Chemical Component Summary

Name3,5,3'TRIIODOTHYRONINE
SynonymsT3; THYROID HORMONE; LIOTHYRONINE
Identifiers(2S)-2-amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid
FormulaC15 H12 I3 N O4
Molecular Weight650.973
TypeNON-POLYMER
Isomeric SMILESc1cc(c(cc1Oc2c(cc(cc2I)C[C@@H](C(=O)O)N)I)I)O
InChIInChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1
InChIKeyAUYYCJSJGJYCDS-LBPRGKRZSA-N

Chemical Details

Formal Charge0
Atom Count35
Chiral Atom Count1
Bond Count36
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB00279 
NameLiothyronine
Groups
  • approved
  • vet_approved
DescriptionLiothyronine is a thyroidal hormone T3 which is normally produced by the thyroid gland in a ratio 4:1 when compared with T4: T3. Liothyronine is the active form of thyroxine which is composed in a basic chemical structure by a tyrosine with bound iodine.[T457] The exogenous liothyronine product was developed by King Pharmaceuticals and FDA approved in 1956.[L5578]
Synonyms
  • L-3,5,3'-Triiodothyronine
  • Liothyroninum
  • 3,5,3'-Triiodothyronine
  • 3,5,3'-Triiodo-L-thyronine
  • 4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine
Brand Names
  • Teva-liothyronine
  • Np Thyroid 30
  • Triostat
  • NP Thyroid 30
  • NP Thyroid 60
IndicationLiothyronine is officially approved for the following indications: - Replacement therapy in primary (thyroidal), secondary (pituitary) and tertiary (hypothalamic) congenital or acquired hypothyroidism. - As an adjunct therapy to surgery and radioiodine in the management of thyroid cancer. - As a diagnostic agent in suppression tests for mild hyperthyroidism or thyroid gland autonomy.[FDA label] In general terms, exogenous liothyronine is used to replace insufficient hormonal production and restore T3 plasma levels.[T457] The lack of liothyronine can be presented as a pale and puffy face, coarse, brittle hair, dry skin, croaky voice and constipation as well as irregular periods, drowsiness, and lethargy.[T457] Liothyronine should never be used in the suppression of benign nodules and nontoxic diffuse goiter in iodine-sufficient patients nor in the treatment of hyperthyroidism during the recovery phase of subacute thyroiditis.[FDA label]
Categories
  • Agents used to treat hypothyroidism
  • Drugs that are Mainly Renally Excreted
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • l-Triiodothyronine
ATC-Code
  • H03AA03
  • H03AA02
CAS number6893-02-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Thyroid hormone receptor alphaMEQKPSKVECGSDPEENSARSPDGKRKRKNGQCSLKTSMSGYIPSYLDKD...unknownagonist
Thyroid hormone receptor betaMTPNSMTENGLTAWDKPKHCPDREHDWKLVGMSEACLHRKSHSERRSTLK...unknownagonist
Proliferating cell nuclear antigenMFEARLVQGSILKKVLEALKDLINEACWDISSSGVNLQSMDSSHVSLVQL...unknownantagonist
UDP-glucuronosyltransferase 1-1MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...unknownsubstrate
TransthyretinMASHRLLLLCLAGLVFVSEAGPTGTGESKCPLMVKVLDAVRGSPAINVAV...unknown
View More
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

Related Resource References

Resource NameReference
Pharos CHEMBL1544
PubChem 5920, 7048703
ChEMBL CHEMBL1544
ChEBI CHEBI:533015, CHEBI:18258
CCDC/CSD LOJLUT