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55-03-8

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55-03-8 Usage

Chemical Properties

Levothyroxine sodium is White Solid

Originator

Synthroid,Flint,US,1953

Uses

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.

Definition

ChEBI: The sodium salt of L-thyoxine. It is used as replacement therapy in the treatment of hypothyroidism.

Indications

Levothyroxine sodium (Levothroid, Synthroid, Levoxine) is the sodium salt of the naturally occurring levorotatory isomer of T4. It is the preparation of choice for maintenance of plasma T4 and T3 concentrations for thyroid hormone replacement therapy in hypothyroid patients. It is absorbed intact from the gastrointestinal tract, and its long half-life allows for convenient oncedaily administration. Since much of the T4 is deiodinated to T3, it is usually unnecessary to use more expensive preparations containing both T4 and T3.The aim is to establish euthyroidism with measured serum concentrations of T4, T3, and TSH within the normal range. The TSH-suppressive effects of exogenous T4 also prove useful in removing the stimulatory effects of TSH on the thyroid gland in the management of simple nonendemic goiter, chronic thyroiditis, and TSHdependent thyroid carcinoma.

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.

Therapeutic Function

Thyroid hormone

General Description

Levothyroxine sodium,O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-2-tyrosinemonosodium salt, hydrate (Synthroid, Letter, Levoxine,Levoid), is the sodium salt of the levo isomer of thyroxine,which is an active physiological principle obtained from thethyroid gland of domesticated animals used for food by humans.It is also prepared synthetically. The salt is a light yellow,tasteless, odorless powder. It is hygroscopic but stablein dry air at room temperature. It is soluble in alkali hydroxides,1:275 in alcohol, and 1:500 in water, to give a pH ofabout 8.9.

Clinical Use

Liothyronine sodium occurs in vivo together withlevothyroxine sodium; it has the same qualitative activitiesas thyroxine but is more active. It is absorbed readily fromthe gastrointestinal tract, is cleared rapidly from the bloodstream,and is bound more loosely to plasma proteins than isthyroxine, probably because of the less acidic phenolic hydroxylgroup.Its uses are the same as those of levothyroxine sodium,including treatment of metabolic insufficiency, male infertility,and certain gynecological disorders.

Veterinary Drugs and Treatments

Levothyroxine sodium is indicated for the treatment of hypothyroidism in all species.

Check Digit Verification of cas no

The CAS Registry Mumber 55-03-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 5 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 55-03:
(4*5)+(3*5)+(2*0)+(1*3)=38
38 % 10 = 8
So 55-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H11I4NO4.Na/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23;/h1-2,4-5,12,21H,3,20H2,(H,22,23);/q;+1

55-03-8 Well-known Company Product Price

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  • TCI America

  • (T0245)  L-Thyroxine Sodium Salt Pentahydrate  >98.0%(T)

  • 55-03-8

  • 100mg

  • 305.00CNY

  • Detail
  • TCI America

  • (T0245)  L-Thyroxine Sodium Salt Pentahydrate  >98.0%(T)

  • 55-03-8

  • 1g

  • 1,550.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001382)  Levothyroxine for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 55-03-8

  • Y0001382

  • 1,880.19CNY

  • Detail

55-03-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name levothyroxine sodium anhydrous

1.2 Other means of identification

Product number -
Other names (S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propionic Acid Sodium Salt Pentahydrate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:55-03-8 SDS

55-03-8Synthetic route

L-thyroxine
51-48-9

L-thyroxine

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
With sodium carbonate In water Reflux;98%
Stage #1: L-thyroxine With sulfuric acid; ammonia In butan-1-ol at 5 - 65℃; for 1h; pH=8;
Stage #2: With sodium hydroxide In propan-1-ol; butan-1-ol at 25 - 50℃; pH=10;
83%
With sodium carbonate Reflux;79.2%
With sodium carbonate In propan-1-ol; water at 80 - 90℃; for 1h;68%
O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine disodium salt

