Sulfanilamid

Bezeichnung:Sulfanilamid

CAS-Nr63-74-1

Englisch Name:Sulfanilamide

CBNumberCB6212562

SummenformelC6H8N2O2S

Molgewicht172.2

MOL-Datei63-74-1.mol

Synonyma

Sulfanilamid

Sulfanilamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	164-166 °C(lit.)
Siedepunkt	400.5±47.0 °C(Predicted)
Dichte	1.08
Dampfdruck	0.00001 hPa (70 °C)
Brechungsindex	1.6490 (estimate)
storage temp.	2-8°C
Löslichkeit	5.37g/l
pka	pKa 10.65(H2O t = 25.0±0.5 I = 0.2) (Uncertain)
Aggregatzustand	powder
Farbe	white to faintly beige
PH	5.8-6.1 (5g/l, H2O, 20℃)
Geruch (Odor)	Odorless
Säure-Base-Indikators(pH-Indikatoren)	5.8 - 6.1 (0.5% aq.sol.)
Wasserlöslichkeit	7.5 g/L at 25 ºC
maximale Wellenlänge (λmax)	257nm(H2O)(lit.)
Merck	14,8925
BRN	511852
InChIKey	FDDDEECHVMSUSB-UHFFFAOYSA-N
LogP	-0.620
CAS Datenbank	63-74-1(CAS DataBase Reference)
NIST chemische Informationen	Benzenesulfonamide, 4-amino-(63-74-1)
EPA chemische Informationen	Sulfanilamide (63-74-1)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	40
S-Sätze:	24/25-36-22
WGK Germany	3
RTECS-Nr.	WO8400000
F	10
TSCA	Yes
HazardClass	8
HS Code	29350090
Giftige Stoffe Daten	63-74-1(Hazardous Substances Data)
Toxizität	LD50 orally in mice: 3.8 g/kg (Marshall)

Gefahreninformationscode (GHS)

Sulfanilamide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S22:Staub nicht einatmen.
Beschreibung
Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.
Chemische Eigenschaften
White granules or powder crystals, odorless. Taste slightly bitter. Slightly soluble in cold water, ethanol, methanol, ether and acetone, easily soluble in boiling water, glycerin, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene and petroleum ether.
Verwenden
Sulfonamide antibacterial Sulfanilamide is an antibacterial and used in the treatment of vaginal yeast infections. It is a competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid. It serves as an intermediate for the preparation of 2,6-disubstituted anilines by electrophilic substitution followed by removal of the sulfonamide blocking group by desulfonation with sulfuric acid.
Verwenden
Sulfanilamide is an antibacterial agent and antimicrobial agent of sulfonamide type (topical and vaginal).
synthetische
Sulfonamide is synthesized from acetanilide by chlorosulfonation, amination, hydrolysis, and neutralization:
Acetanilide is reacted with chlorosulfonic acid at 40～50℃, then cooled, slowly added to water for acid decomposition, precipitated at the same time, dried and filtered to obtain p-acetamidobenzenesulfonyl chloride, and then subjected to ammoniation, and the amination temperature is controlled at 40～ 45 ℃, and then hydrolyzed, acidified to obtain sulfonamide.
Definition
ChEBI: Sulfanilamide is a sulfonamide in which the sulfamoyl functional group is attached to aniline at the 4-position. It has a role as an EC 4.2.1.1 (carbonic anhydrase) inhibitor, an antibacterial agent and a drug allergen. It is a substituted aniline, a sulfonamide antibiotic and a sulfonamide.
Trademarks
Acetonal vaginal;Amidrin;Avc cream suppositoty;Avc/dienestrol;Avril;Azol polvo;Azol pomada;Buco pental;Buco regis;Chemiovis;Daromid;Defonamid;Dorsec;Expseptoplix;Faderma;Fricton;Gagaril sulfamida;Gynaedron;Instilin;Jacosulfon;Medeyol;Mentol sedans sulfamidad;Nasopomada;Odamida;Oestro-gyneadron;Otocaina;Otonasal;Otorrilan;Ovuthricinol;Oxidermiol;Paraseptol;Pental forte;Pentalmicina;Polvo sulfamida leti;Polvo sulfamida orrvan;Polvos wilfe;Pomada heridas;Pomada wilfe;Prontablin;Pulvi bacteramide;Pyodental;Pyodron;Quimpeamida;Rhinamide;Rino glucol sulf;Sulfacromo;Sulfonamid spuman;Sulfonamide-spuman-style;Sulfonanilamid;Sulfosellan-salbe;Ung. vemleigh.
Weltgesundheitsorganisation (WHO)
Sulfanilamide, a sulfonamide anti-infective agent, was introduced in 1936 for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Sulfanilamide is still used in some countries as a pessaries or as vaginal cream.
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 9, p. 71, 1961 DOI: 10.1248/cpb.9.71
Antimicrobial activity
Sulfanilamide is a sulfonamide antibiotic. It is bacteriostatic against Streptococci in vitro at a concentration of 20 μg/ml and inhibits the growth of 106 clinically isolated strains of Gonococcus. Sulfanilamide reduces the concentration of Streptococcus in rabbit plasma ex vivo following four doses of 20 ml of a 2% sulfanilamide solution. Sulfonamide class antibiotics, of which sulfanilamide is a member, are bacteriostatic and inhibit bacterial synthesis of dihydrofolic acid by competing with 4-aminobenzoic acid for binding to dihydropteroate synthase. Formulations containing sulfanilamide have been used to treat T. vaginalis infections.
Allgemeine Beschreibung
White powder. pH of 0.5% aqueous solution: 5.8-6.1.
Air & Water Reaktionen
May be unstable if exposed for long periods air and light . Slightly water soluble.
Reaktivität anzeigen
Sulfanilamide is an amino acid. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May react with azo and diazo compounds to generate toxic gases.
Brandgefahr
Flash point data for Sulfanilamide are not available but Sulfanilamide is probably combustible.
Biochem/physiol Actions
Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.Mode of Action: A competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid.Anti-microbial Spectrum: Gram positive, Gram negative, Chlamydia Mode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Sicherheitsprofil
Poison by intraperitoneal route. Moderately toxic by ingestion, subcutaneous, and intravenous routes. Human teratogenic effects by unspecified route: developmental abnormalities of the blood and lymphatic systems (including the spleen and bone marrow). Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Sulfanilamide Upstream-Materialien And Downstream Produkte

Sulfanilamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

63-74-1, Sulfanilamide Verwandte Suche:

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