Liothyronine
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.

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