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DL-Thyroxin Produkt Beschreibung

L-Thyroxine Struktur
51-48-9
CAS-Nr.
51-48-9
Bezeichnung:
DL-Thyroxin
Englisch Name:
L-Thyroxine
Synonyma:
T4;T44;thx;l-t4;Thyrax;Henning;Tetramet;thyroxin;THYROXINE;NSC 36397
CBNumber:
CB5853720
Summenformel:
C15H11I4NO4
Molgewicht:
776.87
MOL-Datei:
51-48-9.mol

DL-Thyroxin Eigenschaften

Schmelzpunkt:
235 °C
alpha 
-5 º (1N NaOH:EtOH 1:2)
Dichte
2.4440 (estimate)
Flammpunkt:
9℃
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit
Dissolves in 4M ammonium hydroxide in Methanol at 50mg/ml
pka
2.2(at 25℃)
Siedepunkt:
576.3±50.0 °C(Predicted)
Aggregatzustand
Powder
Farbe
White to Pale Brown
Wasserlöslichkeit
insoluble
Sensitive 
Light Sensitive
Merck 
9491
BRN 
2228515
InChIKey
XUIIKFGFIJCVMT-LBPRGKRZSA-N
CAS Datenbank
51-48-9(CAS DataBase Reference)
EPA chemische Informationen
L-Thyroxine (51-48-9)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,T,F
R-Sätze: 40-39/23/24/25-23/24/25-11
S-Sätze: 22-24/25-36-45-36/37-16
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS-Nr. YP2833500
8-10
TSCA  Yes
HazardClass  IRRITANT
HS Code  29379000
Giftige Stoffe Daten 51-48-9(Hazardous Substances Data)
Toxizität TDLo oral in child: 328ug/kg
Bildanzeige (GHS)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H370 Schädigt die Organe. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 1 Achtung P260, P264, P270, P307+P311, P321,P405, P501
Sicherheit
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P370+P378 Bei Brand: zum Löschen verwenden.

DL-Thyroxin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R40:Verdacht auf krebserzeugende Wirkung.

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.

Beschreibung

L-Thyroxine is a synthetic form of the thyroid hormone thyroxine. In vivo, L-thyroxine (0.9 and 2.7 μg) inhibits synthesis and release of thyrotropin induced by thyrotropin-releasing hormone (Item No. 22917) from the anterior pituitary in mice. It also reverses decreases in levels of circulating thymic serum factor (FTS) and the number of T rosette-forming cells in an old age-induced mouse model of hypothyroidism. Formulations containing L-thyroxine have been used in the treatment of hypothyroidism.

Chemische Eigenschaften

Crystalline Solid

Originator

Synthroid,Flint,US,1953

Verwenden

antihypercholesterimic, thyromimetic

Verwenden

One of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroi d hormone, but has been used to treat hyperlipidemia.

Verwenden

Thyroxine is one of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroid hormone, but has been used to treat hyperlipidemia.

Indications

Effects of this drug depend heavily on dosage. In small doses, levothyroxine exhibits anabolic action. In medium doses, it stimulates growth and development of tissue, metabolism of protein, fats, and carbohydrates, increases functional activity of central nervous and cardiovascular systems, as well as kidneys and liver. In large doses, it slows the thyrotropic activity of the hypophysis and suppresses thyroid gland production. Levothyroxine is used for hypothyroidism, myxedema, thyrotoxicosis, erythyroid conditions, and cretinism.

Definition

ChEBI: The L-enantiomer of thyroxine.

Manufacturing Process

A 9.30 g portion of N-acetyl-L-diiodotyrosinamide was suspended in 100 ml of 0.05M boric acid (H3BO3) and 100 ml of 95% ethanol, and the solid was dissolved by adjusting the pH to 10.5 with 2N sodium hydroxide (NaOH). A 15% (by weight) portion of manganese sulfate monohydrate was added and the solution heated at 44°C under conditions of oxygenation while being agitated mechanically. After approximately 24 hours of incubation, the precipitated product was collected and separated from the catalyst, providing the amide of N-acetyl-L-thyroxine in 30.6% yield. On hydrolysis (removal of both amide functions), achieved by refluxing in glacial acetic acid-hydrochloric acid (approximately 2:1), L-thyroxine is obtained. It was isolated as the sodium salt, containing approximately 5 molecules of water of hydration.

Trademarks

Levo-T (Alara); Levolet (Vintage); Levothroid (Lloyd); Levoxyl (Jones); Novothyrox (Genpharm); Synthroid (Abbott); Unithroid (Stevens J).

Therapeutic Function

Thyroid hormone

Pharmakokinetik

Because of its firmer binding to carrier proteins, synthetic crystalline L-T4 sodium salt (levothyroxine sodium, Synthtoid, Euthyrox) has a slower onset of action than crystalline T3 or a desiccated thyroid preparation. Its administration leads to a greater increase in serum T4 but a lesser increase in serum T3 than compared with Thyroid USP. The availability of 11 different tablet strengths, ranging from 25 to 300 μg, allows individual dosing

