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

General Information of Drug (ID: DR0124)
Drug Name
Apremilast
Synonyms
Apremilast; Apremilast (CC-10004); Apremilast (JAN/USAN); Apremilast [USAN:INN]; Apremilast/CC 10004/; OTEZLA; Otezla (TN); QCR-202; SCHEMBL302992; UP7QBP99PN; apremilast-cc-10004; apremilastum; (S)-N-(2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide; 608141-41-9; C22H24N2O7S; CC 10004; CC-10004; CC10004; CHEBI:78540; CHEMBL514800; GTPL7372; HSDB 8221; N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide; UNII-UP7QBP99PN
Indication Psoriasis vulgaris [ICD11: EA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 460.5 Topological Polar Surface Area 128
Heavy Atom Count 32 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
11561674
PubChem SID
16663888 ; 28672022 ; 42703565 ; 50086920 ; 78553422 ; 96025543 ; 103594774 ; 104103394 ; 135195808 ; 135299279 ; 136946493 ; 140792549 ; 144115618 ; 152256090 ; 152258393 ; 160647230 ; 164045129 ; 164194075 ; 176253765 ; 178103944 ; 186014493 ; 187575333 ; 189561506 ; 198938842 ; 198994002 ; 218902332 ; 223380767 ; 223443866 ; 223593318 ; 224603101 ; 226643371 ; 247101845 ; 249492055 ; 249814467 ; 250163167 ; 251962967 ; 251970550 ; 252088578 ; 252160602 ; 252214744 ; 252438251 ; 252451837 ; 252553654
ChEBI ID
CHEBI:78540
CAS Number
608141-41-9
TTD Drug ID
D07ESC
Formula
C22H24N2O7S
Canonical SMILES
CCOC1=C(C=CC(=C1)C(CS(=O)(=O)C)N2C(=O)C3=C(C2=O)C(=CC=C3)NC(=O)C)OC
InChI
1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1
InChIKey
IMOZEMNVLZVGJZ-QGZVFWFLSA-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
Apremilast metabolite M1/2 DM000628 N. A. Unclear 1 [4]
Apremilast metabolite M17 DM000631
54764856
Oxidation - Hydroxylation 1 [4]
Apremilast metabolite M5 DM000641 N. A. Unclear 1 [4]
Apremilast metabolite M7 DM000635 N. A. Oxidation - N-Deacetylation 1 [4]
O-desmethyl Apremilast DM000623
68088610
Oxidation - O-Demethylation 1 [4]
Apremilast metabolite M10 DM000632
57524408
Oxidation - Hydroxylation 2 [4]
Apremilast metabolite M11 DM000636 N. A. Oxidation - Hydroxylation 2 [4]
Apremilast metabolite M13 DM000643
57524487
Conjugation - Glucuronidation 2 [4]
Apremilast metabolite M16 DM000634
57524483
Oxidation - Hydroxylation 2 [4]
Apremilast metabolite M18 DM000629
84885
Hydrolysis - Hydrolysis 2 [4]
Apremilast metabolite M19 DM000627 N. A. Hydrolysis - Hydrolysis 2 [4]
Apremilast metabolite M19 DM000627 N. A. Oxidation - O-Demethylation 2 [4]
Apremilast metabolite M22 DM000642 N. A. Hydrolysis - Hydrolysis 2 [4]
Apremilast metabolite M9 DM000626
91810683
Hydrolysis - Hydrolysis 2 [4]
O-desmethyl Apremilast DM000623
68088610
Oxidation - O-Demethylation 2 [4]
O-desmethyl apremilast glucuronide DM000624
57524484
Conjugation - Glucuronidation 2 [4]
Apremilast metabolite M14 DM000640
57524405
Conjugation - Glucuronidation 3 [4]
Apremilast metabolite M15 DM000625
91810684
Hydrolysis - Hydrolysis 3 [4]
Apremilast metabolite M20 DM000639 N. A. Oxidation - O-Deethylation 3 [4]
Apremilast metabolite M21 DM000633 N. A. Oxidation - Hydroxylation 3 [4]
Apremilast metabolite M23 DM000630
91810656
