Details of the Drug

General Information of Drug (ID: DMRWLB2)

Drug Name
Fluticasone propionate
Synonyms
FLUTICASONE PROPIONATE; Flovent; Cutivate; Flixotide; Flonase; Flixonase; Flovent HFA; Flunase; Flutide; Fluspiral; Flusonal; atemur; Flutivate; Fluinol; Axotide; Asmatil; Brethal; Flovent Diskus 50; Flixotide Disks; Flixotide Disk; Flovent Diskus; Flovent Diskus 100; Flovent Diskus 250; Flixotide Inhaler; Trialona; Rinosone; Inalacor; Cultivate; Ubizol; Zoflut; Flixonase Nasal Spray; Flonase Aq; Fluticasonpropionat Allen; Fluticasone (propionate); UNII-O2GMZ0LF5W; CCI-18781; CCI 18781; MFCD00866007; O2GMZ0LF5W
Indication
Disease Entry ICD 11 Status REF
Allergic asthma CA23.0 Approved [1]
Allergic rhinitis CA08.0 Approved [1]
Bronchiolitis N.A. Approved [1]
Exanthem N.A. Approved [1]
Granuloma annulare N.A. Approved [1]
Intrinsic asthma N.A. Approved [1]
Primary cutaneous T-cell lymphoma N.A. Approved [1]
Pulmonary emphysema CA21.Z Approved [1]
⏷ Show the Full List of Indication(s)
Affected Organisms
Humans and other mammals
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 500.6
Logarithm of the Partition Coefficient (xlogp) 4
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
Clearance
The clearance of drug is 1093 mL/min []
Elimination
The drug is mainly eliminated in the feces with <5% eliminated in the urine [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 7.8 hours []
Metabolism
The drug is metabolized via the hepatic []
Vd
The volume of distribution (Vd) of drug is 4.2 L/kg []
Chemical Identifiers
Formula
C25H31F3O5S
IUPAC Name
[(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
Canonical SMILES
CCC(=O)OC1(C(CC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C)C(=O)SCF
InChI
InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/m1/s1
InChIKey
WMWTYOKRWGGJOA-CENSZEJFSA-N
Cross-matching ID
PubChem CID
444036
ChEBI ID
CHEMBL1473
CAS Number
80474-14-2
UNII
O2GMZ0LF5W
DrugBank ID
DB00588
VARIDT ID
DR01643
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Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Annexin A1 (ANXA1) OT5OFDJC ANXA1_HUMAN Protein Interaction/Cellular Processes [4]
Antileukoproteinase (SLPI) OTUNFUU8 SLPI_HUMAN Gene/Protein Processing [5]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Regulation of Drug Effects [6]
Glutathione hydrolase 5 proenzyme (GGT5) OTDJYEO7 GGT5_HUMAN Gene/Protein Processing [7]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [8]
Osteocalcin (BGLAP) OTK1YLWQ OSTCN_HUMAN Gene/Protein Processing [9]
Vascular cell adhesion protein 1 OTP74K37 VCAM1_HUMAN Protein Interaction/Cellular Processes [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Fluticasone propionate FDA Label
2 Crim C, Pierre LN, Daley-Yates PT: A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate. Clin Ther. 2001 Sep;23(9):1339-54.
3 Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. Toxicol Appl Pharmacol. 2012 May 1;260(3):294-302.
4 Glucocorticoid-induced surface expression of annexin 1 blocks beta2-integrin adhesion of human eosinophils to intercellular adhesion molecule 1 surrogate protein. J Allergy Clin Immunol. 2005 Mar;115(3):493-500. doi: 10.1016/j.jaci.2004.11.010.
5 Glucocorticoid receptor nuclear translocation in airway cells after inhaled combination therapy. Am J Respir Crit Care Med. 2005 Sep 15;172(6):704-12. doi: 10.1164/rccm.200408-1041OC. Epub 2005 Apr 28.
6 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.
7 A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism. J Allergy Clin Immunol. 2001 Jul;108(1):122-4.
8 Identification and validation of novel human pregnane X receptor activators among prescribed drugs via ligand-based virtual screening. Drug Metab Dispos. 2011 Feb;39(2):337-44. doi: 10.1124/dmd.110.035808. Epub 2010 Nov 10.
9 Improved safety with equivalent asthma control in adults with chronic severe asthma on high-dose fluticasone propionate. Respirology. 2001 Sep;6(3):237-46. doi: 10.1046/j.1440-1843.2001.00329.x.
10 Inhibition of VCAM-1 expression in human bronchial epithelial cells by glucocorticoids. Am J Respir Cell Mol Biol. 1999 Apr;20(4):643-50. doi: 10.1165/ajrcmb.20.4.3265.