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Merck

D9016

Sigma-Aldrich

Dicloxacillin sodium salt monohydrate

Sinónimos:

3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolyl penicillin sodium salt monohydrate

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About This Item

Fórmula empírica (notación de Hill):
C19H16Cl2N3NaO5S·H2O
Número de CAS:
Peso molecular:
510.32
EC Number:
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85

form

powder or crystals

Quality Level

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

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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 .

pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Satonori Higuchi et al.
Toxicology letters, 200(3), 139-145 (2010-11-26)
Drug-induced liver injury (DILI) is a major problem in drug development and clinical drug therapy. In most cases, the mechanisms are still unknown. It is difficult to predict DILI in humans due to the lack of experimental animal models. Dicloxacillin
Alexandros Ikonomidis et al.
Antimicrobial agents and chemotherapy, 52(11), 3905-3908 (2008-08-13)
Community-type Staphylococcus aureus strains that are positive for mecA and PBP2a but appear phenotypically susceptible to oxacillin are increasingly reported worldwide. Four S. aureus clinical isolates carrying the mecA gene with oxacillin MICs of <2 microg/ml were tested for oxacillin
Unusual presentation of ORF in an otherwise healthy individual.
Louise S Villadsen et al.
Acta dermato-venereologica, 88(3), 277-278 (2008-05-16)
Hjalti Már Björnsson et al.
Laeknabladid, 95(11), 771-773 (2009-12-10)
We describe a case of a 10 year old boy who developed an contact dermatitis to black henna tattoo. Sixteen days later he was brought to the emergency department because of an presumed superinfection by S. aureus. The infection was
Maria Labrou et al.
Antimicrobial agents and chemotherapy, 56(6), 3388-3391 (2012-03-21)
We compared the activity of dicloxacillin with that of vancomycin against 15 oxacillin-susceptible, methicillin-resistant Staphylococcus aureus (OS-MRSA) clinical isolates. By population analyses, we found that 6 OS-MRSA isolates were able to grow in the presence of up to 8 μg/ml

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