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D9016

Sigma-Aldrich

Dicloxacillin sodium salt monohydrate

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C19H16Cl2N3NaO5S·H2O
Numéro CAS:
13412-64-1
Poids moléculaire :
510.32
Numéro CE :
206-444-3
Numéro MDL:
MFCD00167147
Code UNSPSC :
51102829
ID de substance PubChem :
24894242
Nomenclature NACRES :
NA.85

Forme

powder or crystals

Couleur

white to off-white

Solubilité

H2O: 100 mg/mL

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

cell wall synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

SIGZQNJITOWQEF-VICXVTCVSA-M

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Description générale

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

Actions biochimiques/physiologiques

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 .

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H315,H319,H334,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

S L Nielsen et al.
The Journal of antimicrobial chemotherapy, 42(2), 221-226 (1998-09-17)
The effect of dicloxacillin and fusidic acid used alone and in combination on the extracellular and intracellular killing of four isolates of Staphylococcus aureus in the presence of serum was studied. At the extracellular level, dicloxacillin (8 mg/L) had a
I Vesteinsdottir et al.
European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology, 31(10), 2601-2610 (2012-03-24)
Increased incidence and severity of Clostridium difficile infections (CDIs) is of major concern. However, by minimizing known risk factors, the incidence can be decreased. The aim of this investigation was to calculate the incidence and assess risk factors for CDI
Wendy L Berth et al.
The Journal of reproductive medicine, 54(5), 291-294 (2009-06-13)
To evaluate the quality of care for mastitis managed by telephone without an office or emergency room visit. A word search of electronic medical records allowed for identification of patients managed with a mastitis clinical practice guideline. Comparisons of outcomes
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
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
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