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]
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Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

500.6

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:31441
CAS Number: 80474-14-2
DrugBank ID: DB00588
VARIDT ID: DR01643

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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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]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[7]
Cytochrome P450 3A5 (CYP3A5)	OTSXFBXB	CP3A5_HUMAN	Gene/Protein Processing	[8]
Cytosolic phospholipase A2 (PLA2G4A)	OTE70SOT	PA24A_HUMAN	Protein Interaction/Cellular Processes	[4]
Dual specificity protein phosphatase 1 (DUSP1)	OTN6BR75	DUS1_HUMAN	Gene/Protein Processing	[5]
Glucocorticoid receptor (NR3C1)	OTCI2YDI	GCR_HUMAN	Protein Interaction/Cellular Processes	[5]
Glutathione hydrolase 5 proenzyme (GGT5)	OTDJYEO7	GGT5_HUMAN	Gene/Protein Processing	[9]
Granulocyte-macrophage colony-stimulating factor (CSF2)	OT1M7D28	CSF2_HUMAN	Protein Interaction/Cellular Processes	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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	The inhaled glucocorticoid fluticasone propionate efficiently inactivates cytochrome P450 3A5, a predominant lung P450 enzyme. Chem Res Toxicol. 2010 Aug 16;23(8):1356-64.
8	Regulation of CYP3A genes by glucocorticoids in human lung cells. F1000Res. 2013 Aug 13;2:173.
9	A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism. J Allergy Clin Immunol. 2001 Jul;108(1):122-4.
10	Inhibition of GM-CSF secretion by topical corticosteroids and nedocromil sodium. A comparison study using nasal polyp epithelial cells. Respir Med. 2000 May;94(5):428-31. doi: 10.1053/rmed.1999.0756.