinir

Systematic (IUPAC) name
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
Clinical data
Trade names	Cefzon
AHFS/Drugs.com	monograph
MedlinePlus	a698001
Pregnancy cat.	B (US)
Legal status	Rx only (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	16% to 21% (dose-dependent)
Protein binding	60% to 70%
Metabolism	Negligible
Half-life	1.7 ± 0.6 hours
Excretion	Renal
Identifiers
CAS number	91832-40-5 Y
ATC code	J01DD15
PubChem	CID 6915944
DrugBank	DB00535
ChemSpider	5291705 Y
UNII	CI0FAO63WC Y
KEGG	D00917 Y
ChEBI	CHEBI:3485 Y
ChEMBL	CHEMBL927 Y
Chemical data
Formula	C14H13N5O5S2
Mol. mass	395.416 g/mol
SMILES O=C2N1/C(=C(/C=C)CS[C@@H]1[C@@H]2NC(=O)C(=N\O)/c3nc(sc3)N)C(=O)O
InChI 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 Y Key:RTXOFQZKPXMALH-GHXIOONMSA-N Y
Y (what is this?)  (verify)

Cefdinir is a third generation oral cephalosporin antibiotic. It was discovered by Fujisawa Pharmaceutical Co., Ltd. "Fujisawa" (now Astellas) and introduced in 1991 under the brand name Cefzon.^[1][2] Warner-Lambert licensed this cephalosporin, cefdinir, for marketing in US from Fujisawa, Japan.^[3] Abbott obtained U.S. marketing rights to Omnicef (Cefdinir) in December 1998 through an agreement with Warner-Lambert Company.^[4] It was approved by FDA on Dec 4, 1997.^[5] It is available in US as Omnicef by Abbott Laboratories and in India as Cednir by Abbott, Kefnir by Glenmark and Cefdiel by Ranbaxy.

As of 2008, cefdinir was the highest-selling cephalosporin antibiotic in the United States, with more than US$585 million in retail sales of its generic versions alone.^[6]

Mechanism of action

Indications

Therapeutic uses of cefdinir include otitis media, soft tissue infections, and respiratory tract infections, including sinusitis, strep throat, community-acquired pneumonia and acute exacerbations of bronchitis.

Susceptible organisms

Cefdinir is a bacteriocidal antibiotic. It can be used to treat infections caused by several Gram-negative and Gram-positive bacteria.

Spectrum of 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 μg/mL - 4 μg/mL
• Streptococcus pneumoniae: 0.006 μg/mL - 64 μg/mL
• Streptococcus pyogenes: ≤0.004 μg/mL - 2 μg/mL

^[7]

Side effects

Side effects include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain."^[8]

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.

"Blood" in the stool

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 Clostridium difficile infection caused by the antibiotic could be signified.

Special caution required for pediatric dry powder: Dry powder may take longer for proper mixing

References

External links

• Medline Plus: Cefdinir