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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Levothyroxine
- Accession Number
- DB00451 (APRD00235, EXPT02993)
- Type
- Small Molecule
- Groups
- Approved
- Description
The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism.
- Structure
Structure for DB00451 (Levothyroxine)
- Synonyms
- 3,3',5,5'-Tetraiodo-L-thyronine
- 3,5,3',5'-TETRAIODO-L-thyronine
- 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine
- L-T4
- L-Thyroxine
- Levothyroxin
- LT4
- O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine
- O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine
- T4
- Product Ingredients
Ingredient UNII CAS InChI Key Levothyroxine sodium 054I36CPMN 55-03-8 YDTFRJLNMPSCFM-UHFFFAOYSA-M - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Eltroxin Tablet 200 mcg Oral Aspen Pharmacare Canada Inc. 1997-04-02 Not applicable Canada 
Eltroxin Tablet 150 mcg Oral Aspen Pharmacare Canada Inc. 1974-12-31 Not applicable Canada Eltroxin Tablet 100 mcg Oral Aspen Pharmacare Canada Inc. 1998-11-27 Not applicable Canada Eltroxin Tablet 300 mcg Oral Aspen Pharmacare Canada Inc. 1998-02-11 Not applicable Canada Eltroxin Tablet 50 mcg Oral Aspen Pharmacare Canada Inc. 1951-12-30 Not applicable Canada Eltroxin 150 Tab Tablet 150 mcg Oral Glaxo Canada Inc 1974-12-31 1999-08-12 Canada Eltroxin Tab 100mcg Tablet .1 mg Oral Glaxo Canada Inc 1951-12-31 1999-08-12 Canada Eltroxin Tab 200mcg Tablet .2 mg Oral Glaxo Canada Inc 1960-12-31 1998-07-30 Canada Eltroxin Tab 300mcg Tablet .3 mg Oral Glaxo Canada Inc 1966-12-31 1998-07-30 Canada Eltroxin Tab 50mcg Tablet .05 mg Oral Glaxo Canada Inc 1951-12-31 1998-07-30 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Levothyroxine Tablet 125 ug/1 Oral Northwind Pharmaceuticals 2014-09-14 Not applicable US 
Levothyroxine Sodium Tablet 100 ug/1 Oral Physicians Total Care, Inc. 2007-09-17 Not applicable US Levothyroxine sodium Tablet 50 ug/1 Oral Sandoz 2002-03-01 Not applicable US Levothyroxine sodium Tablet 100 ug/1 Oral bryant ranch prepack 2002-03-01 Not applicable US Levothyroxine sodium Tablet 100 ug/1 Oral Nu Care Pharmaceuticals,inc. 2002-03-01 Not applicable US Levothyroxine Sodium Tablet 175 ug/1 Oral Mylan Pharmaceuticals 2002-11-01 Not applicable US Levothyroxine Sodium Tablet 100 ug/1 Oral Cardinal Health 2010-10-29 Not applicable US Levothyroxine Sodium Tablet .125 mg/1 Oral Physicians Total Care, Inc. 1994-10-06 Not applicable US Levothyroxine sodium Tablet 200 ug/1 Oral Sandoz 2002-03-01 Not applicable US 
Levothyroxine Sodium Tablet 88 ug/1 Oral Remedy Repack 2013-07-05 2016-10-13 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Thyrolar Levothyroxine sodium (12.5 ug/1) + Liothyronine Sodium (3.1 ug/1) Tablet Oral Allergan 1969-11-21 Not applicable US Thyrolar Levothyroxine sodium (50 ug/1) + Liothyronine Sodium (12.5 ug/1) Tablet Oral Allergan 1969-11-21 Not applicable US Thyrolar Levothyroxine sodium (150 ug/1) + Liothyronine Sodium (37.5 ug/1) Tablet Oral Allergan 1969-11-21 Not applicable US Thyrolar Levothyroxine sodium (25 ug/1) + Liothyronine Sodium (6.25 ug/1) Tablet Oral Allergan 1969-11-21 Not applicable US Thyrolar Levothyroxine sodium (100 ug/1) + Liothyronine Sodium (25 ug/1) Tablet Oral Allergan 1969-11-21 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Levothyroxine and Liothyronine Thyroid Levothyroxine (19 ug/1) + Liothyronine (4.5 ug/1) Tablet Oral Westminster 2017-09-19 Not applicable US Levothyroxine and Liothyronine Thyroid Levothyroxine (57 ug/1) + Liothyronine (13.5 ug/1) Tablet Oral Westminster 2017-09-19 Not applicable US Levothyroxine and Liothyronine Thyroid Levothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1) Tablet Oral Westminster 2017-11-15 Not applicable US Levothyroxine and Liothyronine Thyroid Levothyroxine (38 ug/1) + Liothyronine (9 ug/1) Tablet Oral Westminster 2017-09-19 Not applicable US Levothyroxine and Liothyronine Thyroid Levothyroxine (76 ug/1) + Liothyronine (18 ug/1) Tablet Oral Westminster 2017-11-15 Not applicable US NP Thyroid 120 Levothyroxine (76 ug/1) + Liothyronine (18 ug/1) Tablet Oral Acella Pharmaceuticals, LLC 2010-11-11 Not applicable US NP Thyroid 120 Levothyroxine (76 ug/1) + Liothyronine (18 ug/1) Tablet Oral Preferreed Pharmaceuticals Inc. 2017-10-12 Not applicable US NP Thyroid 15 Levothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1) Tablet Oral Preferreed Pharmaceuticals Inc. 2017-10-12 Not applicable US NP Thyroid 15 Levothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1) Tablet Oral Acella Pharmaceuticals, LLC 2010-11-11 Not applicable US NP Thyroid 30 Levothyroxine (19 ug/1) + Liothyronine (4.5 ug/1) Tablet Oral Acella Pharmaceuticals, LLC 2010-11-11 Not applicable US - International/Other Brands
- Eutirox (Merck) / Letrox (Berlin-Chemie) / Levaxin (Nycomed) / Levothyrox (Merck) / Novothyrox / Oroxine (GlaxoSmithKline) / Thyrax (Merck)
- Categories
- Amino Acids
- Amino Acids, Aromatic
- Amino Acids, Cyclic
- Amino Acids, Peptides, and Proteins
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- P-glycoprotein/ABCB1 Inducers
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Thyroid Agents
- Thyroid Hormones
- Thyroid Preparations
- Thyroid Products
- Thyroid Therapy
- Thyroxine
- UNII
- Q51BO43MG4
- CAS number
- 51-48-9
- Weight
- Average: 776.87
Monoisotopic: 776.686681525 - Chemical Formula
- C15H11I4NO4
- InChI Key
- XUIIKFGFIJCVMT-LBPRGKRZSA-N
- InChI
- 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
- IUPAC Name
- (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
- SMILES
- N[[email protected]@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O
Pharmacology
- Indication
For use alone or in combination with antithyroid agents to treat hypothyroidism, goiter, chronic lymphocytic thyroiditis, myxedema coma, and stupor.
