Cloxacillin Chemical Properties

Boiling point:

689.7±55.0 °C(Predicted)

Density 

1.2954 (rough estimate)

refractive index 

1.6100 (estimate)

pka

pKa 2.70±0.07(H2O t=35.0 c=0.0025) (Uncertain)

InChIKey

LQOLIRLGBULYKD-JKIFEVAISA-N

SMILES

N12[C@@]([H])([C@H](NC(C3=C(C)ON=C3C3=CC=CC=C3Cl)=O)C1=O)SC(C)(C)[C@@H]2C(O)=O

Safety Information

Hazardous Substances Data

61-72-3(Hazardous Substances Data)

Cloxacillin Usage And Synthesis

Description

Cloxacillin induced contact dermatitis in a pharmaceutical factory worker with positive reactions to ampicillin but not to penicillin. The chemical formula of this is 3-o-chlorophenyl-5-methyl-4-isoxazolyl penicillin (Knudsen et al., 1962); this differs from oxacillin only by an additional chlorine atom.

Originator

Orbenin,Beecham,UK,1962

Uses

Cloxacillin is a semisynthetic beta-lactamase resistant penicillin antibiotic with antibacterial activity. It is used to treat a wide variety of bacterial infections.

Definition

ChEBI: Cloxacillin is a semisynthetic penicillin antibiotic carrying a 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido group at position 6. It has a role as an antibacterial agent and an antibacterial drug. It is a semisynthetic derivative, a penicillin allergen and a penicillin. It is functionally related to an oxacillin. It is a conjugate acid of a cloxacillin(1-).

Manufacturing Process

The reaction between 6-aminopenicillanic acid (6.5 g) and 3-o-chlorophenyl-5- methylisoxazole4-carbonyl chloride (7.66 g) gave the sodium salt of 3-o-chlorophenyl-5-methyl-4-isoxazolylpenicillin（Cloxacillin） (9.98 g) as a pale yellow solid. Colorimetric assay with hydroxylamine against a benzylpenicillin standard indicated a purity of 68%.The 3-o-chlorophenyl-5-methylisoxazole-4-carboxylic acid, from which the acid chloride was prepared, was obtained by hydrolysis of the ester product of the reaction between o-chlorobenzohydroxamic chloride and ethyl acetoacetate in methanolic sodium methoxide. Reaction with thionyl chloride gave the starting material.

brand name

Allypropymal;Alurate sodium;Aprozal;Isonal;Nervisal;Numal;Somnipron.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Ampicillin and cloxacillin are listed separately in the WHO Model List of Essential Drugs.

Contact allergens

Cloxacillin is a semisynthetic penicillin close to oxacillin. It induced contact dermatitis in a pharmaceutical factory worker with positive reactions to ampicillin, but not to penicillin. In cutaneous drug reactions such as acute generalized exanthematous pustulosis due to amoxicillin, cross-reactivity is frequent to cloxacillin (personal observations).

Side effects

Common side effects include Upset stomach, nausea, vomiting, diarrhea, gas, and mouth sores may occur.

Purification Methods

Purify mandelic acid by Soxhlet extraction with *C6H6 (about 6mL/g) and allow the extract to crystallise. It can also be recrystallised from CHCl3. The S-benzylisothiuronium salt has m 169o (166o) (from H2O). Dry it at room temperature under vacuum. [Beilstein 10 IV 565.]

Cloxacillin(61-72-3)Related Product Information

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