Oxacillin sodium monohydrate

Bezeichnung:Oxacillin sodium monohydrate

CAS-Nr7240-38-2

Englisch Name:Oxacillin sodium monohydrate

CBNumberCB9278851

SummenformelC19H20N3NaO6S

Molgewicht441.43

MOL-Datei7240-38-2.mol

Oxacillin sodium monohydrate physikalisch-chemischer Eigenschaften

Schmelzpunkt	188 C
Siedepunkt	687℃
alpha	D20 +201° (c = 1 in water)
Brechungsindex	205 ° (C=1, H2O)
Flammpunkt	>110°(230°F)
storage temp.	Inert atmosphere,2-8°C
Löslichkeit	Freely soluble in water, soluble in methanol, practically insoluble in methylene chloride.
Farbe	White to Almost white
PH	pH (30g/l, 25℃) : 4.5～7.5
Wasserlöslichkeit	Freely soluble in water
Merck	14,6904
BRN	4287093
CAS Datenbank	7240-38-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	36/37/38-42/43
S-Sätze:	22-26-36/37
WGK Germany	3
HS Code	29411099
Toxizität	LD50 orally in rats: >8000 mg/kg (Goldenthal)

Gefahreninformationscode (GHS)

Oxacillin sodium monohydrate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
Oxacillin was synthesized by Bristol-Myers Laboratories in 1961 starting with 6-aminopenicillanic acid. It was the first orally active and penicillinase-stable semisynthetic penicillin to be introduced clinically. Oxacillin is slightly less stable against gastric acid and shows a lower serum concentration than phenoxymethylpenicillin, but it is highly active against phenoxymethylpenicillinresistant Staphylococcus aureus. Oxacillin has been used by oral and intramuscular administration for therapy of respiratory tract, urinary tract, gynecological, and other infections caused by benzylpenicillin-resistant bacteria.
Chemische Eigenschaften
White or almost white powder.
Originator
Resistopen,Squibb,US,1962
Verwenden
Penicillin antibacterial.
Verwenden
Semi-synthetic antibiotic related to Penicillin. Antibacterial. Dyes and metabolites.
Definition
ChEBI: Oxacillin sodium monohydrate is a hydrate. It contains an oxacillin sodium.
Manufacturing Process
(A) Benzaldoxime: (Reference, Vogel, Textbook of Practical Organic Chemistry, page 883) -Materials: (Theoretical yield, 121.1 grams of free oxime), 106.1 grams (1.0 mol) of benzaldehyde (NF grade), 69.5 grams (1.0 mol) of hydroxylamine hydrochloride (practical grade), 68.0 grams (1.7 mol) of sodium hydroxide (pellet).
Procedure: The sodium hydroxide is dissolved in 200 ml water and the benzaldehyde is added. With continued stirring the hydroxylamine hydrochloride is added in portions. Some heat is developed and eventually the benzaldehyde dissolves. The solution is stirred for 15 minutes and then cooled in an ice-bath. A waxy, crystalline mass separates, and after further cooling it is collected by suction and dried in air. Yield is 86 to 149 grams. This crude material is suitable for step (B).
(B) Benzohydroximic Chloride: [Reference, G.W. Perrold et al, J. Am. Chem. Soc., 79, 462 (1957)] - Materials: 121 grams (0.77 mol) of crude benzaldoxime from step (A), 500 ml of 8.3 N hydrochloric acid, chlorine.
Procedure: The crude product from (A) is suspended in the hydrochloric acid, cooled in an ice-salt mixture, and chlorine is passed into the mixture with stirring for ? to 1 hour. Transient blue and green colors may be noticed in the mixture during this time. The temperature will probably rise to 3° to 5°C. The solid is collected by suction filtration and dried for an hour or so on the filter before use in (C). If at all possible, it should be used on the day of preparation. Yield is 71 grams (after 1? hours on the filter).
(C) 5-Methyl-3-Phenyl-4-Isoxazolecarboxylic Acid: [Reference, A. Quilico and R. Rusco, Gazz. Chim. Ital. 67, 589 (1937); C.A. 32, 21177] - Materials: 71 grams (0.45 mol) of crude benzohydroximic chloride from (E), 78 grams (0.60 mol) of ethyl acetoacetate (practical grade), 34 grams (0.60 mol) of sodium methoxide (95% minimum), 400 ml of methanol (reagent grade).
Procedure: The sodium methoxide is cautiously added in portions to 200 ml of methanol with stirring. Some heat is evolved. To this warm solution is rapidly added the ethyl acetoacetate with continued stirring. The solution is stirred for 10 minutes and then cooled in an ice-salt-acetone mixture (-25°C). If desired a Dry Ice-acetone cooling bath may be used to shorten the addition time. The crude material from (B) is dissolved in 200 ml of methanol. At this point it is probably easier to filter this mixture by suction to remove a large amount of insoluble solid, which is probably sodium chloride. The solid may be rinsed with more methanol.
The filtrate is chilled in ice-water and added to the cooled methanolic solution of the sodium derivative of ethyl acetoacetate at a rate which keeps the temperature of the re. action mixture below 0°C. The addition time will be 15 to 20 minutes if ice-salt-acetone is used as a coolant. This reaction is extremely exothermic.
The reaction mixture is stirred overnight at room temperature and filtered to remove the sodium chloride. The filtrate is stripped in vacuo and the crude ester (literature reports MP 48°C) is dissolved in 150 ml of ethanol; 28 grams (0.70 mol of sodium hydroxide in 90 ml of water is added and the solution is refluxed for 2 hours. After removal of the ethanol in vacuo the residue is dissolved in water and extracted twice with ether. Dissolved ether is removed from the aqueous solution in vacuo and it is acidified to pH 2 with concentrated hydrochloric acid.
The crystalline crude acid is dried briefly and then recrystallized from acetonitrile to give 32 grams of white product; MP 193° to 194.5°C (literature reports 189° to 190°C). Concentration of the mother liquor gives an additional 5 grams of material having a MP of 192.5 to 194°C. The 37 grams of material represents an 18% overall yield from benzaldehyde.
(D) The acid is converted to the acid chloride by reaction with thionyl chloride.
(E) 5-Methyl-3-Phenyl-4-Isoxazolylpenicillin: A solution of
Trademarks
Bactocill (GlaxoSmithKline); Prostaphlin (Apothecon).
Therapeutic Function
Antibacterial
Kontakt-Allergie
Oxacillin is a semisynthetic penicillin of the group M. It is closely related to cloxacillin.

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