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| | 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 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 |
| | 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 Preparation Products And Raw materials |
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