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

Similar Structures

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
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Eltroxin	Tablet	300 mcg	Oral	Aspen Pharmacare Canada Inc.	1998-02-11	Not applicable
Eltroxin	Tablet	50 mcg	Oral	Aspen Pharmacare Canada Inc.	1951-12-30	Not applicable
Eltroxin	Tablet	150 mcg	Oral	Aspen Pharmacare Canada Inc.	1974-12-31	Not applicable
Eltroxin	Tablet	200 mcg	Oral	Aspen Pharmacare Canada Inc.	1997-04-02	Not applicable
Eltroxin	Tablet	100 mcg	Oral	Aspen Pharmacare Canada Inc.	1998-11-27	Not applicable
Eltroxin 150 Tab	Tablet	150 mcg	Oral	Glaxo Canada Inc	1974-12-31	1999-08-12
Eltroxin Tab 100mcg	Tablet	.1 mg	Oral	Glaxo Canada Inc	1951-12-31	1999-08-12
Eltroxin Tab 200mcg	Tablet	.2 mg	Oral	Glaxo Canada Inc	1960-12-31	1998-07-30
Eltroxin Tab 300mcg	Tablet	.3 mg	Oral	Glaxo Canada Inc	1966-12-31	1998-07-30
Eltroxin Tab 50mcg	Tablet	.05 mg	Oral	Glaxo Canada Inc	1951-12-31	1998-07-30

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Levothyroxine	Tablet	125 ug/1	Oral	Northwind Pharmaceuticals	2014-09-14	Not applicable
Levothyroxine Sodium	Tablet	125 ug/1	Oral	Med Health Pharma	2011-02-10	2012-10-31
Levothyroxine Sodium	Tablet	125 ug/1	Oral	Cardinal Health	2010-10-29	Not applicable
Levothyroxine Sodium	Tablet	25 ug/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Levothyroxine sodium	Tablet	50 ug/1	Oral	bryant ranch prepack	2002-03-01	Not applicable
Levothyroxine Sodium	Tablet	100 ug/1	Oral	Preferreed Pharmaceuticals Inc.	2015-04-21	Not applicable
Levothyroxine sodium	Tablet	88 ug/1	Oral	Sandoz Inc.	2002-03-01	Not applicable
Levothyroxine Sodium	Tablet	125 ug/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Levothyroxine sodium	Tablet	88 ug/1	Oral	bryant ranch prepack	2002-03-01	Not applicable
Levothyroxine sodium	Tablet	112 ug/1	Oral	A-S Medication Solutions	2002-03-01	2016-08-31

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Thyrolar	Levothyroxine sodium (50 ug/1) + Liothyronine sodium (12.5 ug/1)	Tablet	Oral	Allergan	1969-11-21	Not applicable
Thyrolar	Levothyroxine sodium (25 ug/1) + Liothyronine sodium (6.25 ug/1)	Tablet	Oral	Allergan	1969-11-21	Not applicable
Thyrolar	Levothyroxine sodium (150 ug/1) + Liothyronine sodium (37.5 ug/1)	Tablet	Oral	Allergan	1969-11-21	Not applicable
Thyrolar	Levothyroxine sodium (12.5 ug/1) + Liothyronine sodium (3.1 ug/1)	Tablet	Oral	Allergan	1969-11-21	Not applicable
Thyrolar	Levothyroxine sodium (100 ug/1) + Liothyronine sodium (25 ug/1)	Tablet	Oral	Allergan	1969-11-21	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Levothyroxine and Liothyronine Thyroid	Levothyroxine (38 ug/1) + Liothyronine (9 ug/1)	Tablet	Oral	Westminster	2017-09-19	Not applicable
Levothyroxine and Liothyronine Thyroid	Levothyroxine (19 ug/1) + Liothyronine (4.5 ug/1)	Tablet	Oral	bryant ranch prepack	2017-09-19	Not applicable
Levothyroxine and Liothyronine Thyroid	Levothyroxine (19 ug/1) + Liothyronine (4.5 ug/1)	Tablet	Oral	Westminster	2017-09-19	Not applicable
Levothyroxine and Liothyronine Thyroid	Levothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1)	Tablet	Oral	Westminster	2017-11-15	Not applicable
Levothyroxine and Liothyronine Thyroid	Levothyroxine (38 ug/1) + Liothyronine (9 ug/1)	Tablet	Oral	bryant ranch prepack	2017-09-19	Not applicable
Levothyroxine and Liothyronine Thyroid	Levothyroxine (76 ug/1) + Liothyronine (18 ug/1)	Tablet	Oral	Westminster	2017-11-15	Not applicable
Levothyroxine and Liothyronine Thyroid	Levothyroxine (57 ug/1) + Liothyronine (13.5 ug/1)	Tablet	Oral	Westminster	2017-09-19	Not applicable
NP Thyroid 120	Levothyroxine (76 ug/1) + Liothyronine (18 ug/1)	Tablet	Oral	Acella Pharmaceuticals, LLC	2017-06-12	Not applicable
NP Thyroid 120	Levothyroxine (76 ug/1) + Liothyronine (18 ug/1)	Tablet	Oral	Preferreed Pharmaceuticals Inc.	2017-10-12	Not applicable
NP Thyroid 15	Levothyroxine (9.5 ug/1) + Liothyronine (2.25 ug/1)	Tablet	Oral	Preferreed Pharmaceuticals Inc.	2017-10-12	Not applicable