O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine disodium salt

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Stage #1: O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine disodium salt With sodium hydroxide In water at 25 - 30℃; pH=~ 12 - 13;
Stage #2: With hydrogenchloride In water pH=2 - 3; Product distribution / selectivity;
92%
With pyrographite; sodium hydroxide; sodium sulfite In water at 20℃; for 0.5h;84%
Stage #1: O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine disodium salt With acetic acid In propan-1-ol; water at 55 - 60℃;
Stage #2: With sodium carbonate In propan-1-ol; water at 80 - 90℃;
81%
3,5-diiodo-l-tyrosine
300-39-0

3,5-diiodo-l-tyrosine

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydroxide / water / 1 h
1.2: 2 h / 20 - 40 °C
2.1: diisopropylamine / water; butan-1-ol / 2 h / 20 - 90 °C
2.2: 2 h / 20 - 30 °C
3.1: acetic acid; hydrogen iodide / 5 h / 100 °C
4.1: methylamine / methanol / 25 - 30 °C
4.2: -8 - 0 °C
4.3: 15 - 20 °C
5.1: sulfuric acid; ammonia / butan-1-ol / 1 h / 5 - 65 °C / pH 8
5.2: 25 - 50 °C / pH 10
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide / water / 0 - 15 °C
2.1: 0.5 h / 20 °C
2.2: 1 h / 20 - 50 °C
3.1: copper(II) perchlorate hexahydrate / dichloromethane / 0.17 h / 25 °C
3.2: 3 h / 25 °C
4.1: acetic acid; hydrogen iodide / 4 h / 120 °C
5.1: sodium iodide / water / 0.08 h / 20 °C / Inert atmosphere
5.2: 0.5 h / 20 °C
5.3: 1.25 h / 20 - 60 °C
6.1: sodium hydroxide; sodium sulfite; pyrographite / water / 0.5 h / 20 °C
View Scheme
3,5-diiodo L-tyrosine copper complex

3,5-diiodo L-tyrosine copper complex

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diisopropylamine / water; butan-1-ol / 2 h / 20 - 90 °C
1.2: 2 h / 20 - 30 °C
2.1: acetic acid; hydrogen iodide / 5 h / 100 °C
3.1: methylamine / methanol / 25 - 30 °C
3.2: -8 - 0 °C
3.3: 15 - 20 °C
4.1: sulfuric acid; ammonia / butan-1-ol / 1 h / 5 - 65 °C / pH 8
4.2: 25 - 50 °C / pH 10
View Scheme
4,4'-dimethoxydiphenyliodonium iodide
6293-71-6

4,4'-dimethoxydiphenyliodonium iodide

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diisopropylamine / water; butan-1-ol / 2 h / 20 - 90 °C
1.2: 2 h / 20 - 30 °C
2.1: acetic acid; hydrogen iodide / 5 h / 100 °C
3.1: methylamine / methanol / 25 - 30 °C
3.2: -8 - 0 °C
3.3: 15 - 20 °C
4.1: sulfuric acid; ammonia / butan-1-ol / 1 h / 5 - 65 °C / pH 8
4.2: 25 - 50 °C / pH 10
View Scheme
2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid
94345-95-6

2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid; hydrogen iodide / 5 h / 100 °C
2.1: methylamine / methanol / 25 - 30 °C
2.2: -8 - 0 °C
2.3: 15 - 20 °C
3.1: sulfuric acid; ammonia / butan-1-ol / 1 h / 5 - 65 °C / pH 8
3.2: 25 - 50 °C / pH 10
View Scheme
L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tert-butylamine; sodium iodide; sodium hypochlorite / methanol / 20 - 30 °C
2: sodium carbonate / water; propan-1-ol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tert-butylamine; sodium iodide; sodium hypochlorite / methanol / 20 - 30 °C
2.1: sodium hydroxide / water; propan-1-ol / 80 - 90 °C
3.1: acetic acid / water; propan-1-ol / 55 - 60 °C
3.2: 80 - 90 °C
View Scheme
{Cu(HOC6H2I2CH2CH(NH2)COO)2}
49553-16-4

{Cu(HOC6H2I2CH2CH(NH2)COO)2}

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 2 h / 90 °C
2: hydrogenchloride / water / 5 h / 100 °C
3: potassium iodide; iodine; sodium hydroxide / water / -10 - 10 °C
4: sodium carbonate / Reflux
View Scheme
2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid
94345-95-6

