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

• ChemBase ID: 164
• Molecular Formular: C15H12I3NO4
• Molecular Mass: 650.97349
• Monoisotopic Mass: 650.79005187
• SMILES: Ic1cc(C[C@H](N)C(=O)O)cc(I)c1Oc1cc(I)c(O)cc1
• Canonical SMILES: OC(=O)[C@H](Cc1cc(I)c(c(c1)I)Oc1ccc(c(c1)I)O)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
• InChIKey: AUYYCJSJGJYCDS-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
• IUPAC Traditional name: liothyronine
• Brand Name: Cytomel; Tresitope; Triostat; Tertroxin
• Synonyms: T3; 3,3′,5-Triiodo-L-thyronine; O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine; Liothyronine; 3,3′,5-Triiodo-L-thyronine; 3,3′,5 Triiodothyronine (T3); 3,3',5-Triiodo-L-thyronine; L-Liothyronine; Liothyronin; Liothyronine Sodium; Triiodothyronine; T3 liothyronine; Liothyronine; T₃; 3,3',5-triiodo-L-thyronine; Triiodothyronine; L-T3; 3,3’,5-Triiodothyronine; T3 (Hormone); Tresitope; 3,3',5-Triiodo-L-thyronine; O-(4-羟基-3-碘苯基)-3,5-二碘代-L-酪氨酸; 碘噻罗宁; 3,3′,5-三碘代-L-甲状腺原氨酸; 3,3′,5-三碘代-L-甲状腺原氨酸; 3,3′,5-三碘甲状腺氨酸 (T3)

Database IDs

• CAS Number: 6893-02-3
• EC Number: 229-999-3
• MDL Number: MFCD00002593
• Beilstein Number: 2710227
• PubChem SID: 46506352; 24900088; 160963627
• PubChem CID: 5920
• CHEBI ID: 18258
• CHEMBL: 1544
• Chemspider ID: 5707
• DrugBank ID: DB00279
• Unique Ingredient Identifier: 06LU7C9H1V
• Wikipedia Title: Triiodothyronine

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.30255273
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.798151
• LogD (pH = 7.4): 2.7648876
• Log P: 2.798505
• Molar Refractivity: 113.4255 cm^3
• Polarizability: 44.90148 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.82
• LOG S: -4.52
• Solubility (Water): 1.95e-02 g/l

PROPERTIES

Physical Property

• Solubility: 3.96 mg/L; DMSO; Ethanol
• Apperance: Off-White Solid; powder
• Melting Point: 200-207°C (dec.); 232-240 °C (dec.); 234-238 °C(lit.); 234-238°C
• Optical Rotation: [α]20/D +23.0°, c = 2 in ethanol or 0.1 N HCl; [α]20/D +25±2°, c = 1% in ethanol/1 M HCl (2:1); [α]25/D +23.0°, c = 2 in 1 N HCl: ethanol, 1:2; +25 (c=1 in 1M HCl/Ethanol 1:2)
• Hydrophobicity(logP): 2.9

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Light Sensitive
• RTECS: AY6750000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C; -70°C

Pharmacology Properties

• Gene Information: human ... THRA(7067), THRB(7068)rat ... Thra(81812), Thrb(24831)

Product Information

• Purity: ≥95% (HPLC); ≥97.0% (sum of enantiomers, HPLC); 95%
• Grade: BCR® certified Reference Material
• Impurities: ≤2% 3,5-diiodo thyronine; ≤2% thyroxine
• Empirical Formula (Hill Notation): C15H12I3NO4

DETAILS

DrugBank - DB00279

• Drug Groups: 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]
• Indication: Used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Absorption: 95% in 4 hours
• Half Life: 2.5 days
• Protein Binding: 99.7%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - T2877

包装
1, 5 g in poly bottle
100, 250, 500 mg in poly bottle

Sigma Aldrich - 564605

Packaging
250 mg in glass bottle

Sigma Aldrich - 91990

Other Notes
Review: Thyroid hormone action at the nuclear level1

Sigma Aldrich - IRMM469

Legal Information
BCR is a registered trademark of European Commission

Toronto Research Chemicals - T795380

One of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.

REFERENCES

• Gross, J., et al.: Lancet I, 439 (1952)
• Roche, J., et al.: Biochim. Biophys. Acta, 11, 215 (1952)
• Chacon, M.A., et al.: J. Pediatr., 99, 758 (1952)
• Chopra, I.J., et al.: Thyroid, 6, 255 (1952)