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
• EC Number: 206-444-3
• MDL number: MFCD00167147
• UNSPSC Code: 51102829
• PubChem Substance ID: 24894242
• NACRES: NA.85

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: ß-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
• Signal Word: Danger
• Hazard Statements: H315,H319,H334,H335
• Precautionary Statements: 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 Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves