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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

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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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
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
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
Unusual presentation of ORF in an otherwise healthy individual.
Louise S Villadsen et al.
Acta dermato-venereologica, 88(3), 277-278 (2008-05-16)
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
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