Liothyroninnatrium

Bezeichnung:Liothyroninnatrium

CAS-Nr55-06-1

Englisch Name:Liothyronine sodium

CBNumberCB3195390

SummenformelC15H11I3NNaO4

Molgewicht672.96

MOL-Datei55-06-1.mol

Synonyma

Liothyroninnatrium

Liothyroninnatrium physikalisch-chemischer Eigenschaften

Schmelzpunkt	205 °C (dec.)(lit.)
alpha	20 º (c=2,alcohol/1.2N HCl)
RTECS-Nr.	YP2836500
storage temp.	-20°C
Löslichkeit	4 M NH₄OH in methanol: 125 g/5mL, clear, yellow-brown
Aggregatzustand	powder
Farbe	White to Pale Brown
Wasserlöslichkeit	Partly miscible in water. Soluble in dimethyl sulfoxide, methanol, sodium hydroxide and ethanol. Practically insoluble in most other organic solvents.
Sensitive	Light Sensitive
Merck	5510
BRN	8179867
InChI	InChI=1/C15H12I3NO4.Na/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22;/h1-4,6,12,20H,5,19H2,(H,21,22);/q;+1/p-1/t12-;/s3
InChIKey	SBXXSUDPJJJJLC-ZLBVLXFENA-M
SMILES	C1(C(I)=CC(C[C@H](N)C([O-])=O)=CC=1I)OC1=CC=C(O)C(I)=C1.[Na+] \|&1:6,r\|
CAS Datenbank	55-06-1(CAS DataBase Reference)
EPA chemische Informationen	L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-, monosodium salt (55-06-1)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22
S-Sätze:	22-24/25-36
WGK Germany	3
F	3-8-10
HS Code	29379000

Gefahreninformationscode (GHS)

Liothyronine sodium Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
white to beige powder
Originator
Cytomel,SKF,US,1956
Verwenden
L-3,3',5-Triiodothyronine, Sodium Salt is shown to stimulate respiratory activity at the mitochondrial level. T3 is a thyroid hormone that increases rates of proteins synthesis, stimulates the breakdown of cholesterol, and effects embryonic development. In cell culture, T3 regulates cell differentiation and protein expression.
Verwenden
One of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.
Indications
Liothyronine sodium (Cytomel) is the sodium salt of the naturally occurring levorotatory isomer of T3. Liothyronine is generally not used for maintenance thyroid hormone replacement therapy because of its short plasma half-life and duration of action. The use of T3alone is recommended only in special situations, such as in the initial therapy of myxedema and myxedema coma and the short-term suppression of TSH in patients undergoing surgery for thyroid cancer. The use of T3 alone may also be useful in patients with the rare condition of 5'-deiodinase deficiency who cannot convert T4 to T3.
Definition
ChEBI: Liothyronine sodium is the sodium salt of liothyronine. Thought to be more active than levothyroxine and with a rapid (few hours) onset and short duration of action, liothyronine sodium is used in the treatment of hypothyroidism, particularly in cases of hypothyroid coma. It contains a 3,3',5-triiodo-L-thyroninate.
Manufacturing Process
The 3,5-diiodo compound used as a starting material is a known material and may be prepared by the method in British Patents 643,089 and 671,070 and in the Journal of the Chemical Society, London, 1949, page 3424.
Synthesis: L-diiodo thyronine (1.05 g) is dissolved in ammonia (specific gravity 0.880) (40 ml) and methanol (40 ml) and iodinated slowly with shaking with N-iodine in KI solution at room temperature. After iodination,most of the ammonia and methanol are removed by evaporation under diminished pressure, water is added to the original volume, the solution is heated to 60°C and brought to pH 4 with hydrochloric acid. A crystalline precipitate is obtained which after cooling to room temperature is collected and washed with water. At this stage, the crude triiodo thyronine is contaminated with thyroxine and a little unchanged diiodo thyronine.
Purification: The crude precipitate is dissolved in boiling 2N HCl (300 ml) and filtered from the relatively insoluble thyroxine hydrochloride. The hot filtrate is brought to pH 4 with 5N NaOH and triiodo thyronine again separates; after chilling at 0° to 4°C it is collected, washed with water and dried. The yield of triiodo thyronine is 70 to 75% of the theoretical. This triiodo thyronine still contains some thyroxine (about 10%).
The final purification consists of chromatographic separation of thyroxine and triiodo thyronine on a kieselguhr column using 20% chloroform in n-butanol equilibrated with 0.5N NaOH as the developing solvent. 80 to 100 mg triiodo thyronine is purified during each run on a 50 g kieselguhr column. Pure Ltriiodo thyronine has MP 236° to 237°C (dec.) and [α]D29.5° = +21.5 in a 4.75% solution in a mixture of 1 part of N HCl and 2 parts of ethanol. Liothyronine is commonly used as the sodium salt.
Trademarks
Thyroid hormone Cytomel (King); Triostat (Jones).
Allgemeine Beschreibung
3,3′,5′-Triiodo-L-thyronine (T₃) is an endocrine hormone produced by the thyroid gland and is regarded as an active thyroid hormone at cellular level. Thyroxine (T₄) serves as a precursor for T₃ and is generated in extrathyroidal tissues.
Biochem/physiol Actions
3,3′,5′-Triiodo-L-thyronine (T3) is a thyroid hormone that increases rates of proteins synthesis, stimulates the breakdown of cholesterol, and effects embryonic development. In cell culture, T3 regulates cell differentiation and protein expression. The interaction of T3 with nonhistone proteins in the chromatin initiates the thyroid hormone activity. Thyroid hormones regulate the differentiation and development of tissues and affect a number of metabolic processes. The level of circulating T3 hormone is reduced in hypothyroidism.

Liothyronine sodium Upstream-Materialien And Downstream Produkte

Liothyroninnatrium Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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