buspirone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anxiolytics, buspirone derivatives 437 36505-84-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • buspirone
  • buspin
  • buspirone hydrochloride
  • buspirone HCl
An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.
  • Molecular weight: 385.51
  • Formula: C21H31N5O2
  • CLOGP: 2.19
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 0
  • TPSA: 69.64
  • ALOGS: -2.82
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
30 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.02 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.59 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 3.90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Sept. 29, 1986 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 465.18 12.61 449 21573 145471 46518569
Anxiety 136.58 12.61 279 21743 181678 46482362
Depression 129.03 12.61 262 21760 169842 46494198
Serotonin syndrome 107.33 12.61 90 21932 24130 46639910
Suicidal ideation 99.95 12.61 128 21894 56254 46607786
Toxicity to various agents 86.32 12.61 257 21765 211509 46452531
Withdrawal syndrome 61.63 12.61 58 21964 18076 46645964
Neuroleptic malignant syndrome 48.57 12.61 41 21981 11081 46652959
Overdose 44.54 12.61 127 21895 101852 46562188
Stiff person syndrome 42.29 12.61 11 22011 174 46663866
Panic attack 39.09 12.61 48 21974 20194 46643846
Agitation 37.96 12.61 82 21940 55333 46608707
Rheumatoid arthritis 37.33 12.61 35 21987 240180 46423860
Tremor 35.85 12.61 128 21894 115511 46548529
Poisoning 35.14 12.61 38 21984 13956 46650084
Drug withdrawal syndrome 33.37 12.61 52 21970 27332 46636708
Cardio-respiratory arrest 32.65 12.61 81 21941 59788 46604252
Insomnia 31.18 12.61 157 21865 164767 46499273
Febrile neutropenia 31.02 12.61 4 22018 94623 46569417
Disturbance in attention 30.50 12.61 54 21968 31506 46632534
Weight increased 29.99 12.61 155 21867 164318 46499722
Anoxia 29.48 12.61 9 22013 260 46663780
Extrapyramidal disorder 29.00 12.61 31 21991 11237 46652803
Neutropenia 27.15 12.61 17 22005 143187 46520853
Mydriasis 27.10 12.61 29 21993 10524 46653516
Hypothermia 27.01 12.61 31 21991 12152 46651888
Plasma cell mastitis 26.90 12.61 5 22017 13 46664027
Respiratory arrest 26.62 12.61 53 21969 33763 46630277
Intentional overdose 25.58 12.61 78 21944 64866 46599174
Drug screen false positive 25.50 12.61 11 22011 866 46663174
Somnolence 24.16 12.61 141 21881 156380 46507660
Treatment failure 24.09 12.61 7 22015 93080 46570960
Thrombocytopenia 24.03 12.61 15 22007 126566 46537474
Migraine 23.85 12.61 80 21942 69946 46594094
Suicide attempt 23.48 12.61 68 21954 54968 46609072
Emotional disorder 23.43 12.61 29 21993 12295 46651745
Anaemia 23.34 12.61 54 21968 255725 46408315
Injection site mass 23.31 12.61 32 21990 15008 46649032
False positive investigation result 23.09 12.61 9 22013 547 46663493
Pre-existing condition improved 22.17 12.61 21 22001 6591 46657449
Panic disorder 21.51 12.61 14 22008 2547 46661493
Product dose omission issue 21.15 12.61 144 21878 168376 46495664
Pancytopenia 20.93 12.61 7 22015 85051 46578989
Suspected suicide 19.98 12.61 17 22005 4644 46659396
Fibromyalgia 19.52 12.61 49 21973 36414 46627626
Sleep apnoea syndrome 18.94 12.61 36 21986 22165 46641875
Anticholinergic syndrome 17.99 12.61 11 22011 1795 46662245
Exposure via ingestion 17.70 12.61 14 22008 3453 46660587
Bipolar disorder 17.17 12.61 19 22003 7158 46656882
Rhabdomyolysis 17.13 12.61 51 21971 41858 46622182
Surgery 16.81 12.61 40 21982 28745 46635295
Mania 16.70 12.61 23 21999 10823 46653217
Exposure during pregnancy 16.51 12.61 16 22006 108196 46555844
Memory impairment 16.30 12.61 76 21946 77261 46586779
Generalised anxiety disorder 16.26 12.61 10 22012 1650 46662390
Bradykinesia 16.05 12.61 14 22008 3952 46660088
Drug intolerance 16.00 12.61 28 21994 147021 46517019
Flat affect 15.80 12.61 9 22013 1289 46662751
Irritability 15.60 12.61 39 21983 28907 46635133
Infusion related reaction 15.40 12.61 15 22007 101193 46562847
Hallucination, auditory 15.35 12.61 22 22000 10734 46653306
Cerebellar infarction 15.25 12.61 10 22012 1842 46662198
Muscle rigidity 15.15 12.61 21 22001 9940 46654100
Anger 15.13 12.61 23 21999 11829 46652211
Autonomic nervous system imbalance 15.04 12.61 11 22011 2415 46661625
Behaviour disorder 14.73 12.61 10 22012 1951 46662089
Sedation 14.66 12.61 33 21989 22877 46641163
Diabetic neuropathy 14.59 12.61 13 22009 3776 46660264
General physical health deterioration 14.55 12.61 20 22002 115749 46548291
Therapy cessation 14.48 12.61 36 21986 26593 46637447
Akathisia 14.42 12.61 18 22004 7696 46656344
Nightmare 14.26 12.61 27 21995 16571 46647469
Depressed mood 14.04 12.61 41 21981 33278 46630762
Narcolepsy 14.01 12.61 8 22014 1151 46662889
Mental disorder 14.01 12.61 32 21990 22393 46641647
Renal impairment 13.85 12.61 9 22013 74363 46589677
Alcoholism 13.62 12.61 10 22012 2208 46661832
Product substitution issue 13.60 12.61 25 21997 15006 46649034
Alcohol withdrawal syndrome 13.52 12.61 7 22015 830 46663210
Hyperhidrosis 13.47 12.61 80 21942 89228 46574812
Cognitive disorder 13.32 12.61 43 21979 36840 46627200
Delusion 13.29 12.61 21 22001 11167 46652873
Illness 13.23 12.61 22 22000 12202 46651838
Macroglossia 13.11 12.61 6 22016 544 46663496
Accidental death 12.94 12.61 9 22013 1826 46662214
Cardiac death 12.77 12.61 6 22016 577 46663463
Lower respiratory tract infection 12.76 12.61 5 22017 55084 46608956
Psychotic disorder 12.74 12.61 31 21991 22590 46641450
Appetite disorder 12.72 12.61 14 22008 5240 46658800

