Identification

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
Thumb
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
IngredientUNIICASInChI Key
Levothyroxine sodium054I36CPMN55-03-8YDTFRJLNMPSCFM-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EltroxinTablet50 mcgOralAspen Pharmacare Canada Inc.1951-12-30Not applicableCanada
EltroxinTablet150 mcgOralAspen Pharmacare Canada Inc.1974-12-31Not applicableCanada
EltroxinTablet300 mcgOralAspen Pharmacare Canada Inc.1998-02-11Not applicableCanada
EltroxinTablet100 mcgOralAspen Pharmacare Canada Inc.1998-11-27Not applicableCanada
EltroxinTablet200 mcgOralAspen Pharmacare Canada Inc.1997-04-02Not applicableCanada
Eltroxin 150 TabTablet150 mcgOralGlaxo Canada Inc1974-12-311999-08-12Canada
Eltroxin Tab 100mcgTablet.1 mgOralGlaxo Canada Inc1951-12-311999-08-12Canada
Eltroxin Tab 200mcgTablet.2 mgOralGlaxo Canada Inc1960-12-311998-07-30Canada
Eltroxin Tab 300mcgTablet.3 mgOralGlaxo Canada Inc1966-12-311998-07-30Canada
Eltroxin Tab 50mcgTablet.05 mgOralGlaxo Canada Inc1951-12-311998-07-30Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Levothyroxine SodiumTablet100 ug/1OralCardinal Health2010-10-29Not applicableUs
Levothyroxine SodiumTablet.112 mg/1OralRemedy Repack2011-06-222016-10-13Us
Levothyroxine SodiumTablet125 ug/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs00378 1813 01 nlmimage10 4823a43d
Levothyroxine SodiumTablet100 ug/1OralA S Medication Solutions2002-11-012017-06-20Us
Levothyroxine SodiumTablet50 ug/1OralPd Rx Pharmaceuticals, Inc.2002-11-01Not applicableUs
Levothyroxine SodiumTablet.2 mg/1OralPhysicians Total Care, Inc.1995-08-07Not applicableUs
Levothyroxine SodiumTablet100 ug/1OralMylan Pharmaceuticals2002-11-01Not applicableUs
Levothyroxine SodiumTablet200 ug/1OralMylan Pharmaceuticals2002-11-01Not applicableUs00378 1819 01 nlmimage10 3f239fbc
Levothyroxine SodiumTablet100 ug/1OralPd Rx Pharmaceuticals, Inc.2002-11-01Not applicableUs
Levothyroxine SodiumTablet.175 mg/1OralPhysicians Total Care, Inc.2001-04-16Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Levothyroxine sodiumTablet50 ug/1OralProficient Rx LP2002-03-01Not applicableUs
International/Other Brands
Eutirox (Merck) / Letrox (Berlin-Chemie) / Levaxin (Nycomed) / Levothyrox (Merck) / Novothyrox / Oroxine (GlaxoSmithKline) / Thyrax (Merck)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Levothyroxine and Liothyronine ThyroidLevothyroxine (57 ug/1) + Liothyronine (13.5 ug/1)TabletOralWestminster2017-09-19Not applicableUs
Levothyroxine and Liothyronine ThyroidLevothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1)TabletOralWestminster2017-11-15Not applicableUs
Levothyroxine and Liothyronine ThyroidLevothyroxine (38 ug/1) + Liothyronine (9 ug/1)TabletOralWestminster2017-09-19Not applicableUs
Levothyroxine and Liothyronine ThyroidLevothyroxine (76 ug/1) + Liothyronine (18 ug/1)TabletOralWestminster2017-11-15Not applicableUs
Levothyroxine and Liothyronine ThyroidLevothyroxine (19 ug/1) + Liothyronine (4.5 ug/1)TabletOralWestminster2017-09-19Not applicableUs
NP Thyroid 120Levothyroxine (76 ug/1) + Liothyronine (18 ug/1)TabletOralAcella Pharmaceuticals, LLC2010-11-11Not applicableUs
NP Thyroid 120Levothyroxine (76 ug/1) + Liothyronine (18 ug/1)TabletOralPreferreed Pharmaceuticals Inc.2017-10-12Not applicableUs
NP Thyroid 15Levothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1)TabletOralPreferreed Pharmaceuticals Inc.2017-10-12Not applicableUs
NP Thyroid 15Levothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1)TabletOralAcella Pharmaceuticals, LLC2010-11-11Not applicableUs
NP Thyroid 30Levothyroxine (19 ug/1) + Liothyronine (4.5 ug/1)TabletOralbryant ranch prepack2010-11-11Not applicableUs
Categories
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.

