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C9393

Sigma-Aldrich

Cloxacillin sodium salt monohydrate

β-lactamase-resistant antibiotic

Synonym(s):

Cloxacillin, Sodium cloxacillin monohydrate

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About This Item

Linear Formula:
C19H17ClN3O5SNa · H2O
CAS Number:
7081-44-9
Molecular Weight:
475.88
EC Number:
211-390-9
MDL number:
MFCD00150735
UNSPSC Code:
51102829
PubChem Substance ID:
24893156
NACRES:
NA.85

form

powder or crystals

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

O.[Na+].Cc1onc(-c2ccccc2Cl)c1C(=O)N[C@H]3[C@H]4SC(C)(C)[C@@H](N4C3=O)C([O-])=O

InChI

1S/C19H18ClN3O5S.Na.H2O/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23;;/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1

InChI key

KCUWTKOTPIUBRI-VICXVTCVSA-M

General description

Chemical structure: ß-lactam

Application

Cloxacillin is effective against infections caused by penicillin G-resistant staphylococci. It was used in studies of topical antibacterial agents for burn and crush wounds.

Biochem/physiol Actions

Cloxacillin is a semi-synthetic antibiotic and a chlorinated derivative of oxacillin. It inhibits the last stage of bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs), which results in cell lysis. Cell lysis is mediated by bacterial cell wall autolytic enzymes. Cloxacillin is often used as AmpC β-lactamase inhibitor in combination with β-lactam antibiotics.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H317,H319,H334,H335

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - 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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A New Antibacterial Agent: Sodium Cloxacillin Monohydrate (Tegopen)
Journal of the American Medical Association, 195, 569-570 (1966)
Anna Stefánsdóttir et al.
Acta orthopaedica, 84(1), 87-91 (2013-02-16)
Prosthetic joint infections can be caused by bacteria derived from the patient's skin. The aim of the study was: (1) to determine which bacteria colonize the nose and groin in patients planned for primary hip or knee arthroplasty, (2) to
Srecko Marusic et al.
International journal of clinical pharmacology and therapeutics, 50(6), 431-433 (2012-06-09)
To present the case of warfarin-cloxacillin interaction that resulted in an increased international normalized ratio (INR). A 70-year-old man had been treated with warfarin for atrial fibrillation. He was hospitalized because of superficial thrombophlebitis of the left median cubital vein
M C Verdier et al.
Journal of chemotherapy (Florence, Italy), 23(5), 277-281 (2011-10-19)
The aim of the present retrospective observational clinical study was to assess the interindividual pharmacokinetic variability of plasma concentrations of amoxicillin or cloxacillin administered in high doses intravenously in critically ill patients, related to renal function or administration method.Four hundred
Ai Lee Lim et al.
The Medical journal of Malaysia, 67(3), 340-341 (2012-10-23)
Lemierre syndrome is an uncommon disease which commonly arise from acute bacterial oropharyngeal infection. This disease was first described in 1900 by Courmont and Cade Lemierre. It is commonly caused by Fusobacterium necrophorum. Lemierre syndrome has been reported to be
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