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| Levothyroxine, also known as L-thyroxine, is a synthetic form of the thyroid hormone thyroxine (T4). It is used to treat thyroid hormone deficiency (hypothyroidism), including a severe form known as myxedema coma. It may also be used to treat and prevent certain types of thyroid tumors. It is not indicated for weight loss. Levothyroxine is taken orally (by mouth) or given by intravenous injection. Levothyroxine has a half-life of 7.5 days when taken daily, so about six weeks is required for it to reach a steady level in the blood.
Side effects from excessive doses include weight loss, trouble tolerating heat, sweating, anxiety, trouble sleeping, tremor, and fast heart rate. Use is not recommended in people who have had a recent heart attack. Use during pregnancy has been found to be safe. Dosing should be based on regular measurements of thyroid-stimulating hormone (TSH) and T4 levels in the blood. Much of the effect of levothyroxine is following its conversion to triiodothyronine (T3).
Levothyroxine was first made in 1927. It is on the World Health Organization's List of Essential Medicines. Levothyroxine is available as a generic medication. In 2022, it was the fourth most commonly prescribed medication in the United States, with more than 82 million prescriptions.
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Read full article at Wikipedia
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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-/m0/s1 |
| XUIIKFGFIJCVMT-LBPRGKRZSA-N |
| N[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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antithyroid drug
A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
thyroid hormone
Any hormone produced by the thyroid gland
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
mitogen
A chemical substance that encourages a cell to commence cell division, triggering mitosis.
(via thyroxine )
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antithyroid drug
A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.
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View more via ChEBI Ontology
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3,3',5,5'-tetraiodo-L-thyronine
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ChemIDplus
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3,5,3',5'-TETRAIODO-L-THYRONINE
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PDBeChem
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3,5,3',5'-tetraiodo-L-thyronine
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ChemIDplus
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4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine
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IUPAC
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L-T4
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ChemIDplus
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L-Thyroxine
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KEGG COMPOUND
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Levothyroxin
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KEGG COMPOUND
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levothyroxine
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ChemIDplus
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LT4
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ChEBI
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O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine
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PDBeChem
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T4
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KEGG COMPOUND
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T4
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ChEBI
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2646
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DrugCentral
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3004
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VSDB
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C01829
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KEGG COMPOUND
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D08125
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KEGG DRUG
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DB00451
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DrugBank
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Levothyroxine
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Wikipedia
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LSM-5447
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LINCS
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T44
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PDBeChem
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| View more database links |
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2228515
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Beilstein Registry Number
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Beilstein
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51-48-9
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CAS Registry Number
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KEGG COMPOUND
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51-48-9
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CAS Registry Number
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ChemIDplus
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7002831
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Beilstein Registry Number
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Beilstein
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Alzoubi KH, Alkadhi KA (2014)
Levothyroxin replacement therapy restores hypothyroidism induced impairment of L-LTP induction: critical role of CREB.
Brain research bulletin 100, 29-37 [PubMed:24216002]
[show Abstract]
Cyclic-AMP response element binding protein (CREB) is a transcription factor crucial for late phase long-term potentiation (L-LTP) induction and maintenance. Upon multiple high frequency stimulation (MHFS), large Ca(2+) influx activates adenylyl cyclase. This, in turn, activates PKA, which by itself or through MAPK p42/p44 can activate (phosphorylate) CREB. Upon phosphorylation, P-CREB activates multiple genes essential for L-LTP generation. Calcium calmodulin kinase IV (CaMKIV) is also activated by calcium and can directly activate CREB. We have shown previously that hypothyroidism impairs L-LTP and reduces the basal protein levels of CREB, MAPK p42/p44, and CaMKIV in area CA1 of the hippocampus. In the present study, levels of these signaling molecules were determined in area CA1 during the induction and maintenance phases of L-LTP. Standard MHFS was used to evoke L-LTP in the CA1 area of hypothyroid, levothyroxin treated hypothyroid and sham control anesthetized adult rats. Chronic levothyroxin treatment reversed hypothyroidism-induced L-LTP impairment. Five minutes after MHFS, western blotting showed an increase in the levels of P-CREB, and P-MAPK p42/p44 in sham-operated control, and levothyroxin treated hypothyroid animals, but not in hypothyroid animals. The protein levels of total CREB, total MAPK p42/p44, BDNF and CaMKIV were not altered in all groups five minutes after MHFS. Four hours after MHFS, the levels of P-CREB, and P-MAPK p42/p44 remained unchanged in hypothyroid animals, while they were elevated in sham-operated control, and levothyroxin treated hypothyroid animals. We conclude that respective normalized phosphorylation of essential kinases such as P-CREB and P-MAPK p42/p44 is correlated with restoration of normal L-LTP induction and maintenance in the CA1 area of levothyroxin-treated hypothyroid animals. | Ianiro G, Mangiola F, Di Rienzo TA, Bibbò S, Franceschi F, Greco AV, Gasbarrini A (2014)
Levothyroxine absorption in health and disease, and new therapeutic perspectives.
