Tiratricol: Difference between revisions

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{{drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
⚫
| UNII_Ref = {{fdacite|changed|FDA}}
⚫
| UNII = 29OQ9EU4R1
| verifiedrevid = 418305814
| verifiedrevid = 418305814
| IUPAC_name = [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
| IUPAC_name = [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
| image = Tiratricol.svg
| image = Tiratricol.svg

<!--Clinical data-->
| tradename =
| Drugs.com = {{drugs.com|international|tiratricol}}
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category =
⚫
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| legal_status =
⚫
| routes_of_administration =

<!--Pharmacokinetic data-->
⚫
| bioavailability =
⚫
| protein_bound = Presumed high
⚫
| metabolism = [[Liver|Hepatic]] [[glucuronidation]]
⚫
| elimination_half-life =
⚫
| excretion = Biliary

<!--Identifiers-->
⚫
| CAS_number = 51-24-1
⚫
| ATC_prefix = H03
⚫
| ATC_suffix = AA04
⚫
| ATC_supplemental = {{ATC|D11|AX08}}
⚫
| PubChem = 5803
⚫
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
⚫
| DrugBank = DB03604
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5598
| ChemSpiderID = 5598
⚫
| UNII_Ref = {{fdacite|changed|FDA}}
⚫
| InChI = 1/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)
⚫
| UNII = 29OQ9EU4R1
⚫
| InChIKey = UOWZUVNAGUAEQC-UHFFFAOYAM
⚫
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫
| smiles = Ic2cc(Oc1c(I)cc(cc1I)CC(=O)O)ccc2O
⚫
| KEGG = D07214
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 41632
| ChEMBL = 41632

<!--Chemical data-->
⚫
| C=14 | H=9 | I=3 | O=4
⚫
| molecular_weight = 621.932 g/mol
⚫
| smiles = Ic2cc(Oc1c(I)cc(cc1I)CC(=O)O)ccc2O
⚫
| InChI = 1/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)
⚫
| InChIKey = UOWZUVNAGUAEQC-UHFFFAOYAM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)
| StdInChI = 1S/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UOWZUVNAGUAEQC-UHFFFAOYSA-N
| StdInChIKey = UOWZUVNAGUAEQC-UHFFFAOYSA-N
⚫
| synonyms = 3,3',5-triiodothyroacetic acid<br>TRIAC
⚫
| CAS_number = 51-24-1
⚫
| ATC_prefix = H03
⚫
| ATC_suffix = AA04
⚫
| ATC_supplemental = {{ATC|D11|AX08}}
⚫
| PubChem = 5803
⚫
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
⚫
| DrugBank = DB03604
⚫
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫
| KEGG = D07214
⚫
| C = 14 | H = 9 | I = 3 | O = 4
⚫
| molecular_weight = 621.932 g/mol
⚫
| synonyms = 3,3',5-triiodothyroacetic acid<br>TRIAC
⚫
| bioavailability =
⚫
| protein_bound = Presumed high
⚫
| metabolism = [[Liver|Hepatic]] [[glucuronidation]]
⚫
| elimination_half-life =
⚫
| excretion = Biliary
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category=
⚫
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| legal_status =
⚫
| routes_of_administration =
}}
}}
'''Tiratricol''' (also known as '''TRIAC''' or triiodothyroacetic acid) is a [[thyroid hormone]] [[analog (chemistry)|analogue]].
'''Tiratricol''' (also known as '''TRIAC''' or triiodothyroacetic acid) is a [[thyroid hormone]] [[analog (chemistry)|analogue]].

Revision as of 07:44, 1 September 2011

Tiratricol
Clinical data
Other names3,3',5-triiodothyroacetic acid
TRIAC
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Protein bindingPresumed high
MetabolismHepatic glucuronidation
ExcretionBiliary
Identifiers
  • [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.079 Edit this at Wikidata
Chemical and physical data
FormulaC14H9I3O4
Molar mass621.932 g/mol g·mol−1
3D model (JSmol)
  • Ic2cc(Oc1c(I)cc(cc1I)CC(=O)O)ccc2O
  • InChI=1S/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20) checkY
  • Key:UOWZUVNAGUAEQC-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tiratricol (also known as TRIAC or triiodothyroacetic acid) is a thyroid hormone analogue.

Uses

It is indicated in the management of thyroid hormone resistance syndrome[1] and is used, in combination with levothyroxine, to suppress thyroid-stimulating hormone production in patients with thyroid cancer.

It has been investigated for use in reducing goiter.[2]

It has also shown some effectiveness in reducing the atrophy caused when using corticosteroids.[3]

Tiratricol has also been widely marketed, under various trade names, as a weight loss aid. In 1999 and 2000, the United States Food and Drug Administration and Health Canada both issued warnings to the public regarding the use of dietary supplements containing tiratricol.[4][5]

Legal status

Tiratricol is not approved for sale in Canada or the United States. It was once an approved drug in Brazil, but its marketing authorization was suspended in 2003, effectively prohibiting its sale.[6]

References

  1. ^ Carvalho GA, Ramos HE (2004). "[Thyroid hormone resistance syndrome]". Arq Bras Endocrinol Metabol (in Portuguese). 48 (1): 83–92. doi:/S0004-27302004000100010. PMID 15611821. {{cite journal}}: Check |doi= value (help) Template:PDFlink
  2. ^ Brenta G, Schnitman M, Fretes O; et al. (2003). "Comparative efficacy and side effects of the treatment of euthyroid goiter with levo-thyroxine or triiodothyroacetic acid". J. Clin. Endocrinol. Metab. 88 (11): 5287–92. doi:10.1210/jc.2003-030095. PMID 14602763. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Yazdanparast P, Carlsson B, Oikarinen A, Risteli J, Lavin T, Faergemann J (2006). "Action of topical thyroid hormone analogue, triiodothyroacetic acid in reversing glucocorticoid-induced skin atrophy in humans". Thyroid. 16 (11): 1157–62. doi:10.1089/thy.2006.16.1157. PMID 17123343. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ "FDA Warns Against Consuming Dietary Supplements Containing Tiratricol" (Press release). U.S. Food and Drug Administration. November 21, 2000. Retrieved 2007-08-08.
  5. ^ "Health Canada issues warning on products containing Tiratricol (TRIAC)" (Press release). Health Canada. December 2, 1999. Retrieved 2007-08-08.
  6. ^ "Anvisa suspende Tiratricol" (in Portuguese). Brazilian Society of Endocrinology and Metabolism. Archived from the original on 2007-10-09. Retrieved 2007-08-08.


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