Identification

Name
Liothyronine
Accession Number
DB00279  (APRD01074)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

The L-triiodothyronine (T3, liothyronine) thyroid hormone is normally synthesized and secreted by the thyroid gland in much smaller quantities than L-tetraiodothyronine (T4, levothyroxine, L-thyroxine). Most T3 is derived from peripheral monodeiodination of T4 at the 5 position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3. [PubChem]

Structure
Thumb
Synonyms
  • 3,3',5-triiodo-L-thyronine
  • 3,5,3'-Triiodo-L-thyronine
  • 3,5,3'-Triiodothyronine
  • 3,5,3'TRIIODOTHYRONINE
  • 4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine
  • L-3,5,3'-Triiodothyronine
  • L-T3
  • Liothyronine
  • Liothyroninum
  • Liotironina
  • O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine
  • T3
  • Tertroxin
  • Tresitope
  • Triiodothyronine
External IDs
NSC-80203
Product Ingredients
IngredientUNIICASInChI Key
Liothyronine SodiumGCA9VV7D2N55-06-1SBXXSUDPJJJJLC-YDALLXLXSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CytomelTablet25 ug/1OralPfizer Laboratories Div Pfizer Inc.1956-05-08Not applicableUs
CytomelTablet25 ug/1OralPhysicians Total Care, Inc.2002-12-30Not applicableUs
CytomelTablet5 mcgOralPfizer1993-12-31Not applicableCanada
CytomelTablet50 ug/1OralPfizer Laboratories Div Pfizer Inc.1956-05-08Not applicableUs
CytomelTablet25 ug/1OralA S Medication Solutions1956-05-082017-06-20Us60793 0116 01 nlmimage10 0039806c
CytomelTablet5 ug/1OralPhysicians Total Care, Inc.2004-05-03Not applicableUs
CytomelTablet5 ug/1OralPfizer Laboratories Div Pfizer Inc.1956-05-08Not applicableUs60793 0115 01 nlmimage10 7b133da9
CytomelTablet5 ug/1OralA S Medication Solutions1956-05-082017-06-20Us
CytomelTablet5 ug/1OralA S Medication Solutions1956-05-082017-06-20Us
CytomelTablet25 mcgOralPfizer1993-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Liothyronine SodiumTablet50 ug/1OralNorthwind Pharmaceuticals2014-12-29Not applicableUs
Liothyronine SodiumTablet25 ug/1Oralbryant ranch prepack2012-11-30Not applicableUs
Liothyronine SodiumTablet25 ug/1OralKaiser Foundations Hospitals2009-08-29Not applicableUs
Liothyronine SodiumTablet50 ug/1OralGolden State Medical Supply2014-08-28Not applicableUs
Liothyronine SodiumTablet5 ug/1OralSigma Pharm Laboratories, Llc2012-11-30Not applicableUs
Liothyronine SodiumTablet25 ug/1OralPaddock Laboratories, Inc.2009-03-23Not applicableUs
Liothyronine sodiumTablet5 ug/1OralMylan Pharmaceuticals2013-01-23Not applicableUs
Liothyronine SodiumTablet25 ug/1OralPd Rx Pharmaceuticals, Inc.2009-03-23Not applicableUs
Liothyronine SodiumTablet25 ug/1OralGolden State Medical Supply2014-08-28Not applicableUs42794 0019 02 nlmimage10 bc40de26
Liothyronine sodiumTablet5 ug/1OralA S Medication Solutions2016-10-032017-06-20Us
International/Other Brands
Tertroxin (Aspen Pharmacare)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Levothyroxine and Liothyronine ThyroidLiothyronine (13.5 ug/1) + Levothyroxine (57 ug/1)TabletOralWestminster2017-09-19Not applicableUs
Levothyroxine and Liothyronine ThyroidLiothyronine (4.5 ug/1) + Levothyroxine (19 ug/1)TabletOralWestminster2017-09-19Not applicableUs
Levothyroxine and Liothyronine ThyroidLiothyronine (9 ug/1) + Levothyroxine (38 ug/1)TabletOralWestminster2017-09-19Not applicableUs
NP Thyroid 120Liothyronine (18 ug/1) + Levothyroxine (76 ug/1)TabletOralAcella Pharmaceuticals, LLC2010-11-11Not applicableUs
NP Thyroid 120Liothyronine (18 ug/1) + Levothyroxine (76 ug/1)TabletOralPreferreed Pharmaceuticals Inc.2017-10-12Not applicableUs
NP Thyroid 15Liothyronine (2.25 ug/1) + Levothyroxine (9.5 ug/1)TabletOralPreferreed Pharmaceuticals Inc.2017-10-12Not applicableUs
NP Thyroid 15Liothyronine (2.25 ug/1) + Levothyroxine (9.5 ug/1)TabletOralAcella Pharmaceuticals, LLC2010-11-11Not applicableUs
NP Thyroid 30Liothyronine (4.5 ug/1) + Levothyroxine (19 ug/1)TabletOralAcella Pharmaceuticals, LLC2010-11-11Not applicableUs
NP Thyroid 30Liothyronine (4.5 ug/1) + Levothyroxine (19 ug/1)TabletTopicalPreferreed Pharmaceuticals Inc.2017-10-12Not applicableUs
NP Thyroid 30Liothyronine (4.5 ug/1) + Levothyroxine (19 ug/1)TabletOralbryant ranch prepack2010-11-11Not applicableUs
Categories
UNII
06LU7C9H1V
CAS number
6893-02-3
Weight
Average: 650.9735
Monoisotopic: 650.790038137
Chemical Formula
C15H12I3NO4
InChI Key
AUYYCJSJGJYCDS-LBPRGKRZSA-N
InChI
InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1
IUPAC Name
(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
SMILES
N[[email protected]@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O

Pharmacology

Indication

Used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis.

