22/02/2020 Levothyroxine - Wikipedia

Levothyroxine
Levothyroxine, also known as L-thyroxine, is a
Levothyroxine
manufactured form of the thyroid hormone thyroxine
(T4).[2][5] It is used to treat thyroid hormone deficiency,
including the severe form known as myxedema coma.[2] It
may also be used to treat and prevent certain types of
thyroid tumors.[2] It is not indicated for weight loss.[2]
Levothyroxine is taken by mouth or given by injection into
a vein.[2] Maximum effect from a specific dose can take up
to six weeks to occur.[2]

Side effects from excessive doses include weight loss,

trouble tolerating heat, sweating, anxiety, trouble sleeping,
tremor, and fast heart rate.[2] Use is not recommended in
people who have had a recent heart attack.[2] Use during Clinical data
pregnancy has been found to be safe.[2] It is recommended Trade names Synthroid, Levoxyl, Thyrax,
that dosing be based on regular measurements of thyroid- others
stimulating hormone (TSH) and T4 levels in the blood. [2]
Other names 3,5,3′,5′-Tetraiodo-L-
Much of the effect of levothyroxine is following its thyronine
conversion to triiodothyronine (T3).[2] AHFS/Drugs.com Monograph (https://www.dr
ugs.com/monograph/levoth
Levothyroxine was first made in 1927.[5] It is on the World
yroxine-sodium.html)
Health Organization's List of Essential Medicines, the
safest and most effective medicines needed in a health MedlinePlus a682461 (https://medlineplu
system.[6] Levothyroxine is available as a generic s.gov/druginfo/meds/a6824
medication.[2] The wholesale cost in the developing world 61.html)
is about US$0.58 to US$12.28 per month.[7] In the United License data EU EMA: by INN (http://ww
States, a typical month of treatment costs less than w.ema.europa.eu/ema/inde
US$25.[8] Levothyroxine was the most commonly x.jsp?curl=%2Fpages%2F
prescribed medication in the United States as of 2016, with medicines%2Flanding%2Fe
more than 114 million prescriptions.[9] par_search.jsp&mid=&sear
chTab=searchByKey&alrea
dyLoaded=true&isNewQuer
Contents y=true&status=Authorised&
status=Withdrawn&status=
Medical use Suspended&status=Refuse
Elderly d&keywordSearch=Submit
Pregnancy and breastfeeding &searchType=inn&taxonom
Children yPath=&treeNumber=&sear
Contraindications chGenericType=generics&k
eyword=Levothyroxine)
Side effects
US DailyMed: Levothyroxine
Interactions
(https://dailymed.nlm.nih.go
Mechanism of action v/dailymed/search.cfm?labe
Pharmacokinetics
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History ltype=all&query=Levothyrox
Society and culture ine)
Economics Pregnancy AU: A [1]
Available forms category
US: N (Not classified yet) [1]
References
Routes of By mouth, intravenous
External links administration
ATC code H03AA01 (WHO (https://ww
w.whocc.no/atc_ddd_inde
Medical use x/?code=H03AA01))
Levothyroxine is typically used to treat Legal status
hypothyroidism, [10] and is the treatment of choice for Legal status US: ℞-only
people with hypothyroidism,[11] who often require lifelong
thyroid hormone therapy.[12] Pharmacokinetic data
Bioavailability 40-80%[2]
It may also be used to treat goiter via its ability to lower Metabolism mainly in liver, kidneys,
thyroid-stimulating hormone (TSH), a hormone that is
brain and muscles
considered goiter-inducing.[13][14] Levothyroxine is also
Elimination ca. 7 days (in
used as interventional therapy in people with nodular half-life
thyroid disease or thyroid cancer to suppress TSH hyperthyroidism 3–4 days,
secretion.[15] A subset of people with hypothyroidism in hypothyroidism 9–
treated with an appropriate dose of levothyroxine will 10 days)
describe continuing symptoms despite TSH levels in the Excretion feces and urine
normal range.[12] In these people, further laboratory and Identifiers
clinical evaluation is warranted as they may have another
IUPAC name
cause for their symptoms.[12] Furthermore, it is important
CAS Number 51-48-9 (http://www.commo
to review their medications and possible dietary
supplements as several medications can affect thyroid nchemistry.org/ChemicalDe
hormone levels.[12] tail.aspx?ref=51-48-9)
6106-07-6 (http://www.com
Levothyroxine is also used to treat subclinical monchemistry.org/Chemical
hypothyroidism which is defined by an elevated TSH level Detail.aspx?ref=6106-07-6
and a normal-range free T4 level without symptoms.[12] &title=) (levothyroxine
Such people may be asymptomatic[12] and whether they sodium hydrate)
should be treated is controversial.[11] One benefit of PubChem CID 5819 (https://pubchem.ncbi.
treating this population with levothyroxine therapy is nlm.nih.gov/compound/581
preventing development of hypothyroidism.[11] As such, it 9)
is recommended that treatment should be taken into
DrugBank DB00451 (https://www.drug
account for patients with initial TSH levels above
10  mIU/L, people with elevated thyroid peroxidase bank.ca/drugs/DB00451)
antibody titers, people with symptoms of hypothyroidism ChemSpider 5614 (http://www.chemspid
and TSH levels between 5–10 mIU/L, and women who are er.com/Chemical-Structure.
pregnant or want to become pregnant.[11] Oral dosing for 5614.html)
patients with subclinical hypothyroidism is
[16] UNII Q51BO43MG4 (https://fdasi
1 μg/kg/day.
s.nlm.nih.gov/srs/srsdirect.j
It is also used to treat myxedema coma, which is a severe sp?regno=Q51BO43MG4)
form of hypothyroidism characterized by mental status KEGG D08125 (http://www.kegg.j
changes and hypothermia.[12] As it is a medical emergency p/entry/D08125)
with a high mortality rate, it should be treated in the
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intensive care unit[12] with thyroid hormone replacement ChEBI CHEBI:18332 (https://www.
and aggressive management of individual organ system ebi.ac.uk/chebi/searchId.d
complications.[11] o?chebiId=CHEBI:18332)
ChEMBL ChEMBL1624 (https://www.
Dosages vary according to the age groups and the
ebi.ac.uk/chembldb/index.p
individual condition of the person, body weight and
hp/compound/inspect/ChE
compliance to the medication and diet. Other predictors of
MBL1624)
the required dosage are sex, BMI, deiodinase activity
(SPINA-GD) and etiology of hypothyroidism.[17] Annual CompTox DTXSID8023214 (https://co
Dashboard (EPA)
or semiannual clinical evaluations and TSH monitoring are mptox.epa.gov/dashboard/
appropriate after dosing has been established.[18] DTXSID8023214)
Levothyroxine is taken on an empty stomach ECHA InfoCard 100.000.093 (https://echa.e
approximately half an hour to an hour before meals.[19] As uropa.eu/substance-inform
such, thyroid replacement therapy is usually taken ation/-/substanceinfo/100.0
30 minutes prior to eating in the morning.[12] For patients 00.093)
with trouble taking levothyroxine in the morning, bedtime
Chemical and physical data
dosing is effective as well.[12] A 2015 study showed
greater efficacy of levothyroxine when taken at Formula C15H11I4NO4
bedtime.[20] Doses of levothyroxine that normalize serum Molar mass 776.874 g·mol−1
TSH may not normalize abnormal levels of LDL 3D model Interactive image (https://ch
cholesterol and total cholesterol.[21] (JSmol)
emapps.stolaf.edu/jmol/jmo
Poor compliance in taking the medicine is the most l.php?model=NC%28Cc1c
common cause of elevated TSH levels in people receiving c%28I%29c%28Oc2cc%28
appropriate doses of levothyroxine.[12] I%29c%28O%29c%28I%29
c2%29c%28I%29c1%29
C%28O%29%3DO)
Elderly Melting point 231 to 233 °C (448 to
For older people (over 50  years old) and people with 451 °F) [4]
known or suspected ischemic heart disease, levothyroxine Solubility in Slightly soluble
therapy should not be initiated at the full replacement water (0.105 mg·mL−1 at
dose.[22] Since thyroid hormone increases the heart's 25 °C)[3] mg/mL (20 °C)
oxygen demand by increasing heart rate and contractility,
SMILES
starting at higher doses may cause an acute coronary
syndrome or an abnormal heart rhythm.[12] InChI

