T44

3,5,3',5'-TETRAIODO-L-THYRONINE

Find entries where: T44

is present as a standalone ligand in 22 entries

as a non-polymer is covalently linked to polymer or other heterogen groups 5 entries

is present in a polymer sequence 2 entries

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Chemical Component Summary
Name	3,5,3',5'-TETRAIODO-L-THYRONINE
Identifiers	(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid
Formula	C₁₅ H₁₁ I₄ N O₄
Molecular Weight	776.87
Type	NON-POLYMER
Isomeric SMILES	c1c(cc(c(c1I)Oc2cc(c(c(c2)I)O)I)I)C[C@@H](C(=O)O)N
InChI	InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1
InChIKey	XUIIKFGFIJCVMT-LBPRGKRZSA-N

Chemical Details
Formal Charge	0
Atom Count	35
Chiral Atom Count	1
Bond Count	36
Aromatic Bond Count	12

Drug Info: DrugBank

DrugBank ID	DB00451 ?
Name	Levothyroxine
Groups	approved
Description	Levothyroxine is a synthetically produced form of thyroxine, a major endogenous hormone secreted by the thyroid gland.[F4633] Also known as L-thyroxine or the brand name product Synthroid, levothyroxine is used primarily to treat hypothyroidism, a condition where the thyroid gland is no longer able to produce sufficient quantities of the thyroid hormones T<sub>4</sub> (tetraiodothyronine or thyroxine) and T<sub>3</sub> (triiodothyronine or [DB00279]), resulting in diminished down-stream effects of these hormones. Without sufficient quantities of circulating thyroid hormones, symptoms of hypothyroidism begin to develop such as fatigue, increased heart rate, depression[A179620], dry skin and hair, muscle cramps, constipation, weight gain, memory impairment, and poor tolerance to cold temperatures.[F4636,A35722] In response to Thyroid Stimulating Hormone (TSH) release by the pituitary gland, a normally functioning thyroid gland will produce and secrete T<sub>4</sub>, which is then converted through deiodination (by type I or type II 5′-deiodinases)[A179941] into its active metabolite T<sub>3</sub>. While T<sub>4</sub> is the major product secreted by the thyroid gland, T<sub>3</sub> exerts the majority of the physiological effects of the thyroid hormones; T<sub>4</sub> and T<sub>3</sub> have a relative potency of ~1:4 (T4:T3).[F4633] T<sub>4</sub> and T<sub>3</sub> act on nearly every cell of the body, but have a particularly strong effect on the cardiac system.[A179935] As a result, many cardiac functions including heart rate, cardiac output, and systemic vascular resistance are closely linked to thyroid status.[A179938] Prior to the development of levothyroxine, [DB09100] or desiccated thyroid, used to be the mainstay of treatment for hypothyroidism. However, this is no longer recommended for the majority of patients due to several clinical concerns including limited controlled trials supporting its use. Desiccated thyroid products contain a ratio of T4 to T3 of 4.2:1, which is significantly lower than the 14:1 ratio of secretion by the human thyroid gland. This higher proportion of T3 in desiccated thyroid products can lead to supraphysiologic levels of T3 which may put patients at risk of thyrotoxicosis if thyroid extract therapy is not adjusted according to the serum TSH.[A35722, F4636]
Synonyms	Levothyroxin O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine Levothyroxine sodium pentahydrate L-T4 3,5,3',5'-Tetraiodo-L-thyronine Thyroxine 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine T4 L-Thyroxine Levothyroxine Levothyroxine sodium LT4 3,3',5,5'-Tetraiodo-L-thyronine O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine
Brand Names	Levo-T 25mcg - Tab Synthroid Tab 125mcg USP Tirosint Eltroxin 150 Tab Levotec 125mcg Tablets USP PMS-levothyroxine Sodium Tab 75mcg Synthroid Tab 100mcg USP Unithroid Ermeza Levo-T 300mcg - Tab Adthyza Thyroid Euthyrox Levothyroxine and Liothyronine Thyroid Levotec 150mcg Tablets USP PMS-levothyroxine Sodium Tab 150mcg PMS-levothyroxine Sodium Tab 50mcg Tirosint SOL PMS-levothyroxine Sodium Tab 100mcg PMS-levothyroxine Sodium Tab 25mcg Levothyroxine Sodium for Injection Synthroid PMS-levothyroxine Sodium Tab 125mcg Levotec 200mcg Tablets USP Levo-T 125mcg - Tab Levo-T 75mcg - Tab Levothroid Thyroid Np Thyroid NP Thyroid 30 Levotec 300mcg Tablets USP Thyrolar NP Thyroid 120 Np Thyroid 30 Synthroid Liq Inj 500mcg/vial USP Eltroxin Tab 300mcg Eltroxin Tab 200mcg Tirocap Levotec 100mcg Tablets USP Levo-T 150mcg - Tab Levotec 175mcg Tablets USP Synthroid Tab 112mcg USP Levothyroxine Np Thyroid 90 Synthroid Tab 200mcg USP NP Thyroid 60 Np Thyroid 60 NP Thyroid 90 Synthroid Tab 300mcg Tab Eltroxin Tab 100mcg Eltroxin Tab 50mcg Levo-T 100mcg - Tab PMS-levothyroxine Sodium Tab 300mcg Apo-levothyroxine PMS-levothyroxine Sodium Tab 200mcg Levo-T Levothyroxine Sodium Injection Synthroid Tab 150mcg USP Eltroxin Synthroid Tab 50mcg USP Adthyza thyroid Levotec 75mcg Tablets USP Novothyrox Levothyroxine sodium Synthroid Tab 25mcg USP Levothyroxine Sodium Thyquidity Levoxyl Synthroid Tab 88mcg USP Levothroxine Sodium NP Thyroid 15 Levotec 25mcg Tablets USP Levo-T 200mcg - Tab Levo-T 50mcg - Tab Synthroid Tab 175mcg USP Levotec 50mcg Tablets USP Synthroid Tab 75mcg USP Levotec 112mcg Tablets USP
Indication	Levothyroxine is indicated as replacement therapy in primary (thyroidal), secondary (pituitary) and tertiary (hypothalamic) congenital or acquired hypothyroidism. It is also indicated as an adjunct to surgery and radioiodine therapy in the management of thyrotropin-dependent well-differentiated thyroid cancer.
Categories	Agents used to treat hypothyroidism Amino Acids Amino Acids, Aromatic Amino Acids, Cyclic Amino Acids, Peptides, and Proteins Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 Enzyme Inhibitors Hormones Hormones, Hormone Substitutes, and Hormone Antagonists Narrow Therapeutic Index Drugs OATP1B1/SLCO1B1 Inhibitors OATP1B3 inhibitors Organic Anion Transporting Polypeptide 2B1 Inhibitors P-glycoprotein inducers Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins Thyroid Products Thyroxine-binding globulin substrates UGT1A1 Substrates UGT1A1 Substrates with a Narrow Therapeutic Index
ATC-Code	H03AA01 H03AA51
CAS number	51-48-9

