Levothyroxine
L-Thyroxine
CAS: 51-48-9
Molecular Formula: C15H11I4NO4
Levothyroxine - Names and Identifiers
| Name | L-Thyroxine |
| Synonyms | l-t4 L-Thyroxine t4(hormone) levothyroxine tetraiodothyronine 3,5,3',5'-tetraiodothyronine 3,5,3',5'-tetraiodothyronine l-3,5,3',5'-tetraiodothyronine 3,3',5,5'-TETRAIODO-L-THYRONIN l-3,5,3',5'-tetraiodothyronine 3,5,3',5'-TETRAIODO-L-THYRONINE o-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine o-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-l-tyrosin O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine β-((3,5-Diiodo-4-hydroxyphenoxy)-3,5-diiodophenyl)alanine 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-alanine beta-[(3,5-diiodo-4-hydroxyphenoxy)-3,5-diiodophenyl]alanine |
| CAS | 51-48-9 |
| EINECS | 200-101-1 |
| InChI | InChI=1/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 |
Levothyroxine - Physico-chemical Properties
| Molecular Formula | C15H11I4NO4 |
| Molar Mass | 776.87 |
| Density | 2.4440 (estimate) |
| Melting Point | 235 °C |
| Boling Point | 576.3±50.0 °C(Predicted) |
| Specific Rotation(α) | -5 º (1N NaOH:EtOH 1:2) |
| Flash Point | 9℃ |
| Water Solubility | insoluble |
| Solubility | Soluble in alkali solution, insoluble in water, ethanol and ether |
| Vapor Presure | 4.02E-14mmHg at 25°C |
| Appearance | White or slightly grayish brown crystals |
| Color | White to Pale Brown |
| Merck | 9491 |
| BRN | 2228515 |
| pKa | 2.2(at 25℃) |
| Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
| Sensitive | Light Sensitive |
| Refractive Index | 1.795 |
| MDL | MFCD00002595 |
| Physical and Chemical Properties | Melting point 223°C (dec.) specific optical rotation -5 ° (1N NaOH:EtOH 1:2) water-soluble insoluble White needle-like crystals, odorless, tasteless. Degeneration in light. Melting point 231-233 °c (decomposition). Do not dissolve in water and ethanol and other common organic solvents. Soluble in ethanol containing inorganic acid or alkali, also soluble in hydroxide alkali and carbonate alkali solution. In its acidic ethanol solution to add sodium nitrite, heating is yellow, plus an excess of ammonia will become pink. |
| Use | It can promote general tissue metabolism, improve nerve excitability and body development. For the treatment of hypothyroidism, myxedema and cretinism. |
| In vivo study | Deiodinases (DIOs), which catalyse the conversion of thyroxine (pro-hormone) to the active thyroid hormone, are associated with thyroid stimulating hormone (TSH) levels. DIO1 and DIO2 catalyze activation of thyroid hormone secretion in contrast to DIO3 playing role inactivation of the secretion. Activities of DIO1 and DIO2 play pivotal role in the negative feedback regulation of pituitary TSH secretion. L-Thyroxine (T4) and Triiodothyronine (T3) hormones are known to modulate the expression of ionic channels, pumps and regulatory contractile proteins. Moreover, thyroid hormones have been shown to influence calcium homeostasis and flux responsible for excitation and contractility, with L-Thyroxine and Triiodothyronine modulating its pharmacological control and secretion. In rats fed 12 weeks with the iodine-free diet, a significant decrease in the levels of both Triiodothyronine and L-Thyroxine is observed when compared to the control group fed with standard diet (p<0.001). In the group treated with low doses of L-Thyroxine, an increase in L-Thyroxine levels is observed (p=0.02) while Triiodothyronine levels remain virtually similar to the control group (p=0.19). Rats treated with high doses of L-Thyroxine display a significant increase in both Triiodothyronine and L-Thyroxine circulating concentrations compared to the non-treated hypothyroid group (p<0.001 and p=0.004, respectively) and a significant increase in L-Thyroxine levels when compared to the control values (p=0.03). |
