Sulfafurazol

Bezeichnung:Sulfafurazol

CAS-Nr127-69-5

Englisch Name:Sulfisoxazole

CBNumberCB1495500

SummenformelC11H13N3O3S

Molgewicht267.3

MOL-Datei127-69-5.mol

Synonyma

Sulfafurazol

Sulfafurazol physikalisch-chemischer Eigenschaften

Schmelzpunkt	195°C
Siedepunkt	482.2±55.0 °C(Predicted)
Dichte	1.3486 (rough estimate)
Brechungsindex	1.6630 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit	acetone: complete50 mg/ml
pka	5.0(at 25℃)
Aggregatzustand	Solid
Farbe	White to Light Brown
Wasserlöslichkeit	<0.1 g/100 mL at 22.5 ºC
maximale Wellenlänge (λmax)	271nm(MeOH)(lit.)
Merck	14,8952
BRN	6737262
Stabilität	Stable. Incompatible with strong oxidizing agents.
CAS Datenbank	127-69-5(CAS DataBase Reference)
NIST chemische Informationen	Benzenesulfonamide, 4-amino-N-(3,4-dimethyl-5-isoxazolyl)-(127-69-5)
IARC	3 (Vol. 24, Sup 7) 1987
EPA chemische Informationen	Sulfisoxazole (127-69-5)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	2
RTECS-Nr.	WO9100000
HazardClass	IRRITANT
HS Code	29350030
Giftige Stoffe Daten	127-69-5(Hazardous Substances Data)
Toxizität	LD50 orally in mice: 6800 mg/kg (Seki)

Gefahreninformationscode (GHS)

Sulfisoxazole Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
white to cream powder
Originator
Gantrisin,Roche,US,1949
Verwenden
Sulfisoxazole is a sulfonamide based antibacterial that exhibits activity against wide spectrum of gram-negative and gram-positive bacterium.
Definition
ChEBI: A sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of gram-negative and gram-positive organisms.
Manufacturing Process
112 parts of 3,4-dimethyl-5-amino-isoxazole were dissolved in a mixture of 100 volume parts of pyridine and 200 volume parts of acetone. The mixture is cooled with cold water and 240 parts p-acetamino-benzene sulfonic acid chloride are added in small portions under stirring at temperatures of below 30°C. The mixture is left standing overnight at 20° to 30°C and then the 5- acetamino-benzene-sulfonylamino-3,4-dimethyl-isoxazole is precipitated by the addition of water. Recrystallized from acetic acid or alcohol it forms small prisms of the melting point 210°C.
100 parts of the 5-acetamino-benzene-sulfonyl-amino-3,4-dimethyl-isoxazole are boiled under reflux with 500 volume parts 15 to 20% aqueous hydrochloric acid for 30 to 45 minutes until all is dissolved. 500 parts crystallized sodium acetate are added and the liquid left cooling for crystallization. The sulfanilamido-3,4-dimethyl-isoxazole is sucked off, washed with water and dried. In the pure state it forms white prisms with the melting point of 193°C.
Trademarks
Gantrisin (Roche).
Therapeutic Function
Antibacterial
Antimicrobial activity
Like all examined sulfanilamides, this drug is effective in treating infections caused by streptococci, gonococci, pneumococci, staphylococci, and also colon bacillus. However, about 90% of it binds with proteins in the plasma after oral administration, and it diffuses mostly to tissues and tissue fluids, which makes it the drug of choice for many systemic infections. Synonyms of this drug are gantrisin, fultrxin, sulfazin, sulfolar, and others.
Allgemeine Beschreibung
Sulfisoxazole’s plasmahalf-life is 6 hours. This compound is a white, odorless,slightly bitter, crystalline powder. Its pKa is 5.0. At pH 6,this sulfonamide has a water solubility of 350 mg in100 mL, and its acetyl derivative has a solubility of 110 mgin 100 mL of water.Sulfisoxazole possesses the action and the uses of othersulfonamides and is used for infections involving sulfonamide-sensitive bacteria. It is claimed to be effective in thetreatment of Gram-negative urinary infections.
Allgemeine Beschreibung
Odorless white to yellowish crystalline powder. Slightly bitter taste. Acid to litmus.
Air & Water Reaktionen
May be sensitive to prolonged exposure to air and light. Sensitive to heat. Slightly soluble in water.
Brandgefahr
Flash point data for Sulfisoxazole are not available; however, Sulfisoxazole is probably combustible.
Pharmazeutische Anwendungen
3,4-Dimethyl-5-sulfanilamidoisoxazole. It is highly soluble, even in acid urine. The spectrum and potency are typical of the group. It is well absorbed, achieving a concentration of around 20 mg/L 3–4 h after a 2 g oral dose.
Side effects are those common to other sulfonamides. It is less prone than some other members of the group to cause renal problems. Its principal use is in urinary tract infection, and is present in some ophthalmic preparations.
Biologische Aktivität
A selective ET A endothelin receptor antagonist (IC 50 values are 600 and 2200 nM for ET A and ET B receptors respectively).
Sicherheitsprofil
Mildly toxic by ingestion. An experimental teratogen. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Synthese
Sulfisoxazole, N1 -(3,4-dimethyl-5-isoxazolyl)sulfanilamide (33.1.19), is synthesized by reacting 4-acetylaminobenzenesulfonyl chloride with 5-amino-3, 4-dimethylisoxazol (33.1.17), which is in turn synthesized by heterocyclization of 2-methylacetylacetonitrile with hydroxylamine, and subsequent acidic hydrolysis (hydrochloric acid) of the protective acetyl group in the resulting product (33.1.18).

Sulfisoxazole Upstream-Materialien And Downstream Produkte

Sulfafurazol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

127-69-5, Sulfisoxazole Verwandte Suche:

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