Tiratricol (BioDeep_00000271446)
代谢物信息卡片
Tiratricol
化学式: C14H9I3O4 (621.7635124)
中文名称: 替拉曲可
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(=O)O)I)I)O
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)
描述信息
H - Systemic hormonal preparations, excl. sex hormones and insulins > H03 - Thyroid therapy > H03A - Thyroid preparations > H03AA - Thyroid hormones
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1553 - Thyroid Agent
D - Dermatologicals
同义名列表
1 个代谢物同义名
数据库引用编号
6 个数据库交叉引用编号
- KEGGdrug: D07214
- PubChem: 5803
- DrugBank: DB03604
- ChEMBL: CHEMBL41632
- CAS: 51-24-1
- PMhub: MS000002465
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Siaw Li Chan, Samuel Refetoff, Nikolina Babic, Ming Jin, Uttam Garg, Kiang-Teck J Yeo. Triiodothyroacetic Acid Cross-Reacts With Measurement of Triiodothyronine (T3) on Various Immunoassay Platforms.
American journal of clinical pathology.
2022 02; 157(2):156-158. doi:
10.1093/ajcp/aqab124. [PMID: 34542585] - Rutchanna M S Jongejan, Evert F S van Velsen, Marcel E Meima, Theo Klein, Sjoerd A A van den Berg, Elske T Massolt, W Edward Visser, Robin P Peeters, Yolanda B de Rijke. Change in Thyroid Hormone Metabolite Concentrations Across Different Thyroid States.
Thyroid : official journal of the American Thyroid Association.
2022 02; 32(2):119-127. doi:
10.1089/thy.2021.0453. [PMID: 34806412] - W E Visser. Therapeutic applications of thyroid hormone analogues.
Annales d'endocrinologie.
2021 Jun; 82(3-4):170-172. doi:
10.1016/j.ando.2020.03.004. [PMID: 32197712] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Riccardo Zucchi. Thyroid Hormone Analogues: An Update.
Thyroid : official journal of the American Thyroid Association.
2020 08; 30(8):1099-1105. doi:
10.1089/thy.2020.0071. [PMID: 32098589] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - Stefan Groeneweg, Robin P Peeters, Carla Moran, Athanasia Stoupa, Françoise Auriol, Davide Tonduti, Alice Dica, Laura Paone, Klara Rozenkova, Jana Malikova, Adri van der Walt, Irenaeus F M de Coo, Anne McGowan, Greta Lyons, Femke K Aarsen, Diana Barca, Ingrid M van Beynum, Marieke M van der Knoop, Jurgen Jansen, Martien Manshande, Roelineke J Lunsing, Stan Nowak, Corstiaan A den Uil, M Carola Zillikens, Frank E Visser, Paul Vrijmoeth, Marie Claire Y de Wit, Nicole I Wolf, Angelique Zandstra, Gautam Ambegaonkar, Yogen Singh, Yolanda B de Rijke, Marco Medici, Enrico S Bertini, Sylvia Depoorter, Jan Lebl, Marco Cappa, Linda De Meirleir, Heiko Krude, Dana Craiu, Federica Zibordi, Isabelle Oliver Petit, Michel Polak, Krishna Chatterjee, Theo J Visser, W Edward Visser. Effectiveness and safety of the tri-iodothyronine analogue Triac in children and adults with MCT8 deficiency: an international, single-arm, open-label, phase 2 trial.
The lancet. Diabetes & endocrinology.
2019 09; 7(9):695-706. doi:
10.1016/s2213-8587(19)30155-x. [PMID: 31377265] - Soledad Bárez-López, Carmen Grijota-Martínez, Xiao-Hui Liao, Samuel Refetoff, Ana Guadaño-Ferraz. Intracerebroventricular administration of the thyroid hormone analog TRIAC increases its brain content in the absence of MCT8.
PloS one.
2019; 14(12):e0226017. doi:
10.1371/journal.pone.0226017. [PMID: 31809508] - Hae Chan Ha, Ji Min Jang, Dan Zhou, Han Gyeol Kim, Moon Jung Back, In Chul Shin, So Yoon Yun, Yongwei Piao, Jong Min Choi, Jong Hoon Won, Dae Kyong Kim. 3, 5, 3'-Triiodothyroacetic acid (TRIAC) is an anti-inflammatory drug that targets toll-like receptor 2.
