sodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate

• ChemBase ID: 154647
• Molecular Formular: C19H18Cl2N3NaO6S
• Molecular Mass: 510.32349
• Monoisotopic Mass: 509.01910595
• SMILES: Cc1c(c(no1)c1c(cccc1Cl)Cl)C(=O)N[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)[O-].O.[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1c(Cl)cccc1Cl.O.[Na+]
• InChI: 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
• InChIKey: SIGZQNJITOWQEF-VICXVTCVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate
• IUPAC Traditional name: sodium dicloxacillin(1-) hydrate
• Synonyms: Dicloxacillin sodium salt hydrate; Dicloxacillin sodium salt monohydrate; 双氯青霉素 钠盐 水合物; 双氯青霉素 钠盐 一水合物

Database IDs

• CAS Number: 13412-64-1
• EC Number: 206-444-3
• MDL Number: MFCD00167147
• Beilstein Number: 4778711
• PubChem SID: 24869911; 24894242; 162248785
• PubChem CID: 23675786

CALCULATED PROPERTIES

• Acid pKa: 3.7486086
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.1539227
• LogD (pH = 7.4): -0.3794561
• Log P: 2.9057844
• Molar Refractivity: 122.279 cm^3
• Polarizability: 43.778053 Å^3
• Polar Surface Area: 115.57 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: XH8925000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2; 3
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H334-H335
• GHS Precautionary statements: P261-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C19H16Cl2N3NaO5S · xH2O; C19H16Cl2N3NaO5S·H2O

DETAILS

Sigma Aldrich - D9016

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 mechanims of penicillinase (β-lactamase) resistance. It is used to study phenylbutazone plasma binding1 and extracellular and intracellular killing of Staphylococcus aureus2
Dicloxacillin is used to study bacterial cell wall biosynthesis at the level of peptidogylcan cross-linking and to study mechanims of penicillinase (β-lactamase) resistance.
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 .

Sigma Aldrich - 46182

Legal Information
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