TargetActionsOrganism
AThyroid hormone receptor alpha
agonist
Human
AThyroid hormone receptor beta
agonist
Human
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
PathwayCategory
Thyroid hormone synthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolLevothyroxine may increase the anticoagulant activities of Acenocoumarol.Approved
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Levothyroxine.Approved
AlaproclateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Alaproclate.Experimental
Aluminum hydroxideThe serum concentration of Levothyroxine can be decreased when it is combined with Aluminum hydroxide.Approved
Ambroxol acefyllinateThe metabolism of Ambroxol acefyllinate can be increased when combined with Levothyroxine.Experimental, Investigational
AmineptineLevothyroxine may increase the arrhythmogenic activities of Amineptine.Illicit, Withdrawn
AminophyllineThe metabolism of Aminophylline can be increased when combined with Levothyroxine.Approved
AmiodaroneThe metabolism of Levothyroxine can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineLevothyroxine may increase the arrhythmogenic activities of Amitriptyline.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Levothyroxine.Approved, Investigational
AmoxapineLevothyroxine may increase the arrhythmogenic activities of Amoxapine.Approved
AprepitantThe serum concentration of Levothyroxine can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Levothyroxine can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Levothyroxine can be decreased when combined with Atomoxetine.Approved
BoceprevirThe metabolism of Levothyroxine can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Levothyroxine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Levothyroxine can be decreased when it is combined with Bosentan.Approved, Investigational
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Levothyroxine.Approved
Calcium AcetateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Acetate.Approved
Calcium CarbonateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Carbonate.Approved
Calcium ChlorideThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Chloride.Approved
Calcium CitrateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Citrate.Approved
Calcium glubionateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium glubionate.Approved
Calcium GluceptateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Gluceptate.Approved
Calcium gluconateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium lactate.Approved, Experimental, Investigational, Vet Approved
Calcium lactate gluconateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium lactate gluconate.Experimental
Calcium laevulateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium laevulate.Experimental
Calcium pangamateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium pangamate.Experimental
Calcium PhosphateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Calcium Phosphate.Approved
CarbamazepineThe serum concentration of Levothyroxine can be decreased when it is combined with Carbamazepine.Approved, Investigational
CaseinThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Casein.Approved
CeritinibThe serum concentration of Levothyroxine can be increased when it is combined with Ceritinib.Approved
ChlorotrianiseneThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Chlorotrianisene.Investigational, Withdrawn
CholestyramineThe serum concentration of Levothyroxine can be decreased when it is combined with Cholestyramine.Approved
CiprofloxacinThe serum concentration of Levothyroxine can be decreased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Citalopram.Approved
ClarithromycinThe metabolism of Levothyroxine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Levothyroxine can be decreased when combined with Clemastine.Approved
ClomipramineLevothyroxine may increase the arrhythmogenic activities of Clomipramine.Approved, Vet Approved
ClorindioneLevothyroxine may increase the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Levothyroxine can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Levothyroxine can be decreased when combined with Cobicistat.Approved
ColesevelamThe serum concentration of Levothyroxine can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Levothyroxine can be decreased when it is combined with Colestipol.Approved
