Dicloxacillin

Penicillinase-resistant isoxazolyl penicillins were developed to survive the beta-lactamase that staphylococci secrete, and dicloxacillin belongs to that group. The molecule, C19H17Cl2N3O5S with a mass near 470.3 g/mol, binds penicillin-binding proteins in the bacterial envelope and halts the transpeptidation step that cross-links peptidoglycan strands. The weakened wall then fails under osmotic pressure and the organism lyses. Clinical use is oral and centres on mild-to-moderate skin and soft-tissue infections attributed to staphylococci and streptococci, where beta-lactamase production would inactivate earlier penicillins. Food markedly reduces absorption of the compound, a pharmacokinetic feature that distinguishes it from several other oral beta-lactams. It is an approved small-molecule antibacterial that has completed the final phase of clinical development.

SMILES

Cc1onc(-c2c(Cl)cccc2Cl)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O

InChI

InChI=1S/C19H17Cl2N3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1