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51-48-9 molecular structure
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(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid

ChemBase ID: 334
Molecular Formular: C15H11I4NO4
Molecular Mass: 776.87002
Monoisotopic Mass: 776.68669984
SMILES and InChIs

SMILES:
Ic1cc(C[C@H](N)C(=O)O)cc(I)c1Oc1cc(I)c(O)c(I)c1
Canonical SMILES:
OC(=O)[C@H](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)/t12-/m0/s1
InChIKey:
XUIIKFGFIJCVMT-LBPRGKRZSA-N

Cite this record

CBID:334 http://www.chembase.cn/molecule-334.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
IUPAC Traditional name
levothyroxine
Brand Name
Thyreoideum
Thyro-tabs
Thyroxevan
Thyroxin
Thyroxinal
Unithroid
Eltroxin
Euthyrox
Laevoxin
Letter
Levaxin
Levolet
Levothroid
Levothyrox
Levoxine
Levoxyl
Novothyrox
Oroxine
Synthroid
Synthroid Sodium
Thyratabs
Thyrax
Synonyms
Thyroxine (T4)
(-)-Thyroxine
3,3',5,5'-Tetraiodo-L-thyronine
L-Thryoxin
L-Thyroxine
Laevothyroxinum
Levo-t
Levothyroxine Sodium
Tetraiodothyronine
THX
Thyroxine iodine
Levothyroxin
T4 levothyroxine
O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine
Levothyroxine
L-Thyroxine
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine
Henning
L-T4
L-Thyroxin
NSC 36397
T4 (hormone)
Thyrax
Thyroxinal
ThyroxineAlso see: T425601
T4
3,3′,5,5″-Tetraiodo-L-thyronine
L-Thyroxine
Levothyroxine
Thyreoideum
Thyroxin
Thyroxine
3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine
L-甲状腺素
甲状腺素 (T4)
3,3′,5,5″-四碘代-L-甲状腺原氨酸
3-[4-(4-羟基-3,5-二碘苯氧基)-3,5-二碘苯基]-L-丙氨酸
L-甲状腺素
CAS Number
51-48-9
EC Number
200-101-1
MDL Number
MFCD00002595
Beilstein Number
2228515
PubChem SID
24900033
46507672
24899990
160963797
PubChem CID
5819

