Reverse triiodothyronine

Reverse triiodothyronine
Names
	IUPAC name O-(4-Hydroxy-3,5-diiodophenyl)-3-iodo-L-tyrosine
	Systematic IUPAC name (2S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid
	Other names reverse triiodothyronine; reverse T3; rT3; 3,3′,5′-triiodothyronine
Identifiers
CAS Number	5817-39-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:11684 ;
ChemSpider	559294 ;
IUPHAR/BPS	2636;
KEGG	C07639 ;
MeSH	Reverse+triiodothyronine
PubChem CID	22069;
UNII	8NZ4Y08T96 ;
CompTox Dashboard (EPA)	DTXSID50859929 DTXSID00274724, DTXSID50859929 ;
	InChI InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1 Key: HZCBWYNLGPIQRK-LBPRGKRZSA-N ; InChI=1/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1 Key: HZCBWYNLGPIQRK-LBPRGKRZBV;
	SMILES C1=CC(=C(C=C1C[C@@H](C(=O)O)N)I)OC2=CC(=C(C(=C2)I)O)I;
Properties
Chemical formula	C15H12I3NO4
Molar mass	650.974
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Reverse triiodothyronine, also known as rT₃, is an isomer of triiodothyronine (T₃).

Reverse T₃ is the third-most common iodothyronine the thyroid gland releases into the bloodstream, at 0.9%; tetraiodothyronine (levothyroxine, T₄) constitutes 90% and T₃ is 9%. However, 95% of rT₃ in human blood is made elsewhere in the body, as enzymes remove a particular iodine atom from T₄.^[1]

The production of hormone by the thyroid gland is controlled by the hypothalamus and pituitary gland. The physiological activity of thyroid hormone is regulated by a system of enzymes that activate, inactivate or simply discard the prohormone T₄ and in turn functionally modify T₃ and rT₃. These enzymes operate under complex direction of systems including neurotransmitters, hormones, markers of metabolism and immunological signals.

The levels of rT₃ increase in conditions such as euthyroid sick syndrome because its clearance decreases while its production stays the same. The decreased clearance is possibly from lower thyroxine 5-deiodinase activity in the peripheral tissue or decreased liver uptake of rT₃.^[2] In addition, increased rT₃ concentrations result from upregulated thyroxine 5-deiodinase activity in critical illness, starvation and fetal life.^[3]

Reactions

Synthesis of Reverse T₃ from T₄ via deiodination. Synthesis of T₃ and T₂ is also shown.

References

^ Chopra IJ (July 1976). "An assessment of daily production and significance of thyroidal secretion of 3,3′,5′-triiodothyronine (reverse T3) in man". J. Clin. Invest. 58 (1): 32–40. doi:10.1172/JCI108456. PMC 333152. PMID 932209.
^ Euthyroid Sick Syndrome at eMedicine
^ Chatzitomaris, Apostolos; Hoermann, Rudolf; Midgley, John E.; Hering, Steffen; Urban, Aline; Dietrich, Barbara; Abood, Assjana; Klein, Harald H.; Dietrich, Johannes W. (20 July 2017). "Thyroid Allostasis–Adaptive Responses of Thyrotropic Feedback Control to Conditions of Strain, Stress, and Developmental Programming". Frontiers in Endocrinology. 8. doi:10.3389/fendo.2017.00163. PMC 5517413. PMID 28775711.

External links

Triiodothyronine, Reverse at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

[Chopra_1976-1] Chopra IJ (July 1976). "An assessment of daily production and significance of thyroidal secretion of 3,3′,5′-triiodothyronine (reverse T3) in man". J. Clin. Invest. 58 (1): 32–40. doi:10.1172/JCI108456. PMC 333152. PMID 932209.

[2] Euthyroid Sick Syndrome at eMedicine

[Chatzitomaris_2017-3] Chatzitomaris, Apostolos; Hoermann, Rudolf; Midgley, John E.; Hering, Steffen; Urban, Aline; Dietrich, Barbara; Abood, Assjana; Klein, Harald H.; Dietrich, Johannes W. (20 July 2017). "Thyroid Allostasis–Adaptive Responses of Thyrotropic Feedback Control to Conditions of Strain, Stress, and Developmental Programming". Frontiers in Endocrinology. 8. doi:10.3389/fendo.2017.00163. PMC 5517413. PMID 28775711.

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Names


IUPAC name O-(4-Hydroxy-3,5-diiodophenyl)-3-iodo-L-tyrosine
Systematic IUPAC name (2S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid
Other names reverse triiodothyronine reverse T₃ rT₃ 3,3′,5′-triiodothyronine
Identifiers
CAS Number	5817-39-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:11684^N
ChemSpider	559294^N
IUPHAR/BPS	2636
KEGG	C07639^N
MeSH	Reverse+triiodothyronine
PubChem CID	22069
UNII	8NZ4Y08T96^Y
CompTox Dashboard (EPA)	DTXSID50859929 DTXSID00274724, DTXSID50859929
InChI InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1^N Key: HZCBWYNLGPIQRK-LBPRGKRZSA-N^N InChI=1/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1 Key: HZCBWYNLGPIQRK-LBPRGKRZBV
SMILES C1=CC(=C(C=C1C[C@@H](C(=O)O)N)I)OC2=CC(=C(C(=C2)I)O)I
Properties
Chemical formula	C₁₅H₁₂I₃NO₄
Molar mass	650.974
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references