Archives of pharmacal research.
2018 Oct; 41(10):995-1008. doi:
10.1007/s12272-018-1057-8. [PMID: 30099678] - Joanne M Donkers, Benno Zehnder, Gerard J P van Westen, Mark J Kwakkenbos, Adriaan P IJzerman, Ronald P J Oude Elferink, Ulrich Beuers, Stephan Urban, Stan F J van de Graaf. Reduced hepatitis B and D viral entry using clinically applied drugs as novel inhibitors of the bile acid transporter NTCP.
Scientific reports.
2017 11; 7(1):15307. doi:
10.1038/s41598-017-15338-0. [PMID: 29127322] - Soledad Bárez-López, Maria Jesus Obregon, Raquel Martínez-de-Mena, Juan Bernal, Ana Guadaño-Ferraz, Beatriz Morte. Effect of Triiodothyroacetic Acid Treatment in Mct8 Deficiency: A Word of Caution.
Thyroid : official journal of the American Thyroid Association.
2016 05; 26(5):618-26. doi:
10.1089/thy.2015.0388. [PMID: 26701289] - Simone Kersseboom, Sigrun Horn, W Edward Visser, Jiesi Chen, Edith C H Friesema, Catherine Vaurs-Barrière, Robin P Peeters, Heike Heuer, Theo J Visser. In vitro and mouse studies supporting therapeutic utility of triiodothyroacetic acid in MCT8 deficiency.
Molecular endocrinology (Baltimore, Md.).
2014 Dec; 28(12):1961-70. doi:
10.1210/me.2014-1135. [PMID: 25389909] - Stefano Stagi, Cristina Manoni, Valentina Cirello, Danila Covelli, Sabrina Giglio, Francesco Chiarelli, Salvatore Seminara, Maurizio de Martino. Diabetes mellitus in a girl with thyroid hormone resistance syndrome: a little recognized interaction between the two diseases.
Hormones (Athens, Greece).
2014 Oct; 13(4):561-7. doi:
10.14310/horm.2002.1502. [PMID: 25402385] - Rosalba Senese, Federica Cioffi, Pieter de Lange, Fernando Goglia, Antonia Lanni. Thyroid: biological actions of 'nonclassical' thyroid hormones.
The Journal of endocrinology.
2014 May; 221(2):R1-12. doi:
10.1530/joe-13-0573. [PMID: 24464019] - B Sjouke, D M Kusters, J J P Kastelein, G K Hovingh. Familial hypercholesterolemia: present and future management.
Current cardiology reports.
2011 Dec; 13(6):527-36. doi:
10.1007/s11886-011-0219-9. [PMID: 21938413] - Ashley Hinther, Dominik Domanski, Saadia Vawda, Caren C Helbing. C-fin: a cultured frog tadpole tail fin biopsy approach for detection of thyroid hormone-disrupting chemicals.
Environmental toxicology and chemistry.
2010 Feb; 29(2):380-388. doi:
10.1002/etc.44. [PMID: 20821457] - Leonardo M Cortez, Ricardo N Farías, Rosana N Chehín. Protective effect of 3,5,3'-triiodothyroacetic and 3,5,3',5'-tetraiodothyroacetic acids on serum albumin fibrillation.
European biophysics journal : EBJ.
2009 Sep; 38(7):857-63. doi:
10.1007/s00249-009-0448-7. [PMID: 19381627] - Warren J L Wood, Travis Geraci, Aaron Nilsen, Andrea E DeBarber, Thomas S Scanlan. Iodothyronamines are oxidatively deaminated to iodothyroacetic acids in vivo.
Chembiochem : a European journal of chemical biology.
2009 Jan; 10(2):361-5. doi:
10.1002/cbic.200800607. [PMID: 19105176] - Serge H Boyer, Hongjian Jiang, Jason D Jacintho, Mali Venkat Reddy, Haiqing Li, Wenyu Li, Jennifer L Godwin, William G Schulz, Edward E Cable, Jinzhao Hou, Rongrong Wu, James M Fujitaki, Scott J Hecker, Mark D Erion. Synthesis and biological evaluation of a series of liver-selective phosphonic acid thyroid hormone receptor agonists and their prodrugs.
Journal of medicinal chemistry.
