Compound Information | SONAR Target prediction |
Name: | CEFUROXIME SODIUM |
Unique Identifier: | SPE01502033 |
MolClass: | Checkout models in ver1.5 and ver1.0 |
Molecular Formula: | |
Molecular Weight: | 431.249 g/mol |
X log p: | 5.927 (online calculus) |
Lipinksi Failures | 1 |
TPSA | 159.93 |
Hydrogen Bond Donor Count: | 0 |
Hydrogen Bond Acceptors Count: | 10 |
Rotatable Bond Count: | 9 |
Canonical Smiles: | [Na+].[O-]C(=O)C1N2C(SCC=1COC(N)=O)C(NC(=O)C(=NOC)c1occc1)C2=O |
Source: | semisynthetic |
Therapeutics: | antibacterial |
Generic_name: | Cefuroxime |
Chemical_iupac_name: | 4-(carbamoyloxymethyl)-8-[2-(2-furyl)-2-methoxyimino-acetyl]amino-7-oxo-2-thia-6-aza bicyclo[4.2.0]oct-4-ene-5-carboxylic acid |
Drug_type: | Approved Drug |
Pharmgkb_id: | PA448868 |
Kegg_compound_id: | C06894 |
Drugbank_id: | APRD00285 |
Melting_point: | 218-225 oC |
H2o_solubility: | Freely soluble as sodium salt (145 mg/L) |
Logp: | -0.921 |
Cas_registry_number: | 55268-75-2 |
Drug_category: | Anti-bacterial Agents; Cephalosporins; ATC:J01DC02 |
Indication: | For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections. |
Pharmacology: | Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. 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. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. |
Mechanism_of_action: | Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefuroxime interferes with an autolysin inhibitor. |
Organisms_affected: | Enteric bacteria and other eubacteria |
2658 |
3-(carbamoyloxymethyl)-7-[[2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct- 2-ene-2-carboxylate |
2659 |
3-(carbamoyloxymethyl)-7-[[2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct- 2-ene-2-carboxylic acid |
41375 |
(6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4. 2.0]oct-2-ene-2-carboxylic acid |
41816 |
sodium (6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4. 2.0]oct-2-ene-2-carboxylate |
5353513 |
3-(carbamoyloxymethyl)-7-[[(2E)-2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0 ]oct-2-ene-2-carboxylate |
5353516 |
3-(carbamoyloxymethyl)-7-[[(2E)-2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0 ]oct-2-ene-2-carboxylic acid |