Tiratricol: Difference between revisions

Tiratricol
Clinical data
Other names	3,3',5-triiodothyroacetic acid; TRIAC
AHFS/Drugs.com	International Drug Names
ATC code	H03AA04 (WHO) D11AX08 (WHO);
Pharmacokinetic data
Protein binding	Presumed high
Metabolism	Hepatic glucuronidation
Excretion	Biliary
Identifiers
	IUPAC name [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid;
CAS Number	51-24-1 ;
PubChem CID	5803;
IUPHAR/BPS	2637;
DrugBank	DB03604 ;
ChemSpider	5598 ;
UNII	29OQ9EU4R1;
KEGG	D07214 ;
ChEBI	CHEBI:40021;
ChEMBL	ChEMBL41632 ;
CompTox Dashboard (EPA)	DTXSID2045232 ;
ECHA InfoCard	100.000.079
Chemical and physical data
Formula	C14H9I3O4
Molar mass	621.935 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Ic2cc(Oc1c(I)cc(cc1I)CC(=O)O)ccc2O;
	InChI 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) ; Key:UOWZUVNAGUAEQC-UHFFFAOYSA-N ;
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Tiratricol (also known as TRIAC or triiodothyroacetic acid) is a thyroid hormone analogue. Triiodothyroacetic acid is also a physiologic thyroid hormone that is present in the normal organism in low concentrations.

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

^ 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. "Free full text" (PDF). (95.3 KiB)
^ 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.
^ 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.
^ "FDA Warns Against Consuming Dietary Supplements Containing Tiratricol" (Press release). U.S. Food and Drug Administration. November 21, 2000. Retrieved 2007-08-08.
^ "Health Canada issues warning on products containing Tiratricol (TRIAC)" (Press release). Health Canada. December 2, 1999. Retrieved 2007-08-08.
^ "Anvisa suspende Tiratricol" (in Portuguese). Brazilian Society of Endocrinology and Metabolism. Archived from the original on 2007-10-09. Retrieved 2007-08-08.
^ Laboratoires DB PHARMA: Teatrois Archived 2015-01-19 at archive.today information

External links

"Tiratricol". Drug Information Portal. U.S. National Library of Medicine.

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This dermatologic drug article is a stub. You can help Wikipedia by expanding it.

[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. "Free full text" (PDF). (95.3 KiB)

[pmid14602763-2] 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.

[pmid17123343-3] 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 Archived 2015-01-19 at archive.today information

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@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
-{{drugbox
+{{about|the drug|the electronic component|TRIAC|the car|Triac (car)}}
+{{Drugbox
 | Verifiedfields = changed
+| verifiedrevid = 470610738
-| UNII_Ref = {{fdacite|changed|FDA}}
+| IUPAC_name = [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
-| UNII = 29OQ9EU4R1
+| image = Tiratricol.svg
-| verifiedrevid = 418305814
+| width = 240
-| IUPAC_name        = [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid
+| image2 = Tiratricol 3D ball.png
-| image             = Tiratricol.svg
+| alt2 = Ball-and-stick model of the tiratricol molecule
+<!--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_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
+| ChEBI = 40021
-| 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_Ref = {{fdacite|correct|FDA}}
-| InChIKey = UOWZUVNAGUAEQC-UHFFFAOYAM
+| UNII = 29OQ9EU4R1
-| smiles = Ic2cc(Oc1c(I)cc(cc1I)CC(=O)O)ccc2O
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D07214
 | ChEMBL_Ref = {{ebicite|correct|EBI}}
 | ChEMBL = 41632
+<!--Chemical data-->
+| C=14 | H=9 | I=3 | O=4
+| smiles = Ic2cc(Oc1c(I)cc(cc1I)CC(=O)O)ccc2O
 | 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
-| CAS_number        = 51-24-1
-| ATC_prefix        = H03
-| ATC_suffix        = AA04
-| ATC_supplemental  = {{ATC|D11|AX08}}
-| PubChem           = 5803
-| DrugBank          =
-| 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]]. Triiodothyroacetic acid is also a physiologic [[thyroid hormone]] that is present in the normal organism in low concentrations.
 ==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=/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]].
+It is indicated in the management of [[thyroid hormone resistance|thyroid hormone resistance syndrome]]<ref>{{cite journal |vauthors=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|doi-access=free }} {{cite web|url= http://www.scielo.br/pdf/abem/v48n1/19522.pdf |title=Free full text }}&nbsp;{{small|(95.3&nbsp;[[Kibibyte|KiB]])}}</ref> 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]].<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 |year=2003 |month=November |pmid=14602763 |doi= 10.1210/jc.2003-030095|url=http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=14602763}}</ref>
+It has been investigated for use in reducing [[goiter]].<ref name="pmid14602763">{{cite journal  |vauthors=Brenta G, Schnitman M, Fretes O, etal |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|doi-access=free }}</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 |year=2006 |month=November |pmid=17123343 |doi=10.1089/thy.2006.16.1157}}</ref>
+It has also shown some effectiveness in reducing the atrophy caused when using [[corticosteroid]]s.<ref name="pmid17123343">{{cite journal |vauthors=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>
+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 = https://www.fda.gov/bbs/topics/ANSWERS/ANS01057.html | title = FDA Warns Against Consuming Dietary Supplements Containing Tiratricol | date = November 21, 2000 | access-date = 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 | access-date = 2007-08-08 | publisher = [[Health Canada]]}}</ref>
 ==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 = 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 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 = | access-date = 2007-08-08 | publisher = Brazilian Society of Endocrinology and Metabolism |archive-url = https://web.archive.org/web/20071009062707/http://www.endocrino.org.br/noticia_g_exibe.php?id=9 <!-- Bot retrieved archive --> |archive-date = 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] {{Webarchive|url=https://archive.today/20150119005506/http://www.db-pharma.com/fiche.cfm?id=24 |date=2015-01-19 }} information</ref> It is available as an [[orphan drug]] to be prescribed by registered specialists in Europe.
 ==References==
-{{Reflist|2}}
+{{Reflist}}
+== External links ==
+* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/tiratricol | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Tiratricol }}
 {{Other dermatological preparations}}
 {{Thyroid therapy}}
+{{Thyroid hormone receptor modulators}}
+{{Thyroid hormone intermediates}}
 [[Category:Orphan drugs]]
-[[Category:Organoiodides]]
+[[Category:Iodobenzene derivatives]]
 [[Category:Phenols]]
 [[Category:Phenol ethers]]
+[[Category:Thyroid hormone receptor agonists]]
 {{systemic-hormonal-drug-stub}}
 {{dermatologic-drug-stub}}
-[[tr:Tiratrikol]]