International/Other Brands

Eutirox (Merck) / Letrox (Berlin-Chemie) / Levaxin (Nycomed) / Levothyrox (Merck) / Oroxine (GlaxoSmithKline) / Thyrax (Merck)

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[C@@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.

Associated Conditions

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	agonist	Humans
AThyroid hormone receptor beta	agonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

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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

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
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(R)-warfarin	The metabolism of Levothyroxine can be decreased when combined with (R)-warfarin.
(S)-Warfarin	The metabolism of Levothyroxine can be decreased when combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Levothyroxine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Levothyroxine.
3-isobutyl-1-methyl-7H-xanthine	The serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Levothyroxine.
3,5-diiodothyropropionic acid	The metabolism of Levothyroxine can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Levothyroxine.
4-hydroxycoumarin	The metabolism of Levothyroxine can be decreased when combined with 4-hydroxycoumarin.
5-androstenedione	The metabolism of Levothyroxine can be decreased when combined with 5-androstenedione.
5-fluorouridine	The therapeutic efficacy of Levothyroxine can be decreased when used in combination with 5-fluorouridine.

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Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Action

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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
Guide to Pharmacology: GtP Drug Page
HET: T44
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 …

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FDA label

Download (54.3 KB)

MSDS

Download (51.7 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Enrolling by Invitation	Prevention	Recurrent Pregnancy Losses	1
1	Completed	Not Available	Drug Drug Interaction (DDI)	1
1	Completed	Not Available	Healthy Volunteers	4
1	Completed	Basic Science	Pharmacokinetics	2
1	Completed	Treatment	Diabetes Mellitus (DM) / Healthy Volunteers	1
1	Completed	Treatment	Healthy Males	1
1	Not Yet Recruiting	Treatment	Healthy Volunteers	1
1, 2	Completed	Treatment	Brain Death	1
1, 2	Recruiting	Other	Healthy Volunteers	1
2	Completed	Not Available	Thyroid Diseases	1
2	Recruiting	Treatment	Biomarkers / Endocrine System Diseases / Hypothyroidism	1
2	Terminated	Treatment	Non-Alcoholic Fatty Liver Disease (NAFLD) / Type 2 Diabetes Mellitus	1
2, 3	Active Not Recruiting	Prevention	Graves' Disease	1
2, 3	Completed	Treatment	Bipolar Disorder (BD)	1
2, 3	Completed	Treatment	Subclinical Hypothyroidism	2
2, 3	Not Yet Recruiting	Treatment	Hypothyroidism / Neoplasms / Postoperative Complications	1
2, 3	Recruiting	Treatment	Hypothyroidism	1
3	Completed	Treatment	Chronic Kidney Disease (CKD) / Subclinical Hypothyroidism	1
3	Completed	Treatment	Hypothyroxinemia	1
3	Completed	Treatment	Hypothyroxinemia / Pregnancy / Subclinical Hypothyroidism	1
3	Not Yet Recruiting	Treatment	Transient Hypothyroxinemia of Prematurity (THOP)	1
3	Recruiting	Treatment	Euthyroid Females	1
3	Unknown Status	Treatment	Dyslipidemias	1