2008 Nov; 51(22):7075-93. doi:
10.1021/jm800824d. [PMID: 18975928] - G Medina-Gomez, R M Calvo, M-J Obregon. Thermogenic effect of triiodothyroacetic acid at low doses in rat adipose tissue without adverse side effects in the thyroid axis.
American journal of physiology. Endocrinology and metabolism.
2008 Apr; 294(4):E688-97. doi:
10.1152/ajpendo.00417.2007. [PMID: 18285526] - Sing-Yung Wu, Daniel H Polk, Wen-Sheng Huang, Eugene Ho, Jaffer M Kattan, Delbert A Fisher. 3'-monoiodothyronine sulfate and Triac sulfate are thyroid hormone metabolites in developing sheep.
Pediatric research.
2008 Feb; 63(2):149-53. doi:
10.1203/pdr.0b013e31815f6551. [PMID: 18091342] - Mario A Pisarev, Gabriela Brenta, Marta Schnitman, Diana L Kleiman de Pisarev. [Triiodothyroacetic acid in euthyroid goiter. New data on its mechanisms of action. Comparison with L-thyroxin].
Bulletin de l'Academie nationale de medecine.
2007 Nov; 191(8):1705-15; discussion 1715. doi:
NULL. [PMID: 18666468] - Masanobu Yamada. [Resistance to thyroid hormone].
Nihon rinsho. Japanese journal of clinical medicine.
2006 Dec; 64(12):2237-42. doi:
NULL. [PMID: 17154085] - A P S Kong, C W Lam, A O K Chan, S F Yiu, S C Tiu. Resistance to thyroid hormone in a Chinese family with R429Q mutation in the thyroid hormone receptor beta gene.
Hong Kong medical journal = Xianggang yi xue za zhi.
2005 Apr; 11(2):125-9. doi:
. [PMID: 15815068] - Gema Medina-Gomez, Rosa-Maria Calvo, Maria-Jesus Obregón. T3 and Triac inhibit leptin secretion and expression in brown and white rat adipocytes.
Biochimica et biophysica acta.
2004 Jun; 1682(1-3):38-47. doi:
10.1016/j.bbalip.2004.01.007. [PMID: 15158754] - Philippe Faure, Lucie Oziol, Yves Artur, Philippe Chomard. Thyroid hormone (T3) and its acetic derivative (TA3) protect low-density lipoproteins from oxidation by different mechanisms.
Biochimie.
2004 Jun; 86(6):411-8. doi:
10.1016/j.biochi.2004.04.009. [PMID: 15283976] - G Brenta, M Schnitman, O Fretes, E Facco, M Gurfinkel, S Damilano, N Pacenza, A Blanco, E Gonzalez, M A Pisarev. Comparative efficacy and side effects of the treatment of euthyroid goiter with levo-thyroxine or triiodothyroacetic acid.
The Journal of clinical endocrinology and metabolism.
2003 Nov; 88(11):5287-92. doi:
10.1210/jc.2003-030095. [PMID: 14602763] - Edith C H Friesema, Sumita Ganguly, Amal Abdalla, Jocelyn E Manning Fox, Andrew P Halestrap, Theo J Visser. Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.
The Journal of biological chemistry.
2003 Oct; 278(41):40128-35. doi:
10.1074/jbc.m300909200. [PMID: 12871948] - L Oziol, P Faure, N Bertrand, P Chomard. Inhibition of in vitro macrophage-induced low density lipoprotein oxidation by thyroid compounds.
The Journal of endocrinology.
2003 Apr; 177(1):137-46. doi:
10.1677/joe.0.1770137. [PMID: 12697045] - F A Verhoeven, H H A G M Van der Putten, G Hennemann, J M J Lamers, T J Visser, M E Everts. Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs.
The Journal of endocrinology.
2002 May; 173(2):247-55. doi:
10.1677/joe.0.1730247. [PMID: 12010632] - L Oziol, P Faure, C Vergely, L Rochette, Y Artur, P Chomard, P Chomard. In vitro free radical scavenging capacity of thyroid hormones and structural analogues.
The Journal of endocrinology.
2001 Jul; 170(1):197-206. doi:
10.1677/joe.0.1700197. [PMID: 11431152] - N Lameloise, C Siegrist-Kaiser, M O'Connell, A Burger. Differences between the effects of thyroxine and tetraiodothyroacetic acid on TSH suppression and cardiac hypertrophy.
