2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

• ChemBase ID: 391
• Molecular Formular: C15H11I4NO4
• Molecular Mass: 776.87002
• Monoisotopic Mass: 776.68669984
• SMILES: Ic1cc(CC(N)C(=O)O)cc(I)c1Oc1cc(I)c(O)c(I)c1
• Canonical SMILES: OC(=O)C(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)
• InChIKey: XUIIKFGFIJCVMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
• IUPAC Traditional name: thyroxine
• Brand Name: Choloxin; Dynothel; Lisolipin; Eulipos
• Synonyms: 3,5,3′,5′-Tetraiodo-d-thyronine Sodium; Dekstrotyroksiininatrium; Dextrothyroxinum Natricum; Dextrotiroxina sódica; Dextrotyroxinnatrium; D-Thyroxine Sodium; Sodium 4-O-(4-hydroxy-3,5-di-iodophenyl)-3,5-di-iodo-d-tyrosinate hydrate; Dextrothyroxine; O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine; DL-THYROXINE, NA; 3,5,3',5'-tetraiodo-L-thyronine; Levothyroxine

Database IDs

• CAS Number: 51-49-0; 51-48-9
• MDL Number: MFCD00063058
• PubChem SID: 160963854
• PubChem CID: 5819; 853
• CHEBI ID: 18332
• ATC CODE: H03AA01
• CHEMBL: 1624
• Chemspider ID: 5614
• DrugBank ID: DB00451
• MeSH Name: Thyroxine
• Unique Ingredient Identifier: Q51BO43MG4
• Wikipedia Title: Levothyroxine

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.27336746
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.722463
• LogD (pH = 7.4): 3.4409168
• Log P: 3.727307
• Molar Refractivity: 126.788 cm^3
• Polarizability: 50.46104 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.15
• LOG S: -4.94
• Solubility (Water): 8.98e-03 g/l

PROPERTIES

Physical Property

• Solubility: slightly soluble (0,105 mg·l^-1 at 25 °C) in water
• Melting Point: 231–233 °C
• Hydrophobicity(logP): 4

Safety Information

• Storage Warning: IRRITANT
• Safety Statements: S22, S24/25
• TSCA Listed: false

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: ~100%
• Excretion: Through feces and urine
• Half Life: ca. 7 days (in hyperthyroidism 3-4 days, in hypothyroidism 9-10 days)
• Metabolism: Mainly in liver, kidneys, brain and muscles
• Legal Status: Rx
• Pregnancy Category: A (US)

DETAILS

MP Biomedicals - 05207619

MP Biomedicals Rare Chemical collection

DrugBank - DB00509

• Drug Groups: approved
• Description: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism. [PubChem]
• Indication: Used to lower high cholesterol levels in the blood.
• Pharmacology: Dextrothyroxine, the dextrorotary isomer of the synthetic thyroxine, is a antihyperlipidemic.
• Toxicity: Symptoms of dextrothyroxine overdose are unknown.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia