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

General Information of Drug (ID: DR1334)
Drug Name
Prednisone
Prodrug Info Prednisone is the prodrug of Prednisolone
Synonyms
Panafcort; Panasol; Paracort; Prednidib; Prednilonga; Prednison; Prednisonum; Prednizon; Pronison; Rectodelt; Servisone; Sterapred; Supercortil; Adasone; Ancortone; Bicortone; Colisone; Cortan; Cortidelt; Cotone; Dacortin; Decortancyl; Decortin; Decortisyl; Dehydrocortisone; Dekortin; Deltacortisone; Deltacortone; Deltasone; Deltison; Deltra; Di-Adreson; Diadreson; Encorton; Encortone; Enkorton; Hostacortin; Liquid Pred; Lisacort; Meticorten; Nurison; Orasone; Ultracorten; Ultracortene; Winpred; Wojtab; Zenadrid; prednisone; 1,2-Dehydrocortisone
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 358.4 Topological Polar Surface Area 91.7
Heavy Atom Count 26 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5865
PubChem SID
9574 ; 75351 ; 811678 ; 6436730 ; 7980378 ; 8153624 ; 10321430 ; 11404403 ; 11466105 ; 11467225 ; 11485950 ; 12159191 ; 14876665 ; 14901277 ; 17389753 ; 24887849 ; 24898748 ; 29224894 ; 46508166 ; 47423771 ; 47499091 ; 47869192 ; 47943330 ; 48094072 ; 48168897 ; 48393454 ; 48414367 ; 48423989 ; 48425558 ; 49681504 ; 49698331 ; 49855473 ; 50085971 ; 50105442 ; 50105443 ; 50793118 ; 53790481 ; 56310878 ; 56312053 ; 56312061 ; 56312554 ; 56314869 ; 56320929 ; 56320930 ; 56352934 ; 56463357 ; 57323004 ; 81093202 ; 85300843 ; 85787889
ChEBI ID
ChEBI:8382
CAS Number
53-03-2
TTD Drug ID
D0IL7L
Formula
C21H26O5
Canonical SMILES
CC12CC(=O)C3C(C1CCC2(C(=O)CO)O)CCC4=CC(=O)C=CC34C
InChI
1S/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
InChIKey
XOFYZVNMUHMLCC-ZPOLXVRWSA-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
17alpha,21-dihydroxy-pregnan-1,4,6-trien-3,11,30-trione (M-XVII) DM002938
22793136
Unclear 1 [4]
20alpha-dihydro-prednisone (M-V) DM002951
71749279
Unclear 1 [4]
20beta-dihydro-prednisone (M-IV) DM002943
14475047
Unclear 1 [4]
6alpha-hydroxy-prednisone (M-XIII) DM002942
101913096
Oxidation - Hydroxylation 1 [4]
6beta-hydroxy-prednisone (M-XII) DM002941
101913093
Oxidation - Hydroxylation 1 [4] , [2]
Prednisolone DM003078
5755
Unclear 1 [4]
17alpha,20xi,21-trihydroxy-5xi-pregn-1-en-3,11-dione(M-XVIII) DM002944
101913094
Unclear 2 [4]
6beta-hydroxy-prednisolone(M-VI) DM002945
14726612
Unclear 2 [2]
20alpha-dihydro-prednisolone (M-III) DM002935
13962390
Unclear 3 [4]
20beta-dihydro-prednisolone (M-II) DM002936
13962391
Unclear 3 [4]
6alpha-hydroxy-prednisolone (M-VII) DM002939
101913091
Unclear 3 [4]
6beta,11beta,17alpha,20alpha,21-pentahydroxypregnan-1,4-diene-3-one (M-IX) DM002947
156621394
Unclear 3 [4]
6beta,11beta,17alpha,20beta,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII) DM002949
156621404
Unclear 3 [4]
6beta,11beta,17alpha,21-tetrahydroxy-5xi-pregn-1-en-3,20-dione (M-XIV) DM002946
101913092
Unclear 3 [4]
Delta6-prednisolone (M-XI) DM002934
224451
Unclear 3 [4]
6alpha,11beta,17alpha,20beta,21-pentahydroxypregnan-1,4-diene-3-one (M-X) DM002940
101913095
Unclear 4 [4]
6beta,11beta,17alpha,20alpha,21-pentahydroxy-5xi-pregn-1-en-3-one (M-XVI) DM002948