- Structured Indications
- Pharmacodynamics
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.
- Mechanism of action
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.
Target Actions Organism AThyroid hormone receptor alpha agonistHuman AThyroid hormone receptor beta agonistHuman - Absorption
Bioavailability varies from 48% to 80%. Human studies have confirmed the importance of an intact jejunum and ileum for levothyroxine absorption and have shown some absorption from the duodenum.
- Volume of distribution
- Not Available
- Protein binding
> 99% to serum proteins, including thyroxine-binding globulin (TBG), thyroxine-binding prealbumin (TBPA), and albumin (TBA)
- Metabolism
Approximately 70% of secreted T4 is deiodinated to equal amounts of T3 and reverse triiodothyronine (rT3), which is calorigenically inactive. Elimination of T4 and T3 involves hepatic conjugation to glucuronic and sulfuric acids. The hormones undergo enterohepatic circulation as conjugates are hydrolyzed in the intestine and reabsorbed. Conjugated compounds that reach the colon are hydrolyzed and eliminated as free compounds in the feces. Other minor T4 metabolites have been identified.
- Route of elimination
Thyroid hormones are primarily eliminated by the kidneys.
- Half life
T4, 6 to 7 days. T3, 1 to 2 days.
- Clearance
- Not Available
- Toxicity
LD50=20 mg/kg (orally in rat). Hypermetabolic state indistinguishable from thyrotoxicosis of endogenous origin. Symptoms of thyrotoxicosis include weight loss, increased appetite, palpitations, nervousness, diarrhea, abdominal cramps, sweating, tachycardia, increased pulse and blood pressure, cardiac arrhythmias, tremors, insomnia, heat intolerance, fever, and menstrual irregularities.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Thyroid hormone synthesis Metabolic Thyroid hormone synthesis Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Acenocoumarol Levothyroxine may increase the anticoagulant activities of Acenocoumarol. Approved, Investigational Afatinib The serum concentration of Afatinib can be decreased when it is combined with Levothyroxine. Approved Alaproclate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Alaproclate. Experimental Aluminum hydroxide The serum concentration of Levothyroxine can be decreased when it is combined with Aluminum hydroxide. Approved, Investigational Ambroxol acefyllinate The metabolism of Ambroxol acefyllinate can be increased when combined with Levothyroxine. Experimental, Investigational Amineptine Levothyroxine may increase the arrhythmogenic activities of Amineptine. Illicit, Withdrawn Aminophylline The metabolism of Aminophylline can be increased when combined with Levothyroxine. Approved Amiodarone The metabolism of Levothyroxine can be decreased when combined with Amiodarone. Approved, Investigational Amitriptyline Levothyroxine may increase the arrhythmogenic activities of Amitriptyline. Approved Amodiaquine The serum concentration of Amodiaquine can be increased when it is combined with Levothyroxine. Approved, Investigational Amoxapine Levothyroxine may increase the arrhythmogenic activities of Amoxapine. Approved Apalutamide The serum concentration of Levothyroxine can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Levothyroxine can be increased when it is combined with Aprepitant. Approved, Investigational Atazanavir The metabolism of Levothyroxine can be decreased when combined with Atazanavir. Approved, Investigational Atomoxetine The metabolism of Levothyroxine can be decreased when combined with Atomoxetine. Approved Boceprevir The metabolism of Levothyroxine can be decreased when combined with Boceprevir. Approved, Withdrawn Bortezomib The metabolism of Levothyroxine can be decreased when combined with Bortezomib. Approved, Investigational Bosentan The serum concentration of Levothyroxine can be decreased when it is combined with Bosentan. Approved, Investigational Brentuximab vedotin The serum concentration of Brentuximab vedotin can be decreased when it is combined with Levothyroxine. Approved, Investigational Calcium Acetate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Acetate. Approved, Investigational Calcium Chloride The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Chloride. Approved Calcium Citrate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Citrate. Approved Calcium glubionate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium glubionate. Approved Calcium Gluceptate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Gluceptate. Approved Calcium gluconate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium gluconate. Approved, Vet Approved Calcium lactate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium lactate. Approved, Experimental, Investigational, Vet Approved Calcium lactate gluconate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium lactate gluconate. Experimental Calcium levulinate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium levulinate. Approved, Experimental Calcium pangamate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium pangamate. Experimental Calcium Phosphate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Phosphate. Approved Carbamazepine The serum concentration of Levothyroxine can be decreased when it is combined with Carbamazepine. Approved, Investigational Casein The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Casein. Approved Ceritinib The serum concentration of Levothyroxine can be increased when it is combined with Ceritinib. Approved Chlorotrianisene The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Chlorotrianisene. Investigational, Withdrawn Cholestyramine The serum concentration of Levothyroxine can be decreased when it is combined with Cholestyramine. Approved, Investigational Ciprofloxacin The serum concentration of Levothyroxine can be decreased when it is combined with Ciprofloxacin. Approved, Investigational Citalopram The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Citalopram. Approved Clarithromycin The metabolism of Levothyroxine can be decreased when combined with Clarithromycin. Approved Clemastine The metabolism of Levothyroxine can be decreased when combined with Clemastine. Approved, Investigational Clomipramine Levothyroxine may increase the arrhythmogenic activities of Clomipramine. Approved, Investigational, Vet Approved Clorindione Levothyroxine may increase the anticoagulant activities of Clorindione. Experimental Clotrimazole The metabolism of Levothyroxine can be decreased when combined with Clotrimazole. Approved, Vet Approved Cobicistat The metabolism of Levothyroxine can be decreased when combined with Cobicistat. Approved Colesevelam The serum concentration of Levothyroxine can be decreased when it is combined with Colesevelam. Approved Colestipol The serum concentration of Levothyroxine can be decreased when it is combined with Colestipol. Approved Conivaptan The serum