U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H11I4NO4
Molecular Weight 776.8706
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOTHYROXINE

SMILES

c1c(cc(c(c1I)Oc2cc(c(c(c2)I)O)I)I)C[C@@]([H])(C(=O)O)N

InChI

InChIKey=XUIIKFGFIJCVMT-LBPRGKRZSA-N
InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.drugs.com/dosage/levothyroxine.html

Levothyroxine (T4) is a synthetically prepared levo isomer of thyroxine, the major hormone secreted from the thyroid gland. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine (T3) which exerts a broad spectrum of stimulatory effects on cell metabolism. Thyroid hormone increases the metabolic rate of cells of all tissues in the body. In the fetus and newborn, thyroid hormone is important for the growth and development of all tissues including bones and the brain. In adults, thyroid hormone helps to maintain brain function, food metabolism, and body temperature, among other effects. The symptoms of thyroid deficiency relieved by levothyroxine include slow speech, lack of energy, weight gain, hair loss, dry thick skin and unusual sensitivity to cold. Levothyroxine acts like the endogenous thyroid hormone thyroxine (T4, a tetra-iodinated tyrosine derivative). In the liver and kidney, T4 is converted to T3, the active metabolite. In order to increase solubility, the thyroid hormones attach to thyroid hormone binding proteins, thyroxin-binding globulin, and thyroxin-binding prealbumin (transthyretin). Transport and binding to thyroid hormone receptors in the cytoplasm and nucleus then takes place. Thus by acting as a replacement for natural thyroxine, symptoms of thyroxine deficiency are relieved. Levothyroxine is used for use alone or in combination with antithyroid agents to treat hypothyroidism, goiter, chronic lymphocytic thyroiditis, myxedema coma, and stupor.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Synthroid

Approved Use

Levothyroxine tablets are used for the following indications: Hypothyroidism As replacement or supplemental therapy in congenital or acquired hypothyroidism of any etiology, except transient hypothyroidism during the recovery phase of subacute thyroiditis. Specific indications include: primary (thyroidal), secondary (pituitary), and tertiary (hypothalamic) hypothyroidism and subclinical hypothyroidism. Primary hypothyroidism may result from functional deficiency, primary atrophy, partial or total congenital absence of the thyroid gland, or from the effects of surgery, radiation, or drugs, with or without the presence of goiter. Pituitary TSH Suppression In the treatment or prevention of various types of euthyroid goiters, including thyroid nodules, subacute or chronic lymphocytic thyroiditis (Hashimoto’s thyroiditis), multinodular goiter and, as an adjunct to surgery and radioiodine therapy in the management of thyrotropin-dependent well differentiated thyroid cancer.

Launch Date

1027382400000
Primary
Synthroid

Approved Use

Levothyroxine tablets are used for the following indications: Hypothyroidism As replacement or supplemental therapy in congenital or acquired hypothyroidism of any etiology, except transient hypothyroidism during the recovery phase of subacute thyroiditis. Specific indications include: primary (thyroidal), secondary (pituitary), and tertiary (hypothalamic) hypothyroidism and subclinical hypothyroidism. Primary hypothyroidism may result from functional deficiency, primary atrophy, partial or total congenital absence of the thyroid gland, or from the effects of surgery, radiation, or drugs, with or without the presence of goiter. Pituitary TSH Suppression In the treatment or prevention of various types of euthyroid goiters, including thyroid nodules, subacute or chronic lymphocytic thyroiditis (Hashimoto’s thyroiditis), multinodular goiter and, as an adjunct to surgery and radioiodine therapy in the management of thyrotropin-dependent well differentiated thyroid cancer.

