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{{drugbox
 
| IUPAC_name       = 2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]<br>acetic acid
{{Drugbox
| image             = Tiratricol.jpg
| Verifiedfields = changed
| CAS_number        = 51-24-1
| verifiedrevid = 470610738
| ATC_prefix        = H03
| IUPAC_name = [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
| ATC_suffix        = AA04
| image = Tiratricol.svg
| ATC_supplemental  = {{ATC|D11|AX08}}
| width = 240
| PubChem          = 5803
| image2 = Tiratricol 3D ball.png
| DrugBank          =
| alt2 = Ball-and-stick model of the tiratricol molecule
| C = 14 | H = 9 | I = 3 | O = 4
<!--Clinical data-->
| molecular_weight  = 621.932 g/mol
| tradename =
| synonyms          = 3,3',5-triiodothyroacetic acid<br>TRIAC
| Drugs.com = {{drugs.com|international|tiratricol}}
| bioavailability  =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| protein_bound    = Presumed high
| pregnancy_US = <!-- A / B            / C / D / X -->
| metabolism        = [[Liver|Hepatic]] [[glucuronidation]]
| pregnancy_category =   
| elimination_half-life =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| excretion        = Biliary
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_category=   
| legal_status =
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| routes_of_administration =
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
 
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
<!--Pharmacokinetic data-->
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| bioavailability = 
| legal_status     =  
| protein_bound = Presumed high
| routes_of_administration =  
| metabolism = [[Liver|Hepatic]] [[glucuronidation]]
| elimination_half-life = 
| excretion = Biliary
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 51-24-1
| ATC_prefix = H03
| ATC_suffix = AA04
| ATC_supplemental =  {{ATC|D11|AX08}}
| PubChem = 5803
| IUPHAR_ligand = 2637
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03604
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5598
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 29OQ9EU4R1
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07214
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| 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 = 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 = UOWZUVNAGUAEQC-UHFFFAOYSA-N
| synonyms = 3,3',5-triiodothyroacetic acid<br>TRIAC
}}
}}
{{SI}}
'''Tiratricol''' (also known as '''TRIAC''' or triiodothyroacetic acid) is a [[thyroid hormone]] [[analog (chemistry)|analogue]].
__NOTOC__


==Uses==
It is indicated in the management of [[thyroid hormone resistance|thyroid hormone resistance syndrome]]<ref>{{cite journal |author=Carvalho GA, Ramos HE |title=[Thyroid hormone resistance syndrome] |language=Portuguese |journal=Arq Bras Endocrinol Metabol |volume=48 |issue=1 |pages=83–92 |year=2004 |pmid=15611821 |doi=10.1590/S0004-27302004000100010}} {{PDFlink|[http://www.scielo.br/pdf/abem/v48n1/19522.pdf Free full text]|95.3&nbsp;[[Kibibyte|KiB]]<!-- application/pdf, 97642 bytes -->}}</ref> and is used, in combination with [[levothyroxine]], to suppress [[thyroid-stimulating hormone]] production in patients with [[thyroid cancer]].


==Overview==
It has been investigated for use in reducing [[goiter]].<ref name="pmid14602763">{{cite journal |author=Brenta G, Schnitman M, Fretes O, ''et al.'' |title=Comparative efficacy and side effects of the treatment of euthyroid goiter with levo-thyroxine or triiodothyroacetic acid |journal=J. Clin. Endocrinol. Metab. |volume=88 |issue=11 |pages=5287–92 |date=November 2003 |pmid=14602763 |doi= 10.1210/jc.2003-030095|url=http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=14602763}}</ref>
'''Tiratricol''' (also known as '''TRIAC''') is a [[thyroid hormone]] [[analog (chemistry)|analogue]]. It is indicated in the management of [[thyroid hormone resistance|thyroid hormone resistance syndrome]]<ref>{{cite journal |author=Carvalho GA, Ramos HE |title=[Thyroid hormone resistance syndrome] |language=Portuguese |journal=Arq Bras Endocrinol Metabol |volume=48 |issue=1 |pages=83–92 |year=2004 |pmid=15611821 |doi=/S0004-27302004000100010}} {{PDFlink|[http://www.scielo.br/pdf/abem/v48n1/19522.pdf Free full text]|95.3&nbsp;[[Kibibyte|KiB]]<!-- application/pdf, 97642 bytes -->}}</ref> and is used, in combination with [[levothyroxine]], to suppress [[thyroid-stimulating hormone]] production in patients with [[thyroid cancer]].


