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6893-02-3 molecular structure
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(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 and InChIs

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

Cite this record

CBID:164 http://www.chembase.cn/molecule-164.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-iodophenoxy)-3,5-diiodophenyl]propanoic acid
IUPAC Traditional name
liothyronine
Brand Name
Cytomel
Tresitope
Triostat
Tertroxin
Synonyms
L-Liothyronine
Liothyronin
Liothyronine Sodium
Triiodothyronine
T3 liothyronine
Liothyronine
T3
3,3',5-triiodo-L-thyronine
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)
L-T3
3,3’,5-Triiodothyronine
T3 (Hormone)
Tresitope
3,3',5-Triiodo-L-thyronine
3,3',5-Triiodo-L-thyronine
Triiodothyronine
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)
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 0.30255273  H Acceptors
H Donor LogD (pH = 5.5) 2.798151 
LogD (pH = 7.4) 2.7648876  Log P 2.798505 
Molar Refractivity 113.4255 cm3 Polarizability 44.90148 Å3
Polar Surface Area 92.78 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 0.82  LOG S -4.52 
Solubility (Water) 1.95e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
3.96 mg/L expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
Apperance
Off-White Solid expand Show data source
powder expand Show data source
Melting Point
200-207°C (dec.) expand Show data source
232-240 °C (dec.) expand Show data source
234-238 °C(lit.) expand Show data source
234-238°C expand Show data source
Optical Rotation
[α]20/D +23.0°, c = 2 in ethanol or 0.1 N HCl expand Show data source
[α]20/D +25±2°, c = 1% in ethanol/1 M HCl (2:1) expand Show data source
[α]25/D +23.0°, c = 2 in 1 N HCl: ethanol, 1:2 expand Show data source
+25 (c=1 in 1M HCl/Ethanol 1:2) expand Show data source
Hydrophobicity(logP)
2.9 expand Show data source
Storage Condition
Refrigerator expand Show data source
Storage Warning
Light Sensitive expand Show data source
RTECS
AY6750000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) 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
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37-60 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
-70°C expand Show data source
Gene Information
human ... THRA(7067), THRB(7068)rat ... Thra(81812), Thrb(24831) expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥97.0% (sum of enantiomers, HPLC) expand Show data source
95% expand Show data source
Grade
BCR® certified Reference Material expand Show data source
Certificate of Analysis
Download expand Show data source
Impurities
≤2% 3,5-diiodo thyronine expand Show data source
≤2% thyroxine expand Show data source
Empirical Formula (Hill Notation)
C15H12I3NO4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00279 external link
Item Information
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 - IRMM469 external link
Legal Information
BCR is a registered trademark of European Commission
Sigma Aldrich - 564605 external link
Packaging
250 mg in glass bottle
Sigma Aldrich - 91990 external link
Other Notes
Review: Thyroid hormone action at the nuclear level1
Sigma Aldrich - T2877 external link
包装
1, 5 g in poly bottle
100, 250, 500 mg in poly bottle
Toronto Research Chemicals - T795380 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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