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

General Information of Drug (ID: DR1572)
Drug Name
Thalidomide
Synonyms
Talargan; Talismol; Telargean; Tensival; Thalinette; Thalomid; Theophilcholine; Valgraine; thalidomide; (+/-)-THALIDOMIDE; Algosediv; Asmadion; Calmorex; Contergan; Corronarobetin; Ectiluran; Enterosediv; Gastrinide; Glutanon; Hippuzon; Neosedyn; Neosydyn; Nerosedyn; Neufatin; Neurodyn; Neurosedin; Neurosedym; Nevrodyn; Noctosediv; Pantosediv; Polygripan; Profarmil; Psycholiquid; Psychotablets; Quetimid; Quietoplex; Sandormin; Sedimide; Sedisperil; Sedoval; Shinnibrol; Softenil; Softenon; 2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione; 50-35-1
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 258.23 Topological Polar Surface Area 83.6
Heavy Atom Count 19 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5426
PubChem SID
10112 ; 111716 ; 398060 ; 398061 ; 482479 ; 596356 ; 5642997 ; 7847819 ; 7980770 ; 8150004 ; 8153340 ; 10321467 ; 10524356 ; 11120267 ; 11120755 ; 11121243 ; 11121763 ; 11122243 ; 11335226 ; 11360465 ; 11362910 ; 11364734 ; 11365472 ; 11367296 ; 11368034 ; 11369858 ; 11371011 ; 11371012 ; 11372649 ; 11372899 ; 11373635 ; 11374612 ; 11375458 ; 11376196 ; 11378022 ; 11428259 ; 11450681 ; 11461437 ; 11466220 ; 11467340 ; 11484629 ; 11485800 ; 11488523 ; 11491530 ; 11492901 ; 11532929 ; 12013404 ; 14798889 ; 17405778 ; 22391552
ChEBI ID
CHEBI:74947
CAS Number
50-35-1
TTD Drug ID
D0U7GK
Formula
C13H10N2O4
Canonical SMILES
C1CC(=O)NC(=O)C1N2C(=O)C3=CC=CC=C3C2=O
InChI
1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
InChIKey
UEJJHQNACJXSKW-UHFFFAOYSA-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
2-phthalimidoglutaramic acid DM004589
98204
Conjugation - Amide Hydrolyation 1 [8] , [3]
4-hydroxythalidomide DM004602
11778087
Oxidation - Hydrolyzationn 1 [4]
4-phthalimidoglutaramic acid DM004583
142761524
Conjugation - Amide Hydrolyation 1 [8] , [3]
5-Hydroxythalidomide DM004595
5743568
Oxidation - Aromatic hydroxylation 1 [2] , [3]
Alpha-(o-carboxybenzamido)glutarimide DM004591
134629
Conjugation - Amide Hydrolyation 1 [8] , [3]
Cis, trans-5'-Hydroxythalidomide DM004598
9878646
Oxidation - Hydrolyzationn 1 [2] , [3]
N-Hydroxythalidomide DM004601
124398
Oxidation - Hydrolyzation 1 [4]
Thalidomide arene oxide DM004599
88553247
Oxidation - Epoxidation 1 [2] , [3]
Thalidomide-5-O-glucuronide DM004600 N. A. Oxidation - Hydrolyzationn 1 [3]
2-(o-carboxybenzamido)glutaramic acid DM004590
134511
Conjugation - Amide Hydrolyation 2 [8]
2-(o-carboxybenzamido)glutaramic acid DM004590
134511
Conjugation - Amide Hydrolyation 2 [3]
2-phthalimidoglutaric acid DM004588
92225
Conjugation - Amide Hydrolyation 2 [8]
4-(o-carboxybenzamido)glutaramic acid DM004584 N. A. Conjugation - Amide Hydrolyation 2 [8]
5-Hydroxythalidomide DM004595
5743568
Conjugation - Glucuronidation 2 [2]
Alpha-aminoglutarimide DM004594
134508
Conjugation - Amide Hydrolyation 2 [3]
Cis,trans-5,5'-dihydroxythalidomide DM004596 N. A. Oxidation - Hydrolyzationn 2 [3]
Phthalic Acid DM004587
1017
Conjugation - Amide Hydrolyation 2 [3]
2-(o-carboxybenzamido)glutaric acid DM004585 N. A. Conjugation - Amide Hydrolyation 3 [8]
2-(o-carboxybenzamido)glutaric acid DM004585 N. A. Conjugation - Amide Hydrolyation 3 [3]
Isoglutamine DM004593
445883
Conjugation - Amide Hydrolyation 3 [3]
L-Glutamine DM001343
5961
Conjugation - Amide Hydrolyation 3 [3]
Phthalic Acid DM004587
1017
Conjugation - Amide Hydrolyation 3 [3]
Glutamate DM000317
33032
Conjugation - Amide Hydrolyation 4 [3]
L-Glutamine DM001343
5961
Conjugation - Amide Hydrolyation 4 [3]
Phthalic Acid DM004587
1017
Conjugation - Amide Hydrolyation 4 [3]
L-Glutamine DM001343
5961
Conjugation - Amide Hydrolyation 5 [3]
Phthalic Acid DM004587
1017
Conjugation - Amide Hydrolyation 5 [3]
⏷ Show the Full List of 27  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004914 Thalidomide 4-phthalimidoglutaramic acid Conjugation - Amide Hydrolyation Non-ME [8], [3]