Pregnancy and breastfeeding

According to the U.S. Food and Drug Administration (FDA)
pregnancy categories, levothyroxine has been assigned Pregnancy
Category A.[22] Given that no increased risk of congenital
abnormalities have been demonstrated in pregnant women taking
levothyroxine, therapy should be continued during pregnancy.[22]
Furthermore, therapy should be immediately administered to women Generic levothyroxine, 25 μg oral
diagnosed with hypothyroidism during pregnancy, as tablet
hypothyroidism is associated with a higher rate of complications,
such as spontaneous abortion, preeclampsia, and premature birth.[22]

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Thyroid hormone requirements increase during and last throughout pregnancy.[12] As such, it is
recommended that pregnant women increase to nine doses of levothyroxine each week, rather than the usual
seven, as soon as their pregnancy is confirmed.[12] Repeat thyroid function tests should be done five weeks
after the dosage is increased.[12]

While a minimal amount of thyroid hormones are found in breast milk, the amount does not influence infant
plasma thyroid levels.[16] Furthermore, levothyroxine was not found to cause any adverse events to the
infant or mother during breastfeeding.[16] As adequate concentrations of thyroid hormone are required to
maintain normal lactation, it is recommended that appropriate levothyroxine doses be administered during
breastfeeding.[16]

Children
Levothyroxine is safe and effective for children with hypothyroidism; the goal of treatment for children with
hypothyroidism is to reach and preserve normal intellectual and physical development.[22]

Contraindications
Levothyroxine is contraindicated in people with hypersensitivity to levothyroxine sodium or any component
of the formulation, people with acute myocardial infarction, and people with thyrotoxicosis of any
etiology.[16] Levothyroxine is also contraindicated for people with uncorrected adrenal insufficiency, as
thyroid hormones may cause an acute adrenal crisis by increasing the metabolic clearance of
glucocorticoids.[22] For oral tablets, the inability to swallow capsules serves as an additional
contraindication.[16]

