5510. Liothyronine

Nomenclature

CAS number: 6893-02-3
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-l-tyrosine; l-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]alanine; 4-(3-iodo-4-hydroxyphenoxy)-3,5-diiodophenylalanine; 3,5,3′-triiodothyronine; T3.
C15H12I3NO4; mol wt 650.97.
C 27.68%, H 1.86%, I 58.48%, N 2.15%, O 9.83%.

Description and 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).

Chemical structure

Properties

Crystals, dec 236-237°. [α]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.

Derivative

Sodium salt.

Nomenclature

CAS number: 55-06-1
Liothyronine sodium; sodium l-triiodothyronine; Cytobin (Pfizer); Cytomel (GSK); Cynomel (GSK); Tertroxin (GSK).
C15H11I3NNaO4; mol wt 672.96.
C 26.77%, H 1.65%, I 56.57%, N 2.08%, Na 3.42%, O 9.51%.

Derivative

Hydrochloride.

Nomenclature

CAS number: 6138-47-2
Thybon (Henning).
C15H12I3NO4.HCl; mol wt 687.43.
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°. [α]D29.5 +21.5° (c = 4.75 in a mixture of 1 vol N HCl and 2 vols ethanol).

Therapeutic Category

Thyroid hormone.

Therapeutic Category (Veterinary)

Thyroid hormone.

Keywords

Antihypothyroid; Thyroid Hormone