Ciclesonide

Identification

Summary

Ciclesonide is a glucocorticoid used in the symptomatic relief of nasal symptoms associated with seasonal and perennial allergic rhinitis in adults and adolescents.

Brand Names
Alvesco, Omnaris, Zetonna
Generic Name
Ciclesonide
DrugBank Accession Number
DB01410
Background

Ciclesonide is a glucocorticoid used to treat obstructive airway diseases. It is marketed under the brand name Alvesco.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 540.697
Monoisotopic: 540.308703757
Chemical Formula
C32H44O7
Synonyms
  • Ciclesonida
  • Ciclesonide
External IDs
  • BI54903
  • RPR-251526
  • RPR251526

Pharmacology

Indication

For the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis in adults and adolescents 12 years of age and older.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAsthmaCombination Product in combination with: Carmoterol (DB15784)••••••••••••••••••
Used in combination to manageAsthmaCombination Product in combination with: Formoterol (DB00983)•••••••••••••••••••
Management ofAsthma••••••••••••••••••••
Used in combination to preventBronchoconstrictionCombination Product in combination with: Tiotropium (DB01409)••••••••••••••••••
Used in combination to manageChronic obstructive pulmonary disease (copd)Combination Product in combination with: Carmoterol (DB15784)••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ciclesonide is a pro-drug that is enzymatically hydrolyzed to a pharmacologically active metabolite, C21-desisobutyryl-ciclesonide (des-ciclesonide or RM1) following intranasal application. Des-ciclesonide has anti-inflammatory activity with affinity for the glucocorticoid receptor that is 120 times higher than the parent compound. The precise mechanism through which ciclesonide affects allergic rhinitis symptoms is not known. Corticosteroids have been shown to have a wide range of effects on multiple cell types (e.g., mast cells, eosinophils, neutrophils, macrophages, and lymphocytes) and mediators (e.g., histamine, eicosanoids, leukotrienes, and cytokines) involved in allergic inflammation.

Mechanism of action

Glucocorticoids such as ciclesonide can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of glucocorticoids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Ciclesonide reduces inflammatory reaction by limiting the capillary dilatation and permeability of the vascular structures. These compounds restrict the accumulation of polymorphonuclear leukocytes and macrophages and reduce the release of vasoactive kinins. Recent research suggests that corticosteroids may inhibit the release of arachidonic acid from phospholipids, thereby reducing the formation of prostaglandins. Ciclesonide is a glucocorticoid receptor agonist. On binding, the corticoreceptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing an increase or decrease in expression of specific target genes, including suppression of IL2 (interleukin 2) expression.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
Absorption

Ciclesonide and des-ciclesonide have negligible oral bioavailability (both less than 1%) due to low gastrointestinal absorption and high first-pass metabolism. The intranasal administration of ciclesonide at recommended doses results in negligible serum concentrations of ciclesonide.

Volume of distribution

Not Available

Protein binding

The percentage of ciclesonide and des-ciclesonide bound to human plasma proteins averaged ≥ 99% each, with ≤ 1% of unbound drug detected in the systemic circulation.

Metabolism

Des-ciclesonide undergoes metabolism in the liver to additional metabolites mainly by the cytochrome P450 (CYP) 3A4 isozyme and to a lesser extent by CYP 2D6.

Route of elimination

Not Available

Half-life

Not Available

Clearance
  • 152 L/hr [Following IV administration of 800 mcg of ciclesonide]
Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Ciclesonide can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ciclesonide can be increased when combined with Abatacept.
AbirateroneThe metabolism of Ciclesonide can be decreased when combined with Abiraterone.
AcarboseThe risk or severity of hyperglycemia can be increased when Ciclesonide is combined with Acarbose.
AcebutololThe metabolism of Ciclesonide can be decreased when combined with Acebutolol.
Food Interactions
No interactions found.

