|Jmol-3D images||Image 1|
|Metabolism||Mainly in liver, kidneys, brain and muscles|
|ca. 7 days (in hyperthyroidism 3-4 days, in hypothyroidism 9-10 days)|
|Excretion||Through feces and urine|
|Molar mass||776.87 g mol−1|
|Melting point||231–233 °C|
|Solubility in water||slightly soluble (0,105 mg·l-1 at 25 °C) |
|Related compounds||Triiodothyronine (tri-iodated)
Thyronine (without iodine)
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Levothyroxine, also L-thyroxine or T4, is a synthetic form of the thyroid hormone thyroxine, which is normally secreted by the follicular cells of the thyroid gland. It is also used to treat thyroid hormone deficiency, and occasionally to prevent the recurrence of thyroid cancer. Like its naturally secreted counterpart, levothyroxine is chemically in the chiral L-form. The related drug dextrothyroxine (D-thyroxine) was used in the past as a treatment for hypercholesterolemia (elevated cholesterol levels) but was withdrawn due to cardiac side-effects.
Thyroxine was first isolated in pure form in 1914 at the Mayo Clinic by Edward Calvin Kendall from extracts of hog thyroid glands. The hormone was synthesised in 1927 by British chemists Charles Robert Harington and George Barger.
Levothyroxine is typically used to treat hypothyroidism. It may also be used to treat goiter via its ability to lower thyroid-stimulating hormone (TSH), a hormone that is considered goiter-inducing. In 1992, President George H.W. Bush told television host Larry King that he had been prescribed levothyroxine as part of a treatment regimen for Graves' disease; the exchange was broadcast live to satellite dish owners tracking and recording backhaul channels.
Dosing, which is generally straight forward, must be controlled to achieve free T4 and free T3 levels within the normal reference range and elimination of hypothyroid and hyperthyroid symptoms. Once patients are stabilized annual or semiannual clinical evaluations and TSH monitoring are appropriate. Long-term suppression of TSH values below normal values will frequently cause cardiac side-effects and contribute to decreases in bone mineral density (low TSH levels are also well known to contribute to osteoporosis).
Patients prescribed too high a dose of levothyroxine may experience effects that mimic hyperthyroidism. Overdose can result in heart palpitations, abdominal pain, nausea, anxiousness, confusion, agitation, insomnia, weight loss, and increased appetite. Allergic reactions to the drug are characterized by symptoms such as difficulty breathing, shortness of breath, or swelling of the face and tongue. Acute overdose may cause fever, hypoglycemia, heart failure, coma and unrecognized adrenal insufficiency.
Acute massive overdose may be life-threatening; treatment should be symptomatic and supportive. Massive overdose can be associated with increased sympathetic activity and thus require treatment with beta-blockers.
The effects of overdosing appear 6 hours to 11 days after ingestion.
There are also foods and other substances that can interfere with absorption of thyroxine replacement. People should avoid taking calcium and iron supplements within 4 hours, as well as soy products within 3 hours of the medication, as these can reduce absorption of the drug. Grapefruit juice may delay the absorption of levothyroxine, but based on a study of 10 healthy people aged 20–30 (8 men, 2 women) it may not have a significant effect on bioavailability in young adults. Other substances that reduce absorption are aluminium and magnesium containing antacids, simethicone or sucralfate, cholestyramine, colestipol, Kayexalate. A study of eight women suggested that coffee may interfere with the intestinal absorption of levothyroxine, though at a level less than eating bran. Different substances cause other adverse effects that may be severe. Ketamine may cause hypertension and tachycardia and tricyclic and tetracyclic antidepressants increase its toxicity. On the other hand lithium can cause hyperthyroidism (but most often hypothyroidism) by affecting iodine metabolism of the thyroid itself and thus inhibits synthetic levothyroxine as well.
Dosages vary according to the age groups and the individual condition of the patient, body weight and compliance to the medication and diet. Monitoring of the patient's condition and adjustment of the dosage is periodical and necessary. Levothyroxine is taken on an empty stomach approximately half an hour to an hour before meals.
Common brand names
Common brand names include Eltroxin, Euthyrox, Letrox, Levaxin, L-thyroxine, Thyrax, and Thyrax Duotab in Europe; Thyrox in South Asia; Eutirox, Levoxyl, Synthroid, and Tirosint in North and South America; and Thyrin and Thyrolar in Bangladesh. There are also numerous generic versions.
- Harington in: Biochem. J. 1926, 20, 310.
- Levothyroxine in the ChemIDplus database
- E.C. Kendall in J. Am. Med. Assoc., 1915, Vol. 64, pp 2042-2043: The isolation in crystalline form of the compound containing iodin, which occurs in the thyroid: Its chemical nature and physiologic activity.
- Vaidya B, Pearce SH. Management of hypothyroidism in adults. BMJ (Clinical research ed.). 2008;337:a801. doi:10.1136/bmj.a801. PMID 18662921.
- Svensson J, Ericsson UB, Nilsson P, et al.. Levothyroxine treatment reduces thyroid size in children and adolescents with chronic autoimmune thyroiditis. The Journal of Clinical Endocrinology and Metabolism. 2006;91(5):1729–34. doi:10.1210/jc.2005-2400. PMID 16507633.
- Dietlein, M.; Wegscheider, K.; Vaupel, R.; Schmidt, M.; Schicha, H. (2007). "Management of multinodular goiter in Germany (Papillon 2005): do the approaches of thyroid specialists and primary care practitioners differ?". Nuklearmedizin. Nuclear medicine 46 (3): 65–75. PMID 17549317.
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- Medscape, Hypothyroidism Treatment & Management - Author: Philip R Orlander, MD; Chief Editor: George T Griffing, MD more...
- Frilling, A; Liu, C; Weber, F (2004). "Benign multinodular goiter". Scandinavian journal of surgery : SJS : official organ for the Finnish Surgical Society and the Scandinavian Surgical Society 93 (4): 278–81. PMID 15658668.
- "Synthroid (Levothyroxine Sodium) Drug Information: Uses, Side Effects, Drug Interactions and Warnings". RxList. Retrieved 2010-07-18.
- Irizarry, Lisandro. WebMd. Toxicity, Thyroid Hormone; 2010-04-23 [Retrieved 2010-10-31].
- Ruth H. Michel, Patricia J. Neafsey, Laura Cox Dzurec. Self Medication Practices among Patients taking Levothyroxine. The Internet Journal of Advanced Nursing Practice. 2004;6.
- Lilja JJ, Laitinen K, Neuvonen PJ. Effects of grapefruit juice on the absorption of levothyroxine. Br J Clin Pharmacol. 2005;60(3):337–41. doi:10.1111/j.1365-2125.2005.02433.x. PMID 16120075.
- Altered Intestinal Absorption of L-Thyroxine Caused by Coffee. Thyroid. March 2008 [Retrieved 2009-05-16];18(3):293–301. doi:10.1089/thy.2007.0222. PMID 18341376.
- Levothyroxine sodium on Drugs.com
- Levothyroxine on MedlinePlus
- Detailed Euthyrox (Levothroid/Levothyroxine) Consumer Information: Uses, Precautions, Side Effects
- U.S. National Library of Medicine: Drug Information Portal - Levothyroxine