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oxytetracyclin

Oxytetracycline Struktur
79-57-2
CAS-Nr.
79-57-2
Bezeichnung:
oxytetracyclin
Englisch Name:
Oxytetracycline
Synonyma:
OXYTETRACYCLINE BASE;Terramycin;oxytetracyclin;oxy-kesso-tetra;Oxytetracycline CRS;4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, 2-Naphthacenecarboxamide;la200;Oxydon;oxypam;tetran
CBNumber:
CB6429340
Summenformel:
C22H24N2O9
Molgewicht:
460.43
MOL-Datei:
79-57-2.mol

oxytetracyclin Eigenschaften

Schmelzpunkt:
183 °C
alpha 
-223 º (c=1 0.03N HCl)
Siedepunkt:
565.29°C (rough estimate)
Dichte
1.6340
Brechungsindex
1.6500 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
L?slichkeit
Sparingly soluble in aqueous solution at 0.6 mg/mL
pka
pKa 3.27/7.32/9.11(H2O,t =25,I<0.01)(Approximate)
Aggregatzustand
Crystalline Powder
Farbe
Beige to light yellow
Wasserl?slichkeit
0.2 g/L
InChIKey
IWVCMVBTMGNXQD-PXOLEDIWSA-N
LogP
-0.900
CAS Datenbank
79-57-2(CAS DataBase Reference)
EPA chemische Informationen
Oxytetracycline (79-57-2)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn,Xi
R-S?tze: 63-36-36/37/38
S-S?tze: 22-24/25-36/37/39-26-36
WGK Germany  2
RTECS-Nr. QI7875000
TSCA  Yes
HS Code  30029090
Giftige Stoffe Daten 79-57-2(Hazardous Substances Data)
Toxizit?t LD50 oral in rat: 4800mg/kg
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H411 Giftig für Wasserorganismen, mit langfristiger Wirkung. Langfristig (chronisch) gew?ssergef?hrdend Kategorie 2
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P273 Freisetzung in die Umwelt vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P308+P313 BEI Exposition oder falls betroffen: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen.
P391 Verschüttete Mengen aufnehmen.

oxytetracyclin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R63:Kann das Kind im Mutterleib m?glicherweise sch?digen.
R36:Reizt die Augen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Beschreibung

Oxytetracycline also is one of the classic tetracyclines. It is produced by fermentation of Streptomyces rimosis and other soil microorganisms. The most hydrophilic tetracycline on the market, it has largely now been replaced by its semisynthetic descendants. It is primarily used today for IM injections.

Chemische Eigenschaften

beige to light yellow crystalline powder

Verwenden

Oxytetracycline(Terramycin) was the second of the broad-spectrum tetracycline group of antibiotics to be discovered. Oxytetracycline works by interfering with the ability of bacteria to produce proteins that are essential to them. Without these proteins t

Definition

ChEBI: A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae /ital> (respiratory infections), and Diplococcus pneumoniae.

Antimicrobial activity

It is slightly less active than other tetracyclines against most common pathogenic bacteria.

Pharmazeutische Anwendungen

A fermentation product of certain strains of Streptomyces rimosus, supplied as the dihydrate or hydrochloride for oral or parenteral administration.

Pharmakokinetik

Oral absorption: c.60%
Cmax 500 mg oral: 3–4 mg/L after 2–4 h
Plasma half-life: c.9 h
Volume of distribution: c.1.8 L/kg
Plasma protein binding: 20–35%
Oxytetracycline is moderately well absorbed from the upper gastrointestinal tract. Food decreases plasma levels by approximately 50%. Although widely distributed in the tissues, it achieves lower concentrations than related agents such as minocycline. Sputum concentrations of 1 mg/L have been recorded on a daily dosage of 2 g. Approximately 60% is excreted in the urine and the half-life is prolonged in renal insufficiency.

Clinical Use

It offers no unique therapeutic advantages, although it is one of the cheaper preparations.

