Drug Information

General Information
Drug ID
DR00173
Drug Name
Liothyronine
Synonyms
(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid; 3,3',5-Triiodo-L-thyronine; 3,3',5-Triiodothyronine; 3,3'5-Triiodo-L-thyronine; 3,5,3'-Tri-iodo-L-thyronine; 3,5,3'-Triiodo-L-thyronine; 3,5,3'-triiodothyronine; 3,5,3'TRIIODOTHYRONINE; 4-(3-Iodo-4-hydroxyphenoxy)-3,5-diiodophenylalanine; 4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine; 4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine; Cytomel (TN); Euthroid-0.5; Euthroid-1; Euthroid-2; Euthroid-3; L-3,3',5-TriioDOThyronine; L-3,5,3'-Triiodothyronine; L-3-(4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl)alanine; L-Liothyronine; L-T3; L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-(9CI); Liothyronin; Liothyronine (INN); Liothyronine I 131; Liothyronine I 131 [USAN]; Liothyronine [INN:BAN]; Liothyroninum; Liothyroninum[INN-Latin]; Liotironina; Liotironina [INN-Spanish]; Lyothyronine; O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine; Rathyronine; T3 (Hormone); T3 (Triiodothyronine); T3 (VAN); T3 (amino acid); T3 liothyronine; THYROID HORMONE; TRIIODOTHYRONINE (T3 OR LIOTHYRONINE, ACTIVE) (6-11%); Tertroxin (TN); Thyrolar-0.25; Thyrolar-0.5; Thyrolar-1; Thyrolar-2; Thyrolar-3; Thyronine, 3,3',5-triiodo-, L-(6CI); Tresitope; Tri-Thyrotope; Triiodo-L-thyronine; Triiodothyronine; Triiodothyronine (T3); Triomet-131; Triothyrone
Drug Type
Small molecular drug
Indication Hypothyroidism [ICD11:5A00.2] Approved [1]
Therapeutic Class
Hormone Replacement Agents
Structure
3D MOL 2D MOL
Formula
C15H12I3NO4
Canonical SMILES
C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(C(=O)O)N)I)I)O
InChI
InChI=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
InChIKey
AUYYCJSJGJYCDS-LBPRGKRZSA-N
CAS Number
CAS 6893-02-3
Pharmaceutical Properties Molecular Weight 650.97 Topological Polar Surface Area 92.8
Heavy Atom Count 23 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
XLogP
1.7
PubChem CID
5920
PubChem SID
10321236 ,11364339 ,11364976 ,11366901 ,11367538 ,11369463 ,11370100 ,11372994 ,11373139 ,11373810 ,11375700 ,11377625 ,11378271 ,11457873 ,11466881 ,11468001 ,11485903 ,11486522 ,11489800 ,11491702 ,11492141 ,11495259 ,11532858 ,14710501 ,14710502 ,14936961 ,14964754 ,24900088 ,26737095 ,26737097 ,26753840 ,29224945 ,4253003 ,46393605 ,46506352 ,46518913 ,47217059 ,47291379 ,47440547 ,47440548 ,47885656 ,5481 ,7890655 ,7980832 ,8002138 ,8145172 ,8153668 ,830311 ,832593 ,854428
ChEBI ID
ChEBI:18258
TTD Drug ID
D0S6JG
DT(s) Transporting This Drug NTCP Transporter Info Sodium/taurocholate cotransporting polypeptide Substrate [2]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [3]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [4]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [5]
OATP1C1 Transporter Info Organic anion transporting polypeptide 1C1 Substrate [6]
OATP4A1 Transporter Info Organic anion transporting polypeptide 4A1 Substrate [7]
OATP4C1 Transporter Info Organic anion transporting polypeptide 4C1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OATP1A2 Transporter Info Km =6.5 microM Oocytes-OATP1A2 [3]
OATP1B1 Transporter Info Km =2.7 microM Oocytes-OATP1B1 [4]
OATP1B3 Transporter Info Km =6.4 microM Oocytes-OATP1B3 [5]
OATP4A1 Transporter Info Km =0.9 microM Oocytes-OATP4A1 [3]
OATP4C1 Transporter Info Km =5.9 microM Madin-Darby canine kidney (MDCK) cells-OATP4C1 [7]
References
1 Liothyronine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Identification of thyroid hormone transporters. Biochem Biophys Res Commun. 1999 Jan 19;254(2):497-501.
3 Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner. Endocrinology. 2001 May;142(5):2005-12.
4 Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1. J Biol Chem. 1999 Jun 11;274(24):17159-63.
5 LST-2, a human liver-specific organic anion transporter, determines methotrexate sensitivity in gastrointestinal cancers. Gastroenterology. 2001 Jun;120(7):1689-99.
6 Involvement of multispecific organic anion transporter, Oatp14 (Slc21a14), in the transport of thyroxine across the blood-brain barrier. Endocrinology. 2004 Sep;145(9):4384-91.
7 Isolation and characterization of a digoxin transporter and its rat homologue expressed in the kidney. Proc Natl Acad Sci U S A. 2004 Mar 9;101(10):3569-74.

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