Structured Indications
Pharmacodynamics

Thyroid hormone drugs are natural or synthetic preparations containing T4 or T3 or both. T4 and T3 are produced in the human thyroid gland by the iodination and coupling of the amino acid tyrosine. Liothyronine (T3) contains three atoms of iodine and is formed by the coupling of one molecule of diiodotyrosine (DIT) with one molecule of monoiodotyrosine (MIT). These hormones enhance oxygen consumption by most tissues of the body and increase the basal metabolic rate and the metabolism of carbohydrates, lipids and proteins. Thus, they exert a profound influence on every organ system in the body and are of particular importance in the development of the central nervous system.

Mechanism of action

The hormones, T4 and T3, are tyrosine-based hormones produced by the thyroid gland. Iodine is an important component in their synthesis. The major form of thyroid hormone in the blood is thyroxine (T4). This is converted to the more active liothyronine form by deiodinases in peripheral tissues. Liothyronine acts on the body to increase the basal metabolic rate, affect protein synthesis and increase the body's sensitivity to catecholamines (such as adrenaline). The thyroid hormones are essential to proper development and differentiation of all cells of the human body. To various extents T4 and T3 regulate protein, fat and carbohydrate metabolism. Their most pronounced effect is on how human cells use energetic compounds. The thyroid hormone derivatives bind to the thyroid hormone receptors initially to initiate their downstream effects.

TargetActionsOrganism
AThyroid hormone receptor alpha
agonist
Human
AThyroid hormone receptor beta
agonist
Human
UProliferating cell nuclear antigenNot AvailableHuman
Absorption