4	Active Not Recruiting	Treatment	Endocrine System Diseases / Hypothyroidism / Thyroid Diseases	2
4	Active Not Recruiting	Treatment	Healthy Volunteers	1
4	Completed	Not Available	Hypothyroidism	1
4	Completed	Prevention	Graves´ Disease	1
4	Completed	Treatment	Atherosclerosis / Heart Failure / Thyroid Dysfunction	2
4	Completed	Treatment	Bone Mineral Density / Fractures, Bone / Osteoporosis / Thyroid Dysfunction	1
4	Completed	Treatment	Depression / Subclinical Hypothyroidism	1
4	Completed	Treatment	Euthyroid Sick Syndromes	1
4	Completed	Treatment	Graves' Disease / Toxic Nodular Goitre	1
4	Completed	Treatment	Hypothyroidism	2
4	Completed	Treatment	Mental Fatigue / Thyroid Dysfunction / Tiredness	1
4	Completed	Treatment	Subclinical Hypothyroidism	1
4	Not Yet Recruiting	Treatment	Goitre	1
4	Recruiting	Not Available	Hypothyroidism	1
4	Recruiting	Treatment	Heart Failure / Subclinical Hyperthyroidism / Subclinical Hypothyroidism	1
4	Recruiting	Treatment	Hypothyroidism	1
4	Recruiting	Treatment	Hypothyroidism;Postablative	1
4	Recruiting	Treatment	Hypothyroidism / Myocardial Infarction	1
4	Recruiting	Treatment	Postsurgical Hypothyroidism / Thyroid Cancers	1
4	Terminated	Supportive Care	Brain Dead Organ Donors	1
4	Unknown Status	Basic Science	Diabetes Mellitus (DM) / Hypothyroidism	1
4	Unknown Status	Treatment	Heart Failure With Reduced Ejection Fraction (HFrEF) / Sub-clinical Hypothyroidism	1
4	Withdrawn	Prevention	Systemic Lupus Erythematosus (SLE)	1
4	Withdrawn	Treatment	Subclinical hypothyroïdism	1
Not Available	Active Not Recruiting	Other	Subclinical Hypothyroidism	1
Not Available	Active Not Recruiting	Treatment	Down Syndrome (DS) / Subclinical Hypothyroidism	1
Not Available	Completed	Not Available	Hypothyroidism	2
Not Available	Completed	Not Available	Recurrent Goiter	1
Not Available	Completed	Not Available	Subclinical Hypothyroidism	1
Not Available	Completed	Basic Science	Hypothyroidism	1
Not Available	Completed	Basic Science	Obesity, Morbid	1
Not Available	Completed	Screening	Pregnancy Loss / Sub Clinical Hypothyroidism / Subclinical hypothyroïdism	1
Not Available	Completed	Treatment	Congenital Hypothyroidism	1
Not Available	Completed	Treatment	Congenital Hypothyroidism / Hypothyroidism	1
Not Available	Completed	Treatment	Depression / Distress / Feeling Anxious / Thyroid Cancers / Tiredness	1
Not Available	Completed	Treatment	Diabetes Mellitus (DM)	1
Not Available	Completed	Treatment	Hypothyroidism / Pregnancy	1
Not Available	Completed	Treatment	Pregnancy / Thyroid Diseases	1
Not Available	Completed	Treatment	Thyroid Nodules	1
Not Available	Enrolling by Invitation	Not Available	Head and Neck Carcinoma / Hypothyroidism; Surgery / Laryngeal Cancer / Laryngeal fistula / Wound Heal	1
Not Available	Not Yet Recruiting	Not Available	Quality of Life / Thyroid; Deficiency	1
Not Available	Recruiting	Not Available	Hypothyroidism	1
Not Available	Recruiting	Not Available	Hypothyroidism / Postsurgical Hypothyroidism	1
Not Available	Recruiting	Treatment	ASCVD / Dyslipidemias / Lipid-Lowering Therapy / Statin / Subclinical hypothyroïdism	1
Not Available	Recruiting	Treatment	Hypothyroidism	1
Not Available	Recruiting	Treatment	Pregnancy Related / Thyroid	1
Not Available	Terminated	Basic Science	Hypothyroidism	1
Not Available	Terminated	Treatment	Hypothyroidism / Neoplasms, Brain	1
Not Available	Unknown Status	Diagnostic	Central Hypothyroidism	1
Not Available	Unknown Status	Treatment	Primary Hypothyroidism	1