Chemical Synthesis

Levothyroxine, L-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl] alanine (25.1.10), is synthesized in a multi-stage synthesis from 4-hydroxy-3-iodo- 5-nitrobenzaldehyde. Reacting this with benzenesulfochloride in pyridine gives the corresponding benzenesulfonate 25.1.1, the benzenesulfonyl group of which is easily replaced with a 4-methoxyphenyloxy- group upon reaction with 4-methoxyphenol. The resulting 3-iodo-4-(4-methoxyphenoxy)benzaldehyde (25.1.2) is reacted further with N-acetylglycine in the presence of sodium acetate in a Knoevenagel reaction, in which the resulting ylidene compound cyclizes to an oxazolone derivative 25.1.3. The oxazolone ring of this compound is opened upon reaction with sodium methoxide, forming the desired cinnamic acid derivative 25.1.4. The nitro group of this product is reduced to an amino group by hydrogen in the presence of a Raney nickel catalyst, forming the corresponding amine, and subsequent diazotation and replacement of the diazo group of which with iodine gives the methyl ester of α-acetamido-3,5-diiodo-4-(4-methoxyphenoxy)crotonic acid (25.1.6). The resulting compound undergoes simultaneous reaction with hydrogen iodide and phosphorous in acetic acid, in which the double bond in the crotonic acid is reduced, and the methoxy protection is removed from the phenol ring. During this, a simultaneous hydrolysis of the acetyl group on the nitrogen atom also takes place, forming D,L-3,5-diiodothyronine (25.1.7). The amino group in this product is once again protected by the reaction with formic acid in the presence of acetic anhydride, which gives D,L-N-formyl-3,5-diiodothyronine. Separation of isomers in the resulting racemic mixture is accomplished using brucine, giving D-(+)-N-formyl-3, 5-diiodothyronine L-(+)-N-formyl-3,5-diiodothyronine (25.1.8). The protecting formyl group is hydrolyzed using hydrobromic acid, giving L-(+)-3,5-diiodothyronine (25.1.9), which undergoes direct iodination using iodine in the presence of potassium iodide in aqueous methylamine, to give the desired levothyroxine.

läuterung methode

Purification is the same as for the D-isomer above. Likely impurities are tyrosine, iodotyrosine, iodothyroxines and iodide. Dissolve it in dilute ammonia at room temperature, then crystallise it by adding di[] 546 +27.8o (c 5, EtOH). [Harrington et al. Biochem J 39 164 1945, Nahm & Siedel Chem Ber 96 1 1963, Reineke & Turner J Biol Chem 161 613 1945, Chalmers et al. J Chem Soc 3424 1949, Beilstein 14 II 378, 14 III 1566, 14 IV 2373.]

DL-Thyroxin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


DL-Thyroxin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 347)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Suzhou Ryan Pharmachem Technology Co.,Ltd.
0512-68780025-8002
0512-68780025-8004 yybi@ryanchem.com;sales@ryanchem.com CHINA 188 58
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20012 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 15419 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com China 9156 55
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
025-85710122 sales@fine-chemtech.com CHINA 890 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26782 60
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29953 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Shanghai Worldyang Chemical Co.,Ltd.
+86-021-56795779
sales@worldyachem.com China 833 58

51-48-9(DL-Thyroxin)Verwandte Suche:


  • 3,5,3’,5’-tetraiodothyronine
  • beta-[(3,5-diiodo-4-hydroxyphenoxy)-3,5-diiodophenyl]alanine
  • l-3,5,3’,5’-tetraiodothyronine
  • l-t4
  • o-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-l-tyrosin
  • β-((3,5-Diiodo-4-hydroxyphenoxy)-3,5-diiodophenyl)alanine
  • 3,5,3',5'-TETRAIODO-L-THYRONINE
  • 3,3',5,5'-TETRAIODO-L-THYRONIN
  • 3,3',5,5'-TETRAIODO-L-THYRONINE
  • 3,3',5,5'-TETRAIODO-L-THYRONINE SODIUM SALT
  • O-(4-HYDROXY-3,5-DIIODOPHENYL)-3,5-DIIODO-L-TYROSINE
  • T4
  • TETRAIODOTHYRONINE, NA
  • (S)-2-AMINO-3-[4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL]PROPIONIC ACID
  • LEVOTHYROXINE
  • L-THYROXIN
  • L-THYROXINE
  • L-THYROXINE NA
  • L-THYROXINE SODIUM
  • l-2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-propanoic acid
  • THYROXINE
  • T4
  • L-THYROXINE CELL CULTURE TESTED
  • L-Thyroxine-[L-Tyr-2H5] hydrochloride
  • L-Thyroxine-[L-Tyr-ring-13C6] hydrochloride
  • DL-thyroxin
  • Levothyroxine (500 mg)
  • L-Thyroxine L-Thyroxine
  • O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-
  • Thyroxine 13C9, 15N (T4)
  • (S)-2-aMino-3-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)propanoic acid
  • T4 LEVOTHYOXINE
  • L-Thyroxine 10
  • (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid
  • (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
  • (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]propionic acid
  • Levothyroxin
  • O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine
  • T44
  • Tetramet
  • Hematopoietic system regulatory peptide
  • THYMOSIN BETA4 human
  • o-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine
  • t4(hormone)
  • tetraiodothyronine
  • thx
  • thyreoideum
  • thyroxin
  • thyroxinal
  • L-Tyrosine, O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-
  • 2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-propanoic acid
  • L-Tyrosine, O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo- (9CI)
  • NSC 36397
  • Thyrax
  • Thyroxine, L- (8CI)
  • 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine
  • TETRADIODOTHYRONINE
  • tetaiodothyronine
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