95% in 4 hours

Volume of distribution
Not Available
Protein binding

99.7%

Metabolism
Route of elimination
Not Available
Half life

2.5 days

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Thyroid hormone synthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcebutololThe serum concentration of Acebutolol can be decreased when it is combined with Liothyronine.Approved
AcenocoumarolLiothyronine may increase the anticoagulant activities of Acenocoumarol.Approved
AcetaminophenThe serum concentration of Acetaminophen can be decreased when it is combined with Liothyronine.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be decreased when it is combined with Liothyronine.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Liothyronine.Approved
AlaproclateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Alaproclate.Experimental
AldosteroneThe serum concentration of Aldosterone can be decreased when it is combined with Liothyronine.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be decreased when it is combined with Liothyronine.Approved, Investigational
AmbrisentanThe serum concentration of Ambrisentan can be decreased when it is combined with Liothyronine.Approved, Investigational
Ambroxol acefyllinateThe metabolism of Ambroxol acefyllinate can be increased when combined with Liothyronine.Experimental
AmineptineLiothyronine may increase the arrhythmogenic activities of Amineptine.Illicit, Withdrawn
AminophyllineThe metabolism of Aminophylline can be increased when combined with Liothyronine.Approved
AmitriptylineThe serum concentration of Amitriptyline can be decreased when it is combined with Liothyronine.Approved
ApixabanThe serum concentration of Apixaban can be decreased when it is combined with Liothyronine.Approved
Arsenic trioxideThe serum concentration of Arsenic trioxide can be decreased when it is combined with Liothyronine.Approved, Investigational
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Liothyronine.Approved, Investigational
AtenololThe serum concentration of Atenolol can be decreased when it is combined with Liothyronine.Approved
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Liothyronine.Approved, Investigational
BelinostatThe serum concentration of Belinostat can be decreased when it is combined with Liothyronine.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
BoceprevirThe serum concentration of Boceprevir can be decreased when it is combined with Liothyronine.Withdrawn
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Liothyronine.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Liothyronine.Approved
BromocriptineThe serum concentration of Bromocriptine can be decreased when it is combined with Liothyronine.Approved, Investigational
CabazitaxelThe serum concentration of Cabazitaxel can be decreased when it is combined with Liothyronine.Approved
CaffeineThe serum concentration of Caffeine can be decreased when it is combined with Liothyronine.Approved
CalciumThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium.Nutraceutical
Calcium AcetateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium Acetate.Approved
Calcium CarbonateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium Carbonate.Approved
Calcium CitrateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium Citrate.Approved
Calcium glubionateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium glubionate.Approved
Calcium GluceptateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium Gluceptate.Approved
Calcium gluconateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium lactate.Approved, Experimental, Vet Approved
Calcium lactate gluconateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium lactate gluconate.Experimental
Calcium laevulateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium laevulate.Experimental
Calcium pangamateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium pangamate.Experimental
Calcium PhosphateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Calcium Phosphate.Approved
CamptothecinThe serum concentration of Camptothecin can be decreased when it is combined with Liothyronine.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be decreased when it is combined with Liothyronine.Approved
CarbamazepineThe serum concentration of Liothyronine can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be decreased when it is combined with Liothyronine.Approved
CaseinThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Casein.Approved
CeritinibThe serum concentration of Ceritinib can be decreased when it is combined with Liothyronine.Approved
CerivastatinThe serum concentration of Cerivastatin can be decreased when it is combined with Liothyronine.Withdrawn
ChlorotrianiseneThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Chlorotrianisene.Withdrawn
ChlorpromazineThe serum concentration of Chlorpromazine can be decreased when it is combined with Liothyronine.Approved, Vet Approved
CholestyramineThe serum concentration of Liothyronine can be decreased when it is combined with Cholestyramine.Approved
CimetidineThe serum concentration of Cimetidine can be decreased when it is combined with Liothyronine.Approved
CisplatinThe serum concentration of Cisplatin can be decreased when it is combined with Liothyronine.Approved
CitalopramThe serum concentration of Citalopram can be decreased when it is combined with Liothyronine.Approved
ClarithromycinThe serum concentration of Clarithromycin can be decreased when it is combined with Liothyronine.Approved
ClobazamThe serum concentration of Clobazam can be decreased when it is combined with Liothyronine.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be decreased when it is combined with Liothyronine.Approved, Investigational
ClomipramineLiothyronine may increase the arrhythmogenic activities of Clomipramine.Approved, Vet Approved
ClonidineThe serum concentration of Clonidine can be decreased when it is combined with Liothyronine.Approved
ClopidogrelThe serum concentration of Clopidogrel can be decreased when it is combined with Liothyronine.Approved, Nutraceutical
ClorindioneLiothyronine may increase the anticoagulant activities of Clorindione.Experimental
ClozapineThe serum concentration of Clozapine can be decreased when it is combined with Liothyronine.Approved
CobimetinibThe serum concentration of Cobimetinib can be decreased when it is combined with Liothyronine.Approved
ColchicineThe serum concentration of Colchicine can be decreased when it is combined with Liothyronine.Approved
ColesevelamThe serum concentration of Liothyronine can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Liothyronine can be decreased when it is combined with Colestipol.Approved
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Liothyronine.Approved
CopanlisibThe serum concentration of Copanlisib can be decreased when it is combined with Liothyronine.Approved
CrizotinibThe serum concentration of Crizotinib can be decreased when it is combined with Liothyronine.Approved
CyclobenzaprineLiothyronine may increase the arrhythmogenic activities of Cyclobenzaprine.Approved
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Liothyronine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Liothyronine.Approved
DabrafenibThe serum concentration of Dabrafenib can be decreased when it is combined with Liothyronine.Approved
DactinomycinThe serum concentration of Dactinomycin can be decreased when it is combined with Liothyronine.Approved
DaidzeinThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Daidzein.Experimental
DapagliflozinThe serum concentration of Dapagliflozin can be decreased when it is combined with Liothyronine.Approved
DapoxetineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Dapoxetine.Investigational
DasatinibThe serum concentration of Dasatinib can be decreased when it is combined with Liothyronine.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Liothyronine.Approved
DebrisoquinThe serum concentration of Debrisoquin can be decreased when it is combined with Liothyronine.Approved
DesipramineLiothyronine may increase the arrhythmogenic activities of Desipramine.Approved
DesvenlafaxineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Desvenlafaxine.Approved
DexamethasoneThe serum concentration of Dexamethasone can be decreased when it is combined with Liothyronine.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be decreased when it is combined with Liothyronine.Approved, Illicit, Vet Approved
DibenzepinLiothyronine may increase the arrhythmogenic activities of Dibenzepin.Experimental
DicoumarolLiothyronine may increase the anticoagulant activities of Dicoumarol.Approved
DienestrolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Dienestrol.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Liothyronine.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Liothyronine.Approved
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Liothyronine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be decreased when it is combined with Liothyronine.Illicit
DiltiazemThe serum concentration of Diltiazem can be decreased when it is combined with Liothyronine.Approved
DiphenadioneLiothyronine may increase the anticoagulant activities of Diphenadione.Experimental
