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

General Information of Drug (ID: DR0948)
Drug Name
Levothyroxine sodium
Synonyms
Levoroxine; Levothyroxine sodique; Levothyroxinum natricum; Novothyrox; Oroxine; Ro-thyroxine; Roxstan; Sodium L-thyroxine; Sodium levothyroxine; Sodium thyroxin; Sodium thyroxinate; Tetroid; Thyradin; Thyradin S; Thyro-Tabs; Thyronamin; Thyroxevan; Thyroxin sodium; Thyroxine sodium; Tiroidina; Tirosint; Tyrosint; Unithroid; l-Thyroxine monosodium salt; Dathroid; Eferox; Euthyrox; L-Thyroxine sodium; L-Thyroxine sodium salt; Laevoxin; Letter; Levaxin; Levo-T; Levolet; [125I]-(-)-Thyroxine; [125I]-CCRIS 6739; [125I]-HSDB 3108;80945-46-6; AC1LD8X6; DTXSID30349358; GTPL4627; [125I]-L-Thyroxin; [125I]-L-Thyroxine; [125I]-Laevothyroxinum (acid); [125I]-Levothyroxine; [125I]-Levothyroxinum (acid); [125I]-Synthroid; [125I]-T4; [125I]-T4 (Hormone); [125I]-THX; [125I]-Tetraiodothyronine; [125I]-Thryroxine, l-; [125I]-Thyratabs; [125I]-Thyrax; [125I]-Thyreoideum; [125I]-Thyroxin; [125I]-Thyroxinal; [125I]-Thyroxine; [125I]-Thyroxine (VAN); [125I]-Thyroxine (l); [125I]-Thyroxine iodine; [125I]thyroxine
Indication Hypothyroidism [ICD11: 5A00] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 798.85 Topological Polar Surface Area 95.6
Heavy Atom Count 25 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
23666112
ChEBI ID
CHEBI:6446
CAS Number
55-03-8
TTD Drug ID
D06RGG
Formula
C15H10I4NNaO4
Canonical SMILES
C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)CC(C(=O)[O-])N.[Na+]
InChI
1S/C15H11I4NO4.Na/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);/q;+1/p-1/t12-;/m0./s1
InChIKey
YDTFRJLNMPSCFM-YDALLXLXSA-M
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
3,3',5-triiodothyronine DM000312
67020329
Oxidation - Deiodination 1 [3]
Levothyroxine glucuronide DM000315 N. A. Conjugation - Conjugation 1 [5]
Levothyroxine sulfate DM000316
131742
Conjugation - Conjugation 1 [5]
Reverse triiodothyronine DM000314
644280
Oxidation - Deiodination 1 [3]
Diiodothyronine DM000313
92859
Oxidation - Deiodination 2 [5]
Diiodothyronine DM000313
92859
Oxidation - Deiodination 2 [5] , [6] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001517 Levothyroxine sodium 3,3',5-triiodothyronine Oxidation - Deiodination DIO3 [3]
MR001518 Levothyroxine sodium Reverse triiodothyronine Oxidation - Deiodination DIO3 [3]
MR001519 Levothyroxine sodium Levothyroxine glucuronide Conjugation - Conjugation Unclear [5]
MR001520 Levothyroxine sodium Levothyroxine sulfate Conjugation - Conjugation Unclear [5]
MR001515 3,3',5-triiodothyronine Diiodothyronine Oxidation - Deiodination Unclear [5], [6], [7]
MR001516 Reverse triiodothyronine Diiodothyronine Oxidation - Deiodination Unclear [5]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Thyroxine 5-deiodinase (DIO3) DME0535 Homo sapiens
IOD3_HUMAN
1.21.99.3
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
References
1 Liothyronine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 [Metabolic interaction between psychopharmaceuticals. Probable cause of exacerbation of hypothyroidism according to a case report]. Lakartidningen. 2002 Jun 20;99(25):2854-6.
3 Local activation and inactivation of thyroid hormones: the deiodinase family Mol Cell Endocrinol. 1999 May 25;151(1-2):103-19. doi: 10.1016/s0303-7207(99)00040-4.
4 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
5 LABEL:EVOTHYROXINE SODIUM injection
6 Development of a microphysiological skin-liver-thyroid Chip3 model and its application to evaluate the effects on thyroid hormones of topically applied cosmetic ingredients under consumer-relevant conditions. Front Pharmacol. 2023 Feb 8;14:1076254. doi: 10.3389/fphar.2023.1076254.
7 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.

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