Cefaclor
Cefaclor
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Cefaclor

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Catalog Number PR53994733
CAS 53994-73-3
Description Cefaclor is a cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug and a drug allergen.
Synonyms Cephaclor; Ceclor; Cefaclor anhydrous
IUPAC Name (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Weight 367.8
Molecular Formula C15H14ClN3O4S
InChI QYIYFLOTGYLRGG-GPCCPHFNSA-N
InChI Key InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
Drug Categories Amides; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; beta-Lactams; BSEP/ABCB11 Substrates; Cephalosporins; Drugs that are Mainly Renally Excreted; Heterocyclic Compounds, Fused-Ring; Lactams; Nephrotoxic agents; OAT3/SLC22A8 Inhibitors; OAT3/SLC22A8 Substrates; Second-Generation Cephalosporins; Sulfur Compounds; Thiazines
Drug Interactions Abacavir-Cefaclor may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab-The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefaclor.
Aceclofenac-The risk or severity of nephrotoxicity can be increased when Cefaclor is combined with Aceclofenac.
Acemetacin-The risk or severity of nephrotoxicity can be increased when Cefaclor is combined with Acemetacin.
Acenocoumarol-The risk or severity of bleeding can be increased when Cefaclor is combined with Acenocoumarol.
Half-Life 0.6-0.9 hour
Isomeric SMILES C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)Cl
Type Small Molecule
Therapeutic Category Antibacterials
Pharmacology

Indications

Cefaclor is indicated for the treatment of specific bacterial infections. These include ailments such as pneumonia, as well as infections of the ear, lung, skin, throat, and urinary tract. The medication is targeted towards bacterial pathogens that are susceptible to this antibiotic.

Pharmacodynamics

Cefaclor functions as a second-generation cephalosporin antibiotic with a spectrum of activity similar to that of first-generation cephalosporins. Its bactericidal effect is achieved through the inhibition of bacterial cell-wall synthesis. Extensive in vitro and in vivo clinical studies have demonstrated its efficacy against a variety of Gram-positive aerobes, including Staphylococci (both coagulase-positive and coagulase-negative strains, along with penicillinase-producing strains), Streptococcus pneumoniae, and Streptococcus pyogenes (group A ß-hemolytic streptococci). Additionally, it is effective against Gram-negative aerobes such as Escherichia coli, Haemophilus influenzae (even those strains resistant to ampicillin due to ß-lactamase production), Klebsiella species, and Proteus mirabilis.

Absorption

Cefaclor is efficiently absorbed following oral administration, with its absorption largely unaffected by food intake. This characteristic facilitates flexible dosing schedules, thereby enhancing patient compliance.

Metabolism

Cefaclor undergoes minimal metabolic transformation in the liver. Approximately 60% to 85% of the administered dose is excreted unchanged in the urine within eight hours, indicating that renal excretion is the primary route of elimination for this drug.

Mechanism of Action

Cefaclor functions as a beta-lactam antibiotic, sharing similarities with penicillins in its mechanism of action. It targets penicillin-binding proteins (PBPs) situated within the bacterial cell wall, thereby disrupting the final stage of cell wall synthesis. This disruption leads to cell lysis, which is facilitated by the activity of autolytic enzymes like autolysins. Additionally, cefaclor may play a role in interfering with autolysin inhibitors, further promoting bacterial cell lysis.

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