DipyridamoleThe serum concentration of Dipyridamole can be decreased when it is combined with Liothyronine.Approved
DocetaxelThe serum concentration of Docetaxel can be decreased when it is combined with Liothyronine.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be decreased when it is combined with Liothyronine.Approved, Investigational, Vet Approved
DosulepinLiothyronine may increase the arrhythmogenic activities of Dosulepin.Approved
DoxepinLiothyronine may increase the arrhythmogenic activities of Doxepin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Liothyronine.Approved, Investigational
DuloxetineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Duloxetine.Approved
DyphyllineThe metabolism of Dyphylline can be increased when combined with Liothyronine.Approved
EdoxabanThe serum concentration of Edoxaban can be decreased when it is combined with Liothyronine.Approved
ElbasvirThe serum concentration of Elbasvir can be decreased when it is combined with Liothyronine.Approved
EletriptanThe serum concentration of Eletriptan can be decreased when it is combined with Liothyronine.Approved, Investigational
EltrombopagThe serum concentration of Liothyronine can be increased when it is combined with Eltrombopag.Approved
EnasidenibThe serum concentration of Enasidenib can be decreased when it is combined with Liothyronine.Approved
EpimestrolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Epimestrol.Experimental
EpinastineThe serum concentration of Epinastine can be decreased when it is combined with Liothyronine.Approved, Investigational
EquolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Equol.Investigational
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Liothyronine.Approved, Investigational
ErythromycinThe serum concentration of Erythromycin can be decreased when it is combined with Liothyronine.Approved, Vet Approved
EscitalopramThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Escitalopram.Approved, Investigational
EsmirtazapineLiothyronine may increase the arrhythmogenic activities of Esmirtazapine.Investigational
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Liothyronine.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be decreased when it is combined with Liothyronine.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be decreased when it is combined with Liothyronine.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Liothyronine.Approved
Ethyl biscoumacetateLiothyronine may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtoperidoneThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Etoperidone.Approved
EtoposideThe serum concentration of Etoposide can be decreased when it is combined with Liothyronine.Approved
EzetimibeThe serum concentration of Ezetimibe can be decreased when it is combined with Liothyronine.Approved
FesoterodineThe serum concentration of Fesoterodine can be decreased when it is combined with Liothyronine.Approved
FexofenadineThe serum concentration of Fexofenadine can be decreased when it is combined with Liothyronine.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be decreased when it is combined with Liothyronine.Approved
FluindioneLiothyronine may increase the anticoagulant activities of Fluindione.Investigational
FluoxetineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Fluoxetine.Approved, Vet Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be decreased when it is combined with Liothyronine.Approved
FluvoxamineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Fluvoxamine.Approved, Investigational
FosphenytoinThe serum concentration of Liothyronine can be decreased when it is combined with Fosphenytoin.Approved
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Liothyronine.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be decreased when it is combined with Liothyronine.Approved
GenisteinThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Genistein.Investigational
GlecaprevirThe serum concentration of Glecaprevir can be decreased when it is combined with Liothyronine.Approved
GrazoprevirThe serum concentration of Grazoprevir can be decreased when it is combined with Liothyronine.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be decreased when it is combined with Liothyronine.Withdrawn
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Liothyronine.Approved
HexestrolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Hexestrol.Withdrawn
HydrocortisoneThe serum concentration of Hydrocortisone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be decreased when it is combined with Liothyronine.Approved
IdelalisibThe serum concentration of Idelalisib can be decreased when it is combined with Liothyronine.Approved
ImatinibThe serum concentration of Imatinib can be decreased when it is combined with Liothyronine.Approved
ImipramineThe serum concentration of Imipramine can be decreased when it is combined with Liothyronine.Approved
IndacaterolThe serum concentration of Indacaterol can be decreased when it is combined with Liothyronine.Approved
IndalpineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Indalpine.Investigational, Withdrawn
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Liothyronine.Approved
IndomethacinThe serum concentration of Indomethacin can be decreased when it is combined with Liothyronine.Approved, Investigational
Inotuzumab ozogamicinThe serum concentration of Inotuzumab ozogamicin can be decreased when it is combined with Liothyronine.Approved
Iodide I-131The therapeutic efficacy of Iodide I-131 can be decreased when used in combination with Liothyronine.Approved
IprindoleLiothyronine may increase the arrhythmogenic activities of Iprindole.Experimental
IrinotecanThe serum concentration of Irinotecan can be decreased when it is combined with Liothyronine.Approved, Investigational
IvermectinThe serum concentration of Ivermectin can be decreased when it is combined with Liothyronine.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be decreased when it is combined with Liothyronine.Approved
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Liothyronine.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be decreased when it is combined with Liothyronine.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Liothyronine.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be decreased when it is combined with Liothyronine.Approved, Investigational
Lanthanum carbonateThe serum concentration of Liothyronine can be decreased when it is combined with Lanthanum carbonate.Approved
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Liothyronine.Approved
LenalidomideThe serum concentration of Lenalidomide can be decreased when it is combined with Liothyronine.Approved
LenvatinibThe serum concentration of Lenvatinib can be decreased when it is combined with Liothyronine.Approved
LevetiracetamThe serum concentration of Levetiracetam can be decreased when it is combined with Liothyronine.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be decreased when it is combined with Liothyronine.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be decreased when it is combined with Liothyronine.Approved
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Liothyronine.Approved
LofepramineLiothyronine may increase the arrhythmogenic activities of Lofepramine.Experimental
LoperamideThe serum concentration of Loperamide can be decreased when it is combined with Liothyronine.Approved
LosartanThe serum concentration of Losartan can be decreased when it is combined with Liothyronine.Approved
MannitolThe serum concentration of Mannitol can be decreased when it is combined with Liothyronine.Approved, Investigational
MestranolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Mestranol.Approved
MethallenestrilThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Methallenestril.Experimental
MethotrexateThe serum concentration of Methotrexate can be decreased when it is combined with Liothyronine.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be decreased when it is combined with Liothyronine.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be decreased when it is combined with Liothyronine.Approved, Illicit
MilnacipranThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Milnacipran.Approved
MirabegronThe serum concentration of Mirabegron can be decreased when it is combined with Liothyronine.Approved
MirtazapineLiothyronine may increase the arrhythmogenic activities of Mirtazapine.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be decreased when it is combined with Liothyronine.Approved, Investigational
MorphineThe serum concentration of Morphine can be decreased when it is combined with Liothyronine.Approved, Investigational
MoxestrolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Moxestrol.Experimental
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Liothyronine.Approved, Investigational
NadololThe serum concentration of Nadolol can be decreased when it is combined with Liothyronine.Approved
NaloxoneThe serum concentration of Naloxone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
NefazodoneThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Nelfinavir can be decreased when it is combined with Liothyronine.Approved
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Liothyronine.Approved