concentration of Conivaptan can be increased when it is combined with Levothyroxine. Approved, Investigational Conjugated estrogens The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Conjugated estrogens. Approved Crizotinib The metabolism of Levothyroxine can be decreased when combined with Crizotinib. Approved Cyclobenzaprine Levothyroxine may increase the arrhythmogenic activities of Cyclobenzaprine. Approved Cyclosporine The metabolism of Levothyroxine can be decreased when combined with Cyclosporine. Approved, Investigational, Vet Approved Dabigatran etexilate The serum concentration of Dabigatran etexilate can be decreased when it is combined with Levothyroxine. Approved Dabrafenib The serum concentration of Levothyroxine can be decreased when it is combined with Dabrafenib. Approved, Investigational Daidzein The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Daidzein. Experimental Dapoxetine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Dapoxetine. Investigational Darunavir The metabolism of Levothyroxine can be decreased when combined with Darunavir. Approved Dasatinib The serum concentration of Levothyroxine can be increased when it is combined with Dasatinib. Approved, Investigational Deferasirox The serum concentration of Levothyroxine can be decreased when it is combined with Deferasirox. Approved, Investigational Delavirdine The metabolism of Levothyroxine can be decreased when combined with Delavirdine. Approved Desipramine Levothyroxine may increase the arrhythmogenic activities of Desipramine. Approved, Investigational Desvenlafaxine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Desvenlafaxine. Approved, Investigational Dibenzepin Levothyroxine may increase the arrhythmogenic activities of Dibenzepin. Experimental Dicoumarol Levothyroxine may increase the anticoagulant activities of Dicoumarol. Approved Dienestrol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Dienestrol. Approved, Investigational Diethylstilbestrol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Diethylstilbestrol. Approved, Investigational Dihydroergotamine The metabolism of Levothyroxine can be decreased when combined with Dihydroergotamine. Approved, Investigational Diltiazem The metabolism of Levothyroxine can be decreased when combined with Diltiazem. Approved, Investigational Diphenadione Levothyroxine may increase the anticoagulant activities of Diphenadione. Experimental Dosulepin Levothyroxine may increase the arrhythmogenic activities of Dosulepin. Approved Doxepin Levothyroxine may increase the arrhythmogenic activities of Doxepin. Approved, Investigational Doxorubicin The serum concentration of Doxorubicin can be decreased when it is combined with Levothyroxine. Approved, Investigational Doxycycline The metabolism of Levothyroxine can be decreased when combined with Doxycycline. Approved, Investigational, Vet Approved Dronedarone The metabolism of Levothyroxine can be decreased when combined with Dronedarone. Approved Duloxetine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Duloxetine. Approved Dyphylline The metabolism of Dyphylline can be increased when combined with Levothyroxine. Approved Enzalutamide The serum concentration of Levothyroxine can be decreased when it is combined with Enzalutamide. Approved Epimestrol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Epimestrol. Experimental Equol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Equol. Investigational Erythromycin The metabolism of Levothyroxine can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Escitalopram The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Escitalopram. Approved, Investigational Esmirtazapine Levothyroxine may increase the arrhythmogenic activities of Esmirtazapine. Investigational Estradiol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estradiol. Approved, Investigational, Vet Approved Estradiol acetate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estradiol acetate. Approved, Investigational, Vet Approved Estradiol cypionate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estradiol cypionate. Approved, Investigational, Vet Approved Estradiol valerate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estradiol valerate. Approved, Investigational, Vet Approved Estriol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estriol. Approved, Investigational, Vet Approved Estrogens, esterified The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estrogens, esterified. Approved Estrone The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estrone. Approved Ethinyl Estradiol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Ethinyl Estradiol. Approved Ethyl biscoumacetate Levothyroxine may increase the anticoagulant activities of Ethyl biscoumacetate. Withdrawn Etoperidone The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Etoperidone. Withdrawn Ferric Carboxymaltose The serum concentration of Levothyroxine can be decreased when it is combined with Ferric Carboxymaltose. Approved Ferric pyrophosphate The serum concentration of Levothyroxine can be decreased when it is combined with Ferric pyrophosphate. Experimental Fluconazole The metabolism of Levothyroxine can be decreased when combined with Fluconazole. Approved, Investigational Fluindione Levothyroxine may increase the anticoagulant activities of Fluindione. Approved, Investigational Fluoxetine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Fluoxetine. Approved, Vet Approved Fluvoxamine The metabolism of Levothyroxine can be decreased when combined with Fluvoxamine. Approved, Investigational Fosamprenavir The metabolism of Levothyroxine can be decreased when combined with Fosamprenavir. Approved Fosaprepitant The serum concentration of Levothyroxine can be increased when it is combined with Fosaprepitant. Approved Fosphenytoin The serum concentration of Levothyroxine can be decreased when it is combined with Fosphenytoin. Approved, Investigational Fusidic Acid The serum concentration of Levothyroxine can be increased when it is combined with Fusidic Acid. Approved, Investigational Genistein The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Genistein. Investigational Hexestrol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Hexestrol. Withdrawn Idelalisib The metabolism of Levothyroxine can be decreased when combined with Idelalisib. Approved Imatinib The metabolism of Levothyroxine can be decreased when combined with Imatinib. Approved Imipramine Levothyroxine may increase the arrhythmogenic activities of Imipramine. Approved Indalpine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Indalpine. Investigational, Withdrawn Indinavir The metabolism of Levothyroxine can be decreased when combined with Indinavir. Approved Iodide I-131 The therapeutic efficacy of Iodide I-131 can be decreased when used in combination with Levothyroxine. Approved, Investigational Iprindole Levothyroxine may increase the