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

General Information of Drug (ID: DR1056)
Drug Name
Methylprednisolone
Synonyms
Medesone; Medixon; Medlone 21; Medrate; Medrol; Medrol adt pak; Medrol dosepak; Medrone; Mesopren; Metastab; Methyleneprednisolone; Methylprednisolon; Methylprednisolonum; Metilbetasone; Metilprednisolona; Metilprednisolone; Metrisone; Metrocort; Metysolon; Moderin; Nirypan; Noretona; Predni N Tablinen; Promacortine; Reactenol; Sieropresol; Artisone-wyeth; Besonia; Dopomedrol; Esametone; Firmacort; Solomet; Suprametil; Urbason; Urbasone; Wyacort; methylprednisolone; 6-alpha-Methylprednisolone; 6alpha-Methylprednisolone; 83-43-2; Lemod
Indication Lymphoblastic Lymphoma [ICD11: 2A70] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 374.5 Topological Polar Surface Area 94.8
Heavy Atom Count 27 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
6741
PubChem SID
82706 ; 811679 ; 855789 ; 7847473 ; 7979947 ; 8154374 ; 10321588 ; 11406050 ; 11466307 ; 11467427 ; 11486113 ; 12159225 ; 14779784 ; 14853277 ; 24870169 ; 24896564 ; 29225690 ; 46504885 ; 47440566 ; 47589248 ; 48259526 ; 48334797 ; 48416259 ; 49698417 ; 50019481 ; 50104073 ; 50139236 ; 50796061 ; 53790220 ; 56311264 ; 56311302 ; 56311303 ; 56311483 ; 56312634 ; 56313960 ; 56313963 ; 56314026 ; 56314034 ; 56424125 ; 57323679 ; 57650805 ; 81093211 ; 85300841 ; 85788445 ; 87560014 ; 92125124 ; 92309029 ; 93576705 ; 103189214 ; 103914078
ChEBI ID
CHEBI:6888
CAS Number
83-43-2
TTD Drug ID
D08PIQ
Formula
C22H30O5
Canonical SMILES
CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
InChI
1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1
InChIKey
VHRSUDSXCMQTMA-PJHHCJLFSA-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
Methylprednisolone M1 Metabolite DM004356
124653
Oxidation - 11-oxidation 1 [2]
Methylprednisolone M13 Metabolite DM004360
101577099
Oxidation - 22-hydroxylation 1 [2]
Methylprednisolone M2 Metabolite DM004363
91667753
Unclear 1 [2]
Methylprednisolone M4 Metabolite DM004353
13932217
Oxidation - 6,7-dehydrogenation 1 [2]
Methylprednisolone M7 Metabolite DM004350
100949811
Oxidation - 6-hydroxylation 1 [2]
Methylprednisolone M10 Metabolite DM004351
100949810
Reduction - 20-reduction 2 [2] , [3]
Methylprednisolone M11 Metabolite DM004357
101577096
Reduction - 20-reduction 2 [2] , [3]
Methylprednisolone M14 Metabolite DM004362
101577098
Reduction - 20-reduction 2 [2] , [3]
Methylprednisolone M15 Metabolite DM004361
101577100
Oxidation - 11-oxidation 2 [2]
Methylprednisolone M3 Metabolite DM004364
91667671
Reduction - 20-reduction 2 [2] , [3]
Methylprednisolone M5 Metabolite DM004354
91667780
Reduction - 20-reduction 2 [2] , [3]
Methylprednisolone M8 Metabolite DM004359
101577095
Oxidation - 16-hydroxylation 2 [2]
Methylprednisolone M12 Metabolite DM004358
101577097
Reduction - 20-reduction 3 [2] , [3]
Methylprednisolone M6 Metabolite DM004355
91667685
Reduction - 20-reduction 3 [2] , [3]
Methylprednisolone M9 Metabolite DM004352
100949812
Reduction - 20-reduction 3 [2] , [3]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004679 Methylprednisolone Methylprednisolone M7 Metabolite Oxidation - 6-hydroxylation Unclear [2]
MR004682 Methylprednisolone Methylprednisolone M4 Metabolite Oxidation - 6,7-dehydrogenation Unclear [2]
MR004685 Methylprednisolone Methylprednisolone M1 Metabolite Oxidation - 11-oxidation HSD11B1 [2]
MR004689 Methylprednisolone Methylprednisolone M13 Metabolite Oxidation - 22-hydroxylation Unclear [2]
MR004692 Methylprednisolone Methylprednisolone M2 Metabolite Unclear Unclear [2]
MR004693 Methylprednisolone Methylprednisolone M3 Metabolite Reduction - 20-reduction kduD [2], [3]
MR004686 Methylprednisolone M1 Metabolite Methylprednisolone M11 Metabolite Reduction - 20-reduction kduD [2], [3]
MR004687 Methylprednisolone M1 Metabolite Methylprednisolone M12 Metabolite Reduction - 20-reduction kduD [2], [3]
MR004688 Methylprednisolone M1 Metabolite Methylprednisolone M8 Metabolite Oxidation - 16-hydroxylation Unclear [2]
MR004690 Methylprednisolone M13 Metabolite Methylprednisolone M15 Metabolite Oxidation - 11-oxidation HSD11B1 [2]
MR004691 Methylprednisolone M13 Metabolite Methylprednisolone M14 Metabolite Reduction - 20-reduction kduD [2], [3]
MR004683 Methylprednisolone M4 Metabolite Methylprednisolone M5 Metabolite Reduction - 20-reduction kduD [2], [3]
MR004684 Methylprednisolone M5 Metabolite Methylprednisolone M6 Metabolite Reduction - 20-reduction kduD [2], [3]
MR004680 Methylprednisolone M7 Metabolite Methylprednisolone M10 Metabolite Reduction - 20-reduction kduD [2], [3]
MR004681 Methylprednisolone M7 Metabolite Methylprednisolone M9 Metabolite Reduction - 20-reduction kduD [2], [3]
⏷ Show the Full List of 15 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
20-ketosteroid reductase (20-hydroxysteroid dehydrogenase) (kduD) DMEN240 Bacteroides fragilis Not Available Not Available [2] , [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
References
1 Methylprednisolone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Urinary profile of methylprednisolone and its metabolites after oral and topical administrations
3 Carbonyl reduction pathways in drug metabolism
4 Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35.

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