Nebenwirkungen

Gastrointestinal intolerance is responsible for most side effects, and tends to be more severe than with other tetracyclines. Esophageal irritation may result from the local effects of the swallowed drug. Potentially serious adverse reactions have included neuromuscular paralysis following intravenous administration to patients with myasthenia gravis. Thrombocytopenic purpura and lupus erythematosus syndrome have been reported, although a direct role for the drug in the latter remains uncertain. Apart from the effect on nitrogen balance common to many tetracyclines, a metabolic effect on glucose homeostasis has been noted in type 1 diabetes mellitus. Allergic contact sensitivity reactions have also been reported.

l?uterung methode

Terramycin crystallises (as dihydrate) from water or aqueous EtOH and is soluble in MeOH, EtOH, Me2CO and H2O (0.25mg/mL at 25o ) but insoluble in Et2O and pet ether. It is amphoteric, and an aqueous solution has pH 2.0-5.0. It has max at 247, 275 and 353nm in 0.1 M phosphate (pH 4.5). [Finlay et al. Science 111 85 1951.] The hydrochloride, [2058-46-0] M 496.9 [Beilstein 14 IV 2630], crystallises from MeOH in needles and from H2O at 50o it forms plates. Terramycin has also been purified via the hydrochloride by dissolving it in H2O, adjusting to pH 6, and the solid is filtered off after 1hour. The crystals of the dihydrate are dried to constant weight in vacuum/CaCl2/25o. Drying at 60o in vacuo gives the anhydrous base m 184.5-185.5o (sintering at 180o). The dihydrate has m 181-182o. Its optical rotation in MeOH decreases from [] D 25 +26o (c 0.5%) to [] D 25 +11.3o after standing for 16hours. It forms a sodium salt and a CaCl2 complex. [Regna et al. J Am Chem Soc 73 4211 1951, Beilstein 14 IV 2633.]

oxytetracyclin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


oxytetracyclin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 438)Lieferanten
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79-57-2(oxytetracyclin)Verwandte Suche:


  • 12,12a-hexahydroxy-6-methyl-1,11-dioxo-10
  • 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-,2-Naphthacenecarboxamide
  • 5-hydroxy-tetracyclin
  • 6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-,(4s-(4-alpha,4a-alpha,5-alpha,5a
  • 6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-,[4s-(4alpha,4aalpha,5alpha,5a
  • 6-beta,12a-alpha))--alph
  • adamycin
  • antibiotictm25
  • berkmycen
  • biostat
  • biostatpa
  • dabicycline
  • fanterrin
  • geomycin(streptomycesrimosus)
  • geomycin(streptomycesvimosus)
  • geotilin
  • imperacin
  • la200
  • lenocycline
  • liquamycinla200
  • macocyn
  • mycoshieldtmqthc20
  • nci-c56473
  • oksisyklin
  • otc(antibiotic)
  • oxitetracyclin
  • Oxydon
  • oxymykoin
  • oxypam
  • oxysteclin
  • oxyterracin
  • oxyterracine
  • oxyterracyne
  • oxytetracyclineamphoteric
  • proteroxyna
  • riomitsin
  • ryomycin
  • solkaciclina
  • stevacin
  • tarosin
  • terrafungine
  • terramitsin
  • terramycinim
  • terramycinq50
  • tetran
  • ursocyclin
  • ursocycline
  • vendarcin
  • OXYTETRACYCLINE
  • OXYTETRACYCLIN 2H2O
  • Hydroxytetracycline
  • Oxytetracycline, 'can be used as secondary standard'
  • 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6S,12aS)-
  • OXYTETRACYCLINE(ANHYDROUS)
  • 2-(AMINO-HYDROXY-METHYLIDENE)-4-DIMETHYLAMINO-5,6,10,11,12A-PENTAHYDROXY-6-METHYL-4,4A,5,5A-TETRAHYDROTETRACENE-1,3,12-TRIONE
  • OXYTETRACYCLINE BASE BP (98)
  • 5-Hydroxytetracycline
  • [4S-(4a,4aa,5aa,6,12a]-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a -octahydro - 3,5,6,10,12,12a -hexa hydroxy-6 -methyl-1,11-dioxo-2 -Naphthacenecarboxamide
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