55-06-1, Liothyronine Sodium,
CAS:55-06-1
C15H11I3NNaO4 / 672.96
MFCD00002594
3,3',5-Triiodo-L-thyronine sodium salt
Liothyronine Sodium is a synthetic form of T3 thyroid hormone, which is normally produced by the thyroid gland in the human body. It is commonly used in clinical settings to treat hypothyroidism, a condition in which the thyroid gland doesn't produce enough of these hormones. Liothyronine sodium is also used in scientific research for various purposes.
Synthesis and Characterization:
Liothyronine sodium is synthesized using chemical reactions that involve iodination, amidation, and esterification. The final product is purified using various techniques such as chromatography, crystallization, and recrystallization. Characterization of the product is done using different spectroscopic techniques, including NMR, IR, and mass spectrometry.
Analytical Methods:
Various analytical methods are used for the detection and quantification of liothyronine sodium. These include high-performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), and spectroscopic techniques such as UV-Vis and fluorescence spectroscopy.
Biological Properties:
Liothyronine sodium binds to the thyroid hormone receptor (THR) and activates gene transcription in various tissues. It has a short half-life of approximately 1.5 days and is rapidly metabolized in the liver. Liothyronine sodium has been shown to increase metabolism, heart rate, and energy expenditure in humans.
Toxicity and Safety in Scientific Experiments:
Liothyronine sodium is generally safe in scientific experiments at low doses. However, at high doses, it can cause adverse effects such as tachycardia, arrhythmia, and hyperthyroidism. Safety guidelines should be followed when handling liothyronine sodium in laboratory settings.
Applications in Scientific Experiments:
Liothyronine sodium is widely used in scientific experiments as a tool to investigate the role of thyroid hormones in various processes, including metabolism, aging, fertility, and development. It is also used in studies on obesity, diabetes, and other metabolic disorders.
Current State of Research:
Recent studies on liothyronine sodium have focused on its potential uses as a treatment for depression, bipolar disorder and postpartum depression. Studies have shown that the use of liothyronine sodium can significantly improve the symptoms of these disorders. Researchers are also exploring the use of liothyronine sodium in combination with other drugs to improve the treatment of cancer.
Potential Implications in Various Fields of Research and Industry:
Liothyronine sodium has potential implications in various fields of research and industry. It can be used in the development of novel therapies for metabolic disorders and hormone-related diseases. It can also be used in the production of thyroid hormone supplements and in the formulation of novel thyroid hormone receptor agonists.
Limitations and Future Directions:
One of the main limitations of liothyronine sodium is its short half-life, which limits its clinical application. Future research is needed to develop new analogs with longer half-lives and improved pharmacological properties. Additionally, more studies are needed to investigate the potential benefits and risks of liothyronine sodium in various settings.
Future Directions:
1. Development of novel analogs with increased half-lives and improved pharmacological properties.
2. Investigation of the potential benefits and risks of combining liothyronine sodium with other drugs.
3. Exploration of the role of liothyronine sodium in the regulation of metabolism and energy expenditure.
4. Investigation of the potential use of liothyronine sodium as a treatment for other hormonal disorders, including diabetes and obesity.
5. Development of more sensitive analytical methods for the detection and quantification of liothyronine sodium.
6. Investigation of the potential role of liothyronine sodium in the regulation of aging and fertility.
7. Development of novel thyroid hormone receptor agonists based on the structure of liothyronine sodium.
8. Investigation of the potential molecular mechanisms underlying the therapeutic effects of liothyronine sodium in depression and other mental disorders.
Title: Liothyronine
CAS Registry Number: 6893-02-3
CAS Name: O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine
Additional Names: L-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]alanine; 4-(3-iodo-4-hydroxyphenoxy)-3,5-diiodophenylalanine; 3,5,3¢-triiodothyronine; T3
Molecular Formula: C15H12I3NO4
Molecular Weight: 650.97
Percent Composition: C 27.68%, H 1.86%, I 58.48%, N 2.15%, O 9.83%
Literature References: 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, q.v. Identification in serum: J. Gross, R. Pitt-Rivers, Lancet I, 439 (1952). Prepn from diiodothyronine: J. Roche et al., Biochim. Biophys. Acta 11, 215 (1953). Isoln from thyroid gland and synthesis: J. Gross, R. Pitt-Rivers, Biochem. J. 53, 645 (1953). Bioactivity: eidem, ibid. 652. Elevated levels of T3 have been noted in victims of sudden infant death syndrome: G. Kocsard-Varo, Med. J. Aust. 2, 789 (1973); M. A. Chacon, J. T. Tildon, J. Pediatr. 99, 758 (1981). Direct determn in serum by RIA: I. J. Chopra et al., Thyroid 6, 255 (1996). Clinical trial in combination with thyroxine: R. Bunevicius et al., N. Engl. J. Med. 340, 424 (1999). Review of pharmacology and clinical uses: E. Sypniewski, Ann. Thorac. Surg. 56, S2-S8 (1993); of clinical trials in depression: R. Aronson et al., Arch. Gen. Psychiatry 53, 842-848 (1996); of use in heart transplantation: V. Jeevanandam, Thyroid 7, 139-145 (1997). Review of T3-receptors and molecular mechanism of action: M. A. Lazar, Endocr. Rev. 14, 184-193 (1993); G. A. Brent, N. Engl. J. Med. 331, 847-853 (1994). Review of biological effects: H. C. Freake, J. H. Oppenheimer, Annu. Rev. Nutr. 15, 263-291 (1995).