Products

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International/Other Brands
Omniair
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlvescoAerosol, metered160 ug/1Respiratory (inhalation)Sunovion Pharmaceuticals Inc.2008-10-012019-12-01US flag
AlvescoAerosol, metered50 mcg / actRespiratory (inhalation)TakedaNot applicableNot applicableCanada flag
AlvescoAerosol, metered80 ug/1Respiratory (inhalation)Covis Pharma US, Inc2018-03-26Not applicableUS flag
AlvescoAerosol, metered160 ug/1Respiratory (inhalation)Sixarp, LLC2018-03-26Not applicableUS flag
AlvescoAerosol, metered80 ug/1Respiratory (inhalation)Sunovion Pharmaceuticals Inc.2008-10-012019-12-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-ciclesonideSpray, metered50 mcg / actNasalApotex Corporation2016-11-25Not applicableCanada flag
CiclesonideAerosol, metered160 ug/1Respiratory (inhalation)Prasco Laboratories2021-05-01Not applicableUS flag
CiclesonideAerosol, metered37 ug/1NasalPrasco Laboratories2022-04-23Not applicableUS flag
CiclesonideAerosol, metered80 ug/1Respiratory (inhalation)Prasco Laboratories2021-05-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DUESONIT 18/200 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 120 ADETCiclesonide (200 mcg) + Tiotropium (18 mcg)PowderRespiratory (inhalation)NEUTEC İLAÇ SAN. TİC. A.Ş.2012-04-26Not applicableTurkey flag
DUESONIT 18/200 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 60 ADETCiclesonide (200 mcg) + Tiotropium (18 mcg)PowderRespiratory (inhalation)NEUTEC İLAÇ SAN. TİC. A.Ş.2012-04-26Not applicableTurkey flag
DUESONIT 18/400 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 120 ADETCiclesonide (400 mcg) + Tiotropium (18 mcg)PowderRespiratory (inhalation)NEUTEC İLAÇ SAN. TİC. A.Ş.2012-04-26Not applicableTurkey flag
DUESONIT 18/400 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 60 ADETCiclesonide (400 mcg) + Tiotropium (18 mcg)PowderRespiratory (inhalation)NEUTEC İLAÇ SAN. TİC. A.Ş.2012-04-26Not applicableTurkey flag
FORLEX 6/200MCG INHALASYON IÇIN ÖLÇÜLÜ DOZLU AEROSOL, 120 DOZCiclesonide (200 mcg) + Formoterol fumarate (6 mcg)AerosolRespiratory (inhalation)NEUTEC İNHALER İLAÇ SAN. VE TİC. A.Ş.2013-09-11Not applicableTurkey flag

Categories

ATC Codes
R03BA08 — CiclesonideR01AD13 — Ciclesonide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 3-oxo delta-1,4-steroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Alpha-acyloxy ketones / 1,3-dioxolanes / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Carboxylic acid esters
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Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Alpha-acyloxy ketone / Carbonyl group
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
S59502J185
CAS number
126544-47-6
InChI Key
LUKZNWIVRBCLON-GXOBDPJESA-N
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
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
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(O[C@@H](O2)C1CCCCC1)C(=O)COC(=O)C(C)C

References

Synthesis Reference

Beate Schmidt, "Process for preparing crystalline ciclesonide with defined particle size." U.S. Patent US20060128954, issued June 15, 2006.

