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

General Information of Drug (ID: DR0248)
Drug Name
Buspirone
Synonyms
Buspirona; Buspirona [INN-Spanish]; Buspirone [INN:BAN]; Buspironum; Buspironum [INN-Latin]; MJ-9022-1; Ansial; Ansiced; Axoren; QWCRAEMEVRGPNT-UHFFFAOYSA-N; TK65WKS8HL; buspirone; 36505-84-7; 8-(4-(4-(2-Pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dione; 8-(4-(4-(Pyrimidin-2-yl)piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione; 8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4.5]decane-7,9-dione; BRN 0964904; C21H31N5O2; CHEBI:3223; CHEMBL49; EINECS 253-072-2; UNII-TK65WKS8HL
Indication Anxiety disorder [ICD11: 6B00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 385.5 Topological Polar Surface Area 69.6
Heavy Atom Count 28 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
2477
PubChem SID
9079 ; 4652644 ; 7978828 ; 8151653 ; 10589701 ; 11110857 ; 11112732 ; 11113821 ; 11336096 ; 11361335 ; 11364650 ; 11367212 ; 11369774 ; 11377936 ; 11462307 ; 11466397 ; 11467517 ; 11486154 ; 11495570 ; 11533496 ; 14902734 ; 24714738 ; 25671043 ; 26751994 ; 29221641 ; 46508113 ; 47365265 ; 47365266 ; 47440338 ; 47589062 ; 47662354 ; 48259310 ; 48259311 ; 48259312 ; 48415667 ; 49698848 ; 49872682 ; 50104669 ; 51066541 ; 51091905 ; 53790629 ; 57321342 ; 85209802 ; 85787807 ; 85788842 ; 90340780 ; 92309215 ; 93166677 ; 103166970 ; 103916226
ChEBI ID
ChEBI:3223
CAS Number
36505-84-7
TTD Drug ID
D0U2OO
Formula
C21H31N5O2
Canonical SMILES
C1CCC2(C1)CC(=O)N(C(=O)C2)CCCCN3CCN(CC3)C4=NC=CC=N4
InChI
1S/C21H31N5O2/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2
InChIKey
QWCRAEMEVRGPNT-UHFFFAOYSA-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
3'-hydroxybuspirone DM000704
59058967
Oxidation - Hydroxylation 1 [7]
5-hydroxybuspirone DM000700
59964599
Oxidation - Hydroxylation 1 [8]
6'-hydroxybuspirone DM000705
9930913
Oxidation - Hydroxylation 1 [7] , [9]
Buspirone N-oxide DM000703
15234439
Oxidation - N-Oxidation 1 [7]
PF-00734200 metabolite M3 DM000702
88747
Oxidation - N-Dealkylation 1 [4] , [7] , [9]
Hydroxy derivatives of Buspirone DM000701 N. A. Unclear 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000522 Buspirone 5-hydroxybuspirone Oxidation - Hydroxylation CYP3A4 [8]
MR000523 Buspirone 1-Pyrimidinylpiperazine Oxidation - N-Dealkylation CYP3A4 [4], [7], [9]
MR000524 Buspirone Buspirone N-oxide Oxidation - N-Oxidation CYP3A4 ... [7]
MR000525 Buspirone 3'-hydroxybuspirone Oxidation - Hydroxylation CYP3A4 [7]
MR000526 Buspirone 6'-hydroxybuspirone Oxidation - Hydroxylation CYP3A4 [7], [9]
MR000521 5-hydroxybuspirone Hydroxy derivatives of Buspirone Unclear Unclear [8]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[2] , [3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[6]
References
1 Buspirone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
3 acillus megaterium SF185 spores exert protective effects against oxidative stress in vivo and in vitro. Sci Rep. 2019 Aug 19;9(1):12082.
4 Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7.
5 Effects of cytochrome P450 (CYP) 3A4 inhibitors on the anxiolytic action of tandospirone in rat contextual conditioned fear. Prog Neuropsychopharmacol Biol Psychiatry. 2007 May 9;31(4):926-31.
6 Drug Interactions Flockhart Table
7 DrugBank(Pharmacology-Metabolism)Buspirone
8 Metabolism and disposition of buspirone Am J Med. 1986 Mar 31;80(3B):41-51. doi: 10.1016/0002-9343(86)90331-1.
9 Interaction of buspirone and its major metabolites with human organic cation transporters. Fundam Clin Pharmacol. 2023 Feb 26. doi: 10.1111/fcp.12883.

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