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 129.65 15.98 147 8005 99345 29844981
Anxiety 115.70 15.98 132 8020 89739 29854587
Serotonin syndrome 85.81 15.98 56 8096 17835 29926491
Suicidal ideation 71.63 15.98 67 8085 36047 29908279
Agitation 55.64 15.98 71 8081 54002 29890324
Electrocardiogram QRS complex prolonged 40.93 15.98 21 8131 4256 29940070
Depression 37.92 15.98 79 8073 90358 29853968
Sedation 37.58 15.98 33 8119 16340 29927986
Insomnia 35.08 15.98 78 8074 93258 29851068
Tremor 34.15 15.98 68 8084 75295 29869031
Irritability 33.23 15.98 36 8116 23014 29921312
Muscle necrosis 32.59 15.98 11 8141 773 29943553
Lens dislocation 28.65 15.98 5 8147 17 29944309
Withdrawal syndrome 28.51 15.98 24 8128 11226 29933100
Akathisia 27.11 15.98 18 8134 5886 29938440
Toxicity to various agents 26.72 15.98 107 8045 177076 29767250
Anger 26.70 15.98 23 8129 11097 29933229
Neuroleptic malignant syndrome 26.24 15.98 27 8125 16268 29928058
Product dose omission issue 25.26 15.98 68 8084 91563 29852763
Nightmare 25.06 15.98 23 8129 12053 29932273
Hypertensive urgency 23.40 15.98 5 8147 58 29944268
Fear of weight gain 22.61 15.98 4 8148 15 29944311
Feeling abnormal 19.70 15.98 46 8106 56710 29887616
Electrocardiogram QT prolonged 19.51 15.98 35 8117 35800 29908526
Seizure 19.48 15.98 65 8087 98410 29845916
Orthostatic tremor 18.33 15.98 3 8149 6 29944320
Atrioventricular block second degree 17.97 15.98 11 8141 3129 29941197
Gynaecomastia 17.51 15.98 16 8136 8335 29935991
Pneumonia 17.46 15.98 41 8111 334265 29610061
Drug withdrawal syndrome 17.25 15.98 24 8128 19785 29924541
Panic attack 16.98 15.98 16 8136 8665 29935661
Feeling of despair 16.42 15.98 7 8145 933 29943393
Dysphoria 16.20 15.98 9 8143 2139 29942187
Bipolar disorder 16.11 15.98 11 8141 3765 29940561

Pharmacologic Action:

SourceCodeDescription
ATC N05BE01 NERVOUS SYSTEM
PSYCHOLEPTICS
ANXIOLYTICS
Azaspirodecanedione derivatives
CHEBI has role CHEBI:35474 minor tranquilisers
CHEBI has role CHEBI:35717 sedatives
CHEBI has role CHEBI:35941 serotonergic agonists
CHEBI has role CHEBI:76779 prolyl oligopeptidase (ec 3.4.21.26) inhibitor
MeSH PA D014151 Anti-Anxiety Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Generalized anxiety disorder indication 21897009 DOID:14320
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.51 Basic
pKa2 2.23 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 1A GPCR PARTIAL AGONIST EC50 7.25 WOMBAT-PK CHEMBL
D(4) dopamine receptor GPCR Ki 7 WOMBAT-PK
Alpha-1D adrenergic receptor GPCR Ki 6.28 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 7.68 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 6.44 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.04 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 6.41 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 6.60 WOMBAT-PK
Cytochrome P450 3A4 Enzyme Ki 5.13 WOMBAT-PK
Solute carrier family 22 member 2 Transporter IC50 4.92 CHEMBL
D(3) dopamine receptor GPCR Ki 6.18 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.40 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 4.34 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 5.77 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.32 WOMBAT-PK
Membrane-associated progesterone receptor component 1 Membrane receptor IC50 5.47 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.21 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 6.86 CHEMBL
D(2) dopamine receptor GPCR Ki 7.36 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Ki 6.76 CHEMBL
Dopamine receptor GPCR IC50 6.92 CHEMBL
Adrenergic receptor alpha-2 GPCR IC50 5 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 4.80 CHEMBL
Alpha-2A adrenergic receptor GPCR IC50 5 CHEMBL
Serotonin 1 (5-HT1) receptor GPCR IC50 7.02 CHEMBL
5-hydroxytryptamine receptor 1B GPCR Ki 7.77 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 8.42 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.32 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 6.75 CHEMBL
D(2) dopamine receptor GPCR Ki 6.92 CHEMBL
5-hydroxytryptamine receptor 2C GPCR IC50 6 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 6.32 CHEMBL
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 6.40 IUPHAR
5-hydroxytryptamine receptor 7 GPCR AGONIST Ki 6.40 IUPHAR

External reference:

IDSource
4019646 VUID
N0000147739 NUI
D00702 KEGG_DRUG
33386-08-2 SECONDARY_CAS_RN
4018813 VANDF
4019646 VANDF
C0006462 UMLSCUI
CHEBI:3223 CHEBI
CHEMBL49 ChEMBL_ID
CHEMBL1200399 ChEMBL_ID
DB00490 DRUGBANK_ID
D002065 MESH_DESCRIPTOR_UI
3456 INN_ID
2477 PUBCHEM_CID
36 IUPHAR_LIGAND_ID
TK65WKS8HL UNII
1827 RXNORM
37673 MMSL
4308 MMSL
d00182 MMSL
001468 NDDF
004586 NDDF
387523009 SNOMEDCT_US
419484002 SNOMEDCT_US
91452003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-0053 TABLET 5 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-0054 TABLET 10 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-1003 TABLET 15 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-5200 TABLET 30 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1140 TABLET 5 mg ORAL ANDA 27 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1145 TABLET 7.50 mg ORAL ANDA 27 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1150 TABLET 10 mg ORAL ANDA 27 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1165 TABLET 15 mg ORAL ANDA 27 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1175 TABLET 30 mg ORAL ANDA 27 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-4575 TABLET 10 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-4595 TABLET 5 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-4596 TABLET 15 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7633 TABLET 5 mg ORAL ANDA 30 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7634 TABLET 10 mg ORAL ANDA 30 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7635 TABLET 15 mg ORAL ANDA 30 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7689 TABLET 15 mg ORAL ANDA 30 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7714 TABLET 5 mg ORAL ANDA 30 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7718 TABLET 10 mg ORAL ANDA 30 sections
Buspirone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6899 TABLET 15 mg ORAL ANDA 22 sections
Buspirone HCl HUMAN PRESCRIPTION DRUG LABEL 1 10544-176 TABLET 10 mg ORAL ANDA 27 sections
BUSPIRONE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-375 TABLET 30 mg ORAL ANDA 27 sections
BUSPIRONE HCl HUMAN PRESCRIPTION DRUG LABEL 1 16590-579 TABLET 15 mg ORAL ANDA 27 sections
BUSPIRONE HUMAN PRESCRIPTION DRUG LABEL 1 16590-600 TABLET 10 mg ORAL ANDA 13 sections
BUSPIRONE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-727 TABLET 7.50 mg ORAL ANDA 26 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-200 TABLET 5 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-201 TABLET 7.50 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-202 TABLET 10 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-203 TABLET 15 mg ORAL ANDA 29 sections
Buspirone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-289 TABLET 30 mg ORAL ANDA 29 sections
Buspirone HCl HUMAN PRESCRIPTION DRUG LABEL 1 21695-172 TABLET 15 mg ORAL ANDA 27 sections