Sulfadiazin

Bezeichnung:Sulfadiazin

CAS-Nr68-35-9

Englisch Name:Sulfadiazine

CBNumberCB4166214

SummenformelC10H10N4O2S

Molgewicht250.28

MOL-Datei68-35-9.mol

Synonyma

Sulfadiazin

Sulfadiazin physikalisch-chemischer Eigenschaften

Schmelzpunkt	253 °C (dec.) (lit.)
Siedepunkt	512.6±52.0 °C(Predicted)
Dichte	1.3780 (rough estimate)
Brechungsindex	1.6440 (estimate)
storage temp.	2-8°C
Löslichkeit	Soluble in dimethyl sulfoxide.
pka	pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain)
Aggregatzustand	powder
Farbe	white
Wasserlöslichkeit	67.13mg/L(25 ºC)
Merck	14,8903
BRN	6733588
BCS Class	4/3
CAS Datenbank	68-35-9(CAS DataBase Reference)
NIST chemische Informationen	Sulfadiazine(68-35-9)
EPA chemische Informationen	Benzenesulfonamide, 4-amino-N-2-pyrimidinyl- (68-35-9)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-36/37/38-42/43-43-42
S-Sätze:	26-36
RIDADR	3249
WGK Germany	3
RTECS-Nr.	WP1925000
F	10
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	29335990
Toxizität	LD50 oral in mouse: 1500mg/kg

Gefahreninformationscode (GHS)

Sulfadiazine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
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 slightly yellow crystalline pow
Originator
Sulfadiazine,Lederle,US ,1941
Verwenden
DMSO soluble potent immunosuppressant, neuroprotective neuroregenerative, in vitro T cell proliferation blocker. disrupts calcineurin-mediated signal transduction in T lymphocytes
Verwenden
Sulfonamide antibacterial.
Verwenden
It is used in the form of silver salts (sulfadiazine silver) as an external antibacterial agent, primarily for treating burns. It is believed that the presence of the silver ion in the molecule facilitates increased antimicrobial and wound-healing action.
Definition
ChEBI: A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.
Manufacturing Process
5.4 parts of 2-amino-pyrimidine were covered with 15 parts of anhydrous pyridine. The reaction mixture was treated with 14 parts of pnitrobenzenesulfonyl chloride and the whole heated briefly on the steam bath and let stand 45 minutes at room temperature. To the reaction mixture were added 80 parts of hot alcohol and the precipitate was filtered off and washed with water. The solid was dissolved in dilute caustic solution and the solution was filtered, cooled and acidified. The 2-(p-nitrobenzenesulfonamido)- pyrimidine precipitated and was collected.
The crude 2-(p-nitrobenzenesulfonamido)-pyrimidine from the preceding step was suspended in 130 parts alcohol and 1.5 parts of concentrated hydrochloric acid were added. The suspension was then heated to reflux and 30 parts of iron powder were added with mechanical stirring. The mixture was refluxed and stirred for 24 hours with occasional addition of concentrated hydrochloric acid. The reaction mixture was then made slightly basic and filtered hot and the residues were extracted with several portions of boiling alcohol. The filtrate and wash solutions were combined and evaporated. The 2- (sulfanilamido)-pyrimidine was recrystallized from boiling water with decolorizing charcoal added, according to US Patent 2,410,793.
Trademarks
Coco-Diazine (Lilly); Eskadiazine (SmithKline Beecham).
Therapeutic Function
Antibacterial
Antimicrobial activity
Sulfadiazine is somewhat more active than other sulphonamides.
Allgemeine Beschreibung
Sulfadiazine’s plasma half-life is 17 hours. It is a white,odorless crystalline powder soluble in water to the extentof 1:8,100 at 37°C and 1:13,000 at 25°C, in human serumto the extent of 1:620 at 37°C, and sparingly soluble in alcoholand acetone. It is readily soluble in dilute mineralacids and bases. Its pKa is 6.3.
Pharmazeutische Anwendungen
Sulfadiazine is almost insoluble in water and unstable on exposure to light. It is administered orally or, as the sodium salt, by intravenous injection. It is a component of several multi-ingredient preparations. Its low solubility in urine led to its general replacement by other compounds. The intravenous solution is highly alkaline and should not be given by any other route.
Biochem/physiol Actions
Sulfadiazine is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfadiazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Pharmakokinetik
Oral absorption： Very good
C_max 3 g oral： c. 50 mg/L after 3–4 h
Plasma half-life ：7–12 h
Volume of distribution： 0.36 L/kg
Plasma protein binding： c. 40%
Absorption and distribution
Adequate blood concentrations are easily achieved and maintained after oral administration. It is well distributed and penetrates in therapeutic concentrations into the CSF, but because of resistance it is no longer the drug of choice in meningitis. It crosses the placenta and enters breast milk to achieve concentrations around 20% of plasma levels.
Metabolism and excretion
Sulfadiazine is subject to acetylation in the liver. The acetyl derivative lacks antibacterial activity and is excreted more slowly (half-life 8–18 h). Parent compound and metabolite are both excreted mainly by glomerular filtration.
Clinical Use
Urinary tract infection
Nocardiasis
Chancroid
Toxoplasmosis (in combination with pyrimethamine)
Meningococcal infections
Prophylaxis of rheumatic fever
Nebenwirkungen
In addition to side effects common to the group, sulfadiazine inhibits the metabolism of phenytoin. The risk of crystalluria can be reduced by high fluid intake and alkalization of the urine.
Sicherheitsprofil
Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by ingestion: hematuria, anuria, general anesthesia, gastrointestinal effects. Experimental teratogenic and reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Synthese
Sulfadiazine, N1 -2-pyrimidinylsulfanilamide (33.1.7), is synthesized by reacting 4-acetylaminobenzenesulfonyl chloride with 2-aminopyrimidine, which gives an acetanilide derivative (33.1.6). The subsequent hydrolysis of this product with a base leads to the formation of the desired sulfadiazine.
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Antibacterials: increased risk of crystalluria with methenamine.
Anticoagulants: effect of coumarins enhanced; metabolism of phenindione possibly inhibited.
Antiepileptics: antifolate effect and concentration of phenytoin increased.
Antimalarials: increased risk of antifolate effect with pyrimethamine.
Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis).
Ciclosporin: reduced levels of ciclosporin; increased risk of nephrotoxicity.
Cytotoxics: increase risk of methotrexate toxicity
Stoffwechsel
Sulfadiazine is metabolised in the liver to the acetylated form, with elimination predominantly via the kidneys. Urinary excretion of sulfadiazine and its acetyl derivative is dependent on pH; when the urine is acidic about 30% is excreted unchanged in both fast and slow acetylators, whereas when the urine is alkaline about 75% is excreted unchanged by slow acetylators.

Sulfadiazine Upstream-Materialien And Downstream Produkte

Sulfadiazin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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