European journal of endocrinology.
2001 Feb; 144(2):145-54. doi:
10.1530/eje.0.1440145. [PMID: 11182751] - D Cortelazzi, P S Morpurgo, P Zamperini, D A Fisher, P Beck-Peccoz, S Y Wu. Maternal compound W serial measurements for the management of fetal hypothyroidsm.
European journal of endocrinology.
1999 Dec; 141(6):570-8. doi:
10.1530/eje.0.1410570. [PMID: 10601958] - A M Saboori, N R Rose, C L Burek. Iodination of human thyroglobulin (Tg) alters its immunoreactivity. II. Fine specificity of a monoclonal antibody that recognizes iodinated Tg.
Clinical and experimental immunology.
1998 Aug; 113(2):303-8. doi:
10.1046/j.1365-2249.1998.00644.x. [PMID: 9717982] - H Liang, C E Juge-Aubry, M O'Connell, A G Burger. Organ-specific effects of 3,5,3'-triiodothyroacetic acid in rats.
European journal of endocrinology.
1997 Nov; 137(5):537-44. doi:
10.1530/eje.0.1370537. [PMID: 9405035] - G Radetti, L Persani, G Molinaro, D Mannavola, D Cortelazzi, V K Chatterjee, P Beck-Peccoz. Clinical and hormonal outcome after two years of triiodothyroacetic acid treatment in a child with thyroid hormone resistance.
Thyroid : official journal of the American Thyroid Association.
1997 Oct; 7(5):775-8. doi:
10.1089/thy.1997.7.775. [PMID: 9349583] - S I Sherman, M D Ringel, M J Smith, H A Kopelen, W A Zoghbi, P W Ladenson. Augmented hepatic and skeletal thyromimetic effects of tiratricol in comparison with levothyroxine.
The Journal of clinical endocrinology and metabolism.
1997 Jul; 82(7):2153-8. doi:
10.1210/jcem.82.7.4054. [PMID: 9215287] - S Ueda, J Takamatsu, S Fukata, K Tanaka, N Shimizu, S Sakata, T Yamaji, K Kuma, N Ohsawa. Differences in response of thyrotropin to 3,5,3'-triiodothyronine and 3,5,3'-triiodothyroacetic acid in patients with resistance to thyroid hormone.
Thyroid : official journal of the American Thyroid Association.
1996 Dec; 6(6):563-70. doi:
10.1089/thy.1996.6.563. [PMID: 9001190] - S B Davidson, S A Dulchavsky, L N Diebel, S Dutta, W J Cullen. Effect of sepsis and 3,5,3'-triiodothyronine replacement on myocardial integrity during oxidant challenge.
Critical care medicine.
1996 May; 24(5):850-4. doi:
10.1097/00003246-199605000-00020. [PMID: 8706464] - M E Everts, T J Visser, E P Moerings, A M Tempelaars, H van Toor, R Docter, M de Jong, E P Krenning, G Hennemann. Uptake of 3,3',5,5'-tetraiodothyroacetic acid and 3,3',5'-triiodothyronine in cultured rat anterior pituitary cells and their effects on thyrotropin secretion.
Endocrinology.
1995 Oct; 136(10):4454-61. doi:
10.1210/endo.136.10.7664665. [PMID: 7664665] - C E Juge-Aubry, O Morin, A T Pernin, H Liang, J Philippe, A G Burger. Long-lasting effects of Triac and thyroxine on the control of thyrotropin and hepatic deiodinase type I.
European journal of endocrinology.
1995 Jun; 132(6):751-8. doi:
10.1530/eje.0.1320751. [PMID: 7788017] - N Yokoyama, G N Walker, A J Main, J L Stanton, M M Morrissey, C Boehm, A Engle, A D Neubert, J M Wasvary, Z F Stephan. Synthesis and structure-activity relationships of oxamic acid and acetic acid derivatives related to L-thyronine.
Journal of medicinal chemistry.
1995 Feb; 38(4):695-707. doi:
10.1021/jm00004a015. [PMID: 7861417] - C Jaffiol, J P Daures, N Nsakala, J Guerenova, L Baldet, P Pujol, D Vannereau, J Bringer. [Long term follow up of medical treatment of differentiated thyroid cancer].
Annales d'endocrinologie.
1995; 56(2):119-26. doi:
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Endocrinology.
