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targets (3) transporters (3)
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Identification
Name Cefdinir
Accession Number DB00535 (APRD00644)
Type small molecule
Groups approved
Description

Cefdinir (marketed by Abbott Laboratories under the brand name Omnicef) is a semi-synthetic, broad-spectrum antibiotic in the third generation of the cephalosporin class, proven effective for common bacterial infections of the ear, sinus, throat, and skin. It was approved by the U.S. Food and Drug Administration (FDA) in December of 1997.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Cefdirnir
  • CFDN
Brand names
  • Cefzon
  • Omnicef
Brand name mixtures Not Available
Categories
  • Anti-Infectives
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 91832-40-5
Weight Average: 395.414
Monoisotopic: 395.035809931
Chemical Formula C14H13N5O5S2
InChI Key InChIKey=RTXOFQZKPXMALH-GHXIOONMSA-N
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
Plain Text
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carboxylic Acids and Derivatives
  • Cephalosporins
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Beta Lactams
  • Enamines
  • Isoprenes
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Imines
  • Azetidines
  • Oximes and Derivatives
Pharmacology
Indication For the treatment of the respiratory, skin, soft tissue, and ENT infections caused by H. influenzae (including b-lactamase producing strains), H. parainfluenzae (including b-lactamase producing strains), S. pneumoniae (penicillin-susceptible strains), S. pyogenes, S. aureus (including b-lactamase producing strains), and M. catarrhalis.
Pharmacodynamics Cefdinir is a third generation cephalosporin with a broad spectrum of activity against enteric gram-negative rods. Cefdinir is stable in the presence of some, but not all, b-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins are susceptible to cefdinir. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal.
Mechanism of action As with other cephalosporins, bactericidal activity of cefdinir results from inhibition of cell wall synthesis by acting on penicillin binding proteins (PBPs).
Absorption Maximal plasma cefdinir concentrations occur 2 to 4 hours postdose following capsule or suspension administration. Estimated bioavailability of cefdinir capsules is 21% following administration of a 300 mg capsule dose, and 16% following administration of a 600 mg capsule dose. Estimated absolute bioavailability of cefdinir suspension is 25%. Absorption is reduced by approximately 15% when administered with a high fat meal.
Volume of distribution
  • 0.35±0.29 L/kg [adult subjects]
  • 0.67±0.38 L/kg [pediatric subjects (age 6 months to 12 years)]
Protein binding 60%-70%, binding is independent of concentration.
Metabolism

Cefdinir is not appreciably metabolized. Activity is primarily due to parent drug.
Route of elimination Cefdinir is not appreciably metabolized. Cefdinir is eliminated principally via renal excretion with a mean plasma elimination half-life (t½) of 1.7 (±0.6) hours.
Half life 1.7 ± 0.6 hours
Clearance
  • renal cl=2 +/- 1 mL/min/kg [healthy]
Toxicity Information on cefdinir overdosage in humans is not available. In acute rodent toxicity studies, a single oral 5600-mg/kg dose produced no adverse effects. Toxic signs and symptoms following overdosage with other b-lactam antibiotics have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric gram-negative rods
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Aurobindo pharma ltd
  • Lupin ltd
  • Orchid healthcare
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Abbott laboratories
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Powder, for suspension Oral
Prices
Unit description Cost Unit
Omnicef 125 mg/5ml Suspension 100ml Bottle 101.59 USD bottle
Cefdinir 125 mg/5ml Suspension 60ml Bottle 53.05 USD bottle
Omnicef 300 mg capsule 6.31 USD capsule
Omnicef 300 mg omni-pac capsule 5.72 USD capsule
Cefdinir 300 mg capsule 5.22 USD capsule
Patents
Country Patent Number Approved Expires
United States 4935507 1994-12-04 2011-12-04
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP -0.2 PhysProp
Predicted Properties
Property Value Source
water solubility 8.78e-02 g/l ALOGPS
logP 0.02 ALOGPS
logP -3.93 ChemAxon Molconvert
logS -3.65 ALOGPS
pKa 3.27 ChemAxon Molconvert
hydrogen acceptor count 8 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 158.21 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 94.34 ChemAxon Molconvert
polarizability 36.12 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Yamanaka H, Shimazaki J, Imai K, Sugiyama Y, Shida K: Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats. Endocrinol Jpn. 1975 Aug;22(4):297-302. Pubmed
External Links
Resource Link
KEGG Drug D00917 Link_out
KEGG Compound C08110 Link_out
PubChem Compound 6915944 Link_out
PubChem Substance 46505573 Link_out
ChemSpider 5291705 Link_out
ChEBI 3485 Link_out
ChEMBL 3485 Link_out
Therapeutic Targets Database DAP000436 Link_out
PharmGKB PA448841 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic2/cefdin.htm Link_out
Drugs.com http://www.drugs.com/cdi/cefdinir.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/omn1519.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefdinir Link_out
ATC Codes
  • J01DD15
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (69.2 KB)
MSDS show (57 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions
  • Avoid taking antacids at same time (up to 2 hours before or after antibiotic).
  • Avoid taking iron preparations at same time (up to 2 hours before or after antibiotic).
  • Take without regard to meals.
Targets

1. Penicillin-binding protein 2

Pharmacological action: yes
Actions: inhibitor

Synthesis of cross-linked peptidoglycan from the lipid intermediates

Organism class: bacterial
UniProt ID: P08149 Link_out
Gene: penA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. Pubmed

2. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q60FT7 Link_out
Gene: pbp3 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. Pubmed

3. Myeloperoxidase

Pharmacological action: no
Actions: inhibitor

Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity

Organism class: human
UniProt ID: P05164 Link_out
Gene: MPO Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. Pubmed
Transporters

1. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed

2. Oligopeptide transporter, small intestine isoform

Actions: substrate, inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. Pubmed
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
  3. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. Pubmed

3. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. Pubmed
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.