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	Intravenous	100 ug/5mL
Injection	Intravenous	500 ug/5mL
Injection, powder, lyophilized, for solution	Intravenous	100 ug/5mL
Injection, powder, lyophilized, for solution	Intravenous	100 ug/1
Injection, powder, lyophilized, for solution	Intravenous	200 ug/5mL
Injection, powder, lyophilized, for solution	Intravenous	500 ug/1
Injection, powder, lyophilized, for solution	Intravenous	500 ug/5mL
Injection, solution	Intravenous	100 ug/1mL
Injection, solution	Intravenous	20 ug/1mL
Injection, solution	Intravenous	40 ug/1mL
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	.150 mg/1
Tablet	Oral	0.025 mg/1
Tablet	Oral	0.05 mg/1
Tablet	Oral	0.050 mg/1
Tablet	Oral	0.075 mg/1
Tablet	Oral	0.088 mg/1
Tablet	Oral	0.1 mg/1
Tablet	Oral	0.100 mg/1
Tablet	Oral	0.112 mg/1
Tablet	Oral	0.125 mg/1
Tablet	Oral	0.137 mg/1
Tablet	Oral	0.15 mg/1
Tablet	Oral	0.150 mg/1
Tablet	Oral	0.175 mg/1
Tablet	Oral	0.2 mg/1
Tablet	Oral	0.200 mg/1
Tablet	Oral	0.3 mg/1
Tablet	Oral	0.300 mg/1
Tablet	Oral	100 ug/1
Tablet	Oral	112 ug/1
Tablet	Oral	125 ug/1
Tablet	Oral	137 ug/1
Tablet	Oral	150 ug/1
Tablet	Oral	175 ug/1
Tablet	Oral	200 ug/1
Tablet	Oral	25 ug/1
Tablet	Oral	300 ug/1
Tablet	Oral	50 ug/1
Tablet	Oral	75 ug/1
Tablet	Oral	88 ug/1
Powder, for solution	Intramuscular; Intravenous	200 mcg
Powder, for solution	Intramuscular; Intravenous	500 mcg
Tablet	Topical
Tablet	Oral	137 mcg
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
Tablet	Oral
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
Solution	Oral	100 ug/1mL
Solution	Oral	112 ug/1mL
Solution	Oral	125 ug/1mL
Solution	Oral	13 ug/1mL
Solution	Oral	137 ug/1mL
Solution	Oral	150 ug/1mL
Solution	Oral	175 ug/1mL
Solution	Oral	200 ug/1mL
Solution	Oral	25 ug/1mL
Solution	Oral	50 ug/1mL
Solution	Oral	75 ug/1mL
Solution	Oral	88 ug/1mL

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

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Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US7723390	No	2010-05-25	2024-03-14
US7101569	No	2006-09-05	2023-10-02
US7067148	No	2006-06-27	2022-02-15
US6555581	No	2003-04-29	2022-02-15
US6399101	No	2002-06-04	2020-03-30
US9168239	No	2015-10-27	2032-08-29
US9168238	No	2015-10-27	2032-08-29
US9006289	No	2015-04-14	2032-10-03
US7691411	No	2010-04-06	2024-03-14

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

Learn more

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive	LC-MS/MS	splash10-0ac9-0591664310-c9b7aec3184ebb20a2da
MS/MS Spectrum - Quattro_QQQ 25V, Positive	LC-MS/MS	splash10-014i-2566449540-35bb942c7bcbcfe41af7
MS/MS Spectrum - Quattro_QQQ 40V, Positive	LC-MS/MS	splash10-00xr-3375497520-9dee3cb0c153e6c6df9e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0059-0001001900-83ff4aafed0b73c6c7b7
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not 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

Details1. Thyroid hormone receptor alpha

Kind: Protein
Organism: Humans
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]

Details2. Thyroid hormone receptor beta

Kind: Protein
Organism: Humans
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

Details1. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
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]
Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]

Details2. UDP-glucuronosyltransferase 1-1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Steroid binding
Specific Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name: UGT1A1
Uniprot ID: P22309
Uniprot Name: UDP-glucuronosyltransferase 1-1
Molecular Weight: 59590.91 Da

References

Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]

Carriers

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	10500	N/A	N/A	19651509

Details1. Transthyretin

Kind: Protein
Organism: Humans
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]

Details2. Thyroxine-binding globulin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

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]

Details3. Serum albumin

Kind: Protein
Organism: Humans
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

Details1. Solute carrier organic anion transporter family member 1C1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

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]
Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Details2. Monocarboxylate transporter 8

Kind: Protein
Organism: Humans
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]

Details3. Multidrug resistance protein 1

Kind: Protein
Organism: Humans
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]

Details4. Solute carrier organic anion transporter family member 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

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]
Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Details5. Solute carrier organic anion transporter family member 1B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

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]
Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Details6. Solute carrier organic anion transporter family member 1B3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

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]
Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Details7. Solute carrier organic anion transporter family member 4A1

Kind: Protein
Organism: Humans
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]

Details8. Solute carrier organic anion transporter family member 4C1

Kind: Protein
Organism: Humans
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]

Details9. Large neutral amino acids transporter small subunit 1

Kind: Protein
Organism: Humans
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]

Details10. Solute carrier organic anion transporter family member 2B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name: SLCO2B1
Uniprot ID: O94956
Uniprot Name: Solute carrier organic anion transporter family member 2B1
Molecular Weight: 76709.98 Da

References

Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Drug created on June 13, 2005 07:24 / Updated on May 20, 2019 07:01

Levothyroxine

Identification

Structure for Levothyroxine (DB00451)

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