arrhythmogenic activities of Iprindole. Experimental Iron The serum concentration of Levothyroxine can be decreased when it is combined with Iron. Approved Iron Dextran The serum concentration of Levothyroxine can be decreased when it is combined with Iron Dextran. Approved, Vet Approved Iron saccharate The serum concentration of Levothyroxine can be decreased when it is combined with Iron saccharate. Approved Isavuconazole The serum concentration of Levothyroxine can be increased when it is combined with Isavuconazole. Approved, Investigational Isavuconazonium The metabolism of Levothyroxine can be decreased when combined with Isavuconazonium. Approved, Investigational Isradipine The metabolism of Levothyroxine can be decreased when combined with Isradipine. Approved, Investigational Itraconazole The metabolism of Levothyroxine can be decreased when combined with Itraconazole. Approved, Investigational Ivacaftor The serum concentration of Levothyroxine can be increased when it is combined with Ivacaftor. Approved Ketoconazole The metabolism of Levothyroxine can be decreased when combined with Ketoconazole. Approved, Investigational Lanthanum carbonate The serum concentration of Levothyroxine can be decreased when it is combined with Lanthanum carbonate. Approved Ledipasvir The serum concentration of Ledipasvir can be decreased when it is combined with Levothyroxine. Approved Levomilnacipran The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Levomilnacipran. Approved, Investigational Linagliptin The serum concentration of Linagliptin can be decreased when it is combined with Levothyroxine. Approved Lofepramine Levothyroxine may increase the arrhythmogenic activities of Lofepramine. Experimental Lopinavir The metabolism of Levothyroxine can be decreased when combined with Lopinavir. Approved Lorpiprazole The serum concentration of Levothyroxine can be increased when it is combined with Lorpiprazole. Approved Lovastatin The metabolism of Levothyroxine can be decreased when combined with Lovastatin. Approved, Investigational Luliconazole The serum concentration of Levothyroxine can be increased when it is combined with Luliconazole. Approved Lumacaftor The metabolism of Levothyroxine can be increased when combined with Lumacaftor. Approved Magnesium hydroxide The serum concentration of Levothyroxine can be decreased when it is combined with Magnesium hydroxide. Approved, Investigational Magnesium oxide The serum concentration of Levothyroxine can be decreased when it is combined with Magnesium oxide. Approved Magnesium salicylate The serum concentration of Levothyroxine can be decreased when it is combined with Magnesium salicylate. Approved Magnesium sulfate The serum concentration of Levothyroxine can be decreased when it is combined with Magnesium sulfate. Approved, Investigational, Vet Approved Mestranol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Mestranol. Approved Methallenestril The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Methallenestril. Experimental Mifepristone The serum concentration of Levothyroxine can be increased when it is combined with Mifepristone. Approved, Investigational Milnacipran The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Milnacipran. Approved, Investigational Mirtazapine Levothyroxine may increase the arrhythmogenic activities of Mirtazapine. Approved Mitotane The serum concentration of Levothyroxine can be decreased when it is combined with Mitotane. Approved Moxestrol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Moxestrol. Experimental Nefazodone The metabolism of Levothyroxine can be decreased when combined with Nefazodone. Approved, Withdrawn Nelfinavir The metabolism of Levothyroxine can be decreased when combined with Nelfinavir. Approved Netupitant The serum concentration of Levothyroxine can be increased when it is combined with Netupitant. Approved, Investigational Nevirapine The metabolism of Levothyroxine can be increased when combined with Nevirapine. Approved Nilotinib The metabolism of Levothyroxine can be decreased when combined with Nilotinib. Approved, Investigational Nortriptyline Levothyroxine may increase the arrhythmogenic activities of Nortriptyline. Approved Olaparib The metabolism of Levothyroxine can be decreased when combined with Olaparib. Approved Opipramol Levothyroxine may increase the arrhythmogenic activities of Opipramol. Investigational Orlistat The serum concentration of Levothyroxine can be decreased when it is combined with Orlistat. Approved, Investigational Osimertinib The serum concentration of Levothyroxine can be increased when it is combined with Osimertinib. Approved Palbociclib The serum concentration of Levothyroxine can be increased when it is combined with Palbociclib. Approved, Investigational Paroxetine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Paroxetine. Approved, Investigational Pentobarbital The metabolism of Levothyroxine can be increased when combined with Pentobarbital. Approved, Investigational, Vet Approved Phenindione Levothyroxine may increase the anticoagulant activities of Phenindione. Approved, Investigational Phenobarbital The metabolism of Levothyroxine can be increased when combined with Phenobarbital. Approved, Investigational Phenprocoumon Levothyroxine may increase the anticoagulant activities of Phenprocoumon. Approved, Investigational Phenytoin The serum concentration of Levothyroxine can be decreased when it is combined with Phenytoin. Approved, Vet Approved Piracetam The risk or severity of adverse effects can be increased when Levothyroxine is combined with Piracetam. Approved, Investigational Pitolisant The serum concentration of Levothyroxine can be decreased when it is combined with Pitolisant. Approved, Investigational Polaprezinc The serum concentration of Levothyroxine can be decreased when it is combined with Polaprezinc. Approved, Investigational Polyestradiol phosphate The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Polyestradiol phosphate. Approved Posaconazole The metabolism of Levothyroxine can be decreased when combined with Posaconazole. Approved, Investigational, Vet Approved Primidone The metabolism of Levothyroxine can be increased when combined with Primidone. Approved, Vet Approved Promestriene The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Promestriene. Investigational Protriptyline Levothyroxine may increase the arrhythmogenic activities of Protriptyline. Approved Quinestrol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Quinestrol. Approved Raloxifene Raloxifene can cause a decrease in the absorption of Levothyroxine resulting in a reduced serum concentration and potentially a decrease in efficacy. Approved, Investigational Ranolazine The metabolism of Levothyroxine can be decreased when combined with Ranolazine. Approved, Investigational Rifabutin The metabolism of Levothyroxine can be increased when combined with