European review for medical and pharmacological sciences 18, 451-456 [PubMed:24610609]
[show Abstract]
Levothyroxine therapy is used in case of deficiency of the thyroid hormones in the human organism. Many conditions, either physiological or paraphysiological or clearly pathological, can alter the levothyroxine absorption in the human body. Levothyroxine absorption can indeed be impaired by age, patient's compliance, fasting, the intake of certain foods (such as dietary fibers, grapes, soybeans, papaya and coffee) or by some drugs (such as proton-pump inhibitors, antacids, sucralfate, et cetera). Additionally, many gastrointestinal diseases, such as the conditions that disrupt the integrity of the intestinal barrier and the diseases that impair gastric acidity, may alter the bioavailability of levothyroxine. Since the enormous, widespread diffusion of thyroid diseases, a large number of patients have to face such issues. Therefore, the development of new levothyroxine oral formulations, other than solid tablets, may represent an interesting therapeutic approach, at the same time simple and effective, to face this problem. Recently, two different levothyroxine formulations have been proposed: the liquid formulation and the softgel formulation. Such formulations represent an innovative, effective and cheap therapeutic approach to hypothyroid patient with problems of impaired absorption of levothyroxine. | Anagnostis P, Efstathiadou ZA, Slavakis A, Selalmatzidou D, Poulasouchidou M, Katergari S, Karathanasi E, Dogramatzi F, Kita M (2014)
The effect of L-thyroxine substitution on lipid profile, glucose homeostasis, inflammation and coagulation in patients with subclinical hypothyroidism.
International journal of clinical practice 68, 857-863 [PubMed:24548294]
[show Abstract]
AimsSubclinical hypothyroidism (SH) is associated with increased risk for atherosclerosis, mainly attributable to dyslipidaemia and hypercoagulability. However, conflicting data exist regarding the effect of L-thyroxine substitution on these parameters. The purpose of this study was to assess the effect of L-thyroxine therapy on lipidaemic profile, coagulation markers, high-sensitivity C-reactive protein (hsCRP) and glucose homoeostasis in SH patients.MethodsIt was a prospective open-label study. The following parameters were measured before and 6 months after intervention: anthropometric data, total cholesterol (TC), low-density lipoprotein cholesterol (LDL-C), high-density lipoprotein cholesterol (HDL-C), triglycerides (TG), apolipoproteins B (apoB) and A1 (apoA1), lipoprotein (a) [Lp(a)], fasting plasma glucose and insulin, homoeostasis model assessment-insulin resistance (HOMA-IR), hsCRP, antithrombin III (AT-III), protein C (PC), protein S (PS), fibrinogen and homocysteine.ResultsThirty-two patients (30 women) aged 52.1 ± 13.9 years with SH completed the study. Baseline mean TSH levels were 6.79 ± 2.58 mIU/ml. Achievement of euthyroidism significantly reduced systolic blood pressure (BP) in patients with SH (from 135.2 ± 18.5 to 129.7 ± 15.8 mmHg, p = 0.03) and diastolic BP only in those with baseline TSH levels > 7 mIU/ml (from 79.5 ± 9.8 to 72.1 ± 7.3 mmHg, p = 0.03). No significant changes in body weight, TC, LDL-C, HDL-C, TG, apoB, glucose, insulin, HOMA-IR, hsCRP, AT-III, PC, PS, fibrinogen or homocysteine levels were noticed after restoration of euthyroidism, except for a decrease in apoA1 (p = 0.04) and an increase in Lp(a) levels (p = 0.02).ConclusionsExcept for a reduction in systolic and diastolic BP, thyroid substitution therapy does not affect lipidaemic profile, systematic inflammation, glucose homoeostasis or coagulation in patients with SH. | Prasad BB, Madhuri R, Tiwari MP, Sharma PS (2010)
Layer-by-layer assembled molecularly imprinted polymer modified silver electrode for enantioselective detection of D- and L-thyroxine.
Analytica chimica acta 681, 16-26 [PubMed:21035598]
[show Abstract]
The present work describes a new, simple, and easy method for the generation of stable molecularly imprinted sites in polymeric film, combining self-assembled monolayer and Layer-by-layer approaches through thermal cross-linking of the layered structures, onto the surface of silver electrode. Modified silver electrodes demonstrate enantiodifferentiation and sensitive (detection limits 0.0060 ng mL(-1) for L- and 0.0062 for D-thyroxine) determination of d- and l-thyroxine with the help of differential pulse anodic stripping voltammetric technique. The binding kinetics of thyroxine was explored using anodic stripping cyclic voltammetry and chronocoulometry. The sensor was also validated for D- and L-thyroxine determinations in biological and pharmaceutical samples. | Prasad BB, Tiwari MP, Madhuri R, Sharma PS (2010)
Enatioselective quantitative separation of D- and L-thyroxine by molecularly imprinted micro-solid phase extraction silver fiber coupled with complementary molecularly imprinted polymer-sensor.
