flucloxacillin   Click here for help

GtoPdb Ligand ID: 10910

Synonyms: BRL-2039 | BRL2039 | floxacillin
Approved drug
flucloxacillin is an approved drug (UK)
Compound class: Synthetic organic
Comment: Flucloxacillin is a narrow-spectrum, semisynthetic penicillin (β-lactam) antibiotic. It is β-lactamase stable.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 138.04
Molecular weight 453.06
XLogP 3.2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C1[C@@H](NC(=O)c2c(C)onc2c2c(F)cccc2Cl)[C@@H]2N1[C@@H](C(=O)O)C(S2)(C)C
Isomeric SMILES O=C1[C@@H](NC(=O)c2c(C)onc2c2c(F)cccc2Cl)[C@@H]2N1[C@@H](C(=O)O)C(S2)(C)C
InChI InChI=1S/C19H17ClFN3O5S/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
InChI Key UIOFUWFRIANQPC-JKIFEVAISA-N
No information available.
Summary of Clinical Use Click here for help
Flucloxacillin is not approved by the EMA or FDA. Generic flucloxacillin is authorised for use in the UK and other countries. UK approval allows flucloxacillin (oral, injection or infusion) to treat infections by penicillinase producing staphylococci and other sensitive Gram-positive organisms, such as osteomyelitis [1-2] and endocarditis. It can also be used prophylactically during major cardiothoracic and orthopaedic surgical procedures if appropriate. Flucloxacillin is ineffective against methicillin-resistant Staphylococcus aureus (MRSA).
External links Click here for help