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 supplement]]s containing tiratricol.<ref>{{cite press release | url = http://www.fda.gov/bbs/topics/ANSWERS/ANS01057.html | title = FDA Warns Against Consuming Dietary Supplements Containing Tiratricol | date = November 21 2000 | accessdate = | publisher = U.S. [[Food and Drug Administration]]}}</ref><ref>{{cite press release | url = http://www.hc-sc.gc.ca/ahc-asc/media/advisories-avis/1999/1999_143_e.html | title = Health Canada issues warning on products containing Tiratricol (TRIAC) | date = December 2 1999 | accessdate = | publisher = Health Canada}}</ref>
It has also shown some effectiveness in reducing the atrophy caused when using [[corticosteroid]]s.<ref name="pmid17123343">{{cite journal |author=Yazdanparast P, Carlsson B, Oikarinen A, Risteli J, Lavin T, Faergemann J |title=Action of topical thyroid hormone analogue, triiodothyroacetic acid in reversing glucocorticoid-induced skin atrophy in humans |journal=Thyroid |volume=16 |issue=11 |pages=1157–62 |date=November 2006 |pmid=17123343 |doi=10.1089/thy.2006.16.1157}}</ref>
 
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 supplement]]s containing tiratricol.<ref>{{cite press release | url = http://www.fda.gov/bbs/topics/ANSWERS/ANS01057.html | title = FDA Warns Against Consuming Dietary Supplements Containing Tiratricol | date = November 21, 2000 | accessdate = 2007-08-08 | publisher = U.S. [[Food and Drug Administration]]}}</ref><ref>{{cite press release | url = http://www.hc-sc.gc.ca/ahc-asc/media/advisories-avis/1999/1999_143_e.html | title = Health Canada issues warning on products containing Tiratricol (TRIAC) | date = December 2, 1999 | accessdate = 2007-08-08 | publisher = [[Health Canada]]}}</ref>


==Legal status==
==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.<ref>{{cite web | url = http://www.endocrino.org.br/noticia_g_exibe.php?id=9 | title = Anvisa suspende Tiratricol | language = Portuguese | date = | accessdate = | publisher = Brazilian Society of Endocrinology and Metabolism}}</ref>
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.<ref>{{cite web | url = http://www.endocrino.org.br/noticia_g_exibe.php?id=9 | title = Anvisa suspende Tiratricol | language = Portuguese | date = | accessdate = 2007-08-08 | publisher = Brazilian Society of Endocrinology and Metabolism |archiveurl = http://web.archive.org/web/20071009062707/http://www.endocrino.org.br/noticia_g_exibe.php?id=9 <!-- Bot retrieved archive --> |archivedate = 2007-10-09}}</ref> Tiratricol is still available in France for therapy of thyroid hormone resistance and adjuvant therapy of thyroid cancer.<ref>Laboratoires DB PHARMA: [http://www.db-pharma.com/fiche.cfm?id=24 Teatrois] information</ref> It is available as an [[orphan drug]] to be prescribed by registered specialists in Europe.


==References==
==References==
{{Reflist}}
{{Reflist|2}}


{{Other dermatological preparations}}
{{Other dermatological preparations}}
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Revision as of 15:07, 13 April 2015

Tiratricol
Ball-and-stick model of the tiratricol molecule
Clinical data
Synonyms3,3',5-triiodothyroacetic acid
TRIAC
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
Protein bindingPresumed high
MetabolismHepatic glucuronidation
ExcretionBiliary
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC14H9I3O4
Molar mass621.932 g/mol
3D model (JSmol)
 ☒N☑Y (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] Tiratricol is still available in France for therapy of thyroid hormone resistance and adjuvant therapy of thyroid cancer.[7] It is available as an orphan drug to be prescribed by registered specialists in Europe.

References

  1. ↑ Carvalho GA, Ramos HE (2004). "[Thyroid hormone resistance syndrome]". Arq Bras Endocrinol Metabol (in Portuguese). 48 (1): 83–92. doi:10.1590/S0004-27302004000100010. PMID 15611821. Template:PDFlink
  2. ↑ Brenta G, Schnitman M, Fretes O; et al. (November 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.
  3. ↑ Yazdanparast P, Carlsson B, Oikarinen A, Risteli J, Lavin T, Faergemann J (November 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.
  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.
  7. ↑ Laboratoires DB PHARMA: Teatrois information

Template:Thyroid therapy


Template:Systemic-hormonal-drug-stub Template:Dermatologic-drug-stub

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