Properties: Crystals, dec 236-237°. [a]D29.5 +21.5° (c = 4.75 in a mixture of 1 part N HCl + 2 parts ethanol). Insol in water, alc, propylene glycol. Sol in dil alkalies with the formation of a brownish, water-soluble, sodium salt.
Optical Rotation: [a]D29.5 +21.5° (c = 4.75 in a mixture of 1 part N HCl + 2 parts ethanol)
Derivative Type: Sodium salt
CAS Registry Number: 55-06-1
Additional Names: Liothyronine sodium; sodium L-triiodothyronine
Trademarks: Cytobin (Pfizer); Cytomel (GSK); Cynomel (GSK); Tertroxin (GSK)
Molecular Formula: C15H11I3NNaO4
Molecular Weight: 672.96
Percent Composition: C 26.77%, H 1.65%, I 56.57%, N 2.08%, Na 3.42%, O 9.51%
Derivative Type: Hydrochloride
CAS Registry Number: 6138-47-2
Trademarks: Thybon (Henning)
Molecular Formula: C15H12I3NO4.HCl
Molecular Weight: 687.43
Percent Composition: C 26.21%, H 1.91%, I 55.38%, N 2.04%, O 9.31%, Cl 5.16%
Properties: Long birefringent needles, dec 202-203°. [a]D29.5 +21.5° (c = 4.75 in a mixture of 1 vol N HCl and 2 vols ethanol).
Optical Rotation: [a]D29.5 +21.5° (c = 4.75 in a mixture of 1 vol N HCl and 2 vols ethanol)
Therap-Cat: Thyroid hormone.
Therap-Cat-Vet: Thyroid hormone.
Keywords: Antihypothyroid; Thyroid Hormone.
CAS Number | 55-06-1 |
Product Name | Liothyronine sodium |
IUPAC Name | sodium;(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid |
Molecular Formula | C15H11I3NNaO4 |
Molecular Weight | 672.96 g/mol |
InChI | InChI=1S/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/t12-;/m0./s1 |
InChI Key | SBXXSUDPJJJJLC-YDALLXLXSA-M |
SMILES | C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(C(=O)O)N)I)I)O.[Na+] |
Synonyms | 3,3',5-Triiodothyronine, Cytomel, Liothyronine, Liothyronine Sodium, T3 Thyroid Hormone, Thyroid Hormone, T3, Triiodothyronine |
Canonical SMILES | C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(C(=O)[O-])N)I)I)O.[Na+] |
Isomeric SMILES | C1=CC(=C(C=C1OC2=C(C=C(C=C2I)C[C@@H](C(=O)[O-])N)I)I)O.[Na+] |
CAS No: 55-06-1 Synonyms: O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine sodium salt3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-L-alanine monosodium saltBasoprocinLiothyronine sodium MDL No: MFCD00002594 Chemical Formula: C15H11I3NNaO4 Molecular Weight: 672.96 |
COA:
Product name: Liothyronine Sodium
M.F.: C15H11I3NNaO4 M.W.: 672.96 CAS: 55-06-1
Items | Standards | Results |
Appearance | Light yellow or buff solid | Complies |
Identification | IR and HPLC | Complies |
Specific rotation | +18 ~ +22° | +19.4° |
Water (Loss weight on dryness) | Max. 4% | 3.8% |
Iodides content | Max. 0.08% | Complies |
Chloride content | 1.2% | 0.1% |
Sodium content | 2.9% ~ 4% | 3% |
pH of saturated solution | 8.5 ~ 9.5 | 9 |
Heavy metals | Max. 20ppm | Complies |
Levothyroxine Sodium | Max. 5% | 2.7% |
Assay by HPLC | 95% ~ 101% | 98.6% |
References:
1. McLaughlin, C., et al., Clin. Endocrinol., 69, 169 (2008)
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