Launch Date

1027382400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
76.64 ng/mL
600 μg single, oral
dose: 600 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOTHYROXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1764.14 ng × h/mL
600 μg single, oral
dose: 600 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOTHYROXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.2 day
unknown, unknown
LEVOTHYROXINE serum
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
7.5 h
unknown, unknown
LEVOTHYROXINE serum
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.04%
unknown, unknown
LEVOTHYROXINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5.7 mg 1 times / day single, oral
Studied dose
Dose: 5.7 mg, 1 times / day
Route: oral
Route: single
Dose: 5.7 mg, 1 times / day
Sources:
healthy, 22 months
Health Status: healthy
Age Group: 22 months
Sex: M
Sources:
Other AEs: Hypertension, Tachycardia...
Other AEs:
Hypertension (grade 1)
Tachycardia (grade 1)
Sources:
18 mg 1 times / day single, oral
Studied dose
Dose: 18 mg, 1 times / day
Route: oral
Route: single
Dose: 18 mg, 1 times / day
Sources:
healthy, 30 months
Health Status: healthy
Age Group: 30 months
Sex: M
Sources:
Other AEs: Hyperthyroidism, Seizures...
Other AEs:
Hyperthyroidism
Seizures
Sources:
600 ug 1 times / day single, oral
Studied dose
Dose: 600 ug, 1 times / day
Route: oral
Route: single
Dose: 600 ug, 1 times / day
Sources:
healthy, mean age 35 years
Health Status: healthy
Age Group: mean age 35 years
Sex: M+F
Sources:
Disc. AE: Alanine aminotransferase increased...
AEs leading to
discontinuation/dose reduction:
Alanine aminotransferase increased (2.8%)
Sources:
50 ug steady, oral
Dose: 50 ug
Route: oral
Route: steady
Dose: 50 ug
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Atrial fibrillation, Palpitations...
Other AEs:
Atrial fibrillation (serious, 1 patient)
Palpitations (below serious, 3 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertension grade 1
5.7 mg 1 times / day single, oral
Studied dose
Dose: 5.7 mg, 1 times / day
Route: oral
Route: single
Dose: 5.7 mg, 1 times / day
Sources:
healthy, 22 months
Health Status: healthy
Age Group: 22 months
Sex: M
Sources:
Tachycardia grade 1
5.7 mg 1 times / day single, oral
Studied dose
Dose: 5.7 mg, 1 times / day
Route: oral
Route: single
Dose: 5.7 mg, 1 times / day
Sources:
healthy, 22 months
Health Status: healthy
Age Group: 22 months
Sex: M
Sources:
Hyperthyroidism
18 mg 1 times / day single, oral
Studied dose
Dose: 18 mg, 1 times / day
Route: oral
Route: single
Dose: 18 mg, 1 times / day
Sources:
healthy, 30 months
Health Status: healthy
Age Group: 30 months
Sex: M
Sources:
Seizures
18 mg 1 times / day single, oral
Studied dose
Dose: 18 mg, 1 times / day
Route: oral
Route: single
Dose: 18 mg, 1 times / day
Sources:
healthy, 30 months
Health Status: healthy
Age Group: 30 months
Sex: M
Sources:
Alanine aminotransferase increased 2.8%
Disc. AE
600 ug 1 times / day single, oral
Studied dose
Dose: 600 ug, 1 times / day
Route: oral
Route: single
Dose: 600 ug, 1 times / day
Sources:
healthy, mean age 35 years
Health Status: healthy
Age Group: mean age 35 years
Sex: M+F
Sources:
Palpitations below serious, 3 patients
50 ug steady, oral
Dose: 50 ug
Route: oral
Route: steady
Dose: 50 ug
Sources:
unhealthy
Health Status: unhealthy
Sources:
Atrial fibrillation serious, 1 patient
50 ug steady, oral
Dose: 50 ug
Route: oral
Route: steady
Dose: 50 ug
Sources:
unhealthy
Health Status: unhealthy
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Improved antibody coating protocol using a second antibody antiserum. Application to total thyroxin immunoassay.
2001
A case of pulmonary metastatic thyroid cancer complicated with Graves' disease.
2001 Apr
Graves' disease presenting as elephantiasic pretibial myxedema and nodules of the hands.
2001 Apr
[Destabilizing effect of chicken selection using the functional adrenal reserves criteria].
2001 Apr
Development of hypertensive status in NISAG rats reared by normotensive Wistar rats.
2001 Aug
Hyperthyroidism affects lipid metabolism in lactating and suckling rats.
2001 Aug
Effect of treatment of hypothyroidism on the plasma concentrations of neuroactive steroids and homocysteine.
2001 Aug
Managing hypothyroidism during pregnancy.
2001 Aug
