dextrothyroxine   Click here for help

GtoPdb Ligand ID: 6951

Synonyms: Choloxin® | D-T4 | D-thyroxine
Approved drug
dextrothyroxine is an approved drug (FDA (1967))
Compound class: Synthetic organic
Comment: The INN record for this compound and the US FDA approval, are for the sodium salt. This drug is the dextrorotary isomer of synthetic thyroxine and acts as an antihyperlipidemic.

dextrothyroxine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 92.78
Molecular weight 776.69
XLogP 3.97
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC(=O)C(Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)N
Isomeric SMILES OC(=O)[C@@H](Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)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-/m1/s1
InChI Key XUIIKFGFIJCVMT-GFCCVEGCSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1967)
IUPAC Name Click here for help
(2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
International Nonproprietary Names Click here for help
INN number INN
1112 dextrothyroxine sodium
Synonyms Click here for help
Choloxin® | D-T4 | D-thyroxine
Database Links Click here for help
CAS Registry No. 51-49-0
ChEBI CHEBI:30659
ChEMBL Ligand CHEMBL559
DrugBank Ligand DB00509
DrugCentral Ligand 846
GtoPdb PubChem SID 178103533
PubChem CID 8730
Search Google for chemical match using the InChIKey XUIIKFGFIJCVMT-GFCCVEGCSA-N
Search Google for chemicals with the same backbone XUIIKFGFIJCVMT
Search PubMed clinical trials dextrothyroxine sodium
Search PubMed titles dextrothyroxine sodium
Search PubMed titles/abstracts dextrothyroxine sodium
UniChem Compound Search for chemical match using the InChIKey XUIIKFGFIJCVMT-GFCCVEGCSA-N
UniChem Connectivity Search for chemical match using the InChIKey XUIIKFGFIJCVMT-GFCCVEGCSA-N
Wikipedia Dextrothyroxine

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MedChemExpress
D-Thyroxine (links to external site)
Cat. No. HY-A0152