Drug Details

General Information of the Drug (ID: DR8725)
Name
Levothyroxine
Synonyms
L-thyroxine; levothyroxine; 51-48-9; thyroxine; thyroxin; Tetraiodothyronine; Thyrax; 3,3',5,5'-Tetraiodo-L-thyronine; synthroid; Thyratabs; Thyreoideum; Thyroxinal; Thyroxine iodine; Levothyroxin; (-)-Thyroxine; L-Thyroxin; 3,5,3',5'-Tetraiodo-L-thyronine; L-T4; Thyroxine (l); Levothyroxine sodium; DL-Thyroxin; O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine; t4; Thyroxine (VAN); 3,5,3',5'-Tetraiodothyronine; Laevothyroxinum; T4 (Hormone); L-3,5,3',5'-Tetraiodothyronine; Levothyroxinum (acid); Laevothyroxinum (acid); Thryroxine, l-; Tetramet; Thyroxine I 125; Forthyron (TN); NSC 36397; Levothyroxinum; 3,3',5,5''-Tetraiodo-L-thyronine; CCRIS 6739; Henning; HSDB 3108; 3,5,3'5'-Tetraiodo-L-thyronine; UNII-Q51BO43MG4; Prestwick_548; L-Tyrosine, O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-; 4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine; CHEBI:18332; O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine; (S)-2-amino-3-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)propanoic acid; 3-(4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)alanine; beta-((3,5-Diiodo-4-hydroxyphenoxy)-3,5-diiodophenyl)alanine; 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine; CHEMBL1624; O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine; (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid; C15H11I4NO4; Q51BO43MG4; 51-48-9 (free); THX; MFCD00002595; NCGC00164336-01; L-Thyroxine, 97+%; DSSTox_CID_3214; DSSTox_RID_76927; DSSTox_GSID_23214; Eutirox; Tyrosine, O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-; LT4; SMR000059176; T44; Levothyroxine (BAN); EINECS 200-101-1; Levothyroxine [INN:BAN]; Synthroid (*Sodium salt*); BRN 2228515; SR-01000759430; NSC-36397; 2ceo; L-Tyrosine,; CAS-51-48-9; Spectrum_001076; 1hk1; 1hk2; 1hk3; 1hk4; 1hk5; 1y0x; CPD000059176; L-Thyroxine, free acid; SpecPlus_000871; Prestwick0_000403; Prestwick1_000403; Prestwick2_000403; Prestwick3_000403; Spectrum2_000573; Spectrum3_000611; Spectrum4_000128; Spectrum5_001500; Thyroxine, L- (8CI); bmse000923; Epitope ID:123889; T-3850; (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid; L-Thyroxine (T4) solution; BIDD:PXR0161; Levothroid (*Sodium salt*); SCHEMBL23098; BSPBio_000326; BSPBio_002142; KBioGR_000516; KBioSS_001556; MLS000028647; MLS002548901; DivK1c_006967; SPECTRUM1500774; SPBio_000386; SPBio_002265; BPBio1_000360; GTPL2635; DTXSID8023214; KBio1_001911; KBio2_001556; KBio2_004124; KBio2_006692; KBio3_001642; HMS1569A08; HMS1921I06; HMS2090P18; HMS2092K12; HMS2096A08; HMS2233J18; HMS3259M11; HMS3713A08; L-Thyroxine, >=98% (HPLC); Pharmakon1600-01500774; ZINC3830993; Tox21_112101; Tox21_302156; BDBM50301375; CCG-38738; NSC757434; s2599; AKOS015905129; Tox21_112101_1; AC-7504; AM83594; CS-1819; DB00451; NC00485; NSC-757434; SDCCGMLS-0066571.P001; 2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-propanoic acid; 3,3'',5,5''-tetraiodo-L-thyronine; 3,5,3'',5''-tetraiodo-L-thyronine; NCGC00094852-03; NCGC00164336-02; NCGC00164336-03; NCGC00164336-04; NCGC00164336-05; NCGC00164336-06; NCGC00255368-01; AC-10465; HY-18341; SBI-0051608.P002; AB0010528; DB-006261; SW196731-3; C01829; D08125; J10324; O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-; AB00052176-08; AB00052176_09; AB00052176_10; 002T595; Q773449; SR-05000001567; SR-01000759430-2; SR-05000001567-1; BRD-K30685142-001-05-5; BRD-K30685142-001-08-9; Thyroxine (T4), IRMM(R) certified Reference Material; L-Thyroxine, powder, BioReagent, suitable for cell culture; UNII-QR0BV3BRIA component XUIIKFGFIJCVMT-LBPRGKRZSA-N; Levothyroxine, United States Pharmacopeia (USP) Reference Standard; Levothyroxine, Pharmaceutical Secondary Standard; Certified Reference Material; L-Thyroxine (T4) solution, 100 mug/mL in methanol with 0.1N NH3, ampule of 1 mL, certified reference material
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Molecular Type
Small molecule
Disease Hypo-thyroidism [ICD-11: 5A00] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Elimination
Approximately 20% of T<sub>4 is eliminated in the stool
Half-life
The concentration or amount of drug in body reduced by one-half in 6 - 7 days (T4), and 1 - 2 days (T3)
Metabolism
The drug is metabolized via sequential deiodination
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.00644 micromolar/kg/day
Water Solubility
The ability of drug to dissolve in water is measured as 0.000585 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H11I4NO4
PubChem CID
5819
Canonical SMILES
C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)CC(C(=O)O)N
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
InChIKey
XUIIKFGFIJCVMT-LBPRGKRZSA-N
CAS Number
CAS 51-48-9
ChEBI ID
CHEBI:18332
TTD Drug ID
D06RGG
DrugBank ID
DB00451
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Selenium      Soil     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 Levothyroxine and selenium combination results in improved therapeutic effects than the levothyroxine monotherapy in preventing CLT progression.
Target and Pathway
Target(s) Thyroid hormone receptor alpha (THRA)  Molecule Info  [3]
KEGG Pathway Neuroactive ligand-receptor interaction Click to Show/Hide
2 Thyroid hormone signaling pathway
Pathway Interaction Database RXR and RAR heterodimerization with other nuclear receptor Click to Show/Hide
Reactome Nuclear Receptor transcription pathway Click to Show/Hide
WikiPathways Endochondral Ossification Click to Show/Hide
2 Nuclear Receptors
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4627).
Reference 2 Levothyroxine monotherapy versus levothyroxine and selenium combination therapy in chronic lymphocytic thyroiditis. J Endocrinol Invest. 2017 Nov;40(11):1243-1250.
Reference 3 Thyroid hormone resistance and pituitary enlargement after thyroid ablation in a woman on levothyroxine treatment. Thyroid. 2008 Oct;18(10):1119-23.
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