156621397
Unclear 4 [4]
6beta,11beta,17alpha,20beta,21-pentahydroxy-5xi-pregn-1-en-3-one (M-XV) DM002950
156621396
Unclear 4 [4]
6beta,11beta,17alpha,21-tetrahydroxy-5xi-pregn-1-en-3,20-dione (M-XIV) DM002946
101913092
Unclear 5 [4]
⏷ Show the Full List of 19  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002769 Prednisone 17alpha,21-dihydroxy-pregnan-1,4,6-trien-3,11,30-trione (M-XVII) Unclear Unclear [4]
MR002770 Prednisone 6beta-hydroxy-prednisone (M-XII) Oxidation - Hydroxylation CYP3A4 [4], [2]
MR002771 Prednisone 6alpha-hydroxy-prednisone (M-XIII) Oxidation - Hydroxylation Unclear [4]
MR002772 Prednisone 20beta-dihydro-prednisone (M-IV) Unclear Unclear [4]
MR002773 Prednisone 20alpha-dihydro-prednisone (M-V) Unclear Unclear [4]
MR002774 Prednisone Prednisolone Unclear CYP3A4 [4]
MR002761 20beta-dihydro-prednisone (M-IV) 17alpha,20xi,21-trihydroxy-5xi-pregn-1-en-3,11-dione(M-XVIII) Unclear Unclear [4]
MR002775 Prednisolone Delta6-prednisolone (M-XI) Unclear Unclear [4]
MR002776 Prednisolone 20alpha-dihydro-prednisolone (M-III) Unclear Unclear [4]
MR002777 Prednisolone 20beta-dihydro-prednisolone (M-II) Unclear Unclear [4]
MR002778 Prednisolone 6alpha-hydroxy-prednisolone (M-VII) Unclear Unclear [4]
MR002779 Prednisolone 6beta-hydroxy-prednisolone(M-VI) Unclear CYP3A4 [2]
MR002762 6beta-hydroxy-prednisolone(M-VI) 6beta,11beta,17alpha,21-tetrahydroxy-5xi-pregn-1-en-3,20-dione (M-XIV) Unclear Unclear [4]
MR002763 6beta-hydroxy-prednisolone(M-VI) 6beta,11beta,17alpha,20alpha,21-pentahydroxypregnan-1,4-diene-3-one (M-IX) Unclear Unclear [4]
MR002764 6beta-hydroxy-prednisolone(M-VI) 6beta,11beta,17alpha,20beta,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII) Unclear Unclear [4]
MR002760 6alpha-hydroxy-prednisolone (M-VII) 6alpha,11beta,17alpha,20beta,21-pentahydroxypregnan-1,4-diene-3-one (M-X) Unclear Unclear [4]
MR002765 6beta,11beta,17alpha,20alpha,21-pentahydroxypregnan-1,4-diene-3-one (M-IX) 6beta,11beta,17alpha,20alpha,21-pentahydroxy-5xi-pregn-1-en-3-one (M-XVI) Unclear Unclear [4]
MR002767 6beta,11beta,17alpha,20beta,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII) 6beta,11beta,17alpha,20beta,21-pentahydroxy-5xi-pregn-1-en-3-one (M-XV) Unclear Unclear [4]
MR002766 6beta,11beta,17alpha,20alpha,21-pentahydroxy-5xi-pregn-1-en-3-one (M-XVI) 6beta,11beta,17alpha,21-tetrahydroxy-5xi-pregn-1-en-3,20-dione (M-XIV) Unclear Unclear [4]
MR002768 6beta,11beta,17alpha,20beta,21-pentahydroxy-5xi-pregn-1-en-3-one (M-XV) 6beta,11beta,17alpha,21-tetrahydroxy-5xi-pregn-1-en-3,20-dione (M-XIV) Unclear Unclear [4]
⏷ Show the Full List of 20 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]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [3]
⏷ Show the Full List of 7  DME(s)
References
1 Prednisone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetic and pharmacoimmunodynamic interactions between prednisolone and sirolimus in adrenalectomized rats. J Pharmacokinet Biopharm. 1999 Feb;27(1):1-21.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS J Mass Spectrom. 2015 Mar;50(3):633-42. doi: 10.1002/jms.3571.

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