Metacyclinhydrochlorid

Bezeichnung:Metacyclinhydrochlorid

CAS-Nr3963-95-9

Englisch Name:Metacycline hydrochloride

CBNumberCB2355197

SummenformelC22H23ClN2O8

Molgewicht478.88

MOL-Datei3963-95-9.mol

Synonyma

Metacyclinhydrochlorid

Metacyclinhydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	>224°C(dec.)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated), Water (Slightly)
Aggregatzustand	Crystalline Powder
Farbe	Yellow
BRN	5470951
CAS Datenbank	3963-95-9
EPA chemische Informationen	Methacycline hydrochloride (3963-95-9)

Sicherheit

S-Sätze:	24/25-22
WGK Germany	2
RTECS-Nr.	QI9276000
HS Code	29413020
Toxizität	LD50 in rats, mice (mg/kg): 252, 288 i.p. (Goldenthal)

Gefahreninformationscode (GHS)

Metacycline hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S22:Staub nicht einatmen.
Beschreibung
Methacycline is a tetracycline-class antibiotic that is active against a wide range of Gram-positive and Gram-negative organisms. It is readily absorbed from the gastrointestinal tract and reaches a maximum concentration at about the fourth hour, declining to a negligible amount in about 24 hours. It is more active than tetracycline against a number of bacteria.
Chemische Eigenschaften
yellow crystalline powder
Originator
Rondomycin ,Pfizer ,UK ,1963
Verwenden
A broad spectrum, anti bacterial, semisynthetic antibiotic related to Tetracycline
Verwenden
analgesic, narcotic antagonist
Verwenden
Methacycline hydrochloride is a salt prepared from methacycline taking advantage of the basic dimethylamino group which protonates and readily forms a salt in hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Like all tetracyclines, methacycline hydrochloride shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis.
Verwenden
Broad spectrum, semisynthetic antibiotic related to Tetracycline. Antibacterial.
Definition
ChEBI: Methacycline hydrochloride is an organic molecular entity.
Manufacturing Process
To a stirred solution of 4.6 g (0.01 mol) of anhydrous oxytetracycline in 40 ml of dry tetrahydrofuran is added 3.5 g (0.021 mol) of pyridine-sulfur trioxide complex. After 16 hours of stirring at room temperature, the resulting suspension is filtered, and the solid is slurried with 25 ml of 2% hydrochloric acid for 10 minutes, filtered and thoroughly washed with methanol followed by ether. The pale yellow crystalline 5-oxytetracycline-6,12-hemiketal-12-sulfuric acid ester melts at 210°C.
500 mg 5-oxytetracycline-6,12-hemiketal-12-sulfuric acid ester, prepared as described, is added to 4 ml dry liquid hydrogen fluoride, and the mixture is stirred for 1.5 hours at ice bath temperature. The hydrogen fluoride is then evaporated in a stream of nitrogen and the resulting gummy solids are triturated with about 15 ml ether and filtered. The resulting solid hydrofluoride salt is further purified by suspending in water, adjusting the pH to about 4, and extracting the 6-methylene-5-oxytetracycline free base from the aqueous phase with ethyl acetate. The extract is separated and evaporated to dryness under reduced pressure. The resulting residue is triturated with ether and filtered, and the solid is recrystallized from methanol-acetone-etherconcentrated hydrochloric acid to obtain the product as a purified hydrochloride, according to US Patent 3,026,354.
Trademarks
Rondomycin (Medpointe).
Therapeutic Function
Antibiotic
Allgemeine Beschreibung
The synthesis of methacycline, 6-deoxy-6-demethyl-6-methylene-5-oxytetracycline hydrochloride (Rondomycin), reportedby Blackwood et al. in 1961, was accomplished bychemical modification of oxytetracycline. It has an antibioticspectrum like that of the other tetracyclines but greater potency;about 600 mg of methacycline is equivalent to 1 g oftetracycline. Its particular value lies in its longer serum halflife;doses of 300 mg produce continuous serum antibacterialactivity for 12 hours. Its toxic manifestations and contraindicationsare similar to those of the other tetracyclines.
The greater stability of methacycline, both in vivo and invitro, results from modification at C-6. Removal of the 6-hydroxy group markedly increases the stability of ring C toboth acids and bases, preventing the formation of isotetracyclinesby bases. Anhydrotetracyclines still can form, however,by acid-catalyzed isomerization under strongly acidicconditions. Methacycline hydrochloride is a yellow to darkyellow, crystalline powder that is slightly soluble in waterand insoluble in nonpolar solvents. It should be stored intight, light-resistant containers in a cool place.

Metacycline hydrochloride Upstream-Materialien And Downstream Produkte

Metacyclinhydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

3963-95-9, Metacycline hydrochloride Verwandte Suche:

Send Inquriy