Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014633
Secondary Accession Numbers
  • HMDB14633
Metabolite Identification
Common NameBuspirone
DescriptionBuspirone is only found in individuals that have used or taken this drug. It is an anxiolytic agent and a serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the benzodiazepines, but it has an efficacy comparable to diazepam. [PubChem]Buspirone binds to 5-HT type 1A serotonin receptors on presynaptic neurons in the dorsal raphe and on postsynaptic neurons in the hippocampus, thus inhibiting the firing rate of 5-HT-containing neurons in the dorsal raphe. Buspirone also binds at dopamine type 2 (DA2) receptors, blocking presynaptic dopamine receptors. Buspirone increases firing in the locus ceruleus, an area of brain where norepinephrine cell bodies are found in high concentration. The net result of buspirone actions is that serotonergic activity is suppressed while noradrenergic and dopaminergic cell firing is enhanced.
Structure
Data?1582753201
Synonyms
ValueSource
8-(4-(4-(2-Pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dioneChEBI
BuspironaChEBI
BuspironumChEBI
Gen-buspironeKegg
AnxutHMDB
BesparHMDB
BuspHMDB
Gen buspironeHMDB
Lin buspironeHMDB
Linson pharma brand OF buspirone hydrochlorideHMDB
N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-1-cyclopentanediacetamideHMDB
Nu buspironeHMDB
Ratio-buspironeHMDB
Armstrong brand OF buspirone hydrochlorideHMDB
Bristol myers squibb brand OF buspirone hydrochlorideHMDB
Bristol-myers squibb brand OF buspirone hydrochlorideHMDB
Buspirone hydrochlorideHMDB
Hexal brand OF buspirone hydrochlorideHMDB
NeurosineHMDB
Novo buspironeHMDB
Novo-buspironeHMDB
Nu pharm brand OF buspirone hydrochlorideHMDB
Apo buspironeHMDB
Apo-buspironeHMDB
Genpharm brand OF buspironeHMDB
Novopharm brand OF buspirone hydrochlorideHMDB
Nu-pharm brand OF buspirone hydrochlorideHMDB
PMS BuspironeHMDB
Ratiopharm brand OF buspirone hydrochlorideHMDB
Apotex brand OF buspirone hydrochlorideHMDB
Bristol myers brand OF buspirone hydrochlorideHMDB
Bristol-myers brand OF buspirone hydrochlorideHMDB
BusparHMDB
Eisai brand OF buspirone hydrochlorideHMDB
Hormosan brand OF buspirone hydrochlorideHMDB
Hydrochloride, buspironeHMDB
Lin-buspironeHMDB
Nu-buspironeHMDB
PMS-BuspironeHMDB
Pharmascience brand OF buspirone hydrochlorideHMDB
UPSA brand OF buspirone hydrochlorideHMDB
Ratio buspironeHMDB
Chemical FormulaC21H31N5O2
Average Molecular Weight385.5031
Monoisotopic Molecular Weight385.247775261
IUPAC Name8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
Traditional Namebuspirone
CAS Registry Number36505-84-7
SMILES
O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1
InChI Identifier
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
InChI KeyQWCRAEMEVRGPNT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • Azaspirodecanedione
  • N-arylpiperazine
  • Azaspirodecane
  • Piperidinedione
  • Dialkylarylamine
  • Aminopyrimidine
  • N-alkylpiperazine
  • Piperidinone
  • Delta-lactam
  • Pyrimidine
  • Piperidine
  • Carboxylic acid imide, n-substituted
  • Heteroaromatic compound
  • Carboxylic acid imide
  • Dicarboximide
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point201.5 - 202.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.59 g/LNot Available
LogP2.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM199.330932474
[M+H]+Not Available197.727http://allccs.zhulab.cn/database/detail?ID=AllCCS00001098
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.59 g/LALOGPS
logP1.95ALOGPS
logP1.78ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)7.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.64 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.89 m³·mol⁻¹ChemAxon
Polarizability44.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.44531661259
DarkChem[M-H]-184.75631661259
DeepCCS[M+H]+186.41230932474
DeepCCS[M-H]-184.05430932474
DeepCCS[M-2H]-217.38730932474
DeepCCS[M+Na]+192.66630932474
AllCCS[M+H]+192.932859911
AllCCS[M+H-H2O]+190.732859911
AllCCS[M+NH4]+195.032859911
AllCCS[M+Na]+195.632859911
AllCCS[M-H]-188.932859911
AllCCS[M+Na-2H]-189.332859911
AllCCS[M+HCOO]-190.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BuspironeO=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N13284.8Standard polar33892256
BuspironeO=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N13175.1Standard non polar33892256
BuspironeO=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N13335.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Buspirone GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-3930000000-f72780a741e10d32e14d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Buspirone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-6940000000-197b8ea9ac79cbda753b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone LC-ESI-qTof , Positive-QTOFsplash10-000f-0930000000-081eac0a05abab8fc5fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOFsplash10-000i-0009000000-429c277f63eb2ab52f572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOFsplash10-000i-0009000000-170a03c9244dada2609b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOFsplash10-00di-0922000000-80c9aa9ae15b661116ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOFsplash10-00di-1900000000-fafa91d49f01314afdf12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone LC-ESI-QTOF , positive-QTOFsplash10-00dj-4900000000-460409b07d20201af4142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone , positive-QTOFsplash10-000f-0930000000-081eac0a05abab8fc5fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 60V, Positive-QTOFsplash10-00di-1900000000-1548c934ed4552c550c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 75V, Positive-QTOFsplash10-00di-4900000000-3f738f9b3afda733fdbb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 30V, Positive-QTOFsplash10-00di-0923000000-0432dbe18a87c4f8aac92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 90V, Positive-QTOFsplash10-00ea-9600000000-c19888c809dc5e1e43452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 90V, Positive-QTOFsplash10-00ea-9600000000-306c03950ac42645d6502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 50V, Positive-QTOFsplash10-00dj-4900000000-460409b07d20201af4142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 40V, Positive-QTOFsplash10-00di-1900000000-cd100d009ef3ee04589b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 40V, Positive-QTOFsplash10-00di-1900000000-fafa91d49f01314afdf12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 30V, Positive-QTOFsplash10-00di-0922000000-80c9aa9ae15b661116ad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 45V, Positive-QTOFsplash10-00di-0910000000-cf8501b071281e076ac42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 15V, Positive-QTOFsplash10-000i-0009000000-f8f22927f54be6364e822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Buspirone 50V, Positive-QTOFsplash10-00di-3900000000-1b0646e8d778da56bd8e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Buspirone 10V, Positive-QTOFsplash10-000i-0029000000-e01810fdca67d6848abc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Buspirone 20V, Positive-QTOFsplash10-0079-5679000000-e3b3f87f2a50016515962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Buspirone 40V, Positive-QTOFsplash10-0a4i-8940000000-0f2042c84fa52ff07a002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Buspirone 10V, Negative-QTOFsplash10-001i-0309000000-0cb92cbc3313c049e2b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Buspirone 20V, Negative-QTOFsplash10-0159-0905000000-852ca5ee117750d57ba32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Buspirone 40V, Negative-QTOFsplash10-014i-4910000000-ae14188467b44ba1ea962016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00490 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00490 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00490
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2383
KEGG Compound IDC06861
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBuspirone
METLIN IDNot Available
PubChem Compound2477
PDB IDNot Available
ChEBI ID3223
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Malt EA, Olafsson S, Aakvaag A, Lund A, Ursin H: Altered dopamine D2 receptor function in fibromyalgia patients: a neuroendocrine study with buspirone in women with fibromyalgia compared to female population based controls. J Affect Disord. 2003 Jun;75(1):77-82. [PubMed:12781354 ]
  2. Boido A, Boido CC, Sparatore F: Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes. Farmaco. 2001 Apr;56(4):263-75. [PubMed:11421254 ]
  3. Nader MA, Hannemann M: Interactions of buspirone or gepirone with nicotine on schedule-controlled behavior of pigeons. Behav Pharmacol. 1993 Jun;4(3):263-268. [PubMed:11224194 ]
  4. Pache DM, Fernandez-Perez S, Sewell RD: Buspirone differentially modifies short-term memory function in a combined delayed matching/non-matching to position task. Eur J Pharmacol. 2003 Sep 23;477(3):205-11. [PubMed:14522358 ]
  5. Fernandez-Perez S, Pache DM, Sewell RD: Co-administration of fluoxetine and WAY100635 improves short-term memory function. Eur J Pharmacol. 2005 Oct 17;522(1-3):78-83. Epub 2005 Oct 7. [PubMed:16214127 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. de Boer SF, Lesourd M, Mocaer E, Koolhaas JM: Selective antiaggressive effects of alnespirone in resident-intruder test are mediated via 5-hydroxytryptamine1A receptors: A comparative pharmacological study with 8-hydroxy-2-dipropylaminotetralin, ipsapirone, buspirone, eltoprazine, and WAY-100635. J Pharmacol Exp Ther. 1999 Mar;288(3):1125-33. [PubMed:10027850 ]
  2. Rehman J, Kaynan A, Christ G, Valcic M, Maayani S, Melman A: Modification of sexual behavior of Long-Evans male rats by drugs acting on the 5-HT1A receptor. Brain Res. 1999 Mar 13;821(2):414-25. [PubMed:10064829 ]
  3. Liang KC: Pre- or post-training injection of buspirone impaired retention in the inhibitory avoidance task: involvement of amygdala 5-HT1A receptors. Eur J Neurosci. 1999 May;11(5):1491-500. [PubMed:10215901 ]
  4. Becker C, Hamon M, Benoliel JJ: Prevention by 5-HT1A receptor agonists of restraint stress- and yohimbine-induced release of cholecystokinin in the frontal cortex of the freely moving rat. Neuropharmacology. 1999 Apr;38(4):525-32. [PubMed:10221756 ]
  5. Dupuis DS, Tardif S, Wurch T, Colpaert FC, Pauwels PJ: Modulation of 5-HT1A receptor signalling by point-mutation of cysteine351 in the rat Galpha(o) protein. Neuropharmacology. 1999 Jul;38(7):1035-41. [PubMed:10428422 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Osei-Owusu P, Scrogin KE: Buspirone raises blood pressure through activation of sympathetic nervous system and by direct activation of alpha1-adrenergic receptors after severe hemorrhage. J Pharmacol Exp Ther. 2004 Jun;309(3):1132-40. Epub 2004 Feb 9. [PubMed:14769835 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]