Details of the Drug

General Information of Drug (ID: DM5NW1E)

Drug Name
Beclomethasone dipropionate
Synonyms
BECLOMETHASONE DIPROPIONATE; Beclometasone dipropionate; Beconase; Beclovent; Vancenase; Beclorhinol; Becloforte; Sanasthmyl; Beclazone; Sanasthmax; Propaderm; Beclomet; Vanceril; Aerobec; Becloturmant; Beclacin; Respocort; Entyderma; Korbutone; Viarox; Rino-clenil; Clenil-A; Beclometasone 17,21-dipropionate; Becotide; Aldecin; Turbinal; Aldecina; Rhinosol; Beclate; Atomase; Alanase; Benconase; Aldecine; Clenil; Spir; Beclocort Nasel; Beclomet Nasal; Propaderm Forte; Rhino Clenil; Inalone O; Inalone R; Qvar; QNASL; Beconase AQ; Qvar 80
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Nasal polyp CA0J Approved [1]
Rhinitis FA20 Approved [1]
Vasomotor/allergic rhinitis CA08 Approved [1]
Asthma CA23 Investigative [1]
Affected Organisms
Humans and other mammals
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 521
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 88 ng/L [2]
Clearance
The clearance of drug is 150 L/h [3]
Elimination
Regardless of the route of administration, beclomethasone dipropionate and its metabolites are predominantly excreted in the feces, with less than 10% of the drug and its metabolites being excreted in the urine [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.5 hours [3]
Metabolism
The drug is metabolized via the esterases CYP3A to form beclomethasone-17-monopropionate (17-BMP), beclomethasone-21-monopropionate (21-BMP), and beclomethasone (BOH) [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.055 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.13% [5]
Vd
The volume of distribution (Vd) of drug is 20 L [3]
Chemical Identifiers
Formula
C28H37ClO7
IUPAC Name
[2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
Canonical SMILES
CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)OC(=O)CC
InChI
InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
InChIKey
KUVIULQEHSCUHY-XYWKZLDCSA-N
Cross-matching ID
PubChem CID
21700
ChEBI ID
CHEMBL3002
CAS Number
5534-09-8
UNII
5B307S63B2
DrugBank ID
DB00394
VARIDT ID
DR01665
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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 [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [7]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Gene/Protein Processing [8]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [9]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [10]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [10]
C-C motif chemokine 4 (CCL4) OT6B8P25 CCL4_HUMAN Gene/Protein Processing [10]
C-C motif chemokine 5 (CCL5) OTSCA5CK CCL5_HUMAN Gene/Protein Processing [11]
Eosinophil cationic protein (RNASE3) OTVE2XD1 ECP_HUMAN Gene/Protein Processing [12]
Glutathione hydrolase 5 proenzyme (GGT5) OTDJYEO7 GGT5_HUMAN Gene/Protein Processing [13]
Interleukin-2 receptor subunit alpha (IL2RA) OT0MWCHG IL2RA_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Beclomethasone dipropionate FDA Label
2 QVAR? (beclomethasone dipropionate HFA) for oral inhalation use - FDA Label
3 Beclomethasone dipropionate: absolute bioavailability, pharmacokinetics and metabolism following intravenous, oral, intranasal and inhaled administration in man. Br J Clin Pharmacol. 2001 May;51(5):400-9. doi: 10.1046/j.0306-5251.2001.01374.x.
4 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
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. Toxicol Appl Pharmacol. 2012 May 1;260(3):294-302.
7 Induction of drug-metabolizing enzymes and transporters in human bronchial epithelial cells by beclomethasone dipropionate. IUBMB Life. 2004 Jun;56(6):355-9.
8 Biochemical interaction between effects of beclomethasone dipropionate and salbutamol or formoterol in sputum cells from mild to moderate asthmatics. Allergy. 2005 Mar;60(3):323-9. doi: 10.1111/j.1398-9995.2005.00702.x.
9 Modulation of p-glycoprotein and breast cancer resistance protein by some prescribed corticosteroids. Eur J Pharmacol. 2006 Feb 15;531(1-3):25-33. doi: 10.1016/j.ejphar.2005.12.010. Epub 2006 Jan 25.
10 Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. Leuk Res. 2010 Jul;34(7):917-24. doi: 10.1016/j.leukres.2009.12.002. Epub 2010 Feb 8.
11 Expression of RANTES by human bronchial epithelial cells in vitro and in vivo and the effect of corticosteroids. Am J Respir Cell Mol Biol. 1996 Jan;14(1):27-35. doi: 10.1165/ajrcmb.14.1.8534483.
12 Effect of inhaled beclomethasone dipropionate and budesonide dry powder on pulmonary function and serum eosinophil cationic protein in adult asthmatics. J Investig Allergol Clin Immunol. 1999 Jul-Aug;9(4):241-7.
13 A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism. J Allergy Clin Immunol. 2001 Jul;108(1):122-4.
14 Inhaled beclomethasone dipropionate downregulates airway lymphocyte activation in atopic asthma. Am J Respir Crit Care Med. 1994 Jan;149(1):86-90. doi: 10.1164/ajrccm.149.1.8111605.