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

General Information of Drug (ID: DR0319)
Drug Name
Ciclesonide
Prodrug Info Ciclesonide is the prodrug of Desisobutyrylciclesonide
Synonyms
Ciclesonide; Ciclesonide [INN]; Omnair; Omnaris; Omnaris HFA; Alvesco; Alvesco HFA; Osonase; Osonide; RPR 251526; RPR-251526; RPR251526; S59502J185; Zetonna; (R)-11beta,16alpha,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde, 21-isobutyrate; 126544-47-6; 141845-82-1; AC1MIWNR; Pregna-1,4-diene-3,20-dione, 16,17-((cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha(R))-; UNII-S59502J185
Indication Asthma [ICD11: CA23] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 540.7 Topological Polar Surface Area 99.1
Heavy Atom Count 39 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
6918155
PubChem SID
7848766 ; 12014485 ; 14763472 ; 14910303 ; 17194708 ; 43529548 ; 50069804 ; 50113016 ; 53790514 ; 57371818 ; 75476862 ; 92719025 ; 93307925 ; 93815124 ; 126592968 ; 126621149 ; 126652709 ; 135211289 ; 135805250 ; 137002365 ; 137619495 ; 144206039 ; 152134121 ; 160668474 ; 162183036 ; 162258877 ; 164788141 ; 175266964 ; 184545966 ; 187051772 ; 187072300 ; 196106072 ; 210279779 ; 210282102 ; 223657022 ; 224423934 ; 226395815 ; 251915931 ; 251917279 ; 252215142 ; 252347327
ChEBI ID
CHEBI:31397
CAS Number
141845-82-1
TTD Drug ID
D0K7HU
Formula
C32H44O7
Canonical SMILES
CC(C)C(=O)OCC(=O)C12C(CC3C1(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)OC(O2)C6CCCCC6
InChI
1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29+,30-,31-,32+/m0/s1
InChIKey
LUKZNWIVRBCLON-GXOBDPJESA-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
Desisobutyrylciclesonide DM001836
6918281
Hydrolysis - Hydrolysis 1 [3] , [4] , [5] , [6]
C21-Lipid conjugation DM001837 N. A. Other reaction - Esterification 2 [7]
Ciclesonide metabolite M2 DM001839 N. A. Unclear 2 [7]
Ciclesonide metabolite M3 DM001838 N. A. Unclear 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003207 Ciclesonide Desisobutyrylciclesonide Hydrolysis - Hydrolysis ES [3], [4], [5], [6]
MR003204 Desisobutyrylciclesonide C21-Lipid conjugation Other reaction - Esterification Unclear [7]
MR003205 Desisobutyrylciclesonide Ciclesonide metabolite M3 Unclear CYP3A4 ... [7]
MR003206 Desisobutyrylciclesonide Ciclesonide metabolite M2 Unclear CYP3A4 ... [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Ciclesonide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of enzymes involved in phase I metabolism of ciclesonide by human liver microsomes. Eur J Drug Metab Pharmacokinet. 2005 Oct-Dec;30(4):275-86.
3 Ciclesonide Drugs. 2004;64(5):511-9; discussion 520-1. doi: 10.2165/00003495-200464050-00005.
4 Deposition and metabolism of inhaled ciclesonide in the human lung Eur Respir J. 2010 Nov;36(5):1113-9. doi: 10.1183/09031936.00172309.
5 LC-HRMS/MS study of the prodrug ciclesonide and its active metabolite desisobutyryl-ciclesonide in plasma after an inhalative administration to horses for doping control purposes. Drug Test Anal. 2022 Feb;14(2):252-261. doi: 10.1002/dta.3174.
6 Visualizing the spatial localization of ciclesonide and its metabolites in rat lungs after inhalation of 1-m aerosol of ciclesonide by desorption electrospray ionization-time of flight mass spectrometry imaging. Int J Pharm. 2021 Feb 15;595:120241. doi: 10.1016/j.ijpharm.2021.120241.
7 In Vitro metabolism of ciclesonide in human lung and liver precision-cut tissue slices Biopharm Drug Dispos. 2006 May;27(4):197-207. doi: 10.1002/bdd.500.

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