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]
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
CHEBI:3002
CAS Number
5534-09-8
DrugBank ID
DB00394
VARIDT ID
DR01665
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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
11-beta-hydroxysteroid dehydrogenase type 2 (HSD11B2) OTHF4H9U DHI2_HUMAN Regulation of Drug Effects [7]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [8]
B1 bradykinin receptor (BDKRB1) OT1DHSVQ BKRB1_HUMAN Gene/Protein Processing [9]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Gene/Protein Processing [10]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [11]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [12]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [12]
C-C motif chemokine 4 (CCL4) OT6B8P25 CCL4_HUMAN Gene/Protein Processing [12]
C-C motif chemokine 5 (CCL5) OTSCA5CK CCL5_HUMAN Gene/Protein Processing [13]
C-X-C motif chemokine 10 (CXCL10) OTTLQ6S0 CXL10_HUMAN Protein Interaction/Cellular Processes [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 Metabolism of synthetic steroids by the human placenta. Placenta. 2007 Jan;28(1):39-46.
8 Induction of drug-metabolizing enzymes and transporters in human bronchial epithelial cells by beclomethasone dipropionate. IUBMB Life. 2004 Jun;56(6):355-9.
9 Comparison of kinin B(1) and B(2) receptor expression in neutrophils of asthmatic and non-asthmatic subjects. Int Immunopharmacol. 2007 Dec 20;7(14):1862-8. doi: 10.1016/j.intimp.2007.07.012. Epub 2007 Aug 6.
10 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.
11 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.
12 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.
13 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.
14 The role of IFN-gamma in regulation of IFN-gamma-inducible protein 10 (IP-10) expression in lung epithelial cell and peripheral blood mononuclear cell co-cultures. Respir Res. 2007 Nov 8;8(1):80. doi: 10.1186/1465-9921-8-80.