Rifabutin. Approved, Investigational Rifampicin The serum concentration of Levothyroxine can be decreased when it is combined with Rifampicin. Approved Rifapentine The metabolism of Levothyroxine can be increased when combined with Rifapentine. Approved, Investigational Rucaparib The metabolism of Levothyroxine can be decreased when combined with Rucaparib. Approved, Investigational Saquinavir The metabolism of Levothyroxine can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Sarilumab. Approved, Investigational Secoisolariciresinol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Secoisolariciresinol. Investigational Sertraline The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Sertraline. Approved Sevelamer The serum concentration of Levothyroxine can be decreased when it is combined with Sevelamer. Approved Sildenafil The metabolism of Levothyroxine can be decreased when combined with Sildenafil. Approved, Investigational Siltuximab The serum concentration of Levothyroxine can be decreased when it is combined with Siltuximab. Approved, Investigational Simeprevir The serum concentration of Levothyroxine can be increased when it is combined with Simeprevir. Approved Sofosbuvir The serum concentration of Sofosbuvir can be decreased when it is combined with Levothyroxine. Approved St. John's Wort The serum concentration of Levothyroxine can be decreased when it is combined with St. John's Wort. Approved, Investigational, Nutraceutical Stiripentol The serum concentration of Levothyroxine can be increased when it is combined with Stiripentol. Approved Sucralfate The serum concentration of Levothyroxine can be decreased when it is combined with Sucralfate. Approved Sulfisoxazole The metabolism of Levothyroxine can be decreased when combined with Sulfisoxazole. Approved, Vet Approved Synthetic Conjugated Estrogens, A The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Synthetic Conjugated Estrogens, A. Approved Synthetic Conjugated Estrogens, B The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Synthetic Conjugated Estrogens, B. Approved Telaprevir The metabolism of Levothyroxine can be decreased when combined with Telaprevir. Approved, Withdrawn Telithromycin The metabolism of Levothyroxine can be decreased when combined with Telithromycin. Approved Theophylline The metabolism of Theophylline can be increased when combined with Levothyroxine. Approved Tianeptine Levothyroxine may increase the arrhythmogenic activities of Tianeptine. Approved, Investigational Tibolone The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Tibolone. Approved, Investigational Ticlopidine The metabolism of Levothyroxine can be decreased when combined with Ticlopidine. Approved Tioclomarol Levothyroxine may increase the anticoagulant activities of Tioclomarol. Experimental Tocilizumab The serum concentration of Levothyroxine can be decreased when it is combined with Tocilizumab. Approved Tolevamer The serum concentration of Levothyroxine can be decreased when it is combined with Tolevamer. Approved, Investigational Trimipramine Levothyroxine may increase the arrhythmogenic activities of Trimipramine. Approved Vemurafenib The serum concentration of Levothyroxine can be decreased when it is combined with Vemurafenib. Approved Venlafaxine The metabolism of Levothyroxine can be decreased when combined with Venlafaxine. Approved Verapamil The metabolism of Levothyroxine can be decreased when combined with Verapamil. Approved Vincristine The serum concentration of Vincristine can be decreased when it is combined with Levothyroxine. Approved, Investigational Voriconazole The metabolism of Levothyroxine can be decreased when combined with Voriconazole. Approved, Investigational Warfarin Levothyroxine may increase the anticoagulant activities of Warfarin. Approved Zeranol The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Zeranol. Vet Approved Zimelidine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Zimelidine. Withdrawn Ziprasidone The metabolism of Levothyroxine can be decreased when combined with Ziprasidone. Approved - Food Interactions
- Absorption increased in fasting state and decreased in malabsorption states.
- Consistent administration in relation to meals is recommended.
- No iron or calium carbonate within 4 hours of taking this medication.
- Oral administration with infant soybean formula, soybean flour, cotton seed meal, walnuts, foods containing large amounts of fiber, ferrous sulfate, and antacids may decrease drug absorption.
- Take 30-60 minutes before breakfast.
References
- Synthesis Reference
Jivn-Ren Chen, Dimitri C. Papadimitriou, "Stable dosage of levothyroxine sodium and process of production." U.S. Patent US5225204, issued November, 1991.
US5225204- General References
- Uchino H, Kanai Y, Kim DK, Wempe MF, Chairoungdua A, Morimoto E, Anders MW, Endou H: Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition. Mol Pharmacol. 2002 Apr;61(4):729-37. [PubMed:11901210]
- External Links
- Human Metabolome Database
- HMDB0000248
- KEGG Drug
- D08125
- KEGG Compound
- C01829
- PubChem Compound
- 5819
- PubChem Substance
- 46507672
- ChemSpider
- 5614
- BindingDB
- 50301375
- ChEBI
- 18332
- ChEMBL
- CHEMBL1624
- Therapeutic Targets Database
- DAP000083
- PharmGKB
- PA450221
- IUPHAR
- 2635
- Guide to Pharmacology
- GtP Drug Page
- HET
- T44
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Levothyroxine
- ATC Codes
- H03AA01 — Levothyroxine sodium
- AHFS Codes
- 68:36.04 — Thyroid Agents
- PDB Entries
- 1eta / 1etb / 1f86 / 1hk1 / 1hk2 / 1hk3 / 1hk4 / 1hk5 / 1ict / 1ie4 … show 12 more
- FDA label
- Download (54.3 KB)
- MSDS
- Download (51.7 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Institute biochimique sa (ibsa)
- Institut biochimique sa ibsa
- Vintage pharmaceuticals llc
- Alara pharmaceutical corporation
- Lloyd inc
- Merck kgaa
- Mylan pharmaceuticals inc
- King pharmaceuticals inc
- Abbott laboratories
- Jerome stevens pharmaceuticals inc
- Packagers
- Abbott Laboratories Ltd.
- Advanced Pharmaceutical Services Inc.
- Akrimax Pharmaceuticals
- Amerisource Health Services Corp.
- Apotheca Inc.
- APP Pharmaceuticals
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- BASF Corp.
- Bedford Labs
- Ben Venue Laboratories Inc.
- Bryant Ranch Prepack
- Cardinal Health
- Caremark LLC
- Comprehensive Consultant Services Inc.
- Corepharma LLC
- Direct Dispensing Inc.
- Direct Pharmaceuticals Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Forest Pharmaceuticals
- Genpharm LP
- Giant Food Inc.
- H.E. Butt Grocery Co.
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Innovative Manufacturing and Distribution Services Inc.
- Jerome Stevens Pharmaceuticals Inc.
- JMI Daniels Pharmaceuticals Inc.
- Kaiser Foundation Hospital
- King Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Lannett Co. Inc.
- Liberty Pharmaceuticals
- Lloyd Pharmaceuticals
- Macnary Ltd.
- Major Pharmaceuticals
- Mckesson Corp.
