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D9016

Sigma-Aldrich

Dicloxacillin sodium salt monohydrate

Synonym(s):

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

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About This Item

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

form

powder or crystals

Quality Level

200

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
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Anne Sandberg et al.
Antimicrobial agents and chemotherapy, 55(4), 1443-1452 (2011-02-02)
The small-colony-variant (SCV) phenotype of Staphylococcus aureus has been associated with difficult-to-treat infections, reduced antimicrobial susceptibility, and intracellular persistence. This study represents a detailed intra- and extracellular investigation of a clinical wild-type (WT) S. aureus strain and its counterpart with
Anne Sandberg et al.
Antimicrobial agents and chemotherapy, 54(6), 2391-2400 (2010-03-24)
Antibiotic treatment of Staphylococcus aureus infections is often problematic due to the slow response and recurrences. The intracellular persistence of the staphylococci offers a plausible explanation for the treatment difficulties because of the impaired intracellular efficacies of the antibiotics. The
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