ConivaptanThe serum concentration of Levothyroxine can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated estrogensThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Conjugated estrogens.Approved
CrizotinibThe metabolism of Levothyroxine can be decreased when combined with Crizotinib.Approved
CyclobenzaprineLevothyroxine may increase the arrhythmogenic activities of Cyclobenzaprine.Approved
CyclosporineThe metabolism of Levothyroxine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Levothyroxine.Approved
DabrafenibThe serum concentration of Levothyroxine can be decreased when it is combined with Dabrafenib.Approved
DaidzeinThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Daidzein.Experimental
DapoxetineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Dapoxetine.Investigational
DarunavirThe metabolism of Levothyroxine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Levothyroxine can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Levothyroxine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Levothyroxine can be decreased when combined with Delavirdine.Approved
DesipramineLevothyroxine may increase the arrhythmogenic activities of Desipramine.Approved
DesvenlafaxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Desvenlafaxine.Approved
DibenzepinLevothyroxine may increase the arrhythmogenic activities of Dibenzepin.Experimental
DicoumarolLevothyroxine may increase the anticoagulant activities of Dicoumarol.Approved
DienestrolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Dienestrol.Approved, Investigational
DiethylstilbestrolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Diethylstilbestrol.Approved, Investigational
DihydroergotamineThe metabolism of Levothyroxine can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Levothyroxine can be decreased when combined with Diltiazem.Approved
DiphenadioneLevothyroxine may increase the anticoagulant activities of Diphenadione.Experimental
DosulepinLevothyroxine may increase the arrhythmogenic activities of Dosulepin.Approved
DoxepinLevothyroxine may increase the arrhythmogenic activities of Doxepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Levothyroxine.Approved, Investigational
DoxycyclineThe metabolism of Levothyroxine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Levothyroxine can be decreased when combined with Dronedarone.Approved
DuloxetineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Duloxetine.Approved
DyphyllineThe metabolism of Dyphylline can be increased when combined with Levothyroxine.Approved
EnzalutamideThe serum concentration of Levothyroxine can be decreased when it is combined with Enzalutamide.Approved
EpimestrolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Epimestrol.Experimental
EquolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Equol.Investigational
ErythromycinThe metabolism of Levothyroxine can be decreased when combined with Erythromycin.Approved, Vet Approved
EscitalopramThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Escitalopram.Approved, Investigational
EsmirtazapineLevothyroxine may increase the arrhythmogenic activities of Esmirtazapine.Investigational
EstradiolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estradiol.Approved, Investigational, Vet Approved
EstriolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estriol.Approved, Investigational, Vet Approved
Estrogens, esterifiedThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estrogens, esterified.Approved
EstroneThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estrone.Approved
Ethinyl EstradiolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Ethinyl Estradiol.Approved
Ethyl biscoumacetateLevothyroxine may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtoperidoneThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Etoperidone.Withdrawn
Ferric CarboxymaltoseThe serum concentration of Levothyroxine can be decreased when it is combined with Ferric Carboxymaltose.Approved
Ferric CitrateThe serum concentration of Levothyroxine can be decreased when it is combined with Ferric Citrate.Approved, Investigational
Ferric pyrophosphateThe serum concentration of Levothyroxine can be decreased when it is combined with Ferric pyrophosphate.Approved
FluconazoleThe metabolism of Levothyroxine can be decreased when combined with Fluconazole.Approved
FluindioneLevothyroxine may increase the anticoagulant activities of Fluindione.Investigational
FluoxetineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Levothyroxine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Levothyroxine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Levothyroxine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Levothyroxine can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Levothyroxine can be increased when it is combined with Fusidic Acid.Approved
GenisteinThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Genistein.Investigational
HexestrolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Hexestrol.Withdrawn
ImatinibThe metabolism of Levothyroxine can be decreased when combined with Imatinib.Approved
ImipramineLevothyroxine may increase the arrhythmogenic activities of Imipramine.Approved
IndalpineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Indalpine.Investigational, Withdrawn
IndinavirThe metabolism of Levothyroxine can be decreased when combined with Indinavir.Approved
Iodide I-131The therapeutic efficacy of Iodide I-131 can be decreased when used in combination with Levothyroxine.Approved
IprindoleLevothyroxine may increase the arrhythmogenic activities of Iprindole.Experimental
IronThe serum concentration of Levothyroxine can be decreased when it is combined with Iron.Approved
Iron DextranThe serum concentration of Levothyroxine can be decreased when it is combined with Iron Dextran.Approved, Vet Approved
Iron saccharateThe serum concentration of Levothyroxine can be decreased when it is combined with Iron saccharate.Approved
IsavuconazoniumThe metabolism of Levothyroxine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Levothyroxine can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Levothyroxine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Levothyroxine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Levothyroxine can be decreased when combined with Ketoconazole.Approved, Investigational
Lanthanum carbonateThe serum concentration of Levothyroxine can be decreased when it is combined with Lanthanum carbonate.Approved
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Levothyroxine.Approved
LevomilnacipranThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Levomilnacipran.Approved
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Levothyroxine.Approved
LofepramineLevothyroxine may increase the arrhythmogenic activities of Lofepramine.Experimental
LopinavirThe metabolism of Levothyroxine can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Levothyroxine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Levothyroxine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Levothyroxine can be increased when combined with Lumacaftor.Approved
Magnesium HydroxideThe serum concentration of Levothyroxine can be decreased when it is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe serum concentration of Levothyroxine can be decreased when it is combined with Magnesium oxide.Approved
Magnesium salicylateThe serum concentration of Levothyroxine can be decreased when it is combined with Magnesium salicylate.Approved
Magnesium SulfateThe serum concentration of Levothyroxine can be decreased when it is combined with Magnesium Sulfate.Approved, Vet Approved
MestranolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Mestranol.Approved
MethallenestrilThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Methallenestril.Experimental
MifepristoneThe serum concentration of Levothyroxine can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Milnacipran.Approved
MirtazapineLevothyroxine may increase the arrhythmogenic activities of Mirtazapine.Approved
MitotaneThe serum concentration of Levothyroxine can be decreased when it is combined with Mitotane.Approved
MoxestrolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Moxestrol.Experimental
NefazodoneThe metabolism of Levothyroxine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Levothyroxine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Levothyroxine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Levothyroxine can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Levothyroxine can be decreased when combined with Nilotinib.Approved, Investigational
NortriptylineLevothyroxine may increase the arrhythmogenic activities of Nortriptyline.Approved
OlaparibThe metabolism of Levothyroxine can be decreased when combined with Olaparib.Approved
OpipramolLevothyroxine may increase the arrhythmogenic activities of Opipramol.Investigational
