Menadionnatriumbisulfit

Bezeichnung:Menadionnatriumbisulfit

CAS-Nr130-37-0

Englisch Name:Menadione sodium bisulfite

CBNumberCB9741616

SummenformelC11H11NaO5S

Molgewicht278.25

MOL-Datei130-37-0.mol

Synonyma

Menadionnatriumbisulfit

Menadionnatriumbisulfit physikalisch-chemischer Eigenschaften

Schmelzpunkt	121-124°C
storage temp.	-20°C
Löslichkeit	H2O: ≥50mg/mL, clear, colorless to faintly yellow
InChI	InChI=1S/C11H10O5S.Na.H/c1-11(17(14,15)16)6-9(12)7-4-2-3-5-8(7)10(11)13;;/h2-5H,6H2,1H3,(H,14,15,16);;
InChIKey	JWNUEPMMANLFQO-UHFFFAOYSA-N
SMILES	O=C1C(CC(=O)C2=CC=CC=C12)(C)S(O)(=O)=O.[NaH]
EPA chemische Informationen	Menadione sodium bisulfite (130-37-0)

Sicherheit

Kennzeichnung gefährlicher	Xi,N
R-Sätze:	36-50/53-36/38
S-Sätze:	26-61-60-24/25
RIDADR	UN 3077 9 / PGIII
WGK Germany	3

Gefahreninformationscode (GHS)

Menadione sodium bisulfite Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36:Reizt die Augen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Menadione sodium bisulfite (MSB, also known as vitamin K3), is a crucial growth regulator mediating plant defense response. This substance is used clinically in China to treat hemorrhagic diseases caused by vitamin K deficiency and globally as a vitamin K supplement. This compound and its complex (MSBC) are water-soluble compounds. Menadione and the menadione sodium bisulfite complex are the sources of vitamin K activity in commercial laboratory rodent diets. Menadione possesses high biological activity, but its absorption depends on the amount of fat in the diet. Compared with Menadione, the menadione sodium bisulfite complex is more readily absorbed and is almost as active on a molar basis as phylloquinone. XTT, a tetrazolium salt, could converted to formazan in the presence of an electron coupling reagent such as menadione sodium bisulfite. The formed formazan does not need to be solubilized. Hence, the XTT test, a cytotoxicity evaluation method, is quicker and safer compared with MTT[1-2].
Chemische Eigenschaften
white powder
Originator
Kavitol,Lannacher Heilmittel
Verwenden
Menadione sodium bisulfite has been used:
- as a priming agent in tomato for improving salt tolerance
- to induce reactive oxygen species (ROS) in human lung epithelium BEAS-2B microtissues
- to induce endogenous superoxide production in mouse C17.2 neural stem cells
Definition
ChEBI: An organic sodium salt that is the monosodium salt of menadione sulfonate. A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation i vivo.
Manufacturing Process
The 2-naphthalenesulfonic acid, 1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-, sodium salt, trihydrate can be prepared by mixing the 2-methyl-1,4- naphthoquinone with the bisulphite salt in the presence of water. Ordinarily gentle warming of the aqueous mixture is preferred to facilitate solution. The mixture of 2-methyl-1,4-naphthoquinone (250 mg; 1 molar equivalent); sodium bisulphite (149 mg; 1 molar equivalent); distilled water (250 ml) or 2- methyl-1,4-naphthoquinone (250 mg; 1 molar equivalent); potassium bisulphate (349 mg; 2 molar equivalent); distilled water 250 ml may be used. These examples representing preferred ratios of ingredients are merely illustrative and are not to be interpreted as limiting.
The bisulphite addition compounds have been found to be stable in sunlight and also to be heat stable. Tests, for example, carried out in ampoules have shown aqueous solutions of the compounds not to be decomposed after exposure to a month's sunlight, while other tests have shown the solutions of such compounds to retain their original potency (a) when stored in an oven at 60°C for 15 days or (b) when sterilized at 15 pounds for 0.5 hour in an autoclave at about 122°C. These properties emphasize the radical differences between the stable salts and the properties of 2-methyl-1,4-naphthoquinone, the characteristic instability of which is illustrated by its sensitivity, i. e., decomposition, when exposed to light.
The bisulphite addition compounds have a vitamin K activity equal to that of the 2-methyl-1,4-naphthoquinone contained in the molecule. The compounds, although suitable for oral administration, are particularly adaptable in aqueous solution for parenteral administration in the treatment of hemorrhagic conditions.
Trademarks
Hykinone (Abbott); Klotogen (Abbott).
Therapeutic Function
Prothrombogenic vitamin
Biochem/physiol Actions
Menadione sodium bisulfite is a water-soluble form of menadione, which belongs to the Vitamin K class of compounds. These are necessary for the biosynthesis of prothrombin and other blood clotting factors. Menadione is a prothrombogenic compound and is used as a model quinone in cell culture and in vivo investigations. Menadione has been shown to affect gap-junctional intercellular communication by mediation of tyrosine phosphorylation. Menadione has demonstrated cytotoxic activity against a variety of cell lines and can induce apoptosis in cultured cells, such as osteoclasts and osteoblasts, via elevation of peroxide and superoxide radical levels.An HPLC method for detection of menadione sodium bisulfite in multivitamin formulations has been published. A chemiluminescence assay for menadione sodium bisulfite in pharmaceutical preparations and biological fluids has been reported.
Nebenwirkungen
Inflammation of the walls of a vein
Facial flushing
Cardiovascular collapse
Severe shock-like reactions
Sweating Injection site reactions
Chest constriction
Pain
Shortness of breath
Bluish discoloration of the skin
Einzelnachweise
[1] Zhang Y, et al. Menadione sodium bisulfite inhibits the toxic aggregation of amyloid-β(1-42). Biochimica et Biophysica Acta (BBA) - General Subjects, 2018; 1862: 2226-2235.
[2] Lustgarten M, et al. An Objective Appraisal of the Free Radical Theory of Aging. Handbook of the Biology of Aging, 2011; 177-202.

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