Hydrolysis - Hydrolysis 3 [4]
Apremilast metabolite M8 DM000637 N. A. Unclear 3 [4]
Apremilast metabolite M8 DM000637 N. A. Oxidation - Hydroxylation 3 [4]
⏷ Show the Full List of 23  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000276 Apremilast O-desmethyl Apremilast Oxidation - O-Demethylation CYP1A2 ... [4]
MR000277 Apremilast Apremilast metabolite M1/2 Unclear Unclear [4]
MR000278 Apremilast Apremilast metabolite M17 Oxidation - Hydroxylation Unclear [4]
MR000279 Apremilast Apremilast metabolite M7 Oxidation - N-Deacetylation Unclear [4]
MR000280 Apremilast Apremilast metabolite M5 Unclear Unclear [4]
MR000261 Apremilast metabolite M1/2 Apremilast metabolite M9 Hydrolysis - Hydrolysis Unclear [4]
MR000262 Apremilast metabolite M1/2 Apremilast metabolite M18 Hydrolysis - Hydrolysis Unclear [4]
MR000264 Apremilast metabolite M17 Apremilast metabolite M10 Oxidation - Hydroxylation Unclear [4]
MR000265 Apremilast metabolite M17 Apremilast metabolite M16 Oxidation - Hydroxylation Unclear [4]
MR000273 Apremilast metabolite M5 Apremilast metabolite M19 Hydrolysis - Hydrolysis Unclear [4]
MR000274 Apremilast metabolite M5 Apremilast metabolite M22 Hydrolysis - Hydrolysis Unclear [4]
MR000275 Apremilast metabolite M5 Apremilast metabolite M13 Conjugation - Glucuronidation Unclear [4]
MR000267 Apremilast metabolite M7 Apremilast metabolite M11 Oxidation - Hydroxylation Unclear [4]
MR000268 Apremilast metabolite M7 Apremilast metabolite M4 Oxidation - O-Demethylation Unclear [4]
MR000257 O-desmethyl Apremilast O-desmethyl apremilast glucuronide Conjugation - Glucuronidation Unclear [4]
MR000258 O-desmethyl Apremilast Apremilast metabolite M9 Hydrolysis - Hydrolysis Unclear [4]
MR000259 O-desmethyl Apremilast Apremilast metabolite M19 Oxidation - O-Demethylation Unclear [4]
MR000266 Apremilast metabolite M10 Apremilast metabolite M21 Oxidation - Hydroxylation Unclear [4]
MR000269 Apremilast metabolite M11 Apremilast metabolite M8 Oxidation - Hydroxylation Unclear [4]
MR000263 Apremilast metabolite M18 Apremilast metabolite M23 Hydrolysis - Hydrolysis Unclear [4]
MR000270 Apremilast metabolite M4 Apremilast metabolite M8 Unclear Unclear [4]
MR000271 Apremilast metabolite M4 Apremilast metabolite M20 Oxidation - O-Deethylation Unclear [4]
MR000272 Apremilast metabolite M4 Apremilast metabolite M14 Conjugation - Glucuronidation Unclear [4]
MR000260 O-desmethyl apremilast glucuronide Apremilast metabolite M15 Hydrolysis - Hydrolysis Unclear [4]
⏷ Show the Full List of 24 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Apremilast was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Apremilast (Otezla): a new oral treatment for adults with psoriasis and psoriatic arthritis. P T. 2015 Aug;40(8):495-500.
3 Apremilast, an oral phosphodiesterase 4 (PDE4) inhibitor: a novel treatment option for nurse practitioners treating patients with psoriatic disease. J Am Assoc Nurse Pract. 2016 Dec;28(12):683-695.
4 Disposition, metabolism and mass balance of [(14)C]apremilast following oral administration. Xenobiotica. 2011 Dec;41(12):1063-75.

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