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Integrin alpha-V	MAFPPRRRLRLGPRGLPLLLSGLLLPLCRAFNLDVDSPAEYSGPEGSYFG...	unknown
Integrin beta-3	MRARPRPRPLWATVLALGALAGVGVGGPNICTTRGVSSCQQCLAVSPMCA...	unknown
Thyroid hormone receptor alpha	MEQKPSKVECGSDPEENSARSPDGKRKRKNGQCSLKTSMSGYIPSYLDKD...	unknown	agonist
Thyroid hormone receptor beta	MTPNSMTENGLTAWDKPKHCPDREHDWKLVGMSEACLHRKSHSERRSTLK...	unknown	agonist
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inducer
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
Transthyretin	MASHRLLLLCLAGLVFVSEAGPTGTGESKCPLMVKVLDAVRGSPAINVAV...	unknown
Thyroxine-binding globulin	MSPFLYLVLLVLGLHATIHCASPEGKVTACHSSQPNATLYKMSSINADFA...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown
Solute carrier organic anion transporter family member 1C1	MDTSSKENIQLFCKTSVQPVGRPSFKTEYPSSEEKQPCCGELKVFLCALS...	unknown	substrate
Monocarboxylate transporter 8	MALQSQASEEAKGPWQEADQEQQEPVGSPEPESEPEPEPEPEPVPVPPPE...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inducer
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	substrate
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	inhibitor
Solute carrier organic anion transporter family member 4A1	MPLHQLGDKPLTFPSPNSAMENGLDHTPPSRRASPGTPLSPGSLRSAAHS...	unknown	substrate
Large neutral amino acids transporter small subunit 1	MAGAGPKRRALAAPAAEEKEEAREKMLAAKSADGSAPAGEGEGVTLQRNI...	unknown
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682