MR004921 Thalidomide 2-phthalimidoglutaramic acid Conjugation - Amide Hydrolyation Non-ME [8], [3]
MR004925 Thalidomide Alpha-(o-carboxybenzamido)glutarimide Conjugation - Amide Hydrolyation Non-ME [8], [3]
MR004934 Thalidomide 5-Hydroxythalidomide Oxidation - Aromatic hydroxylation CYP2C19 [2], [3]
MR004937 Thalidomide Cis, trans-5'-Hydroxythalidomide Oxidation - Hydrolyzationn CYP2C19 [2], [3]
MR004939 Thalidomide Thalidomide arene oxide Oxidation - Epoxidation CYP1A1 ... [2], [3]
MR004941 Thalidomide Thalidomide-5-O-glucuronide Oxidation - Hydrolyzationn Unclear [3]
MR004942 Thalidomide N-Hydroxythalidomide Oxidation - Hydrolyzation Unclear [4]
MR004943 Thalidomide 4-hydroxythalidomide Oxidation - Hydrolyzationn Unclear [4]
MR004922 2-phthalimidoglutaramic acid 2-(o-carboxybenzamido)glutaramic acid Conjugation - Amide Hydrolyation Non-ME [8]
MR004924 2-phthalimidoglutaramic acid 2-phthalimidoglutaric acid Conjugation - Amide Hydrolyation Non-ME [8]
MR004915 4-phthalimidoglutaramic acid 4-(o-carboxybenzamido)glutaramic acid Conjugation - Amide Hydrolyation Non-ME [8]
MR004919 4-phthalimidoglutaramic acid 2-phthalimidoglutaric acid Conjugation - Amide Hydrolyation Non-ME [8]
MR004926 Alpha-(o-carboxybenzamido)glutarimide 2-(o-carboxybenzamido)glutaramic acid Conjugation - Amide Hydrolyation Non-ME [3]
MR004932 Alpha-(o-carboxybenzamido)glutarimide Phthalic Acid Conjugation - Amide Hydrolyation Non-ME [3]
MR004933 Alpha-(o-carboxybenzamido)glutarimide Alpha-aminoglutarimide Conjugation - Amide Hydrolyation Non-ME [3]
MR004938 Cis, trans-5'-Hydroxythalidomide Cis,trans-5,5'-dihydroxythalidomide Oxidation - Hydrolyzationn Unclear [3]
MR004940 Thalidomide arene oxide 5-Hydroxythalidomide Conjugation - Glucuronidation Unclear [2]
MR004930 2-(o-carboxybenzamido)glutaramic acid L-Glutamine Conjugation - Amide Hydrolyation Non-ME [3]
MR004931 2-(o-carboxybenzamido)glutaramic acid Phthalic Acid Conjugation - Amide Hydrolyation Non-ME [3]
MR014136 2-(o-carboxybenzamido)glutaramic acid 2-(o-carboxybenzamido)glutaric acid Conjugation - Amide Hydrolyation Non-ME [8]
MR004920 2-phthalimidoglutaric acid 2-(o-carboxybenzamido)glutaric acid Conjugation - Amide Hydrolyation Non-ME [3]
MR004916 4-(o-carboxybenzamido)glutaramic acid 2-(o-carboxybenzamido)glutaric acid Conjugation - Amide Hydrolyation Non-ME [8]
MR004928 4-(o-carboxybenzamido)glutaramic acid Isoglutamine Conjugation - Amide Hydrolyation Non-ME [3]
MR004929 4-(o-carboxybenzamido)glutaramic acid Phthalic Acid Conjugation - Amide Hydrolyation Non-ME [3]
MR004917 2-(o-carboxybenzamido)glutaric acid Glutamic acid Conjugation - Amide Hydrolyation Non-ME [3]
MR004918 2-(o-carboxybenzamido)glutaric acid Phthalic Acid Conjugation - Amide Hydrolyation Non-ME [3]
MR014138 2-(o-carboxybenzamido)glutaric acid L-Glutamine Conjugation - Amide Hydrolyation Non-ME [3]
MR014135 Glutamic acid Phthalic Acid Conjugation - Amide Hydrolyation Non-ME [3]
MR014139 L-Glutamine L-Glutamine Conjugation - Amide Hydrolyation Non-ME [3]
⏷ Show the Full List of 30 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[7]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[2]
⏷ Show the Full List of 11  DME(s)
References
1 Thalidomide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 Thalidomide metabolism and hydrolysis: mechanisms and implications
4 Metabolism of thalidomide in human microsomes, cloned human cytochrome P-450 isozymes, and Hansen's disease patients. J Biochem Mol Toxicol. 2000;14(3):140-7.
5 Thalidomide metabolism by the CYP2C subfamily. Clin Cancer Res. 2002 Jun;8(6):1964-73.
6 Human liver microsomal cytochrome P450 3A enzymes involved in thalidomide 5-hydroxylation and formation of a glutathione conjugate. Chem Res Toxicol. 2010 Jun 21;23(6):1018-24.
7 Pharmacogenetic associations of CYP2C19 genotype with in vivo metabolisms and pharmacological effects of thalidomide. Cancer Biol Ther. 2002 Nov-Dec;1(6):669-73.
8 Chiral inversion and hydrolysis of thalidomide: mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites

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