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Liothyronine.Approved
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Liothyronine.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be decreased when it is combined with Liothyronine.Approved
NizatidineThe serum concentration of Nizatidine can be decreased when it is combined with Liothyronine.Approved
NortriptylineLiothyronine may increase the arrhythmogenic activities of Nortriptyline.Approved
OdanacatibThe serum concentration of Odanacatib can be decreased when it is combined with Liothyronine.Investigational
OlanzapineThe serum concentration of Olanzapine can be decreased when it is combined with Liothyronine.Approved, Investigational
OmbitasvirThe serum concentration of Ombitasvir can be decreased when it is combined with Liothyronine.Approved
OpipramolLiothyronine may increase the arrhythmogenic activities of Opipramol.Investigational
OsimertinibThe serum concentration of Osimertinib can be decreased when it is combined with Liothyronine.Approved
PaclitaxelThe serum concentration of Paclitaxel can be decreased when it is combined with Liothyronine.Approved, Vet Approved
PanobinostatThe serum concentration of Panobinostat can be decreased when it is combined with Liothyronine.Approved, Investigational
ParoxetineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Paroxetine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Liothyronine.Approved
PhenindioneLiothyronine may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Liothyronine.Approved
PhenprocoumonLiothyronine may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe serum concentration of Liothyronine can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PibrentasvirThe serum concentration of Pibrentasvir can be decreased when it is combined with Liothyronine.Approved
PiracetamThe risk or severity of adverse effects can be increased when Piracetam is combined with Liothyronine.Approved
PitavastatinThe serum concentration of Pitavastatin can be decreased when it is combined with Liothyronine.Approved
Polyestradiol phosphateThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Polyestradiol phosphate.Approved
PomalidomideThe serum concentration of Pomalidomide can be decreased when it is combined with Liothyronine.Approved
PonatinibThe serum concentration of Ponatinib can be decreased when it is combined with Liothyronine.Approved
PravastatinThe serum concentration of Pravastatin can be decreased when it is combined with Liothyronine.Approved
PrazosinThe serum concentration of Prazosin can be decreased when it is combined with Liothyronine.Approved
PrednisoloneThe serum concentration of Prednisolone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
PromestrieneThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Promestriene.Investigational
PropranololThe serum concentration of Propranolol can be decreased when it is combined with Liothyronine.Approved, Investigational
ProtriptylineLiothyronine may increase the arrhythmogenic activities of Protriptyline.Approved
QuetiapineThe serum concentration of Quetiapine can be decreased when it is combined with Liothyronine.Approved
QuinestrolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Quinestrol.Approved
QuinidineThe serum concentration of Quinidine can be decreased when it is combined with Liothyronine.Approved
QuinineThe serum concentration of Quinine can be decreased when it is combined with Liothyronine.Approved
RanitidineThe serum concentration of Ranitidine can be decreased when it is combined with Liothyronine.Approved
ReserpineThe serum concentration of Reserpine can be decreased when it is combined with Liothyronine.Approved
RifampicinThe serum concentration of Liothyronine can be decreased when it is combined with Rifampicin.Approved
RisperidoneThe serum concentration of Risperidone can be decreased when it is combined with Liothyronine.Approved, Investigational
RitonavirThe serum concentration of Ritonavir can be decreased when it is combined with Liothyronine.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be decreased when it is combined with Liothyronine.Approved
RomidepsinThe serum concentration of Romidepsin can be decreased when it is combined with Liothyronine.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be decreased when it is combined with Liothyronine.Approved, Vet Approved
SaquinavirThe serum concentration of Saquinavir can be decreased when it is combined with Liothyronine.Approved, Investigational
SecoisolariciresinolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Secoisolariciresinol.Investigational
SelexipagThe serum concentration of Selexipag can be decreased when it is combined with Liothyronine.Approved
SertralineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Sertraline.Approved
SilodosinThe serum concentration of Silodosin can be decreased when it is combined with Liothyronine.Approved
SimeprevirThe serum concentration of Simeprevir can be decreased when it is combined with Liothyronine.Approved
SitagliptinThe serum concentration of Sitagliptin can be decreased when it is combined with Liothyronine.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Liothyronine.Approved
SorafenibThe serum concentration of Sorafenib can be decreased when it is combined with Liothyronine.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be decreased when it is combined with Liothyronine.Approved
SphingosineThe serum concentration of Sphingosine can be decreased when it is combined with Liothyronine.Experimental
Synthetic Conjugated Estrogens, AThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Synthetic Conjugated Estrogens, B.Approved
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Liothyronine.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be decreased when it is combined with Liothyronine.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be decreased when it is combined with Liothyronine.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be decreased when it is combined with Liothyronine.Approved
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Liothyronine.Withdrawn
TemsirolimusThe serum concentration of Temsirolimus can be decreased when it is combined with Liothyronine.Approved
TeriflunomideThe serum concentration of Liothyronine can be increased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Theophylline can be increased when combined with Liothyronine.Approved
TianeptineLiothyronine may increase the arrhythmogenic activities of Tianeptine.Approved
TiboloneThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Tibolone.Approved
TicagrelorThe serum concentration of Ticagrelor can be decreased when it is combined with Liothyronine.Approved
TimololThe serum concentration of Timolol can be decreased when it is combined with Liothyronine.Approved
TioclomarolLiothyronine may increase the anticoagulant activities of Tioclomarol.Experimental
TolevamerThe serum concentration of Liothyronine can be decreased when it is combined with Tolevamer.Approved
TolvaptanThe serum concentration of Tolvaptan can be decreased when it is combined with Liothyronine.Approved
TopotecanThe serum concentration of Topotecan can be decreased when it is combined with Liothyronine.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be decreased when it is combined with Liothyronine.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be decreased when it is combined with Liothyronine.Approved
TrimipramineLiothyronine may increase the arrhythmogenic activities of Trimipramine.Approved
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Liothyronine.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be decreased when it is combined with Liothyronine.Approved
VecuroniumThe serum concentration of Vecuronium can be decreased when it is combined with Liothyronine.Approved
VelpatasvirThe serum concentration of Velpatasvir can be decreased when it is combined with Liothyronine.Approved
VenetoclaxThe serum concentration of Venetoclax can be decreased when it is combined with Liothyronine.Approved
VenlafaxineThe serum concentration of Venlafaxine can be decreased when it is combined with Liothyronine.Approved
VerapamilThe serum concentration of Verapamil can be decreased when it is combined with Liothyronine.Approved
VinblastineThe serum concentration of Vinblastine can be decreased when it is combined with Liothyronine.Approved
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Liothyronine.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be decreased when it is combined with Liothyronine.Approved
VoxilaprevirThe serum concentration of Voxilaprevir can be decreased when it is combined with Liothyronine.Approved
WarfarinLiothyronine may increase the anticoagulant activities of Warfarin.Approved
ZeranolThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Zeranol.Vet Approved
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Liothyronine.Approved
ZimelidineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Zimelidine.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Martin Beasley, David Hause, Irwin Klein, Charles Pamplin, David Reynolds, Kevin Sills, "Controlled release pharmaceutical compositions of liothyronine and methods of making and using the same." U.S. Patent US20060246133, issued November 02, 2006.