OrlistatThe serum concentration of Levothyroxine can be decreased when it is combined with Orlistat.Approved, Investigational
OsimertinibThe serum concentration of Levothyroxine can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Levothyroxine can be increased when it is combined with Palbociclib.Approved
ParoxetineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Paroxetine.Approved, Investigational
PentobarbitalThe metabolism of Levothyroxine can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenindioneLevothyroxine may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe metabolism of Levothyroxine can be increased when combined with Phenobarbital.Approved
PhenprocoumonLevothyroxine may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe serum concentration of Levothyroxine can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PiracetamThe risk or severity of adverse effects can be increased when Piracetam is combined with Levothyroxine.Approved, Investigational
PolaprezincThe serum concentration of Levothyroxine can be decreased when it is combined with Polaprezinc.Approved, Investigational
Polyestradiol phosphateThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Polyestradiol phosphate.Approved
PosaconazoleThe metabolism of Levothyroxine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Levothyroxine can be increased when combined with Primidone.Approved, Vet Approved
PromestrieneThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Promestriene.Investigational
ProtriptylineLevothyroxine may increase the arrhythmogenic activities of Protriptyline.Approved
QuinestrolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Quinestrol.Approved
RaloxifeneRaloxifene can cause a decrease in the absorption of Levothyroxine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
RanolazineThe metabolism of Levothyroxine can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Levothyroxine can be increased when combined with Rifabutin.Approved
RifampicinThe serum concentration of Levothyroxine can be decreased when it is combined with Rifampicin.Approved
RifapentineThe metabolism of Levothyroxine can be increased when combined with Rifapentine.Approved
SaquinavirThe metabolism of Levothyroxine can be decreased when combined with Saquinavir.Approved, Investigational
SecoisolariciresinolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Secoisolariciresinol.Investigational
SertralineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Sertraline.Approved
SevelamerThe serum concentration of Levothyroxine can be decreased when it is combined with Sevelamer.Approved
SildenafilThe metabolism of Levothyroxine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Levothyroxine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Levothyroxine can be increased when it is combined with Simeprevir.Approved
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Levothyroxine.Approved
St. John's WortThe serum concentration of Levothyroxine can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Levothyroxine can be increased when it is combined with Stiripentol.Approved
SucralfateThe serum concentration of Levothyroxine can be decreased when it is combined with Sucralfate.Approved
SulfisoxazoleThe metabolism of Levothyroxine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
Synthetic Conjugated Estrogens, AThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Synthetic Conjugated Estrogens, B.Approved
TelaprevirThe metabolism of Levothyroxine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Levothyroxine can be decreased when combined with Telithromycin.Approved
TheophyllineThe metabolism of Theophylline can be increased when combined with Levothyroxine.Approved
TianeptineLevothyroxine may increase the arrhythmogenic activities of Tianeptine.Approved, Investigational
TiboloneThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Tibolone.Approved, Investigational
TiclopidineThe metabolism of Levothyroxine can be decreased when combined with Ticlopidine.Approved
TioclomarolLevothyroxine may increase the anticoagulant activities of Tioclomarol.Experimental
TocilizumabThe serum concentration of Levothyroxine can be decreased when it is combined with Tocilizumab.Approved
TolevamerThe serum concentration of Levothyroxine can be decreased when it is combined with Tolevamer.Approved
TrimipramineLevothyroxine may increase the arrhythmogenic activities of Trimipramine.Approved
