8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione

• ChemBase ID: 373
• Molecular Formular: C21H31N5O2
• Molecular Mass: 385.50314
• Monoisotopic Mass: 385.24777526
• SMILES: O=C1N(C(=O)CC2(CCCC2)C1)CCCCN1CCN(CC1)c1ncccn1
• Canonical SMILES: O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)c1ncccn1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
• IUPAC Traditional name: buspirone
• Brand Name: Ansial; Ansiced; Anxiron; Axoren; Bespar; Buspar; Buspimen; Buspinol; Buspisal; Censpar; Lucelan; Narol; Travin; Wellbutrin XL
• Synonyms: Buspirona [INN-Spanish]; Buspirone HCL; Buspironum [INN-Latin]; Buspirone; Buspirone; 8-(4-(4-(PyriMidin-2-yl)piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione

Database IDs

• CAS Number: 36505-84-7
• PubChem SID: 46508113; 160963836
• PubChem CID: 2477
• CHEBI ID: 3223
• ATC CODE: N05BE01
• CHEMBL: 49
• Chemspider ID: 2383
• DrugBank ID: DB00490
• IUPHAR ligand ID: 36
• KEGG ID: D07593
• Unique Ingredient Identifier: TK65WKS8HL
• Wikipedia Title: Buspirone
• Medline Plus: a688005

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.32954732
• LogD (pH = 7.4): 1.351795
• Log P: 1.7767332
• Molar Refractivity: 108.8906 cm^3
• Polarizability: 41.61726 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.95
• LOG S: -2.82
• Solubility (Water): 5.88e-01 g/l

PROPERTIES

Physical Property

• Solubility: 21.4 mg/L
• Hydrophobicity(logP): 2.3

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 5%
• Excretion: Urine (29-63%), Feces (18-38%)
• Half Life: 2-3 hours
• Metabolism: Hepatic
• Protein Bound: 95%
• Legal Status: Rx-only
• Pregnancy Category: B (US)

Product Information

• Purity: 97%

DETAILS

DrugBank - DB00490

• Drug Groups: approved; investigational
• Description: 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]
• Indication: For the management of anxiety disorders or the short-term relief of the symptoms of anxiety, and also as an augmention of SSRI-treatment against depression.
• Pharmacology: Buspirone is used in the treatment of generalized anxiety where it has advantages over other antianxiety drugs because it does not cause sedation (drowsiness) and does not cause tolerance or physical dependence. Buspirone differs from typical benzodiazepine anxiolytics in that it does not exert anticonvulsant or muscle relaxant effects. It also lacks the prominent sedative effect that is associated with more typical anxiolytics. in vitro preclinical studies have shown that buspirone has a high affinity for serotonin (5-HT_1A) receptors. Buspirone has no significant affinity for benzodiazepine receptors and does not affect GABA binding in vitro or in vivo when tested in preclinical models. Buspirone has moderate affinity for brain D2-dopamine receptors. Some studies do suggest that buspirone may have indirect effects on other neurotransmitter systems.
• Toxicity: Oral, rat LD₅₀ = 136 mg/kg. Symptoms of overdose include dizziness, drowsiness, nausea or vomiting, severe stomach upset, and unusually small pupils.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized hepatically, primarily by oxidation by cytochrome P450 3A4 producing several hydroxylated derivatives and a pharmacologically active metabolite, 1-pyrimidinylpiperazine (1-PP)
• Absorption: Rapidly absorbed in man. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism.
• Half Life: 2-3 hours (although the action of a single dose is much longer than the short halflife indicates).
• Protein Binding: 95% (approximately 70% bound to albumin, 30% bound to alpha 1 -acid glycoprotein)
• Elimination: In a single-dose study using 14C-labeled buspirone, 29% to 63% of the dose was excreted in the urine within 24 hours, primarily as metabolites; fecal excretion accounted for 18% to 38% of the dose.
• External Links: Wikipedia; RxList; Drugs.com