Journal of chromatography. A 1217, 4255-4266 [PubMed:20483419]
[show Abstract]
Thyroxine is a known disease biomarker which demands a highly sensitive and selective technique to measure ultratrace level with enantiodifferentiation of its optical isomers (d- and l-), in real samples. In this work, an approach of hyphenation between molecularly imprinted micro-solid phase extraction and a complementary molecularly imprinted polymer-sensor was adopted for enantioseparation, preconcentration, and analysis of d- and l-thyroxine. In both techniques, the same imprinted polymer, coated on a vinyl functionalized self-assembled monolayer modified silver wire, was used as the respective extraction fiber as well as sensor material. This combination enabled enhanced preconcentration of test analyte substantially so as to achieve the stringent limit [limit of detection: 0.0084 ng mL(-1), RSD=0.81%, S/N=3 (d-thyroxine); 0.0087 ng mL(-1), RSD=0.63%, S/N=3 (l-thyroxine)] of clinical detection of thyroid-related diseases, without any problems of non-specific false-positive contribution and cross-reactivity. | Pabla D, Akhlaghi F, Zia H (2009)
A comparative pH-dissolution profile study of selected commercial levothyroxine products using inductively coupled plasma mass spectrometry.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 72, 105-110 [PubMed:18996189]
[show Abstract]
Levothyroxine (T4) is a narrow therapeutic index drug with classic bioequivalence problem between various available products. Dissolution of a drug is a crucial step in its oral absorption and bioavailability. The dissolution of T4 from three commercial solid oral dosage forms: Synthroid (SYN), generic levothyroxine sodium by Sandoz Inc. (GEN) and Tirosint (TIR) was studied using a sensitive ICP-MS assay. All the three products showed variable and pH-dependent dissolution behaviors. The absence of surfactant from the dissolution media decreased the percent T4 dissolved for all the three products by 26-95% (at 30 min). SYN dissolution showed the most pH dependency, whereas GEN and TIR showed the fastest and highest dissolution, respectively. TIR was the most consistent one, and was minimally affected by pH and/or by the presence of surfactant. Furthermore, dissolution of T4 decreased considerably with increase in the pH, which suggests a possible physical interaction in patients concurrently on T4 and gastric pH altering drugs, such as proton pump inhibitors. Variable dissolution of T4 products can, therefore, impact the oral absorption and bioavailability of T4 and may result in bioequivalence problems between various available products. | Shionoya H, Sugihara Y, Okano K, Sagami F, Mikami T, Katayama K (2004)
Studies on experimental iodine allergy: 1. Antigen recognition of guinea pig anti-iodine antibody.
The Journal of toxicological sciences 29, 131-136 [PubMed:15206581]
[show Abstract]
It has generally been thought that iodine allergy is cross-sensitive to various iodine-containing chemicals. However, this concept seems to deviate from the immunological principle that immune recognition is specific. To solve this contradiction, we hypothesize that iodine allergy is an immunological reaction to iodinated autologous proteins produced in vivo by iodination reaction from various iodine-containing chemicals. Antisera to iodine were obtained from guinea pigs immunized subcutaneously with iodine-potassium iodide solution emulsified in complete Freund's adjuvant (CFA). The specificity of guinea pig anti-iodine antiserum was determined by enzyme-linked immunosorbent assay (ELISA) inhibition experiments using microplates coated with iodinated guinea pig serum albumin (I-GSA). Antibody activities were inhibited by I-GSA, diiodo-L-tyrosine, and thyroxine, but not by potassium iodide, monoiodo-L-tyrosine, 3,5,3'-triiodothyronine, monoiodo-L-histidine, or diiodo-L-histidine, or by ionic or non-ionic iodinated contrast media. The results that antigen recognition of anti-iodine antibody is specific to iodinated protein support our hypothesis. While protein iodination usually takes place both at histidine residues as well as at tyrosine residues, only iodinated tyrosine acted as an antigenic determinant and no antibody activities to iodinated histidine were detected in our experimental iodine allergy model. | Sandhu GS, Steele R, Gonnella NC (1991)
Effect of L-thyroxine (LT4) and D-thyroxine (DT4) on cardiac function and high-energy phosphate metabolism: a 31P NMR study.
Magnetic resonance in medicine 18, 237-243 [PubMed:2062236]
[show Abstract]
31P NMR spectroscopy was used to monitor the cardiac energy metabolism in hypothyroid rat hearts. Differential alterations in phosphocreatine and inorganic phosphate levels were observed upon treatment of hypothyroid animals with DT4 and LT4, while both agents were equipotent in reducing cholesterol. These results show potential for NMR spectroscopy as a technique to determine therapeutic selectivity. |
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