Cloxacillin

Cloxacillin Basic information
Product Name:Cloxacillin
Synonyms:4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(3-(o-chlorophenyl)-s-me;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo- (8CI);6-(3-o-Chlorophenyl-5-methylisoxazol-4-ylamido) penicillanic acid;6-(5-Methyl-3-o-chlorophenylisoxazole-4-carboxamido) penicillanic acid;6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6-[3-(o-Chlorophenyl)-5-methyl-4-isoxazolylcarboxamido]penicillanic acid
CAS:61-72-3
MF:C19H18ClN3O5S
MW:435.88
EINECS:200-514-7
Product Categories:
Mol File:61-72-3.mol
Cloxacillin Structure
Cloxacillin Chemical Properties
Boiling point 689.7±55.0 °C(Predicted)
density 1.2954 (rough estimate)
refractive index 1.6100 (estimate)
pkapKa 2.70±0.07(H2O t=35.0 c=0.0025) (Uncertain)
InChIKeyLQOLIRLGBULYKD-JKIFEVAISA-N
SMILESN12[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 Data61-72-3(Hazardous Substances Data)
MSDS Information
Cloxacillin Usage And Synthesis
DescriptionCloxacillin 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.
OriginatorOrbenin,Beecham,UK,1962
UsesCloxacillin is a semisynthetic beta-lactamase resistant penicillin antibiotic with antibacterial activity. It is used to treat a wide variety of bacterial infections.
DefinitionChEBI: 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 ProcessThe 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 nameAllypropymal;Alurate sodium;Aprozal;Isonal;Nervisal;Numal;Somnipron.
Therapeutic FunctionAntibacterial
World Health Organization (WHO)Ampicillin and cloxacillin are listed separately in the WHO Model List of Essential Drugs.
Contact allergensCloxacillin 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 effectsCommon side effects include Upset stomach, nausea, vomiting, diarrhea, gas, and mouth sores may occur.
Purification MethodsPurify 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 Preparation Products And Raw materials
Raw materials6-Aminopenicillanic acid-->Ethyl acetoacetate
Flucloxacillin sodium Cloxacillin (Compacted) CLOXACILLIN BENZATHINE,Benzathine cloxacillin CLOXACILLIN SODIUM IMP. D (EP): 3-(2-CHLOROPHENYL)-5-METHYLISOXAZOLE-4-CARBOXYLIC ACID Cloxacillin acid Cloxacillin (Micro) Ampicillin Sodium+Cloxacillin Sodium CLOXACILLIN NA ANTI-CLOXACILLIN,ANTI-CLOXACILLIN (INCLUDES BSA CONJUGATE) Dicloxacillin sodium Cloxacillin-13C4 SodiuM Salt cloxacillin sulfone CLOXACILLIN SODIUM FOR ORAL Dicloxacillin Cloxacillin Flucloxacillin Sodium cloxacillin monohydrate Cloxacillin sodium sterile

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