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

General Information of Drug (ID: DR0819)
Drug Name
Hydrocortisone
Synonyms
Hycort; Hycortol; Hycortole; Hydrasson; Hydro-Adreson; Hydrocortisyl; Hydrocortone; Hytone; Hytone lotion; Incortin-H; Kendall's compound F; Acticort; Cetacort; Cleiton; Cobadex; Cortanal; Cortef; Cortenema; Corticreme; Cortifan; Cortiment; Cortisol; Cortispray; Cortonema; Cortril; Dermacort; Dermolate; Dihydrocostisone; Efcorbin; Efcortelan; Ficortril; Genacort; Hidro-Colisona; Permicort; Polcort H; Proctocort; Reichstein's substance M; Scheroson F; Signef; Tarcortin; Traumaide; hydrocortisone; 17-Hydroxycorticosterone; 50-23-7; Alacort; Optef
Indication Uncontrolled gout [ICD11: FA25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 362.5 Topological Polar Surface Area 94.8
Heavy Atom Count 26 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5754
PubChem SID
3998 ; 75748 ; 841765 ; 855803 ; 3154635 ; 4266384 ; 7847156 ; 7979545 ; 8138524 ; 8144588 ; 8153531 ; 10321360 ; 11404513 ; 11466475 ; 11467595 ; 11486169 ; 12013447 ; 14828390 ; 14852592 ; 17405156 ; 22391546 ; 24278466 ; 24715473 ; 24895394 ; 24895401 ; 24895415 ; 24895560 ; 24895778 ; 26737242 ; 26738006 ; 26751519 ; 26751520 ; 29224790 ; 46488041 ; 46505089 ; 47275088 ; 47348953 ; 47423772 ; 47646134 ; 47646135 ; 48393456 ; 48413873 ; 49698498 ; 49703922 ; 49846290 ; 49857418 ; 53777700 ; 53790729 ; 53801089 ; 53813055
ChEBI ID
ChEBI:17650
CAS Number
50-23-7
TTD Drug ID
D0KR5B
Formula
C21H30O5
Canonical SMILES
CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O
InChI
1S/C21H30O5/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/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
InChIKey
JYGXADMDTFJGBT-VWUMJDOOSA-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
5-alpha Tetrahydrocortisol DM004774
12816693
Reduction - Reduction 1 [2] , [3]
5-beta Tetrahydrocortisol DM004773
164838
Reduction - Reduction 1 [2] , [3]
6-beta-hydrocortisol DM004772
10091061
Oxidation - 6-beta-hydroxylation 1 [9]
6alpha-hydroxy hydrocortisone DM004775 N. A. Unclear 1 [10]
Cortisone DM004769
222786
Oxidation - Oxidationn 1 [2] , [5]
Tetrahydrocortisol Glucuronide 1 DM004765 N. A. Conjugation - O-glucuronidation 1 [5]
Dihydrocortisol DM004770
20056650
Reduction - Reduction 2 [11]
Tetrahydrocortisol Glucuronide 2 DM004766 N. A. Conjugation - O-glucuronidation 2 [5]
Tetrahydrocortisone DM004771
5866
Reduction - Reduction 2 [11]
Tetrahydrocortisone Glucuronide 1 DM004767 N. A. Conjugation - O-glucuronidation 3 [5]
Tetrahydrocortisone Glucuronide 2 DM004768 N. A. Conjugation - O-glucuronidation 4 [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005124 Hydrocortisone Tetrahydrocortisol Glucuronide 1 Conjugation - O-glucuronidation Unclear [5]
MR005125 Hydrocortisone Tetrahydrocortisol Glucuronide 2 Conjugation - O-glucuronidation Unclear [5]
MR005126 Hydrocortisone Tetrahydrocortisone Glucuronide 1 Conjugation - O-glucuronidation Unclear [5]
MR005127 Hydrocortisone Tetrahydrocortisone Glucuronide 2 Conjugation - O-glucuronidation Unclear [5]
MR005128 Hydrocortisone Cortisone Oxidation - Oxidationn HSD11B1 ... [2], [5]
MR005129 Cortisone Dihydrocortisol Reduction - Reduction Unclear [11]
MR005130 Cortisone Tetrahydrocortisone Reduction - Reduction Unclear [11]
MR005131 Cortisone 6-beta-hydrocortisol Oxidation - 6-beta-hydroxylation CYP3A [9]
MR005132 Cortisone 5-beta Tetrahydrocortisol Reduction - Reduction AKR1D1 [2], [3]
MR005133 Cortisone 5-alpha Tetrahydrocortisol Reduction - Reduction SRD5A2 [2], [3]
MR005134 Cortisone 6alpha-hydroxy hydrocortisone Unclear Unclear [10]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1D1 (AKR1D1) DME0400 Homo sapiens
AK1D1_HUMAN
1.3.1.3
[2] , [3]
Aldosterone synthase (CYP11B2) DME0036 Homo sapiens
C11B2_HUMAN
1.14.15.4
[4]
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) DME0199 Homo sapiens
DHI1_HUMAN
1.1.1.146
[2] , [5]
Corticosteroid 11-beta-dehydrogenase 2 (HSD11B2) DME0419 Homo sapiens
DHI2_HUMAN
1.1.1.B40
[2] , [5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[8]
Steroid 11-beta-hydroxylase (CYP11B1) DME0027 Homo sapiens
C11B1_HUMAN
1.14.15.4
[4]
Steroid 5-alpha-reductase 2 (SRD5A2) DME0218 Homo sapiens
S5A2_HUMAN
1.3.1.22
[2] , [3]
⏷ Show the Full List of 9  DME(s)
References
1 Hydrocortisone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cortisol metabolism in healthy young adults: sexual dimorphism in activities of A-ring reductases, but not 11beta-hydroxysteroid dehydrogenases
3 Subcellular distribution of 3H--hydrocortisone and its metabolites in the liver and kidneys of normal and alloxan diabetic rats
4 Studies on the origin of circulating 18-hydroxycortisol and 18-oxocortisol in normal human subjects. J Clin Endocrinol Metab. 2004 Sep;89(9):4628-33.
5 Metabolite profiling and pharmacokinetic evaluation of hydrocortisone in a perfused three-dimensional human liver bioreactor
6 Regulation of the CYP3A4 gene by hydrocortisone and xenobiotics: role of the glucocorticoid and pregnane X receptors. Drug Metab Dispos. 2000 May;28(5):493-6.
7 CYP3A5 genotype is associated with elevated blood pressure. Pharmacogenet Genomics. 2005 Oct;15(10):737-41.
8 Steroid hydroxylation by human fetal CYP3A7 and human NADPH-cytochrome P450 reductase coexpressed in insect cells using baculovirus. Res Commun Mol Pathol Pharmacol. 1998 Apr;100(1):15-28.
9 Cortisol metabolism in vitro--III. Inhibition of microsomal 6 beta-hydroxylase and cytosolic 4-ene-reductase. J Steroid Biochem Mol Biol. 1993 Dec;46(6):827-32.
10 Biotechnological transformation of hydrocortisone to 16-hydroxy hydrocortisone by Streptomyces roseochromogenes
11 DrugBank(Pharmacology-Metabolism):Hydrocortisone

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