- Medisca Inc.
- Merck KGaA
- Monarch Pharmacy
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Neuman Distributors Inc.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Patheon Inc.
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmacy Service Center
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Prescript Pharmaceuticals
- Qualitest
- Rebel Distributors Corp.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Rite Aid Corp.
- Sandhills Packaging Inc.
- Sandoz
- Simildiet SL
- Southwood Pharmaceuticals
- Stat Scripts LLC
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Va Cmop Dallas
- Watson Pharmaceuticals
- Dosage forms
Form Route Strength Tablet Oral .1 mg Tablet Oral .2 mg Tablet Oral .3 mg Tablet Oral .05 mg Injection, powder, lyophilized, for solution Intravenous 100 ug/5mL Injection, powder, lyophilized, for solution Intravenous 200 ug/5mL Injection, powder, lyophilized, for solution Intravenous 500 ug/5mL Tablet Oral .025 mg/1 Tablet Oral .05 mg/1 Tablet Oral .075 mg/1 Tablet Oral .088 mg/1 Tablet Oral .1 mg/1 Tablet Oral .112 mg/1 Tablet Oral .125 mg/1 Tablet Oral .137 mg/1 Tablet Oral .15 mg/1 Tablet Oral .175 mg/1 Tablet Oral .2 mg/1 Tablet Oral .3 mg/1 Tablet Oral 112 ug/1 Tablet Oral 125 ug/1 Tablet Oral 175 ug/1 Tablet Oral 25 ug/1 Tablet Oral 50 ug/1 Tablet Oral 75 ug/1 Powder, for solution Intramuscular; Intravenous 200 mcg Powder, for solution Intramuscular; Intravenous 500 mcg Tablet Oral Tablet Oral 100 ug/1 Tablet Oral 137 ug/1 Tablet Oral 137 mcg Tablet Oral 150 ug/1 Tablet Oral 200 ug/1 Tablet Oral 300 ug/1 Tablet Oral 88 ug/1 Liquid Intravenous 500 mcg Tablet Oral 100 mcg Tablet Oral 112 mcg Tablet Oral 125 mcg Tablet Oral 150 mcg Tablet Oral 175 mcg Tablet Oral 200 mcg Tablet Oral 25 mcg Tablet Oral 300 mcg Tablet Oral 50 mcg Tablet Oral 75 mcg Tablet Oral 88 mcg Capsule Oral 100 ug/1 Capsule Oral 112 ug/1 Capsule Oral 125 ug/1 Capsule Oral 13 ug/1 Capsule Oral 137 ug/1 Capsule Oral 150 ug/1 Capsule Oral 175 ug/1 Capsule Oral 200 ug/1 Capsule Oral 25 ug/1 Capsule Oral 50 ug/1 Capsule Oral 75 ug/1 Capsule Oral 88 ug/1 - Prices
Unit description Cost Unit Levothyroxine sodium powder 159.12USD g Levothyroxine 200 mcg vial 24.0USD vial Levothyroxine 500 mcg vial 24.0USD vial Levoxyl 300 mcg tablet 2.34USD tablet Synthroid 300 mcg tablet 1.29USD tablet Synthroid 175 mcg tablet 1.07USD tablet Synthroid 200 mcg tablet 0.99USD tablet Synthroid 137 mcg tablet 0.87USD tablet Synthroid 112 mcg tablet 0.84USD tablet Synthroid 125 mcg tablet 0.84USD tablet Synthroid 150 mcg tablet 0.83USD tablet Levothyroxine Sodium 300 mcg tablet 0.77USD tablet Synthroid 100 mcg tablet 0.73USD tablet Synthroid 75 mcg tablet 0.72USD tablet Synthroid 88 mcg tablet 0.71USD tablet Levoxyl 200 mcg tablet 0.7USD tablet Levoxyl 175 mcg tablet 0.69USD tablet Unithroid 300 mcg tablet 0.69USD tablet Synthroid 50 mcg tablet 0.65USD tablet Levoxyl 137 mcg tablet 0.62USD tablet Unithroid 200 mcg tablet 0.62USD tablet Levoxyl 112 mcg tablet 0.61USD tablet Synthroid 25 mcg tablet 0.61USD tablet Unithroid 175 mcg tablet 0.61USD tablet Levoxyl 150 mcg tablet 0.59USD tablet Levoxyl 125 mcg tablet 0.58USD tablet Levothyroxine Sodium 175 mcg tablet 0.57USD tablet Levothyroxine Sodium 200 mcg tablet 0.57USD tablet Levothyroxine 175 mcg tablet 0.55USD tablet Unithroid 150 mcg tablet 0.55USD tablet Levoxyl 88 mcg tablet 0.54USD tablet Unithroid 112 mcg tablet 0.53USD tablet Unithroid 125 mcg tablet 0.53USD tablet Levoxyl 75 mcg tablet 0.52USD tablet Levothroid 300 mcg tablet 0.51USD tablet Levoxyl 100 mcg tablet 0.51USD tablet Levothyroxine Sodium 100 mcg tablet 0.5USD tablet Levothyroxine Sodium 150 mcg tablet 0.5USD tablet Levothyroxine Sodium 88 mcg tablet 0.5USD tablet Levoxyl 50 mcg tablet 0.49USD tablet Unithroid 88 mcg tablet 0.49USD tablet Unithroid 100 mcg tablet 0.47USD tablet Unithroid 75 mcg tablet 0.47USD tablet Levothyroxine Sodium 125 mcg tablet 0.47USD tablet Levothyroxine Sodium 137 mcg tablet 0.47USD tablet Levothyroxine Sodium 50 mcg tablet 0.47USD tablet Levothyroxine Sodium 75 mcg tablet 0.47USD tablet Levothyroxine Sodium 112 mcg tablet 0.46USD tablet Levothyroxine 137 mcg tablet 0.45USD tablet Levoxyl 25 mcg tablet 0.45USD tablet Levothyroxine 112 mcg tablet 0.44USD tablet Levothyroxine Sodium 25 mcg tablet 0.43USD tablet Unithroid 50 mcg tablet 0.43USD tablet Unithroid 25 mcg tablet 0.42USD tablet Unithroid direct 100 mcg tablet 0.42USD tablet Unithroid direct 112 mcg tablet 0.42USD tablet Unithroid direct 125 mcg tablet 0.42USD tablet Unithroid direct 150 mcg tablet 0.42USD tablet Unithroid direct 175 mcg tablet 0.42USD tablet Unithroid direct 200 mcg tablet 0.42USD tablet Unithroid direct 25 mcg tablet 0.42USD tablet Unithroid direct 300 mcg tablet 0.42USD tablet Unithroid direct 50 mcg tablet 0.42USD tablet Unithroid direct 75 mcg tablet 0.42USD tablet Unithroid