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 0.27336746  H Acceptors
H Donor LogD (pH = 5.5) 3.722463 
LogD (pH = 7.4) 3.4409168  Log P 3.727307 
Molar Refractivity 126.788 cm3 Polarizability 50.46104 Å3
Polar Surface Area 92.78 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 1.15  LOG S -4.94 
Solubility (Water) 8.98e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.105 mg/mL expand Show data source
Methanol expand Show data source
Apperance
powder expand Show data source
Tan Solid expand Show data source
Melting Point
~235 °C (dec.) expand Show data source
>300°C (dec.) expand Show data source
223 °C (dec.)(lit.) expand Show data source
235-236°C (decomposes) expand Show data source
Optical Rotation
[α]20/D -5.3±0.5°, c = 1% in ethanol/1 M NaOH (2:1) expand Show data source
Hydrophobicity(logP)
4 expand Show data source
Storage Condition
0°C expand Show data source
-20°C expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
YP2833500 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
-70°C expand Show data source
Gene Information
human ... TTR(7276) expand Show data source
human ... TTR(7276)mouse ... Cnr2(12802)rat ... Cnr1(25248) expand Show data source
Purity
≥97.0% (sum of enantiomers, HPLC) expand Show data source
≥98% (HPLC) expand Show data source
Grade
BCR® certified Reference Material expand Show data source
Salt Data
Free Base expand Show data source
Potency
5-50 ng/mL expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
suitable for cell culture expand Show data source
Product Line
BioReagent expand Show data source
Linear Formula
HOC6H2(I)2OC6H2(I)2CH2CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02152145 external link
Free Acid
Crystalline
DrugBank - DB00451 external link
Item Information
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 For use alone or in combination with antithyroid agents to treat hypothyroidism, goiter, chronic lymphocytic thyroiditis, myxedema coma, and stupor.
Pharmacology Levothyroxine (T4) is a synthetically prepared levo isomer of thyroxine, the major hormone secreted from the thyroid gland. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine (T3) which exerts a broad spectrum of stimulatory effects on cell metabolism. Thyroid hormone increases the metabolic rate of cells of all tissues in the body. In the fetus and newborn, thyroid hormone is important for the growth and development of all tissues including bones and the brain. In adults, thyroid hormone helps to maintain brain function, food metabolism, and body temperature, among other effects. The symptoms of thyroid deficiency relieved by levothyroxine include slow speech, lack of energy, weight gain, hair loss, dry thick skin and unusual sensitivity to cold.
Toxicity LD50=20 mg/kg (orally in rat). Hypermetabolic state indistinguishable from thyrotoxicosis of endogenous origin. Symptoms of thyrotoxicosis include weight loss, increased appetite, palpitations, nervousness, diarrhea, abdominal cramps, sweating, tachycardia, increased pulse and blood pressure, cardiac arrhythmias, tremors, insomnia, heat intolerance, fever, and menstrual irregularities.
Affected Organisms
Humans and other mammals
Biotransformation Approximately 70% of secreted T4 is deiodinated to equal amounts of T3 and reverse triiodothyronine (rT3), which is calorigenically inactive. Elimination of T4 and T3 involves hepatic conjugation to glucuronic and sulfuric acids. The hormones undergo enterohepatic circulation as conjugates are hydrolyzed in the intestine and reabsorbed. Conjugated compounds that reach the colon are hydrolyzed and eliminated as free compounds in the feces. Other minor T4 metabolites have been identified.
Absorption Bioavailability varies from 48% to 80%. Human studies have confirmed the importance of an intact jejunum and ileum for levothyroxine absorption and have shown some absorption from the duodenum.
Half Life T4, 6 to 7 days. T3, 1 to 2 days.
Protein Binding > 99% to serum proteins, including thyroxine-binding globulin (TBG), thyroxine-binding prealbumin (TBPA), and albumin (TBA)
Elimination Thyroid hormones are primarily eliminated by the kidneys.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S2599 external link
Research Area: Endocrinology
Biological Activity:
L-Thyroxine is a synthetic form of thyroxine and a hormone replacement drug. L-Thyroxine is typically used to treat hypothyroidism. L-Thyroxine may also be used to treat goiter via its ability to lower thyroid-stimulating hormone (TSH), a hormone that is considered goiter-inducing.
Sigma Aldrich - T2376 external link
Biochem/physiol Actions
L-Thyroxine (T4) and triiodo-L-thyronine (T3) are iodine-containing hormones produced from thyroglobulin in the thyroid follicular cells. The stimulation of metabolic rate and regulation of growth and development by these hormones appear to be due to their effects on DNA transcription and, thus, protein synthesis.
Packaging
1, 5 g in glass bottle
100, 500 mg in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T2376.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich - T1775 external link
Biochem/physiol Actions
L-Thyroxine (T4) and triiodo-L-thyronine (T3) are iodine-containing hormones produced from thyroglobulin in the thyroid follicular cells. The stimulation of metabolic rate and regulation of growth and development by these hormones appear to be due to their effects on DNA transcription and, thus, protein synthesis.
Reconstitution
To prepare 20 μg/ml stock solution, dissolve in 50 ml sterile culture medium per mg thyroxine.
Physical form
powder-0 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw, solution stable 2-8 °C, 30 days
Sigma Aldrich - IRMM468 external link
Biochem/physiol Actions
L-Thyroxine (T4) and triiodo-L-thyronine (T3) are iodine-containing hormones produced from thyroglobulin in the thyroid follicular cells. The stimulation of metabolic rate and regulation of growth and development by these hormones appear to be due to their effects on DNA transcription and, thus, protein synthesis.
Legal Information
BCR is a registered trademark of European Commission
Sigma Aldrich - 89405 external link
Biochem/physiol Actions
L-Thyroxine (T4) and triiodo-L-thyronine (T3) are iodine-containing hormones produced from thyroglobulin in the thyroid follicular cells. The stimulation of metabolic rate and regulation of growth and development by these hormones appear to be due to their effects on DNA transcription and, thus, protein synthesis.
Other Notes
Review1
Toronto Research Chemicals - T425600 external link
One of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the p

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Post, A., et al.: Anal. Profiles Drug Subs., 5, 225 (1976)
  • • Nelson, J.C., et al.: Clin. Chem., 34, 1737 (1976)
  • • Fischer, D.A., et al.: Clin. Chem., 42, 135 (1976)
  • • Cavalieri, R.R., et al.: Thyroid, 7, 177 (1976)
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PATENTS

PATENTS

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