US20060246133
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
HMDB00265
KEGG Compound
C02465
PubChem Compound
5920
PubChem Substance
46506352
ChemSpider
5707
BindingDB
18860
ChEBI
18258
ChEMBL
CHEMBL1544
Therapeutic Targets Database
DAP000082
PharmGKB
PA164778866
IUPHAR
2634
Guide to Pharmacology
GtP Drug Page
HET
T3
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Liothyronine
ATC Codes
H03AA03 — Combinations of levothyroxine and liothyronineH03AA02 — Liothyronine sodium
AHFS Codes
  • 68:36.04 — Thyroid Agents
PDB Entries
1bsx / 1sn5 / 1xzx / 2h77 / 2h79 / 2piv / 2piw / 3gws / 3uvv / 3vkx
show 4 more
FDA label
Download (40.8 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentMultiple Sclerosis, Primary Progressive / Relapsing Remitting Multiple Sclerosis (RRMS) / Secondary Progressive Multiple Sclerosis (SPMS)1
1CompletedNot AvailableDepressive State1
1CompletedPreventionNonvalvular Atrial Fibrillation1
1CompletedTreatmentHead and Neck Carcinoma1
1CompletedTreatmentHealthy Males1
1CompletedTreatmentHealthy Volunteers1
1RecruitingTreatmentDisseminated Sclerosis1
1RecruitingTreatmentProstate Cancer1
1, 2Not Yet RecruitingOtherHealthy Volunteers1
2CompletedNot AvailableThyroid Diseases1
2CompletedTreatmentHypothyroidism1
2CompletedTreatmentNeoplasms, Thyroid1
2RecruitingTreatmentAbnormal Glucose Metabolism / Diabetes Mellitus (DM) / Insulin Resistance1
2, 3RecruitingTreatmentHypothyroidism1
3CompletedTreatmentBipolar Disorder (BD) / Depressive State1
3CompletedTreatmentBipolar Disorder (BD) / Major Depressive Disorder (MDD) / Unipolar Depression1
3CompletedTreatmentPostoperative; Dysfunction Following Cardiac Surgery2
3RecruitingTreatmentDefect, Congenital Heart1
4CompletedTreatmentDepressive State1
4CompletedTreatmentDepressive State / Quality of Life1
4CompletedTreatmentHyperlipidemias / Hypopituitarism / Secondary Hypothyroidism1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4TerminatedTreatmentMajor Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingTreatmentBMI >30 kg/m2 / Obese experiencing rapid weight loss1
Not AvailableCompletedBasic ScienceMajor Depressive Disorder (MDD)1
Not AvailableCompletedSupportive CareNon-thyroidal Illness Syndrome1
Not AvailableCompletedTreatmentFibromyalgia1
Not AvailableCompletedTreatmentHeart Failure, Unspecified / Low T3 Syndrome1
Not AvailableCompletedTreatmentHypothyroidism1
Not AvailableCompletedTreatmentMajor Depressive Disorder (MDD)1
Not AvailableCompletedTreatmentThyroid Cancers1
Not AvailableRecruitingOtherSubclinical Hypothyroidism1
Not AvailableTerminatedTreatmentHypothyroidism / Neoplasms, Brain1
Not AvailableWithdrawnTreatmentCancer, Breast / Metastatic Breast Cancer (MBC)1

