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

• ChemBase编号: 164
• 分子式: C15H12I3NO4
• 平均质量: 650.97349
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
• IUPAC传统名: liothyronine
• 商标名: Cytomel; Tresitope; Triostat; Tertroxin
• 别名: 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); 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

登记号

• CAS号: 6893-02-3
• EC号: 229-999-3
• MDL号: MFCD00002593
• Beilstein号: 2710227
• PubChem SID: 46506352; 160963627; 24900088
• PubChem CID: 5920
• CHEBI ID: 18258
• CHEMBL: 1544
• Chemspider ID: 5707
• DrugBank ID: DB00279
• 美国药典/FDA物质标识码: 06LU7C9H1V
• 维基百科标题: Triiodothyronine

理论计算性质

JChem

• Acid pKa: 0.30255273
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 2.798151
• LogD (pH = 7.4): 2.7648876
• Log P: 2.798505
• 摩尔折射率: 113.4255 cm^3
• 极化性: 44.90148 Å^3
• 极化表面积: 92.78 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 0.82
• LOG S: -4.52
• 溶解度: 1.95e-02 g/l

分子性质

理化性质

• 溶解度: 3.96 mg/L; DMSO; Ethanol
• 外观: Off-White Solid; powder
• 熔点: 200-207°C (dec.); 232-240 °C (dec.); 234-238 °C(lit.); 234-238°C
• 比旋光度: [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)
• 疏水性(logP): 2.9

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Light Sensitive
• RTECS编号: AY6750000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37-60
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C; 2-8°C; -70°C

药理学性质

• 相关基因信息: human ... THRA(7067), THRB(7068)rat ... Thra(81812), Thrb(24831)

产品相关信息

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

详细说明

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

包装
250 mg in glass bottle

Sigma Aldrich - 91990

Other Notes
Review: Thyroid hormone action at the nuclear level1

Sigma Aldrich - IRMM469

法律信息
BCR 注册商标 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.

参考文献

• 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)