Details of the Drug

General Information of Drug (ID: DM2NA4K)

Drug Name
Ciclesonide
Synonyms
Alvesco; Omnair; Omnaris; Osonase; Osonide; Alvesco HFA; Ciclesonide [INN]; Omnaris HFA; RPR 251526; Alvesco (TN); BTR-15; BTR-15K; BY-9010; BYK-20426; KS-1165; Omnaris (TN); Omniair (TN); TBN-15; B-9207-015; Ciclesonide (JAN/USAN/INN); (R)-11beta,16alpha,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde, 21-isobutyrate
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Asthma CA23 Approved [2]
Obstructive airway disease CB40.Y Approved [3]
Seasonal allergic rhinitis CA08.01 Approved [1]
Coronavirus Disease 2019 (COVID-19) 1D6Y Phase 3 [4]
Therapeutic Class
Antiallergic Agents
Affected Organisms
Humans and other mammals
ATC Code
R01AD13: Ciclesonide
R01AD: Corticosteroids
R01A: DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
R01: NASAL PREPARATIONS
R: RESPIRATORY SYSTEM
R03BA08: Ciclesonide
R03BA: Glucocorticoids
R03B: OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
R03: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R: RESPIRATORY SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 540.7
Logarithm of the Partition Coefficient (xlogp) 5.3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [5]
Clearance
The drug present in the plasma can be removed from the body at the rate of 33.3 mL/min/kg [6]
Elimination
0% of drug is excreted from urine in the unchanged form [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.04 hours [6]
Metabolism
The drug is metabolized via the liver []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.000001 micromolar/kg/day [7]
Unbound Fraction
The unbound fraction of drug in plasma is 0.01% [6]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 2.9 L/kg [6]
Water Solubility
The ability of drug to dissolve in water is measured as 0.0002 mg/mL [5]
Chemical Identifiers
Formula
C32H44O7
IUPAC Name
[2-[(1S,2S,4R,6R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 2-methylpropanoate
Canonical SMILES
CC(C)C(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@H]4[C@H]3CCC5=CC(=O)C=C[C@]45C)O)C)O[C@H](O2)C6CCCCC6
InChI
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
Cross-matching ID
PubChem CID
6918155
ChEBI ID
CHEMBL2040682
CAS Number
126544-47-6
UNII
S59502J185
DrugBank ID
DB01410
TTD ID
D0K7HU
VARIDT ID
DR01408
INTEDE ID
DR0319
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Corticosteroid-binding globulin (SERPINA6) TTJL8VG CBG_HUMAN Binder [8]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [10]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ciclesonide (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Levalbuterol DM5YBO1 Minor Increased risk of hypokalemia by the combination of Ciclesonide and Levalbuterol. Asthma [CA23] [12]
Troleandomycin DMUZNIG Moderate Decreased metabolism of Ciclesonide caused by Troleandomycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [13]
Tucatinib DMBESUA Moderate Decreased metabolism of Ciclesonide caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [13]
Vilanterol DMF5EK1 Minor Increased risk of hypokalemia by the combination of Ciclesonide and Vilanterol. Chronic obstructive pulmonary disease [CA22] [12]
Indacaterol DMQJHR7 Minor Increased risk of hypokalemia by the combination of Ciclesonide and Indacaterol. Chronic obstructive pulmonary disease [CA22] [13]
Stiripentol DMMSDOY Moderate Decreased metabolism of Ciclesonide caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [13]
Boceprevir DMBSHMF Moderate Decreased metabolism of Ciclesonide caused by Boceprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [13]
Telaprevir DMMRV29 Moderate Decreased metabolism of Ciclesonide caused by Telaprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [13]
Cobicistat DM6L4H2 Moderate Decreased metabolism of Ciclesonide caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [13]
Ceritinib DMB920Z Moderate Decreased metabolism of Ciclesonide caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [13]
Idelalisib DM602WT Moderate Decreased metabolism of Ciclesonide caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [13]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive immunosuppressive effects by the combination of Ciclesonide and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [14]
Abametapir DM2RX0I Moderate Decreased metabolism of Ciclesonide caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [15]
Lefamulin DME6G97 Moderate Decreased metabolism of Ciclesonide caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [16]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Ciclesonide caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [13]
Fostamatinib DM6AUHV Moderate Decreased clearance of Ciclesonide due to the transporter inhibition by Fostamatinib. Thrombocytopenia [3B64] [17]
⏷ Show the Full List of 16 DDI Information of This Drug

References

1 Ciclesonide FDA Label
2 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (NDA) 202129
3 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7469).
4 ClinicalTrials.gov (NCT04377711) A Study of the Safety and Efficacy of Ciclesonide in the Treatment of Non-hospitalized COVID-19 Patients. U.S. National Institutes of Health.
5 BDDCS applied to over 900 drugs
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8 Novel human corticosteroid-binding globulin variant with low cortisol-binding affinity. J Clin Endocrinol Metab. 2000 Jan;85(1):361-7.
9 Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. Toxicol Appl Pharmacol. 2012 May 1;260(3):294-302.
10 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.
11 Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. Toxicol Appl Pharmacol. 2012 May 1;260(3):294-302. doi: 10.1016/j.taap.2012.03.008. Epub 2012 Mar 23.
12 Cerner Multum, Inc. "Australian Product Information.".
13 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
14 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
15 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
16 Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
17 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.