Noncompliance with medical treatment: pseudomalabsorption of levothyroxine.
2001 Aug
Lack of substantial effects of raloxifene on thyroxine-binding globulin in postmenopausal women: dependency on thyroid status.
2001 Aug
Effects of thyroid hormone deficiency on electrocardiogram findings of congenitally hypothyroid neonates.
2001 Aug
Management practices among primary care physicians and thyroid specialists in the care of hypothyroid patients.
2001 Aug
Tall cell papillary thyroid carcinoma metastatic to femur: evidence for thyroid hormone synthesis within the femur.
2001 Aug
Thyroid hormones and thyroid antibodies in infertile males.
2001 Aug
Developmental landmarks in offspring of rats exposed singly and in combination to Aroclor 1016 and levothyroxine.
2001 Aug
The human type 2 iodothyronine deiodinase is a selenoprotein highly expressed in a mesothelioma cell line.
2001 Aug 10
Confusion over levothyroxine settled.
2001 Aug 15
Congenital hypothyroidism in a child with unsuspected familial dysalbuminemic hyperthyroxinemia caused by a mutation (R218H) in the human albumin gene.
2001 Dec
Characterization of human liver thermostable phenol sulfotransferase (SULT1A1) allozymes with 3,3',5-triiodothyronine as the substrate.
2001 Dec
The role of thyroid hormone administration in potential organ donors.
2001 Dec
Coronary bypass surgery in patients with Sheehan's syndrome.
2001 Dec
Bone mass after long-term euthyroidism in former hyperthyroid women treated with (131)I influence of menopausal status.
2001 Fall
Thyroid hormone deficiency determines predisposition to catalepsy in rats.
2001 Jul
Age-related changes of protein- and RNA-synthetic processes in experimental hyper- and hypothyroidism.
2001 Jul
Association between weight gain, blood parameters, and thyroid hormones and the development of ascites syndrome in broiler chickens.
2001 Jul
Stimulated healing of recalcitrant wounds by topical application of enriched cell culture medium: a clinical report.
2001 Jul
What is going on with levothyroxine.
2001 Jul 9
[Treatment of euthyroid goiter in the elderly].
2001 Jul-Aug
[Euthyroid Graves' disease (problems of diagnosis and treatment)].
2001 Jul-Aug
Five-year mortality in men and women with atrial fibrillation.
2001 Jun
The use of oral radiographic contrast agents in the management of hyperthyroidism.
2001 Jun
[The changes of PCBs and PCDFs as well as symptoms in Yusho patients for 30 years].
2001 May
[Morphological characteristics of placenta and hormonal balance in hyperthyroidism of pregnancy].
2001 May-Jun
Use of soy protein supplement and resultant need for increased dose of levothyroxine.
2001 May-Jun
Usefulness of recombinant human thyrotropin in the radiometabolic treatment of selected patients with thyroid cancer.
2001 Nov
I take Synthroid for my underactive thyroid. What should I do if it is discontinued?
2001 Nov
Treatment of hypothyroidism.
2001 Nov 15
Papillary carcinoma in thyroglossal duct cyst.
2001 Nov-Dec
Thyroid function test abnormalities in newly admitted psychiatric patients residing in an iodine-deficient area: patterns and clinical significance.
2001 Oct
The acute effect of calcium carbonate on the intestinal absorption of levothyroxine.
2001 Oct
Effect of 131 iodine therapy on the course of Graves' ophthalmopathy: a quantitative analysis of extraocular muscle volumes using orbital magnetic resonance imaging.
2001 Oct
Functional evidence for the presence of type II 5'-deiodinase in somatotropes and its adaptive role in hypothyroidism.
2001 Oct
Prevalence and characteristics of postpartum thyroid dysfunction in Tehran.
2001 Oct
Abbott files NDA, will continue to distribute synthroid.
2001 Oct 1
Thyroid hormones modify susceptibility to lidocaine-kindling in rats.
2001 Oct 19
[Screening for thyroid disease. Occurrence of hypothyroidism and hyperthyroidism in patients admitted to a geriatric department].
2001 Oct 8
Acute aortic dissection associated with Sheehan's syndrome.
2001 Sep
Molecular cloning and sequence of Sparus aurata skeletal myosin light chains expressed in white muscle: developmental expression and thyroid regulation.
2001 Sep
Soluble Fas is increased in hyperthyroidism independent of the underlying thyroid disease.
2001 Sep
[RTH syndrome--resistance to thyroid hormone syndrome].
2001 Sep 10
Patents

