Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0180)
Drug Name
Beclomethasone dipropionate
Synonyms
Aerobec; Alanase; Aldecin; Aldecina; Aldecine; Atomase; BECLOMETHASONE DIPROPIONATE; Beclacin; Beclate; Beclazone; Beclocort Nasel; Becloforte; Beclomet; Beclomet Nasal; Beclometasone 17,21-dipropionate; Beclometasone dipropionate; Beclorhinol; Becloturmant; Beclovent; Beconase; Beconase AQ; Becotide; Benconase; Clenil; Clenil-A; Entyderma; Inalone O; Inalone R; Korbutone; Propaderm; Propaderm Forte; QNASL; Qvar; Qvar 80; Respocort; Rhino Clenil; Rhinosol; Rino-clenil; Sanasthmax; Sanasthmyl; Spir; Turbinal; Vancenase; Vanceril; Viarox; Beclomethasone; Beclometasone; Beclometasonum; Beclometasona; 4419-39-0; Beclometasonum [INN-Latin]; Beclometasona [INN-Spanish]; UNII-KGZ1SLC28Z; C22H29ClO5; MLS000028668; Beclometasone [INN]; BMJ 5800; EINECS 224-585-9; KGZ1SLC28Z; SMR000058899; 9-Chloro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione; CHEBI:3001; Beclometasone (INN); (8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one; 5534/9/8
Indication Allergic rhinitis [ICD11: CA08] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 521 Topological Polar Surface Area 107
Heavy Atom Count 36 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
21700
ChEBI ID
CHEBI:3002
CAS Number
5534-09-8
TTD Drug ID
D07DVK
Formula
C28H37ClO7
Canonical SMILES
CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)OC(=O)CC
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
6beta-OH-BDP DM017733 N. A. Unclear - Unclear 1 [4]
Beclomethasone dipropionate Metabolite M5 DM005646
44306855
Unclear - Unclear 1 [4]
Beclomethasone-17-monopropionate (17-BMP) DM005642
62965
Hydrolysis - Hydrolysis 1 [8]
Beclomethasone-21-monopropionate (21-BMP) DM005644
9934186
Hydrolysis - Hydrolysis 1 [5]
Beclomethasone (BOH) DM005643
20469
Hydrolysis - Esterase hydrolysis 2 [5]
Beclomethasone dipropionate Metabolite D-2 DM015092
91242
Hydrolysis - Esterase hydrolysis 2 [5]
Beclomethasone dipropionate Metabolite D-3 DM016429
92030122
Unclear - Unclear 2 [5]
Beclomethasone-21-monopropionate (21-BMP) DM005644
9934186
Unclear - Unclear 2 [5]
Beclomethasone (BOH) DM005643
20469
Hydrolysis - Esterase hydrolysis 3 [5]
Beclomethasone dipropionate Metabolite D-2 DM015092
91242
Unclear - Unclear 3 [5]
Beclomethasone dipropionate Metabolite D-3 DM016429
92030122
Unclear - Unclear 3 [5]
Beclomethasone dipropionate Metabolite D-2 DM015092
91242
Unclear - Unclear 4 [5]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009246 Beclomethasone dipropionate Beclomethasone-17-monopropionate (17-BMP) Hydrolysis - Hydrolysis CES ... [8]
MR009251 Beclomethasone dipropionate Beclomethasone-21-monopropionate (21-BMP) Hydrolysis - Hydrolysis CYP3A4 ... [5]
MR009253 Beclomethasone dipropionate 6beta-OH-BDP Unclear - Unclear CYP3A4 ... [4]
MR009254 Beclomethasone dipropionate Delta6-BDP Unclear - Unclear CYP3A4 ... [4]
MR009247 Beclomethasone-17-monopropionate (17-BMP) Beclomethasone-21-monopropionate (21-BMP) Unclear - Unclear Unclear [5]
MR009252 Beclomethasone-17-monopropionate (17-BMP) Beclomethasone dipropionate Metabolite D-2 Hydrolysis - Esterase hydrolysis Unclear [5]
MR009248 Beclomethasone-21-monopropionate (21-BMP) Beclomethasone dipropionate Metabolite D-3 Unclear - Unclear Unclear [5]
MR009250 Beclomethasone-21-monopropionate (21-BMP) Beclomethasone (BOH) Hydrolysis - Esterase hydrolysis Unclear [5]
MR009249 Beclomethasone dipropionate Metabolite D-3 Beclomethasone dipropionate Metabolite D-2 Unclear - Unclear Unclear [5]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Corticosteroid 11-beta-dehydrogenase 2 (HSD11B2) DME0419 Homo sapiens
DHI2_HUMAN
1.1.1.B40
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A43 (CYP3A43) DME0022 Homo sapiens
CP343_HUMAN
1.14.14.1
[6] , [7]
Cytochrome P450 3A43 (CYP3A43) DME0022 Homo sapiens
CP343_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6] , [7]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[6] , [7]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
⏷ Show the Full List of 10  DME(s)
References
1 Beclomethasone Dipropionate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Involvement of esterases in the pulmonary metabolism of beclomethasone dipropionate and the potential influence of cannabis use
3 Metabolism of synthetic steroids by the human placenta. Placenta. 2007 Jan;28(1):39-46.
4 Metabolism of beclomethasone dipropionate by cytochrome P450 3A enzymes. J Pharmacol Exp Ther. 2013 May;345(2):308-16.
5 Comparative kinetics of metabolism of beclomethasone propionate esters in human lung homogenates and plasma
6 Activation of beclomethasone dipropionate by hydrolysis to beclomethasone-17-monopropionate
7 Degradation products of beclomethasone dipropionate in human plasma
8 DrugBank(Pharmacology-Metabolism):Beclomethasone dipropionate

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