Levothyroxine - Risk and Safety
| Risk Codes | R40 - Limited evidence of a carcinogenic effect R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. |
| UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 3 |
| RTECS | YP2833500 |
| FLUKA BRAND F CODES | 8-10 |
| TSCA | Yes |
| HS Code | 29379000 |
| Hazard Class | IRRITANT |
| Toxicity | TDLo oral in child: 328ug/kg |
Levothyroxine - Reference
| Reference Show more | 1. Feng, Jia, Hua, Ke, Zhao, Xu, et al. Protective effect of Liuwei Dihuang pill on liver injury induced by thyroxine in mice with Yin deficiency syndrome [J]. Shanghai Journal of Traditional Chinese Medicine 2019(11). 2. Fan, Tao-Bo, Liu, Zhejiang-Bo, et al. Effects of thyroid hormone levels in pregnant rats on apoptosis of fetal rat cardiomyocytes [J]. Chongqing Medical Journal, 2020, 3 (7):1036-1041. 3. Shan, Tong, et al. "Proteomics-Based Mongolian Medicine Modified Sugmul-7 Mechanism of regulatory Endocrine Function in Hyperplasia of the Breast." Clinical Medicine Research 9.1 (2020): 11. Does: 10.11648/j.cmr.20200901.13 4. [IF = 3.079] Nabi Ghulam et al."Circulating concentrations of thyroid hormones and cortisol in wild and semi-natural Yangtze finless porpoise (Neophocaena asiaeorientalis)."Conserv Physiol. 2021 Jan;9(1): |
Levothyroxine - Reference Information
| Biological activity | L-Thyroxine (NSC 36397) is a synthetic form of thyroxine and a hormone replacement drug. |
| target | Human Endogenous Metabolite |
| in vivo research | Deiodinases (DIOs), which catalyse the conversion of thyroxine (pro-hormone) to the active thyroid hormone, are associated with thyroid stimulating hormone (TSH) levels. DIO1 and DIO2 catalyze activation of thyroid hormone secretion in contrast to DIO3 playing role inactivation of the secretion. Activities of DIO1 and DIO2 play pivotal role in the negative feedback regulation of pituitary TSH secretion. L-Thyroxine (T4) and Triiodothyronine (T3) hormones are known to modulate the expression of ionic channels, pumps and regulatory contractile proteins. Moreover, thyroid hormones have been shown to influence calcium homeostasis and flux responsible for excitation and contractility, with L-Thyroxine and Triiodothyronine modulating its pharmacological control and secretion. in ratfed 12 weeks with the iodine-free diet, a significant decrease in the levels of both Triiodothyronine and L-Thyroxine is observed when compared to the control group fed with standard diet (p<0.001). in the group treated with low dos of L-Thyroxine, an increase in L-Thyroxine levels is observed (p = 0.02) while Triiodothyronine levels remain virtually similar to the control group (p = 0.19). Rats treated with high doses of L-Thyroxine display a significant increase in both Triiodothyronine and L-Thyroxine circulating concentrations compared to the non-treated hypothyroid group (p<0.001 and p = 0.004, respectively) and a significant increase in L-Thyroxine levels when compared to the control values (p = 0.03). |
| chemical properties | white crystal. Mp235-236 ℃ (decomposition), specific rotation [α]20D-4.4 (3%,0.13 mol/L sodium hydroxide, 70% ethanol), maximum absorption at 325nm wavelength in 0.4 mol/L NaOH solution and 295nm wavelength in 0.4 mol/L HCl solution. This product is soluble in alkali solution, insoluble in water, ethanol and ether. |
| use | biochemical research; thyroxine drugs. L-thyroxine (T4) and triindole-L-thyroogenine (triiodo-L-thyronine,T3) are indole-containing hormones, which are produced by thyroglobulin in thyroid follicular cells. L-thyroxine stimulates metabolism and regulates growth and development by affecting DNA transcription and protein synthesis. |
| production method | using 3, 5-diiodo-L-tyrosine as the main raw material. |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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