Sample Use Guides

Usual Adult Dose for Hypothyroidism
Route of Administration: Oral
Addition of Levothyroxine at concentrations of 100-200 nM rescued rat cerebellar granule neurons (CGNs) from cell death in K5 in a dose-dependent manner. 200 nM T4 was also effective in maintaining the neurites of CGNs in K5.
Name Type Language
LEVOTHYROXINE
HSDB   USP-RS   VANDF   WHO-DD  
Common Name English
LIOTHYRONINE SODIUM IMPURITY A [EP]
Common Name English
SYNTHETIC LEVOTHYROXINE
Common Name English
LEVOTHYROXINE [VANDF]
Common Name English
O-(4-HYDROXY-3,5-DIIODOPHENYL)-3,5-DIIODO-L-TYROSINE
Systematic Name English
SK&F 1-6528
Code English
LEVOTHYROXINE [USP-RS]
Common Name English
LEVOTHYROXIN
Common Name English
L-THYROXINE
Common Name English
NSC-36397
Code English
THYROXINE, L-
Common Name English
3,5,3',5'-TETRAIODO-L-THYRONINE
Systematic Name English
T4
Common Name English
L-TYROSINE, O-(4-HYDROXY-3,5-DIIODOPHENYL)-3,5-DIIODO-
Systematic Name English
THYROXINE
MI  
Common Name English
LEVOTHYROXINE [WHO-DD]
Common Name English
(-)-3-(4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL)ALANINE
Systematic Name English
LEVOTHYROXINE [HSDB]
Common Name English
THYROXINE [MI]
Common Name English
Classification Tree Code System Code
LOINC 14921-1
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 73557-1
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
CFR 21 CFR 520.1248
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LOINC 27000-9
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LOINC 35228-6
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LOINC 14920-3
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LOINC 3024-7
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
CFR 21 CFR 862.1685
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 18.8
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LOINC 83121-4
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LOINC 3028-8
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LOINC 83119-8
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WHO-ATC H03AA03
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NDF-RT N0000007632
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LIVERTOX 958
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 20451-1
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LOINC 6892-4
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LOINC 31145-6
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LOINC 31144-9
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LOINC 35226-0
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NCI_THESAURUS C1553
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LOINC 83120-6
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LOINC 70217-5
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
NCI_THESAURUS C886
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 38506-2
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
WHO-VATC QH03AA03
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 70152-4
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LOINC 53350-5
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CFR 21 CFR 862.1700
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 83122-2
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 3027-0
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
CFR 21 CFR 862.1695
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 53349-7
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 3025-4
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
LOINC 3026-2
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
NDF-RT N0000175945
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
Code System Code Type Description
FDA UNII
Q51BO43MG4
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
CAS
51-48-9
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
NCI_THESAURUS
C62080
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
DRUG BANK
DB00451
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL1624
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
LACTMED
Levothyroxine
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
DRUG CENTRAL
2646
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
HSDB
3108
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-101-1
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
EVMPD
SUB02917MIG
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
USP_CATALOG
1365000
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY USP-RS
RXCUI
10582
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY RxNorm
IUPHAR
2635
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
WIKIPEDIA
LEVOTHYROXINE
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
MERCK INDEX
M10840
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY Merck Index
MESH
D013974
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
EPA CompTox
51-48-9
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
EVMPD
SUB127246
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY
PUBCHEM
5819
Created by admin on Fri Jun 25 21:46:30 UTC 2021 , Edited by admin on Fri Jun 25 21:46:30 UTC 2021
PRIMARY