This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Fluticasone
Accession Number
DB13867
Type
Small Molecule
Groups
Approved, Experimental
Description

Fluticasone is a synthetic glucocorticoid which is used in some countries to treat nasal symptoms. Both the furoate and propanoate esters, fluticasone furoate and fluticasone propionate, are also used as topical anti-inflammatories and inhaled corticosteroids, and are used much more commonly in comparison.

Structure
Thumb
Synonyms
  • Fluticason
  • Fluticasona
  • Fluticasone
  • Fluticasonum
Categories
UNII
CUT2W21N7U
CAS number
90566-53-3
Weight
Average: 444.51
Monoisotopic: 444.158215012
Chemical Formula
C22H27F3O4S
InChI Key
MGNNYOODZCAHBA-GQKYHHCASA-N
InChI
InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
IUPAC Name
(1R,2R,3aS,3bS,5S,9aS,9bR,10S,11aS)-5,9b-difluoro-1-{[(fluoromethyl)sulfanyl]carbonyl}-1,10-dihydroxy-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)SCF

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Fluticasone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Fluticasone.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Fluticasone.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Fluticasone.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Fluticasone.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Fluticasone.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Fluticasone.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Fluticasone.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Fluticasone.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Fluticasone.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D07981
KEGG Compound
C07815
ChemSpider
4470631
ChEBI
5134
ChEMBL
CHEMBL1201396
Wikipedia
Fluticasone
ATC Codes
R03AK11 — Formoterol and fluticasoneR01AD08 — FluticasoneR01AD58 — Fluticasone, combinationsR03AK06 — Salmeterol and fluticasoneR03BA05 — FluticasoneD07AC17 — Fluticasone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAllergic Rhinitis (AR)1
3Not Yet RecruitingTreatmentAllergies1
3RecruitingTreatmentAsthma Bronchial1
4CompletedTreatmentAsthma Bronchial3
4Not Yet RecruitingTreatmentOtitis Media With Effusion1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0344 mg/mLALOGPS
logP2.69ALOGPS
logP2.58ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity107.87 m3·mol-1ChemAxon
Polarizability43.16 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inhibitor
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. NCI/NIH [Link]
  2. FDA reports [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
  2. FDA reports [Link]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA reports [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. FDA reports [Link]

Drug created on July 04, 2017 18:00 / Updated on November 02, 2018 07:47