direct 88 mcg tablet 0.42USD tablet Levothroid 200 mcg tablet 0.4USD tablet Levothroid 175 mcg tablet 0.38USD tablet Levothyroxine 88 mcg tablet 0.38USD tablet Levothroid 125 mcg tablet 0.36USD tablet Levothroid 150 mcg tablet 0.36USD tablet Levothroid 100 mcg tablet 0.35USD tablet Levothroid 137 mcg tablet 0.35USD tablet Levothroid 112 mcg tablet 0.34USD tablet Levothroid 75 mcg tablet 0.33USD tablet Levothroid 88 mcg tablet 0.33USD tablet Levothyroxine 300 mcg tablet 0.32USD tablet Levothroid 25 mcg tablet 0.31USD tablet Unithroid 137 mcg tablet 0.31USD tablet Levothroid 50 mcg tablet 0.3USD tablet Levothyroxine 200 mcg tablet 0.29USD tablet Levothyroxine 150 mcg tablet 0.24USD tablet Levothyroxine 125 mcg tablet 0.22USD tablet Levothyroxine 100 mcg tablet 0.2USD tablet Levothyroxine 75 mcg tablet 0.2USD tablet Levothyroxine 50 mcg tablet 0.18USD tablet Synthroid 0.137 mg Tablet 0.18USD tablet Levothyroxine 25 mcg tablet 0.17USD tablet Synthroid 0.3 mg Tablet 0.12USD tablet Synthroid 0.175 mg Tablet 0.11USD tablet Synthroid 0.075 mg Tablet 0.1USD tablet Synthroid 0.088 mg Tablet 0.1USD tablet Synthroid 0.112 mg Tablet 0.1USD tablet Synthroid 0.125 mg Tablet 0.1USD tablet Synthroid 0.025 mg Tablet 0.09USD tablet Synthroid 0.2 mg Tablet 0.09USD tablet Synthroid 0.1 mg Tablet 0.08USD tablet Synthroid 0.15 mg Tablet 0.08USD tablet Eltroxin 0.3 mg Tablet 0.07USD tablet Synthroid 0.05 mg Tablet 0.06USD tablet Eltroxin 0.2 mg Tablet 0.05USD tablet Eltroxin 0.1 mg Tablet 0.04USD tablet Eltroxin 0.15 mg Tablet 0.04USD tablet Eltroxin 0.05 mg Tablet 0.03USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US7723390 No 2004-03-14 2024-03-14 US US7101569 No 2003-10-02 2023-10-02 US US7067148 No 2002-02-15 2022-02-15 US US6555581 No 2002-02-15 2022-02-15 US US6399101 No 2000-03-30 2020-03-30 US US9168239 No 2012-08-29 2032-08-29 US US9168238 No 2012-08-29 2032-08-29 US US9006289 No 2012-10-03 2032-10-03 US US7691411 No 2004-03-14 2024-03-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 235.5 °C PhysProp water solubility 0.105 mg/mL Not Available logP 4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00898 mg/mL ALOGPS logP 1.15 ALOGPS logP 3.73 ChemAxon logS -4.9 ALOGPS pKa (Strongest Acidic) 0.27 ChemAxon pKa (Strongest Basic) 9.43 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 92.78 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 126.79 m3·mol-1 ChemAxon Polarizability 49.4 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.7212 Blood Brain Barrier - 0.6886 Caco-2 permeable - 0.653 P-glycoprotein substrate Non-substrate 0.5321 P-glycoprotein inhibitor I Non-inhibitor 0.9175 P-glycoprotein inhibitor II Non-inhibitor 0.9709 Renal organic cation transporter Non-inhibitor 0.8891 CYP450 2C9 substrate Non-substrate 0.8309 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6847 CYP450 1A2 substrate Non-inhibitor 0.5924 CYP450 2C9 inhibitor Non-inhibitor 0.7037 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8459 Ames test Non AMES toxic 0.7591 Carcinogenicity Non-carcinogens 0.9148 Biodegradation Not ready biodegradable 0.9693 Rat acute toxicity 2.7082 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9697 hERG inhibition (predictor II) Non-inhibitor 0.8508
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Phenylalanine and derivatives
- Alternative Parents
- Diphenylethers / Phenylpropanoic acids / Diarylethers / Amphetamines and derivatives / L-alpha-amino acids / Phenoxy compounds / Phenol ethers / O-iodophenols / Aralkylamines / Iodobenzenes show 10 more
- Substituents
- Phenylalanine or derivatives / Diphenylether / Diaryl ether / 3-phenylpropanoic-acid / Alpha-amino acid / Amphetamine or derivatives / L-alpha-amino acid / Phenoxy compound / Phenol ether / 2-halophenol show 27 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- non-proteinogenic L-alpha-amino acid, L-phenylalanine derivative, iodophenol, 2-halophenol, thyroxine (CHEBI:18332) / thyroxine, Other amino acids, Biogenic amines (C01829)
Targets
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Isoform Alpha-1: Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.Isoform Al...
- Gene Name
- THRA
- Uniprot ID
- P10827
- Uniprot Name
- Thyroid hormone receptor alpha
- Molecular Weight
- 54815.055 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Bernal J: Thyroid hormone receptors in brain development and function. Nat Clin Pract Endocrinol Metab. 2007 Mar;3(3):249-59. [PubMed:17315033]
- Nakajima Y, Yamada M, Horiguchi K, Satoh T, Hashimoto K, Tokuhiro E, Onigata K, Mori M: Resistance to thyroid hormone due to a novel thyroid hormone receptor mutant in a patient with hypothyroidism secondary to lingual thyroid and functional characterization of the mutant receptor. Thyroid. 2010 Aug;20(8):917-26. doi: 10.1089/thy.2009.0389. [PubMed:20615127]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.