US20060128954
General References
  1. Mutch E, Nave R, McCracken N, Zech K, Williams FM: The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol. 2007 May 15;73(10):1657-64. Epub 2007 Jan 28. [Article]
  2. TITCK Product Information: Tivenos (ciclesonide/tiotropium bromide) powder for inhalation [Link]
KEGG Drug
D01703
PubChem Compound
6918155
PubChem Substance
46508553
ChemSpider
5293368
BindingDB
50247997
RxNav
274964
ChEBI
31397
ChEMBL
CHEMBL2040682
ZINC
ZINC000003915154
Therapeutic Targets Database
DAP000423
PharmGKB
PA164781399
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ciclesonide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAllergic Rhinitis (AR)2
4CompletedTreatmentAsthma4
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentPerennial Allergic Rhinitis (PAR)2
4RecruitingPreventionAsthma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • 3M Health Care
  • Nycomed Inc.
  • Physicians Total Care Inc.
  • Sepracor Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
PowderRespiratory (inhalation)200 mcg
PowderRespiratory (inhalation)400 mcg
AerosolBuccal0.840 mg
Aerosol, meteredRespiratory (inhalation)100 mcg / act
Aerosol, meteredRespiratory (inhalation)160 ug/1
Aerosol, meteredRespiratory (inhalation)160 MCG
Aerosol, meteredRespiratory (inhalation)200 mcg / act
Aerosol, meteredRespiratory (inhalation)40 MCG
Aerosol, meteredRespiratory (inhalation)50 mcg / act
Aerosol, meteredRespiratory (inhalation)80 MCG
Aerosol, meteredRespiratory (inhalation)80 ug/1
Aerosol, meteredOropharyngeal160 mcg
Aerosol, spray160 mcg
Aerosol; solutionRespiratory (inhalation)160 mcg
Aerosol, meteredRespiratory (inhalation)160 Mikrogramm
GasRespiratory (inhalation)160 UG
Aerosol, meteredOropharyngeal80 mcg
Aerosol, spray80 mcg/spray
Aerosol, spray80 mcg
Aerosol; solutionRespiratory (inhalation)80 mcg
Aerosol, meteredRespiratory (inhalation)80 Mikrogramm
GasRespiratory (inhalation)80 UG
AerosolRespiratory (inhalation)0.34 % w/w
AerosolRespiratory (inhalation)80 mcg
SuspensionOral; Respiratory (inhalation)160 mcg
SuspensionRespiratory (inhalation)160 mcg
SuspensionRespiratory (inhalation)80 mcg
Aerosol, meteredRespiratory (inhalation)160 MICROGRAMMI
Aerosol, meteredRespiratory (inhalation)320 MICROGRAMMI
Aerosol, meteredRespiratory (inhalation)80 MICROGRAMMI
SolutionRespiratory (inhalation)160 mcg
SolutionRespiratory (inhalation)80 mcg
AerosolRespiratory (inhalation)160 mcg
SuspensionIntrasinal; Nasal50 mcg
AerosolRespiratory (inhalation)
PowderRespiratory (inhalation)
SprayNasal50 ug/1
Spray, meteredNasal50 mcg / act
SuspensionNasal0.714 mg
Spray, suspensionNasal50 mcg/1dose
Spray, metered; spray, suspensionNasal50 mcg/spray
Spray, metered; spray, suspensionNasal
Aerosol, meteredNasal50 mcg / act
SprayNasal50 mcg
Spray, suspensionNasal0.05 mg
SuspensionIntrasinal; Nasal0.714 mg
PowderRespiratory (inhalation)
Spray, suspensionNasal50 mcg
Aerosol, meteredNasal37 ug/1
Aerosol, meteredRespiratory (inhalation)160 mcg/1dose
Aerosol, meteredRespiratory (inhalation)80 mcg/1dose
Prices
Unit descriptionCostUnit
Alvesco 160 mcg/act Aerosol 6.1 gm Inhaler162.24USD inhaler
Alvesco 80 mcg/act Aerosol 6.1 gm Inhaler162.24USD inhaler
Alvesco 160 mcg inhaler31.1USD g
Alvesco 80 mcg inhaler31.1USD g
Omnaris 50 mcg nasal spray11.01USD g
Alvesco 200 mcg/dose Metered Dose Aerosol0.66USD dose
Alvesco 100 mcg/dose Metered Dose Aerosol0.4USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5695743No1997-12-092010-07-06US flag
CA2388325No2007-09-182020-10-20Canada flag
CA2050812No2003-07-292011-09-06Canada flag
US5775321No1998-07-072015-07-07US flag
US5482934No1996-01-092017-10-24US flag
US8371292No2013-02-122028-02-01US flag
US7235247No2007-06-262019-04-21US flag
US6767901No2004-07-272020-10-21US flag
US6939559No2005-09-062019-04-21US flag
US8383611No2013-02-262020-10-20US flag
US6264923No2001-07-242018-05-13US flag
US6006745No1999-12-282016-12-28US flag
US6120752No2000-09-192018-05-13US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00157 mg/mLALOGPS
logP4.08ALOGPS
logP5.32Chemaxon
logS-5.5ALOGPS
pKa (Strongest Acidic)14.78Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area99.13 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity146.28 m3·mol-1Chemaxon
Polarizability60.18 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9907
Blood Brain Barrier+0.9439
Caco-2 permeable-0.6847
P-glycoprotein substrateSubstrate0.7787
P-glycoprotein inhibitor IInhibitor0.8247
P-glycoprotein inhibitor IIInhibitor0.9476
Renal organic cation transporterNon-inhibitor0.7744
CYP450 2C9 substrateNon-substrate0.8232
CYP450 2D6 substrateNon-substrate0.915
CYP450 3A4 substrateSubstrate0.774
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.7104
CYP450 2D6 inhibitorNon-inhibitor0.9407
CYP450 2C19 inhibitorNon-inhibitor0.9151
CYP450 3A4 inhibitorNon-inhibitor0.6192
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8478
Ames testNon AMES toxic0.9032
CarcinogenicityNon-carcinogens0.9367
BiodegradationNot ready biodegradable0.9897
Rat acute toxicity3.5547 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9738
hERG inhibition (predictor II)Non-inhibitor0.595
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0077-0104960000-afad4e3dad1343274b4e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-3000390000-a2b8cf8066ae7983ac77
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0h2g-2302940000-36f32222e0a9cc04555c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f79-9000810000-db052c2b6645fbb6304e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-6120910000-e7d343ec2a4e492eb9fb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-2941420000-2140ef4def0d6417d1f7
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-245.3986459
predicted
DarkChem Lite v0.1.0
[M-H]-226.19966
predicted
DeepCCS 1.0 (2019)
[M+H]+244.3375459
predicted
DarkChem Lite v0.1.0
[M+H]+228.09508
predicted
DeepCCS 1.0 (2019)
[M+Na]+233.87302
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Barnes NC: The properties of inhaled corticosteroids: similarities and differences. Prim Care Respir J. 2007 Jun;16(3):149-54. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Mutch E, Nave R, McCracken N, Zech K, Williams FM: The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol. 2007 May 15;73(10):1657-64. Epub 2007 Jan 28. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [Article]
  2. Bohmer GM, Drollmann A, Gleiter CH, Nave R: Effect of coadministered ketoconazole, a strong cytochrome P450 3A4 enzyme inhibitor, on the pharmacokinetics of ciclesonide and its active metabolite desisobutyryl-ciclesonide. Clin Pharmacokinet. 2008;47(5):343-9. doi: 10.2165/00003088-200847050-00005. [Article]
  3. Nave R, McCracken N: Metabolism of ciclesonide in the upper and lower airways: review of available data. J Asthma Allergy. 2008 Sep 7;1:11-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Peet CF, Enos T, Nave R, Zech K, Hall M: 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. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at July 17, 2007 12:38 / Updated at March 18, 2024 16:48