Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0959)
Drug Name
Liothyronine
Synonyms
Liothyronin; Liothyronine [INN:BAN]; Liothyroninum; Liotironina; Lyothyronine; T3 (Hormone); T3 (amino acid); Tresitope; Triiodo-L-thyronine; L-3,3',5-TriioDOThyronine; L-3,5,3'-Triiodothyronine; L-Liothyronine; liothyronine; triiodothyronine; triothyrone; (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid; 3,3',5-Triiodo-L-thyronine; 3,3',5-Triiodothyronine; 3,5,3'-Triiodo-L-thyronine; 3,5,3'-triiodothyronine; 3,5,3'TRIIODOTHYRONINE; L-T3; O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine; T3
Indication Hypothyroidism [ICD11: 5A00] Approved [1]
Structure
3D MOL 2D MOL
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
Cross-matching ID
PubChem CID
5920
PubChem SID
5481 ; 830311 ; 832593 ; 854428 ; 4253003 ; 7890655 ; 7980832 ; 8002138 ; 8145172 ; 8153668 ; 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 ; 46393605 ; 46506352 ; 46518913 ; 47217059 ; 47291379 ; 47440547 ; 47440548 ; 47885656
ChEBI ID
ChEBI:18258
CAS Number
6893-02-3
TTD Drug ID
D0S6JG
Formula
C15H12I3NO4
Canonical SMILES
C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(C(=O)O)N)I)I)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Diiodothyronine DM000313
92859
Oxidation - Dehalogenation 1 [4]
Iodine DM000366
807
Unclear 1 [5]
Tiratricol DM000365
5803
Oxidation - Deamination 1 [5]
Triiodothyronine sulfate DM000364
122196
Conjugation - Conjugation 1 [4]
Monoiodothyronine DM000363
53477717
Oxidation - Dehalogenation 2 [4] , [6] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001574 Liothyronine Diiodothyronine Oxidation - Dehalogenation Unclear [4]
MR001575 Liothyronine Triiodothyronine sulfate Conjugation - Conjugation Unclear [4]
MR001576 Liothyronine Tiratricol Oxidation - Deamination Unclear [5]
MR001577 Liothyronine Iodine Unclear Unclear [5]
MR001573 Diiodothyronine Monoiodothyronine Oxidation - Dehalogenation SULT1A1 [4], [6], [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Sulfotransferase 1A1 (SULT1A1) DME0008 Km = 0.084 microM
ST1A1_HUMAN
[2]
References
1 Liothyronine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of human liver thermostable phenol sulfotransferase (SULT1A1) allozymes with 3,3',5-triiodothyronine as the substrate. J Endocrinol. 2001 Dec;171(3):525-32.
3 FDA Label of Liothyronine sodium. The 2020 official website of the U.S. Food and Drug Administration.
4 DrugBank(Pharmacology-Metabolism)Liothyronine
5 Ashley C. and Dunleavy A. (2014). The renal drug handbook. Caroline Ashley and Aileen Dunleavy.
6 Role and Clinical Significance of Monocarboxylate Transporter 8 (MCT8) During Pregnancy. Reprod Sci. 2023 Jun;30(6):1758-1769. doi: 10.1007/s43032-022-01162-z.
7 Binding Characteristics of Thyroid Hormone Distributor Proteins to Thyroid Hormone Metabolites. Thyroid. 2022 Aug;32(8):990-999. doi: 10.1089/thy.2021.0588.

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