VenlafaxineThe metabolism of Levothyroxine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Levothyroxine can be decreased when combined with Verapamil.Approved
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Levothyroxine.Approved, Investigational
VoriconazoleThe metabolism of Levothyroxine can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinLevothyroxine may increase the anticoagulant activities of Warfarin.Approved
ZeranolThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Zeranol.Vet Approved
ZimelidineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Zimelidine.Withdrawn
ZiprasidoneThe 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
  1. 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
HMDB00248
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
PhaseStatusPurposeConditionsCount
0Enrolling by InvitationPreventionRecurrent Pregnancy Losses1
1CompletedNot AvailableDrug Interactions1
1CompletedNot AvailableHealthy Volunteers4
1CompletedBasic SciencePharmacokinetics2
1CompletedTreatmentDiabetes Mellitus (DM) / Healthy Volunteers1
1CompletedTreatmentHealthy Males1
1, 2CompletedTreatmentBrain Death1
1, 2Not Yet RecruitingOtherHealthy Volunteers1
2CompletedNot AvailableThyroid Diseases1
2TerminatedTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD) / Type 2 Diabetes Mellitus1
2, 3Active Not RecruitingPreventionGraves' Disease1
2, 3CompletedTreatmentBipolar Disorder (BD)1
2, 3CompletedTreatmentSubclinical Hypothyroidism2
2, 3Not Yet RecruitingTreatmentHypothyroidism / Neoplasms / Postoperative Complications1
2, 3RecruitingTreatmentHypothyroidism1
3Active Not RecruitingTreatmentHypothyroxinemia1
3CompletedTreatmentCongenital Hypothyroidism / Hypothyroidism1
3CompletedTreatmentHypothyroxinemia / Pregnancy / Subclinical Hypothyroidism1
3Not Yet RecruitingTreatmentTransient Hypothyroxinemia of Prematurity (THOP)1
3Unknown StatusTreatmentDyslipidemias1
4Active Not RecruitingTreatmentEndocrine System Diseases / Hypothyroidism / Thyroid Diseases2
4Active Not RecruitingTreatmentMental Fatigue / Thyroid Dysfunction / Tiredness1
4CompletedNot AvailableHypothyroidism1
4CompletedPreventionGraves´ Disease1
4CompletedTreatmentAtherosclerosis / Heart Failure, Unspecified / Thyroid Dysfunction2
4CompletedTreatmentBone destruction / Bone Mineral Density / Fractures, Bone / Thyroid Dysfunction1
4CompletedTreatmentEuthyroid Sick Syndromes1
4CompletedTreatmentGraves' Disease / Toxic Nodular Goitre1
4CompletedTreatmentHypothyroidism1
4CompletedTreatmentSubclinical Hypothyroidism1
4Not Yet RecruitingTreatmentGoitre1
4Not Yet RecruitingTreatmentHypothyroidism;Postablative1
4RecruitingNot AvailableHypothyroidism1
4RecruitingPreventionHypothyroidism1
4RecruitingTreatmentDepression / Subclinical Hypothyroidism1
4RecruitingTreatmentHeart Failure, Unspecified / Subclinical Hyperthyroidism1
4RecruitingTreatmentHypothyroidism1
4RecruitingTreatmentHypothyroidism / Myocardial Infarction (MI)1
4RecruitingTreatmentPostsurgical Hypothyroidism / Thyroid Cancers1
4Unknown StatusBasic ScienceDiabetes Mellitus (DM) / Hypothyroidism1
4Unknown StatusSupportive CareBrain Dead Organ Donors1
4Unknown StatusTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF) / Sub-clinical Hypothyroidism1
4WithdrawnPreventionSystemic Lupus Erythematosus (SLE)1
4WithdrawnTreatmentSubclinical hypothyroïdism1
Not AvailableActive Not RecruitingNot AvailableHead and Neck Carcinoma / Hypothyroidism; Surgery / Laryngeal Cancer / Laryngeal fistula / Wound Heal1
Not AvailableActive Not RecruitingTreatmentDown Syndrome (DS) / Subclinical Hypothyroidism1
Not AvailableCompletedNot AvailableRecurrent Goiter1
Not AvailableCompletedNot AvailableSubclinical Hypothyroidism1
Not AvailableCompletedBasic ScienceHypothyroidism1
Not AvailableCompletedBasic ScienceObesity, Morbid1
Not AvailableCompletedTreatmentCongenital Hypothyroidism1
Not AvailableCompletedTreatmentDiabetes Mellitus (DM)1
Not AvailableCompletedTreatmentHypothyroidism1
Not AvailableCompletedTreatmentHypothyroidism / Pregnancy1
Not AvailableCompletedTreatmentPregnancy / Thyroid Diseases1
Not AvailableCompletedTreatmentThyroid Nodules1
Not AvailableRecruitingNot AvailableHypothyroidism2
Not AvailableRecruitingNot AvailableHypothyroidism / Postsurgical Hypothyroidism1
Not AvailableRecruitingOtherSubclinical Hypothyroidism1
Not AvailableRecruitingTreatmentDepression / Distress / Feeling Anxious / Thyroid Cancers / Tiredness1
Not AvailableRecruitingTreatmentHypothyroidism1
Not AvailableRecruitingTreatmentPregnancy Related / Thyroid1
