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.]
