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]
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Therapeutic Class

Antiallergic Agents

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:31397
CAS Number: 126544-47-6
DrugBank ID: DB01410
TTD ID: D0K7HU
VARIDT ID: DR01408
INTEDE ID: DR0319

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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Drug Transporter (DTP)

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

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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[11]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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]
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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.