Synonym
Spiperone; E 525; E-525; E525; R 5147; R-5147; R5147; NSC 170983; NSC-170983; NSC170983;
IUPAC/Chemical Name
8-(4-(4-fluorophenyl)-4-oxobutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
InChi Key
DKGZKTPJOSAWFA-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29)
SMILES Code
O=C1NCN(C2=CC=CC=C2)C13CCN(CCCC(C4=CC=C(F)C=C4)=O)CC3
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Spiperone is a potent dopamine D2, serotonin 5-HT1A, and serotonin 5-HT2A antagonist.
In vitro activity:
The findings of this study suggest that antipsychotics decrease dopamine release by reducing vesicular dopamine content. In PC12 cells, spiperone, haloperidol, pimozide, aripiprazole, and risperidone inhibited high potassium-evoked dopamine release. Spiperone, haloperidol, pimozide, aripiprazole, and reserpine transiently increased extracellular levels of dopamine metabolites. Additionally, spiperone, haloperidol, pimozide, aripiprazole, and risperidone reduced intracellular dopamine levels.
Reference: BMC Pharmacol. 2009 Nov 30;9:13. https://pubmed.ncbi.nlm.nih.gov/20460122/
In vivo activity:
In a murine model of chronic obstructive pulmonary disease (COPD), results suggest that spiperone mediated endothelial regeneration and could be a novel therapeutic approach for treatment of emphysema associated with COPD. Spiperone increased the number of capillaries and the expression of the CD31 in the alveolar tissue. Spiperone prevented alveolar wall destruction and reduced the area of emphysema.
Reference: Int J Chron Obstruct Pulmon Dis. 2021 Dec 30;16:3575-3591. https://pubmed.ncbi.nlm.nih.gov/35002229/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
33.3 |
84.28 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
395.47
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Matsuo T, Izumi Y, Wakita S, Kume T, Takada-Takatori Y, Sawada H, Akaike A. Haloperidol, spiperone, pimozide and aripiprazole reduce intracellular dopamine content in PC12 cells and rat mesencephalic cultures: Implication of inhibition of vesicular transport. Eur J Pharmacol. 2010 Aug 25;640(1-3):68-74. doi: 10.1016/j.ejphar.2010.04.043. Epub 2010 May 9. PMID: 20460122.
2. Lu D, Carson DA. Spiperone enhances intracellular calcium level and inhibits the Wnt signaling pathway. BMC Pharmacol. 2009 Nov 30;9:13. doi: 10.1186/1471-2210-9-13. PMID: 19948059; PMCID: PMC2789054.
3. Skurikhin E, Pershina O, