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Buspiron
BUSPIRONE HCL · buspar · 8-[4-[4-(2-PYRIMIDINYL)-1-PIPERAZINYL]BUTYL]-8-AZASPIRO[4,5]DECANE-7,9-DIONE · Buspisal · Buspimen · BUSPIRONE · Nard：Tmvin · BUPROPIONHCL
Identifikatoren & physikalische Daten
| CAS No. | 36505-84-7 |
|---|---|
| Summenformel | C21H31N5O2 |
| Durchschnittliche Molmasse | 385,5 g/mol |
| Monoisotopische Masse | 385,24777523 g/mol |
| SMILES | O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(c2ncccn2)CC1 |
| InChIKey | QWCRAEMEVRGPNT-UHFFFAOYSA-N |
| PubChem CID | 2477 |
| ChEMBL | CHEMBL49 |
| ChEBI | CHEBI:3223 |
| EC No. | 253-072-2 |
| DTXSID | DTXSID2022707 |
| Lokaler Name | Buspiron |
Chemische & physikalische Eigenschaften
| XLogP | 2,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 69,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 28 |
| Formalladung | 0 |
| Komplexität | 529 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 2.3 |
| Löslichkeit | 5.88e-01 g/L |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Anxiety AgentsSerotonin AgonistsPharmaceuticals |
| Schmelzpunkt | 201.5-202.5201.5 - 202.5 °C105-107 °C(Solv: ethyl acetate (141-78-6)) |
| Physical Description | Solid |
| Ionization Efficiency | Positive4.3347297742.7Thermo LTQElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 7.6 |
| Collision Cross Section | 196.8 Ų [M]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID2022707]195.97 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]199.3 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| Siedepunkt | 511.93°C (rough estimate) |
| Dichte | 1.1527 (rough estimate) |
| Brechungsindex | 1.7600 (estimate) |
| Lagerbedingungen | Sealed in dry,2-8°C |
| pKa (Säurekonstante) | pKa 7.60±0.01(H2O t=25.0 I=0.1(NaCl)) (Uncertain) |
| Aggregatzustand | Solid |
| Farbe | White to off-white |
| BCS Class | 1 |
| CAS Datenbank | 36505-84-7(CAS DataBase Reference) |
| NIST chemische Informationen | 8-Azaspiro[4.5]decane-7,9-dione, 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-(36505-84-7) |
| EPA chemische Informationen | 8-Azaspiro[4.5]decane-7,9-dione, 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]- (36505-84-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 4 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 01-09-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31319 |
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Treatment | General symptomatic and supportive measures should be used along with immediate gastric lavage. Respiration, pulse, and blood pressure should be monitored as in all cases of drug overdosage. No specific antidote is known to buspirone, and dialyzability of buspirone has not been determined. (L1712) |
| Hepatotoxicity | Buspirone has been associated with infrequent serum aminotransferase elevations, but has not been linked to instances of clinically apparent liver injury in the published literature. Indeed, buspirone is often used as a control, noncytotoxic agent in assessment of other psychotropic drugs in vitro and in vivo. Buspirone is, nevertheless, metabolized in the liver by the P450 system (CYP 3A4) and has the potential of causing drug-drug interactions. |
| Unerwünschte Wirkungen | Dizziness is a common side effect that occurs in over 10% of patients. |
| Expositionspfade | Oral. Rapidly absorbed in man. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism. |
| Toxizitätsübersicht | Relative to other anxiolytics, buspirone has low toxicity and potential for abuse. There have been no deaths reported from a buspirone overdose alone. In pharmacological trials, healthy male patients were given up to 375 mg daily and developed nausea, vomiting, dizziness, drowsiness, miosis, and gastric distress. While buspirone overdose typically resolves with complete recovery, high suspicion of other medication overdoses should be maintained and investigated. In a literature review, multiple reports of movement disorders, including dyskinesia, akathisia, myoclonus, parkinsonism, and dystonia, have been reported.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. |
| Signs and Symptoms | Symptoms of overdose include dizziness, drowsiness, nausea or vomiting, severe stomach upset, and unusually small pupils. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)buspironeBuSpar®Anxiolytics3less-DILI-concern drugs |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Toxicity Data | LD50: 136 mg/kg (Oral, rat) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| RTECS-Nr. | CL9915000 |
| R-Sätze (R) | 25 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 45 |
Anwendungen & Verwendung
Verwenden
Buspirone is an extremely specific drug that could possibly represent a new chemical class of anxiolytics—azaspirones. As an anxiolytic, its activity is equal to that of benzodiazepines; however, it is devoid of anticonvulsant and muscle relaxant properties, which are characteristic of benzodiazepines.