- Gene Name
- THRB
- Uniprot ID
- P10828
- Uniprot Name
- Thyroid hormone receptor beta
- Molecular Weight
- 52787.16 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Marazuela M, Nattero L, Moure D, Garcia-Polo I, Figueroa-Vega N, Guijarro C: Thyroid hormone resistance and pituitary enlargement after thyroid ablation in a woman on levothyroxine treatment. Thyroid. 2008 Oct;18(10):1119-23. doi: 10.1089/thy.2007.0375. [PubMed:18816177]
- Sivakumar T, Chaidarun S: Resistance to thyroid hormone in a patient with coexisting Graves' disease. Thyroid. 2010 Feb;20(2):213-6. doi: 10.1089/thy.2009.0175. [PubMed:20151830]
- Grasberger H, Ringkananont U, Croxson M, Refetoff S: Resistance to thyroid hormone in a patient with thyroid dysgenesis. Thyroid. 2005 Jul;15(7):730-3. [PubMed:16053391]
Enzymes
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Carriers
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- No
- General Function
- Identical protein binding
- Specific Function
- Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
- Gene Name
- TTR
- Uniprot ID
- P02766
- Uniprot Name
- Transthyretin
- Molecular Weight
- 15886.88 Da
References
- Eneqvist T, Lundberg E, Karlsson A, Huang S, Santos CR, Power DM, Sauer-Eriksson AE: High resolution crystal structures of piscine transthyretin reveal different binding modes for triiodothyronine and thyroxine. J Biol Chem. 2004 Jun 18;279(25):26411-6. Epub 2004 Apr 13. [PubMed:15082720]
- Palha JA: Transthyretin as a thyroid hormone carrier: function revisited. Clin Chem Lab Med. 2002 Dec;40(12):1292-300. [PubMed:12553433]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- No
- General Function
- Serine-type endopeptidase inhibitor activity
- Specific Function
- Major thyroid hormone transport protein in serum.
- Gene Name
- SERPINA7
- Uniprot ID
- P05543
- Uniprot Name
- Thyroxine-binding globulin
- Molecular Weight
- 46324.12 Da
References
- Palha JA: Transthyretin as a thyroid hormone carrier: function revisited. Clin Chem Lab Med. 2002 Dec;40(12):1292-300. [PubMed:12553433]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- No
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Palha JA: Transthyretin as a thyroid hormone carrier: function revisited. Clin Chem Lab Med. 2002 Dec;40(12):1292-300. [PubMed:12553433]
Transporters
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Thyroid hormone transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-gluc...
- Gene Name
- SLCO1C1
- Uniprot ID
- Q9NYB5
- Uniprot Name
- Solute carrier organic anion transporter family member 1C1
- Molecular Weight
- 78695.625 Da
References
- Westholm DE, Stenehjem DD, Rumbley JN, Drewes LR, Anderson GW: Competitive inhibition of organic anion transporting polypeptide 1c1-mediated thyroxine transport by the fenamate class of nonsteroidal antiinflammatory drugs. Endocrinology. 2009 Feb;150(2):1025-32. doi: 10.1210/en.2008-0188. Epub 2008 Oct 9. [PubMed:18845642]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
- Pizzagalli F, Hagenbuch B, Stieger B, Klenk U, Folkers G, Meier PJ: Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter. Mol Endocrinol. 2002 Oct;16(10):2283-96. [PubMed:12351693]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transporter activity
- Specific Function
- Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu,...
- Gene Name
- SLC16A2
- Uniprot ID
- P36021
- Uniprot Name
- Monocarboxylate transporter 8
- Molecular Weight
- 59510.86 Da
References
- Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. [PubMed:12871948]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Siegmund W, Altmannsberger S, Paneitz A, Hecker U, Zschiesche M, Franke G, Meng W, Warzok R, Schroeder E, Sperker B, Terhaag B, Cascorbi I, Kroemer HK: Effect of levothyroxine administration on intestinal P-glycoprotein expression: consequences for drug disposition. Clin Pharmacol Ther. 2002 Sep;72(3):256-64. [PubMed:12235446]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Thyroid hormone transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate.
- Gene Name
- SLCO4A1
- Uniprot ID
- Q96BD0
- Uniprot Name
- Solute carrier organic anion transporter family member 4A1
- Molecular Weight
- 77192.505 Da
References
- Fujiwara K, Adachi H, Nishio T, Unno M, Tokui T, Okabe M, Onogawa T, Suzuki T, Asano N, Tanemoto M, Seki M, Shiiba K, Suzuki M, Kondo Y, Nunoki K, Shimosegawa T, Iinuma K, Ito S, Matsuno S, Abe T: Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner. Endocrinology. 2001 May;142(5):2005-12. [PubMed:11316767]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Organic anion transporter, capable of transporting pharmacological substances such as digoxin, ouabain, thyroxine, methotrexate and cAMP. May participate in the regulation of membrane transport of ...
- Gene Name
- SLCO4C1
- Uniprot ID
- Q6ZQN7
- Uniprot Name
- Solute carrier organic anion transporter family member 4C1
- Molecular Weight
- 78947.525 Da
References
- Mikkaichi T, Suzuki T, Onogawa T, Tanemoto M, Mizutamari H, Okada M, Chaki T, Masuda S, Tokui T, Eto N, Abe M, Satoh F, Unno M, Hishinuma T, Inui K, Ito S, Goto J, Abe T: Isolation and characterization of a digoxin transporter and its rat homologue expressed in the kidney. Proc Natl Acad Sci U S A. 2004 Mar 9;101(10):3569-74. Epub 2004 Mar 1. [PubMed:14993604]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Peptide antigen binding
- Specific Function
- Sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Involved in cellular a...
- Gene Name
- SLC7A5
- Uniprot ID
- Q01650
- Uniprot Name
- Large neutral amino acids transporter small subunit 1
- Molecular Weight
- 55009.62 Da
References
- Uchino H, Kanai Y, Kim DK, Wempe MF, Chairoungdua A, Morimoto E, Anders MW, Endou H: Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition. Mol Pharmacol. 2002 Apr;61(4):729-37. [PubMed:11901210]
Drug created on June 13, 2005 07:24 / Updated on April 23, 2018 23:00