Pharmacoeconomics

Manufacturers
  • X gen pharmaceuticals inc
  • Jhp pharmaceuticals llc
  • King pharmaceuticals inc
  • Coastal pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral25 mcg
TabletOral5 mcg
Injection, solutionIntravenous10 ug/mL
TabletOral25 ug/1
TabletOral5 ug/1
TabletOral50 1/1
TabletOral50 ug/1
TabletOral
TabletTopical
InjectionIntravenous10 ug/mL
Prices
Unit descriptionCostUnit
Triostat 10 mcg/ml vial627.9USD ml
Cytomel 50 mcg tablet1.89USD tablet
Liothyronine Sodium 50 mcg tablet1.69USD tablet
Liothyronine sod 50 mcg tablet1.62USD tablet
Cytomel 25 mcg tablet1.21USD tablet
Cytomel 25 mcg Tablet1.2USD tablet
Cytomel 5 mcg Tablet1.11USD tablet
Liothyronine Sodium 25 mcg tablet1.09USD tablet
Liothyronine sod 25 mcg tablet1.06USD tablet
Cytomel 5 mcg tablet0.89USD tablet
Liothyronine Sodium 5 mcg tablet0.84USD tablet
Liothyronine sod 5 mcg tablet0.81USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)236-237U.S. Patent 2,823,164.
water solubility3.96 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.9Not Available
logS-5.22ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0195 mg/mLALOGPS
logP0.82ALOGPS
logP2.8ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)0.3ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.43 m3·mol-1ChemAxon
Polarizability43.92 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, N/ALC-MS/MSsplash10-000i-0009001000-1d47041336da63b556e4
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-000i-1009001000-15f70073b9018f013c9c
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-000i-0009000000-71c231d7a3ab505815ff
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0udi-0000009000-f932659d1e6d8a622985
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0udi-0000009000-6506a7a71dab928abfb0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0fc0-0700119000-1df6db0e3031eb2739fa
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-004i-0900000000-973fc871534b19242cc8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-004i-0900000000-ac3c4a198bb017dc7ccc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0udi-0000009000-2770ece749a9fa1042f4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0udi-0000009000-881174c66da97022d645
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0a4i-0000019000-6f798ae76702a3053339
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a4i-0000219000-d2ca9f0cc3c1b47176b5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-056r-0021915000-6f3810619f383bce651a
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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0000009000-f932659d1e6d8a622985
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0000009000-6506a7a71dab928abfb0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0fc0-0700119000-1df6db0e3031eb2739fa
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-973fc871534b19242cc8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-ac3c4a198bb017dc7ccc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0000009000-2770ece749a9fa1042f4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0000009000-881174c66da97022d645
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0000019000-6f798ae76702a3053339
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0000219000-178f8aeb4d7fe4223eb6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-056r-0021915000-6f3810619f383bce651a
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 / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines
show 11 more
Substituents
Phenylalanine or derivatives / Diphenylether / Diaryl ether / 3-phenylpropanoic-acid / Alpha-amino acid / Amphetamine or derivatives / L-alpha-amino acid / Phenoxy compound / 2-iodophenol / 2-halophenol
show 28 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
iodothyronine, iodophenol, 2-halophenol (CHEBI:18258) / thyroxine, Other amino acids (C02465)

