Cloxacillin

Bezeichnung:Cloxacillin

CAS-Nr61-72-3

Englisch Name:Cloxacillin

CBNumberCB7163623

SummenformelC19H18ClN3O5S

Molgewicht435.88

MOL-Datei61-72-3.mol

Synonyma

Cloxacillin

Cloxacillin physikalisch-chemischer Eigenschaften

Siedepunkt	689.7±55.0 °C(Predicted)
Dichte	1.2954 (rough estimate)
Brechungsindex	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

Sicherheit

Giftige Stoffe Daten

61-72-3(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Cloxacillin Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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
Verwenden
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.
Trademarks
Allypropymal;Alurate sodium;Aprozal;Isonal;Nervisal;Numal;Somnipron.
Therapeutic Function
Antibacterial
Weltgesundheitsorganisation (WHO)
Ampicillin and cloxacillin are listed separately in the WHO Model List of Essential Drugs.
Kontakt-Allergie
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).
Nebenwirkungen
Common side effects include Upset stomach, nausea, vomiting, diarrhea, gas, and mouth sores may occur.
läuterung methode
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 Upstream-Materialien And Downstream Produkte

Cloxacillin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

61-72-3, Cloxacillin Verwandte Suche:

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