v t e Other dermatological preparations (D11)
Anti-seborrheics	Antiandrogens Bicalutamide Cyproterone acetate Flutamide Spironolactone Antifungals Bifonazole Cetrimonium bromide (cetrimide) Ciclopirox olamine (ciclopirox) Climbazole Clotrimazole Ketoconazole Miconazole Piroctone olamine Selenium disulfide (selenium sulfide) Xenysalate Zinc pyrithione (pyrithione zinc) Antihistamines Calcineurin inhibitors Cyclosporin Pimecrolimus Tacrolimus Isotretinoin Keratolytics Coal tar Resorcinol Salicylic acid Sulfur Urea (urea-containing cream) Lithium salts Lithium gluconate Lithium succinate Topical corticosteroids (e.g., hydrocortisone)
Skin lightening	Hydroquinone Mequinol Monobenzone
Skin darkening	Afamelanotide Melanotan II
Anti-inflammatories	Alitretinoin Gamolenic acid Oxaceprol Pimecrolimus Tacrolimus Topical corticosteroids (e.g., hydrocortisone)
Alopecia treatments	5α-Reductase inhibitors Alfatradiol Dutasteride Finasteride Saw palmetto extract Antiandrogens Bicalutamide Cyproterone acetate Flutamide Spironolactone Topilutamide (fluridil) Potassium channel openers Minoxidil Others Nepidermin Ritlecitinib
Hair growth inhibitors	5α-Reductase inhibitors Dutasteride Finasteride Antiandrogens Bicalutamide Cyproterone acetate Flutamide Spironolactone Eflornithine
Others	Abrocitinib Aminobenzoate potassium Androgens (e.g., testosterone) Benzoylperoxide Brimonidine Caffeine Calcium gluconate Collagen Crisaborole Cromoglicic acid Delgocitinib Deoxycholic acid Diclofenac Dupilumab Estrogens (e.g., estradiol) Glycopyrronium bromide Glycopyrronium tosylate Hyaluronic acid Hydrogen peroxide Ivermectin Lebrikizumab Lokivetmab Magnesium sulfate Metandienone Nemolizumab Oclacitinib Oxymetazoline Povidone-iodine Pregnenolone acetate Progestogens (e.g., progesterone) Ruxolitinib Tiratricol Tralokinumab

v t e Thyroid hormone metabolic intermediates
Tyrosine / iodotyrosine	3-Iodotyrosine Diiodotyrosine
Thyronine / iodothyronine	3'-Monoiodothyronine 3,3'-Diiodothyronine 3,5-Diiodothyronine 3,3',5-Triiodothyronine (T₃) 3,3',5'-Triiodothyronine (Reverse T₃) 3,5,3',5'-Tetraiodothyronine (Thyroxine, T₄)
Thyronamine / iodothyronamine	3-Iodothyronamine 3,3',5-Triiodothyronamine
Iodothyroacetate / iodothyroacetic acid	Triiodothyroacetate (TRIAC)