Side effects
Adverse events are generally caused by incorrect dosing. 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).[23]

Too high a dose of levothyroxine causes hyperthyroidism.[19][24][25] Overdose can result in heart
palpitations, abdominal pain, nausea, anxiousness, confusion, agitation, insomnia, weight loss, and increased
appetite.[26][24] 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.[19]

The effects of overdosing appear 6 hours to 11 days after ingestion.[26]

Interactions
There are many foods and other substances that can interfere with absorption of thyroxine. Substances that
reduce absorption are aluminium and magnesium containing antacids, simethicone, sucralfate,
cholestyramine, colestipol, and polystyrene sulfonate. 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.[27][28] A study of eight women suggested that coffee
may interfere with the intestinal absorption of levothyroxine, though at a level less than eating bran.[29]
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Certain other substances can cause adverse effects that may be severe. Combination of levothyroxine with
ketamine may cause hypertension and tachycardia;[30] 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.[31] Soy,
cottonseed meal, walnuts, fiber, calcium supplements and iron supplements can also adversely affect
absorption.[27] A study found that cow's milk reduces levothyroxine absorption.[32]

To minimize interactions, a manufacturer of levothyroxine recommends waiting 30 minutes to one hour

before eating or drinking anything that is not water. They further recommend to take it in the morning on an
empty stomach.[27]

Mechanism of action
Levothyroxine is a synthetic form of thyroxine (T4), an endogenous hormone secreted by the thyroid gland,
which is converted to its active metabolite, L-triiodothyronine (T3).[22] T4 and T3 bind to thyroid receptor
proteins in the cell nucleus and cause metabolic effects through the control of DNA transcription and protein
synthesis.[22] Like its naturally secreted counterpart, levothyroxine is a chiral compound in the L-form.

Pharmacokinetics
Absorption of orally administered levothyroxine from the gastrointestinal tract ranges from 40 to 80%, with
the majority of the drug absorbed from the jejunum and upper ileum.[22] Levothyroxine absorption is
increased by fasting and decreased in certain malabsorption syndromes, by certain foods, and with age. The
bioavailability of the drug is decreased by dietary fiber.[22]

Greater than 99% of circulating thyroid hormones are bound to plasma proteins including thyroxine-binding
globulin, transthyretin (previously called 'thyroxine-binding prealbumin'), and albumin.[16] Only free
hormone is metabolically active.[16]

The primary pathway of thyroid hormone metabolism is through sequential deiodination.[22] The liver is the
main site of T4 deiodination, and along with the kidneys are responsible for about 80% of circulating T3.[33]
In addition to deiodination, thyroid hormones are also excreted through the kidneys and metabolized
through conjugation and glucuronidation and excreted directly into the bile and the gut where they undergo
enterohepatic recirculation.[16]

Half-life elimination is 6–7  days for people with normal lab results; 9–10  days for people with
hypothyroidism; 3–4 days for people with hyperthyroidism.[16] Thyroid hormones are primarily eliminated
by the kidneys (approximately 80%), with urinary excretion decreasing with age.[16] The remaining 20% of
T4 eliminated in the stool.[16]

History
Thyroxine was first isolated in pure form in 1914 at the Mayo Clinic by Edward Calvin Kendall from
extracts of hog thyroid glands.[34] The hormone was synthesized in 1927 by British chemists Charles Robert
Harington and George Barger.

Society and culture

Economics
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As of 2011, levothyroxine was the second most commonly prescribed medication in the U.S.,[35] with
23.8 million prescriptions filled each year.[36]

In 2016, it became the most commonly prescribed medication in the U.S., with more than 114 million
prescriptions.[9]

Available forms
Levothyroxine for systemic administration is available as an oral tablet, an intramuscular injection, and as a
solution for intravenous infusion.[16] Furthermore, levothyroxine is available as both brand-name and
generic products.[12] While the FDA approved the use of generic levothyroxine for brand-name
levothyroxine in 2004, the decision was met with disagreement by several medical associations.[12] The
American Association of Clinical Endocrinologists (AACE), the Endocrine Society, and the American
Thyroid Association did not agree with the FDA that brand-name and generic formulations of levothyroxine
were bioequivalent.[12] As such, it was recommended that people be started and kept on either brand-name
or generic levothyroxine formulations and not changed back and forth from one to the other.[12] For people
who do switch products, it is recommended that their TSH and free T4 levels be tested after six weeks to
check that they are within normal range.[12]

Common brand names include Eltroxin, Euthyrox, Eutirox, Letrox, Levaxin, Lévothyrox, Levoxyl, L-
thyroxine, Thyrax, and Thyrax Duotab in Europe; Thyrox, Thyronorm in South Asia; Unithroid, Eutirox,
Synthroid, and Tirosint in North and South America; and Thyrin and Thyrolar in Bangladesh. There are also
numerous generic versions.

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.

References
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External links
"Levothyroxine" (https://druginfo.nlm.nih.gov/drugportal/name/levothyroxine). Drug Information
Portal. U.S. National Library of Medicine.

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