Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H10I4NO4.Na.H2O |
Molecular Weight | 816.8671 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C([O-])=O
InChI
InChIKey=ANMYAHDLKVNJJO-LTCKWSDVSA-M
InChI=1S/C15H11I4NO4.Na.H2O/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);;1H2/q;+1;/p-1/t12-;;/m0../s1
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | HO |
Molecular Weight | 17.0073 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C15H11I4NO4 |
Molecular Weight | 776.87 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00451Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/levothyroxine.html
Sources: http://www.drugbank.ca/drugs/DB00451
Curator's Comment: Description was created based on several sources, including
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1860 Sources: http://www.drugbank.ca/drugs/DB00451 |
|||
Target ID: CHEMBL1947 Sources: http://www.drugbank.ca/drugs/DB00451 |
0.136 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Synthroid Approved UseLevothyroxine 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 Date1.02738238E12 |
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Primary | Synthroid Approved UseLevothyroxine 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 Date1.02738238E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
76.64 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30153382 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1764.14 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30153382 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.04% |
unknown, unknown |
LEVOTHYROXINE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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 n = 1 Health Status: healthy Age Group: 22 months Sex: M Population Size: 1 Sources: |
Other AEs: Hypertension, Tachycardia... Other AEs: Hypertension (grade 1) Sources: Tachycardia (grade 1) |
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 n = 1 Health Status: healthy Age Group: 30 months Sex: M Population Size: 1 Sources: |
Other AEs: Hyperthyroidism, Seizures... |
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 n = 36 Health Status: healthy Age Group: mean age 35 years Sex: M+F Population Size: 36 Sources: |
Disc. AE: Alanine aminotransferase increased... AEs leading to discontinuation/dose reduction: Alanine aminotransferase increased (2.8%) Sources: |
50 ug steady, oral (total daily dose) Dose: 50 ug Route: oral Route: steady Dose: 50 ug Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Graves Disease Population Size: 30 Sources: |
Other AEs: Atrial fibrillation, Palpitations... Other AEs: Atrial fibrillation (serious, 1 patient) Sources: Palpitations (below serious, 3 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 n = 1 Health Status: healthy Age Group: 22 months Sex: M Population Size: 1 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 n = 1 Health Status: healthy Age Group: 22 months Sex: M Population Size: 1 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 n = 1 Health Status: healthy Age Group: 30 months Sex: M Population Size: 1 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 n = 1 Health Status: healthy Age Group: 30 months Sex: M Population Size: 1 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 n = 36 Health Status: healthy Age Group: mean age 35 years Sex: M+F Population Size: 36 Sources: |
Palpitations | below serious, 3 patients | 50 ug steady, oral (total daily dose) Dose: 50 ug Route: oral Route: steady Dose: 50 ug Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Graves Disease Population Size: 30 Sources: |
Atrial fibrillation | serious, 1 patient | 50 ug steady, oral (total daily dose) Dose: 50 ug Route: oral Route: steady Dose: 50 ug Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Graves Disease Population Size: 30 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15258100/ |
no | |||
no | ||||
weak | ||||
weak | ||||
yes [IC50 15.4 uM] | ||||
yes [IC50 3.3 uM] | ||||
yes [IC50 4.9 uM] | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
Sources: https://go.drugbank.com/drugs/DB00451 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
[Hereditary thyroxin-binding globulin deficiency--changed thyroid function tests]. | 2001 Apr 30 |
|
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 |
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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 |
|
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 |
|
[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 |
|
[Concentration of thyrotropic hormone and free thyroxin in children with Down's syndrome]. | 2001 Jun |
|
[High levels of carcinoembryonic antigen in a woman with hypothyroidism]. | 2001 Jun 2 |
|
[The changes of PCBs and PCDFs as well as symptoms in Yusho patients for 30 years]. | 2001 May |
|
The various effects of amiodarone on thyroid function. | 2001 May |
|
[Morphological characteristics of placenta and hormonal balance in hyperthyroidism of pregnancy]. | 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/levothyroxine.html
Usual Adult Dose for Hypothyroidism
Average full replacement dose: 1.7 mcg/kg/day (e.g., 100 to 125 mcg/day for a 70 kg adult) orally
Older patients may require less than 1 mcg/kg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25447738
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 00:10:00 UTC 2023
by
admin
on
Sat Dec 16 00:10:00 UTC 2023
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Record UNII |
B82379R9W0
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Record Status |
Validated (UNII)
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Record Version |
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-
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English |
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23667619
Created by
admin on Sat Dec 16 00:10:00 UTC 2023 , Edited by admin on Sat Dec 16 00:10:00 UTC 2023
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PRIMARY | |||
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LEVOTHYROXINE SODIUM MONOHYDRATE
Created by
admin on Sat Dec 16 00:10:00 UTC 2023 , Edited by admin on Sat Dec 16 00:10:00 UTC 2023
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PRIMARY | Description: An almost white or slightly coloured powder, or a fine, slightly coloured, crystalline powder; odourless. Solubility: Very slightly soluble in water; slightly soluble in ethanol (~750 g/L) TS; practically insoluble in acetone R and ether R. It dissolves in solutions of alkali hydroxides. Category: Thyroid hormone. Storage: Levothyroxine sodium should be kept in a tightly closed container, protected from light.Additional information: Levothyroxine sodium may contain a variable quantity of water of crystallization; anhydrous levothyroxine sodium is hygroscopic.Definition: Levothyroxine sodium contains not less than 97.0% and not more than 101.0% of C15H10I4NNaO4, calculated with reference to the dried substance. | ||
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31178-59-3
Created by
admin on Sat Dec 16 00:10:00 UTC 2023 , Edited by admin on Sat Dec 16 00:10:00 UTC 2023
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PRIMARY | |||
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B82379R9W0
Created by
admin on Sat Dec 16 00:10:00 UTC 2023 , Edited by admin on Sat Dec 16 00:10:00 UTC 2023
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PRIMARY |
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