Not AvailableTerminatedBasic ScienceHypothyroidism1
Not AvailableTerminatedTreatmentHypothyroidism / Neoplasms, Brain1
Not AvailableUnknown StatusDiagnosticCentral Hypothyroidism1
Not AvailableUnknown StatusTreatmentPrimary Hypothyroidism1

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
Dosage forms
FormRouteStrength
TabletOral.1 mg
TabletOral.2 mg
TabletOral.3 mg
TabletOral.05 mg
Injection, powder, lyophilized, for solutionIntravenous100 ug/5mL
Injection, powder, lyophilized, for solutionIntravenous200 ug/5mL
Injection, powder, lyophilized, for solutionIntravenous500 ug/5mL
TabletOral.025 mg/1
TabletOral.05 mg/1
TabletOral.075 mg/1
TabletOral.088 mg/1
TabletOral.1 mg/1
TabletOral.112 mg/1
TabletOral.125 mg/1
TabletOral.137 mg/1
TabletOral.15 mg/1
TabletOral.175 mg/1
TabletOral.2 mg/1
TabletOral.3 mg/1
TabletOral112 ug/1
TabletOral125 ug/1
TabletOral175 ug/1
TabletOral25 ug/1
TabletOral50 ug/1
TabletOral75 ug/1
Powder, for solutionIntramuscular; Intravenous200 mcg
Powder, for solutionIntramuscular; Intravenous500 mcg
TabletOral
TabletOral100 ug/1
TabletOral137 ug/1
TabletOral137 mcg
TabletOral150 ug/1
TabletOral200 ug/1
TabletOral300 ug/1
TabletOral88 ug/1
LiquidIntravenous500 mcg
TabletOral100 mcg
TabletOral112 mcg
TabletOral125 mcg
TabletOral150 mcg
TabletOral175 mcg
TabletOral200 mcg
TabletOral25 mcg
TabletOral300 mcg
TabletOral50 mcg
TabletOral75 mcg
TabletOral88 mcg
CapsuleOral100 ug/1
CapsuleOral112 ug/1
CapsuleOral125 ug/1
CapsuleOral13 ug/1
CapsuleOral137 ug/1
CapsuleOral150 ug/1
CapsuleOral175 ug/1
CapsuleOral200 ug/1
CapsuleOral25 ug/1
CapsuleOral50 ug/1
CapsuleOral75 ug/1
CapsuleOral88 ug/1
Prices
Unit descriptionCostUnit
Levothyroxine sodium powder159.12USD g
Levothyroxine 200 mcg vial24.0USD vial
Levothyroxine 500 mcg vial24.0USD vial
Levoxyl 300 mcg tablet2.34USD tablet
Synthroid 300 mcg tablet1.29USD tablet
Synthroid 175 mcg tablet1.07USD tablet
Synthroid 200 mcg tablet0.99USD tablet
Synthroid 137 mcg tablet0.87USD tablet
Synthroid 112 mcg tablet0.84USD tablet
Synthroid 125 mcg tablet0.84USD tablet
Synthroid 150 mcg tablet0.83USD tablet
Levothyroxine Sodium 300 mcg tablet0.77USD tablet
Synthroid 100 mcg tablet0.73USD tablet
Synthroid 75 mcg tablet0.72USD tablet
Synthroid 88 mcg tablet0.71USD tablet
Levoxyl 200 mcg tablet0.7USD tablet
Levoxyl 175 mcg tablet0.69USD tablet
Unithroid 300 mcg tablet0.69USD tablet
Synthroid 50 mcg tablet0.65USD tablet
Levoxyl 137 mcg tablet0.62USD tablet
Unithroid 200 mcg tablet0.62USD tablet
Levoxyl 112 mcg tablet0.61USD tablet
Synthroid 25 mcg tablet0.61USD tablet
Unithroid 175 mcg tablet0.61USD tablet
Levoxyl 150 mcg tablet0.59USD tablet
Levoxyl 125 mcg tablet0.58USD tablet
Levothyroxine Sodium 175 mcg tablet0.57USD tablet
Levothyroxine Sodium 200 mcg tablet0.57USD tablet
Levothyroxine 175 mcg tablet0.55USD tablet
Unithroid 150 mcg tablet0.55USD tablet
Levoxyl 88 mcg tablet0.54USD tablet
Unithroid 112 mcg tablet0.53USD tablet
Unithroid 125 mcg tablet0.53USD tablet
Levoxyl 75 mcg tablet0.52USD tablet
Levothroid 300 mcg tablet0.51USD tablet
Levoxyl 100 mcg tablet0.51USD tablet
Levothyroxine Sodium 100 mcg tablet0.5USD tablet
Levothyroxine Sodium 150 mcg tablet0.5USD tablet
Levothyroxine Sodium 88 mcg tablet0.5USD tablet
Levoxyl 50 mcg tablet0.49USD tablet
Unithroid 88 mcg tablet0.49USD tablet
Unithroid 100 mcg tablet0.47USD tablet
Unithroid 75 mcg tablet0.47USD tablet
Levothyroxine Sodium 125 mcg tablet0.47USD tablet
Levothyroxine Sodium 137 mcg tablet0.47USD tablet
Levothyroxine Sodium 50 mcg tablet0.47USD tablet
Levothyroxine Sodium 75 mcg tablet0.47USD tablet
Levothyroxine Sodium 112 mcg tablet0.46USD tablet
Levothyroxine 137 mcg tablet0.45USD tablet
Levoxyl 25 mcg tablet0.45USD tablet
Levothyroxine 112 mcg tablet0.44USD tablet
Levothyroxine Sodium 25 mcg tablet0.43USD tablet
Unithroid 50 mcg tablet0.43USD tablet
Unithroid 25 mcg tablet0.42USD tablet
Unithroid direct 100 mcg tablet0.42USD tablet
Unithroid direct 112 mcg tablet0.42USD tablet
Unithroid direct 125 mcg tablet0.42USD tablet
Unithroid direct 150 mcg tablet0.42USD tablet
Unithroid direct 175 mcg tablet0.42USD tablet
Unithroid direct 200 mcg tablet0.42USD tablet
Unithroid direct 25 mcg tablet0.42USD tablet
Unithroid direct 300 mcg tablet0.42USD tablet
Unithroid direct 50 mcg tablet0.42USD tablet
Unithroid direct 75 mcg tablet0.42USD tablet
Unithroid direct 88 mcg tablet0.42USD tablet
Levothroid 200 mcg tablet0.4USD tablet
Levothroid 175 mcg tablet0.38USD tablet