1994 Dec; 135(6):2700-7. doi:
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The Journal of clinical endocrinology and metabolism.
1993 Jul; 77(1):221-8. doi:
10.1210/jcem.77.1.8325946. [PMID: 8325946] - S I Sherman, P W Ladenson. Organ-specific effects of tiratricol: a thyroid hormone analog with hepatic, not pituitary, superagonist effects.
The Journal of clinical endocrinology and metabolism.
1992 Sep; 75(3):901-5. doi:
10.1210/jcem.75.3.1517383. [PMID: 1517383] - C Mechelany, M Schlumberger, C Challeton, E Comoy, C Parmentier. TRIAC (3,5,3'-triiodothyroacetic acid) has parallel effects at the pituitary and peripheral tissue levels in thyroid cancer patients treated with L-thyroxine.
Clinical endocrinology.
1991 Aug; 35(2):123-8. doi:
10.1111/j.1365-2265.1991.tb03509.x. [PMID: 1934526] - P Beck-Peccoz, R Roncoroni, S Mariotti, G Medri, C Marcocci, G Brabant, F Forloni, A Pinchera, G Faglia. Sex hormone-binding globulin measurement in patients with inappropriate secretion of thyrotropin (IST): evidence against selective pituitary thyroid hormone resistance in nonneoplastic IST.
The Journal of clinical endocrinology and metabolism.
1990 Jul; 71(1):19-25. doi:
10.1210/jcem-71-1-19. [PMID: 2370293] - P A Schueler, H L Schwartz, K A Strait, C N Mariash, J H Oppenheimer. Binding of 3,5,3'-triiodothyronine (T3) and its analogs to the in vitro translational products of c-erbA protooncogenes: differences in the affinity of the alpha- and beta-forms for the acetic acid analog and failure of the human testis and kidney alpha-2 products to bind T3.
Molecular endocrinology (Baltimore, Md.).
1990 Feb; 4(2):227-34. doi:
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Acta endocrinologica.
1989 Nov; 121(5):651-8. doi:
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The Journal of clinical endocrinology and metabolism.
1989 Aug; 69(2):461-6. doi:
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Endocrinology.
1989 Jul; 125(1):433-43. doi:
10.1210/endo-125-1-433. [PMID: 2737157] - C J Mirell, M Yanagisawa, J M Hershman. Triac reduces serum TSH without decreasing alpha and beta TSH messenger RNAs.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
1989 Mar; 21(3):123-6. doi:
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Clinical physiology and biochemistry.
1989; 7(6):310-4. doi:
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Clinical endocrinology.
1988 May; 28(5):497-507. doi:
10.1111/j.1365-2265.1988.tb03684.x. [PMID: 3214942] - H W Mueller-Gaertner, C Schneider. 3,5,3'-Triiodothyroacetic acid minimizes the pituitary thyrotrophin secretion in patients on levo-thyroxine therapy after ablative therapy for differentiated thyroid carcinoma.
Clinical endocrinology.
1988 Apr; 28(4):345-51. doi:
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Journal of endocrinological investigation.
1988 Feb; 11(2):113-8. doi:
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Biochemical pharmacology.
1986 May; 35(10):1691-6. doi:
10.1016/0006-2952(86)90325-4. [PMID: 3707599] - R W Evans, L E Braverman. Use of 125I-triiodothyroacetic acid to measure nuclear thyroid hormone receptor.
Endocrine research.
1986; 12(1):37-47. doi:
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Brain research.
1985 Mar; 328(2):259-70. doi:
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Endocrinology.
1983 Oct; 113(4):1459-63. doi:
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Comptes rendus des seances de la Societe de biologie et de ses filiales.
1982; 176(2):178-83. doi:
NULL. [PMID: 6212104] - L A Gavin, B M Livermore, R R Cavalieri, M E Hammond, J N Castle. Serum concentration, metabolic clearance, and production rates of 3,5,3'-triiodothyroacetic acid in normal and athyreotic man.
The Journal of clinical endocrinology and metabolism.
1980 Sep; 51(3):529-34. doi:
10.1210/jcem-51-3-529. [PMID: 7410532] - H C Smith, S E Robinson, C J Eastman. Binding of endogenous iodothyronines to isolated liver cell nuclei.
Endocrinology.
1980 Apr; 106(4):1133-6. doi:
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