2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 5 h / 100 °C
2: potassium iodide; iodine; sodium hydroxide / water / -10 - 10 °C
3: sodium carbonate / Reflux
View Scheme
4,4'-dimethoxy-diphenyliodonium bromide
19231-06-2

4,4'-dimethoxy-diphenyliodonium bromide

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 2 h / 90 °C
2: hydrogenchloride / water / 5 h / 100 °C
3: potassium iodide; iodine; sodium hydroxide / water / -10 - 10 °C
4: sodium carbonate / Reflux
View Scheme
N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester
83249-56-3

N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid; hydrogen iodide / 4 h / 120 °C
2.1: sodium iodide / water / 0.08 h / 20 °C / Inert atmosphere
2.2: 0.5 h / 20 °C
2.3: 1.25 h / 20 - 60 °C
3.1: sodium hydroxide; sodium sulfite; pyrographite / water / 0.5 h / 20 °C
View Scheme
N-acetyl-3,5-diiodo-L-tyrosine
1027-28-7

N-acetyl-3,5-diiodo-L-tyrosine

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 0.5 h / 20 °C
1.2: 1 h / 20 - 50 °C
2.1: copper(II) perchlorate hexahydrate / dichloromethane / 0.17 h / 25 °C
2.2: 3 h / 25 °C
3.1: acetic acid; hydrogen iodide / 4 h / 120 °C
4.1: sodium iodide / water / 0.08 h / 20 °C / Inert atmosphere
4.2: 0.5 h / 20 °C
4.3: 1.25 h / 20 - 60 °C
5.1: sodium hydroxide; sodium sulfite; pyrographite / water / 0.5 h / 20 °C
View Scheme
N-acetyl-3,5-diiodo-L-tyrosine ethyl ester
21959-36-4

N-acetyl-3,5-diiodo-L-tyrosine ethyl ester

L-thyroxine sodium
55-03-8

L-thyroxine sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: copper(II) perchlorate hexahydrate / dichloromethane / 0.17 h / 25 °C
1.2: 3 h / 25 °C
2.1: acetic acid; hydrogen iodide / 4 h / 120 °C
3.1: sodium iodide / water / 0.08 h / 20 °C / Inert atmosphere
3.2: 0.5 h / 20 °C
3.3: 1.25 h / 20 - 60 °C
4.1: sodium hydroxide; sodium sulfite; pyrographite / water / 0.5 h / 20 °C
View Scheme
L-thyroxine sodium
55-03-8

L-thyroxine sodium

O-[6-{6-[4-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-oxobutyl]aminohexanoyl}aminohexanoyl]gramicidin A

O-[6-{6-[4-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-oxobutyl]aminohexanoyl}aminohexanoyl]gramicidin A

O-[6-[(6-[3-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethylaminocarbonyl}propionylamino]-1-oxohexyl)amino]-1-oxohexyl]gramicidin A

O-[6-[(6-[3-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethylaminocarbonyl}propionylamino]-1-oxohexyl)amino]-1-oxohexyl]gramicidin A

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane at 20℃; for 16h;63%
L-thyroxine sodium
55-03-8

L-thyroxine sodium

O-[6-(6-[6-{6-[4-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-oxobutyl]aminohexanoyl}aminohexanoyl]aminohexanoyl)aminohexanoyl]gramicidin A

O-[6-(6-[6-{6-[4-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-oxobutyl]aminohexanoyl}aminohexanoyl]aminohexanoyl)aminohexanoyl]gramicidin A

O-{6-[6-({6-[(6-[3-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethylaminocarbonyl}propionylamino]-1-oxohexyl)amino]-1-oxohexyl}amino)-1-oxohexyl]amino-1-oxohexyl}gramicidin A

O-{6-[6-({6-[(6-[3-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethylaminocarbonyl}propionylamino]-1-oxohexyl)amino]-1-oxohexyl}amino)-1-oxohexyl]amino-1-oxohexyl}gramicidin A

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane at 20℃; for 16h;51%
L-thyroxine sodium
55-03-8