Levothyroxine 88 mcg tablet0.38USD tablet
Levothroid 125 mcg tablet0.36USD tablet
Levothroid 150 mcg tablet0.36USD tablet
Levothroid 100 mcg tablet0.35USD tablet
Levothroid 137 mcg tablet0.35USD tablet
Levothroid 112 mcg tablet0.34USD tablet
Levothroid 75 mcg tablet0.33USD tablet
Levothroid 88 mcg tablet0.33USD tablet
Levothyroxine 300 mcg tablet0.32USD tablet
Levothroid 25 mcg tablet0.31USD tablet
Unithroid 137 mcg tablet0.31USD tablet
Levothroid 50 mcg tablet0.3USD tablet
Levothyroxine 200 mcg tablet0.29USD tablet
Levothyroxine 150 mcg tablet0.24USD tablet
Levothyroxine 125 mcg tablet0.22USD tablet
Levothyroxine 100 mcg tablet0.2USD tablet
Levothyroxine 75 mcg tablet0.2USD tablet
Levothyroxine 50 mcg tablet0.18USD tablet
Synthroid 0.137 mg Tablet0.18USD tablet
Levothyroxine 25 mcg tablet0.17USD tablet
Synthroid 0.3 mg Tablet0.12USD tablet
Synthroid 0.175 mg Tablet0.11USD tablet
Synthroid 0.075 mg Tablet0.1USD tablet
Synthroid 0.088 mg Tablet0.1USD tablet
Synthroid 0.112 mg Tablet0.1USD tablet
Synthroid 0.125 mg Tablet0.1USD tablet
Synthroid 0.025 mg Tablet0.09USD tablet
Synthroid 0.2 mg Tablet0.09USD tablet
Synthroid 0.1 mg Tablet0.08USD tablet
Synthroid 0.15 mg Tablet0.08USD tablet
Eltroxin 0.3 mg Tablet0.07USD tablet
Synthroid 0.05 mg Tablet0.06USD tablet
Eltroxin 0.2 mg Tablet0.05USD tablet
Eltroxin 0.1 mg Tablet0.04USD tablet
Eltroxin 0.15 mg Tablet0.04USD tablet
Eltroxin 0.05 mg Tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7723390No2004-03-142024-03-14Us
US7101569No2003-10-022023-10-02Us
US7067148No2002-02-152022-02-15Us
US6555581No2002-02-152022-02-15Us
US6399101No2000-03-302020-03-30Us
US9168239No2012-08-292032-08-29Us
US9168238No2012-08-292032-08-29Us
US9006289No2012-10-032032-10-03Us
US7691411No2004-03-142024-03-14Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)235.5 °CPhysProp
water solubility0.105 mg/mLNot Available
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00898 mg/mLALOGPS
logP1.15ALOGPS
logP3.73ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.27ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.79 m3·mol-1ChemAxon
Polarizability49.4 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7212
Blood Brain Barrier-0.6886
Caco-2 permeable-0.653
P-glycoprotein substrateNon-substrate0.5321
P-glycoprotein inhibitor INon-inhibitor0.9175
P-glycoprotein inhibitor IINon-inhibitor0.9709
Renal organic cation transporterNon-inhibitor0.8891
CYP450 2C9 substrateNon-substrate0.8309
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6847
CYP450 1A2 substrateNon-inhibitor0.5924
CYP450 2C9 inhibitorNon-inhibitor0.7037
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8459
Ames testNon AMES toxic0.7591
CarcinogenicityNon-carcinogens0.9148
BiodegradationNot ready biodegradable0.9693
Rat acute toxicity2.7082 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9697
hERG inhibition (predictor II)Non-inhibitor0.8508
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0ac9-0591664310-c9b7aec3184ebb20a2da
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-014i-2566449540-35bb942c7bcbcfe41af7
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00xr-3375497520-9dee3cb0c153e6c6df9e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0059-0001001900-83ff4aafed0b73c6c7b7
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
  1. 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]
  2. 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]
  3. Bernal J: Thyroid hormone receptors in brain development and function. Nat Clin Pract Endocrinol Metab. 2007 Mar;3(3):249-59. [PubMed:17315033]
  4. 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]
  5. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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
  1. 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
  1. 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

Details
1. Transthyretin
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
  1. 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]
  2. 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
  1. 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
  1. 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
  1. 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]
  2. 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]
  3. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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 December 10, 2017 17:18