D9016

Dicloxacillin sodium salt monohydrate

• Synonym(s): 3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolyl penicillin sodium salt monohydrate
• Empirical Formula (Hill Notation): C₁₉H₁₆Cl₂N₃NaO₅S·H₂O
• CAS Number: 13412-64-1
• Molecular Weight: 510.32
• NACRES: NA.85
• PubChem Substance ID: 24894242
• UNSPSC Code: 51102829
• EC Number: 206-444-3
• MDL number: MFCD00167147

Properties

• form: powder or crystals
• color: white to off-white
• solubility: H₂O: 100 mg/mL
• antibiotic activity spectrum: Gram-negative bacteria, Gram-positive bacteria
• mode of action: cell wall synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: O.[Na+].Cc1onc(c1C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C([O-])=O)-c4c(Cl)cccc4Cl
• InChI: 1S/C19H17Cl2N3O5S.Na.H2O/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);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1
• InChI key: SIGZQNJITOWQEF-VICXVTCVSA-M

Description

General description

Chemical structure: β-lactam

Application

Dicloxacillin is a β-lactamase resistant penicillin similar to oxacillin. Dicloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. It is resistant to penicillinase. It is used to study bacterial cell wall biosynthesis at the level of peptidogylcan cross-linking and to study mechanisms of penicillinase (β-lactamase) resistance. It is used to study phenylbutazone plasma binding and extracellular and intracellular killing of Staphylococcus aureus

Biochem/physiol Actions

Docloxacillin binds to specific penicillin-binding proteins (PBPs) in the bacterial cell wall and therefore inhibits the last stage of bacterial cell wall synthesis. Cell lysis, mediated by bacterial cell wall autolytic enzymes, is the result. Dicloxacillin may interfere with autolysin inhibitors .

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H315,H319,H334,H335
• pcodes: P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves