| Candidate ID: | R0180 |
| Source ID: | DB00535 |
| Source Type: | approved |
| Compound Type: |
small molecule
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| Compound Name: |
Cefdinir
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| Synonyms: |
(6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; CFDN
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| Molecular Formula: |
C14H13N5O5S2
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| SMILES: |
[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O
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| Structure: |
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| DrugBank Description: |
Cefdinir, also known as Omnicef, is a semi-synthetic, broad-spectrum antibiotic belonging to the third generation of the cephalosporin class. It has been proven to be effective for the treatment of common bacterial infections in the ear, sinus, throat, lungs, and skin. Cefdinir was approved by the FDA in 1997 to treat a variety of mild to moderate infections and was initially marketed by Abbvie. Because of its chemical structure, it is effective against organisms that are resistant to first-line cephalosporin therapy due to the production of beta-lactamase enzymes.
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| CAS Number: |
91832-40-5
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| Molecular Weight: |
395.414
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| DrugBank Indication: |
Cefdinir is indicated to treat acute bacterial otitis media, acute maxillary sinusitis, community-acquired (CA) pneumonia, acute bacterial exacerbations of chronic bronchitis, pharyngitis/tonsillitis, and uncomplicated skin and skin structure infections in children and adults.
The organisms susceptible to cefdinir have been listed below in addition to their associated clinical condition that may be treated with cefdinir. Various beta-lactamase producing organisms may be treated, as indicated in certain sections below.
**Respiratory**
Acute bacterial exacerbations of chronic bronchitis caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis
Community-acquired pneumonia caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis
**Ear, nose, and throat**
Acute bacterial otitis media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pneumoniae (penicillin-susceptible only)
Tonsillitis caused by Streptococcus pyogenes
Pharyngitis caused by Streptococcus pyogenes
Acute maxillary sinusitis caused by Haemophilus pneumoniae and Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis
**Skin and skin structure infections**
Uncomplicated skin and skin structure infections caused by Staphylococcus aureus and Streptococcus pyogenes
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| DrugBank Pharmacology: |
Cefdinir is a bactericidal agent that treats bacterial infections by interfering with cell wall synthesis.
Cefdinir exerts broad-spectrum activity against a variety of gram-positive and gram-negative bacterial infections. It is effective against several beta-lactamase enzyme producing bacteria. As a result, many organisms that are resistant to other cephalosporins may be susceptible to cefdinir.
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| DrugBank MoA: |
Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. This This 6-member ring enables cefdinir and other cephalosporins to resist inactivation by certain bacterial enzymes.
With a mechanism similar to other beta-lactam antibiotics, the bactericidal activity of cefdinir is caused by the inhibition of cell wall synthesis via binding to penicillin-binding proteins (PBPs). Cefdinir, like other cephalosporins, penetrates the bacterial cell wall, combats inactivation by beta-lactamase enzymes, and inactivates penicillin-binding proteins. This interferes with the final step of transpeptidation in cell walls, eventually leading to cell lysis, which eventually leads to the death of bacteria that are susceptible to this drug. Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. It has also been shown to inhibit transpeptidase enzymes of various bacteria, which may play a role in its bactericidal action. One in vitro study suggests that cefdinir inhibits myeloperoxidase release extracellularly. The impact of this potential drug target in relation to its mechanism of action is unknown.
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| Targets: |
Penicillin-binding protein 2 inhibitor; PBP3 inhibitor; Myeloperoxidase inhibitor; Peptidoglycan transpeptidase inhibitor
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| Inclusion Criteria: |
Indication associated
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