L-thyroxine sodium

O-succinylgramicidin A

O-succinylgramicidin A

O-[4-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethyl}amino-4-oxobutanoyl]gramicidin A

O-[4-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethyl}amino-4-oxobutanoyl]gramicidin A

Conditions
ConditionsYield
Stage #1: O-succinylgramicidin A With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: L-thyroxine sodium In tetrahydrofuran; water at 20℃;
19%
L-thyroxine sodium
55-03-8

L-thyroxine sodium

O-[6-[4-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-oxobutyl]aminohexanoyl]gramicidin A

O-[6-[4-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-oxobutyl]aminohexanoyl]gramicidin A

O-[6-[3-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethylaminocarbonyl}propionylamino]-1-oxohexyl]gramicidin A

O-[6-[3-{(1S)-1-hydroxycarbonyl-2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]ethylaminocarbonyl}propionylamino]-1-oxohexyl]gramicidin A

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane at 20℃; for 18h;20 mg
L-thyroxine sodium
55-03-8

L-thyroxine sodium

N-trifluoroacetyl thyroxine

N-trifluoroacetyl thyroxine

Conditions
ConditionsYield
With sodium chloride; trifluoroacetic acid; trifluoroacetic anhydride In methanol; chloroform; ethyl acetate; Petroleum ether
L-thyroxine sodium
55-03-8

L-thyroxine sodium

L-thyroxine
51-48-9

L-thyroxine

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid In water; glycerol
With ethylenediaminetetraacetic acid In water; glycerol
With ethylenediaminetetraacetic acid In water; glycerol
With ethylenediaminetetraacetic acid In water; glycerol
With ethylenediaminetetraacetic acid In glycerol
L-thyroxine sodium
55-03-8

L-thyroxine sodium

O2,O3-diacetyl-tartaric acid anhydride
122376-19-6

O2,O3-diacetyl-tartaric acid anhydride

C23H19I4NO11

C23H19I4NO11

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20 - 25℃; for 1h;900 mg

55-03-8Downstream Products

55-03-8Relevant articles and documents

Preparation method of levothyroxine sodium

-

, (2019/06/05)

The invention belongs to the field of pharmaceutical synthesis, and discloses a preparation method of levothyroxine sodium. The preparation method comprises the following steps: (1) taking 3,5-diiodo-L-tyrosine as a raw material, and preparing N-acetyl-L-tyrosine by firstly introducing acetyl protection to an amino group; (2) then preparing N-acetyl-3,5-diiodo-L-tyrosine ethyl ester under the action of thionyl chloride; (3) preparing N-acetyl-O-(4-methyoxyphenyl)-3,3-diiodo-L-tyrosine ethyl ester by carrying out Chan-Lam reaction through copper catalysis; (4) removing a protective group undera strong acidity condition, thus obtaining O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine; (5) then reacting with iodine, and preparing O-(4-hydroxy-3,5-diiodo phenyl)-3,5-diiodo-L-tyrosine disodium salt under the action of sodium hydroxide; (6) finally, regulating pH (Potential of Hydrogen) through glacial acetic acid, thus obtaining the levothyroxine sodium. According to the preparation method disclosed by the invention, the key Chan-Lam reaction and other reaction steps are optimized, so that the reaction time can be greatly shortened, and the reaction yield can be increased; the preparation method is simple in technology, convenient to operate and suitable for industrial production.

A PROCESS FOR PREPARATION OF LEVOTHYROXINE AND SALTS THEREOF

-

, (2015/11/30)

The present invention relates to a process for the preparation of Levothyroxine and salts thereof. The process described in the present invention provides increase in the yields and purity comprising the use of sodium iodide and sodium hypochlorite as iodinating agent.

Process for the preparation of thyroid hormones and derivatives thereof

-

Page/Page column 6, (2011/07/09)

The present invention generally refers to a process for the preparation of L-thyroxine derivatives. More in particular, the present invention relates to a iodination reaction of an aromatic derivative with an appropriate iodinating agent, so to afford the related iodinated compound as disodium salt, which may represent a useful intermediate for the synthesis of the L-thyroxine mono-sodium salt, and the free form thereof.

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