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. Jiang W, Miyamoto T, Kakizawa T, Sakuma T, Nishio S, Takeda T, Suzuki S, Hashizume K: Expression of thyroid hormone receptor alpha in 3T3-L1 adipocytes; triiodothyronine increases the expression of lipogenic enzyme and triglyceride accumulation. J Endocrinol. 2004 Aug;182(2):295-302. [PubMed:15283690]
  2. Kariv R, Enden A, Zvibel I, Rosner G, Brill S, Shafritz DA, Halpern Z, Oren R: Triiodothyronine and interleukin-6 (IL-6) induce expression of HGF in an immortalized rat hepatic stellate cell line. Liver Int. 2003 Jun;23(3):187-93. [PubMed:12955882]
  3. Mai W, Janier MF, Allioli N, Quignodon L, Chuzel T, Flamant F, Samarut J: Thyroid hormone receptor alpha is a molecular switch of cardiac function between fetal and postnatal life. Proc Natl Acad Sci U S A. 2004 Jul 13;101(28):10332-7. Epub 2004 Jul 6. [PubMed:15240882]
  4. Sciaudone MP, Yao L, Schaller M, Zinn SA, Freake HC: Diethylenetriaminepentaacetic acid enhances thyroid hormone action by a transcriptional mechanism. Biol Trace Elem Res. 2004 Summer;99(1-3):219-31. [PubMed:15235154]
  5. Timmer DC, Bakker O, Wiersinga WM: Triiodothyronine affects the alternative splicing of thyroid hormone receptor alpha mRNA. J Endocrinol. 2003 Nov;179(2):217-25. [PubMed:14596673]
  6. 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. Bernal J: Thyroid hormone receptors in brain development and function. Nat Clin Pract Endocrinol Metab. 2007 Mar;3(3):249-59. [PubMed:17315033]
  2. Gonzalez-Sancho JM, Garcia V, Bonilla F, Munoz A: Thyroid hormone receptors/THR genes in human cancer. Cancer Lett. 2003 Mar 31;192(2):121-32. [PubMed:12668276]
  3. 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]
  4. 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]
  5. Yen PM, Feng X, Flamant F, Chen Y, Walker RL, Weiss RE, Chassande O, Samarut J, Refetoff S, Meltzer PS: Effects of ligand and thyroid hormone receptor isoforms on hepatic gene expression profiles of thyroid hormone receptor knockout mice. EMBO Rep. 2003 Jun;4(6):581-7. [PubMed:12776178]
  6. 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]
  7. Wu SY, Sadow PM, Refetoff S, Weiss RE: Tissue responses to thyroid hormone in a kindred with resistance to thyroid hormone harboring a commonly occurring mutation in the thyroid hormone receptor beta gene (P453T). J Lab Clin Med. 2005 Aug;146(2):85-94. [PubMed:16099238]
  8. 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
Auxiliary protein of DNA polymerase delta and is involved in the control of eukaryotic DNA replication by increasing the polymerase's processibility during elongation of the leading strand. Induces a robust stimulatory effect on the 3'-5' exonuclease and 3'-phosphodiesterase, but not apurinic-apyrimidinic (AP) endonuclease, APEX2 activities. Has to be loaded onto DNA in order to be able to stimulate APEX2. Plays a key role in DNA damage response (DDR) by being conveniently positioned at the replication fork to coordinate DNA replication with DNA repair and DNA damage tolerance pathways (PubMed:24939902). Acts as a loading platform to recruit DDR proteins that allow completion of DNA replication after DNA damage and promote postreplication repair: Monoubiquitinated PCNA leads to recruitment of translesion (TLS) polymerases, while 'Lys-63'-linked polyubiquitination of PCNA is involved in error-free pathway and employs recombination mechanisms to synthesize across the lesion.
Specific Function
Chromatin binding
Gene Name
PCNA
Uniprot ID
P12004
Uniprot Name
Proliferating cell nuclear antigen
Molecular Weight
28768.48 Da
References
  1. Punchihewa C, Inoue A, Hishiki A, Fujikawa Y, Connelly M, Evison B, Shao Y, Heath R, Kuraoka I, Rodrigues P, Hashimoto H, Kawanishi M, Sato M, Yagi T, Fujii N: Identification of small molecule proliferating cell nuclear antigen (PCNA) inhibitor that disrupts interactions with PIP-box proteins and inhibits DNA replication. J Biol Chem. 2012 Apr 20;287(17):14289-300. doi: 10.1074/jbc.M112.353201. Epub 2012 Mar 1. [PubMed:22383522]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
Unknown
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
Unknown
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
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. 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]
  2. Friesema EC, Docter R, Moerings EP, Stieger B, Hagenbuch B, Meier PJ, Krenning EP, Hennemann G, Visser TJ: Identification of thyroid hormone transporters. Biochem Biophys Res Commun. 1999 Jan 19;254(2):497-501. [PubMed:9918867]
  3. 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
Actions
Substrate
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. Abe T, Kakyo M, Tokui T, Nakagomi R, Nishio T, Nakai D, Nomura H, Unno M, Suzuki M, Naitoh T, Matsuno S, Yawo H: Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1. J Biol Chem. 1999 Jun 11;274(24):17159-63. [PubMed:10358072]
  2. 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
Actions
Substrate
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]
  2. Abe T, Unno M, Onogawa T, Tokui T, Kondo TN, Nakagomi R, Adachi H, Fujiwara K, Okabe M, Suzuki T, Nunoki K, Sato E, Kakyo M, Nishio T, Sugita J, Asano N, Tanemoto M, Seki M, Date F, Ono K, Kondo Y, Shiiba K, Suzuki M, Ohtani H, Shimosegawa T, Iinuma K, Nagura H, Ito S, Matsuno S: LST-2, a human liver-specific organic anion transporter, determines methotrexate sensitivity in gastrointestinal cancers. Gastroenterology. 2001 Jun;120(7):1689-99. [PubMed:11375950]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
Actions
Substrate
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
References
  1. Friesema EC, Docter R, Moerings EP, Stieger B, Hagenbuch B, Meier PJ, Krenning EP, Hennemann G, Visser TJ: Identification of thyroid hormone transporters. Biochem Biophys Res Commun. 1999 Jan 19;254(2):497-501. [PubMed:9918867]
Kind
Protein
Organism
Human
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
  1. Tohyama K, Kusuhara H, Sugiyama Y: Involvement of multispecific organic anion transporter, Oatp14 (Slc21a14), in the transport of thyroxine across the blood-brain barrier. Endocrinology. 2004 Sep;145(9):4384-91. Epub 2004 May 27. [PubMed:15166123]
  2. 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
Substrate
Inhibitor
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]
  2. 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
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T: Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier. J Pharmacol Exp Ther. 2004 Jun;309(3):1273-81. Epub 2004 Feb 4. [PubMed:14762099]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]
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. Ashida K, Katsura T, Motohashi H, Saito H, Inui K: Thyroid hormone regulates the activity and expression of the peptide transporter PEPT1 in Caco-2 cells. Am J Physiol Gastrointest Liver Physiol. 2002 Apr;282(4):G617-23. [PubMed:11897620]
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 October 23, 2017 14:13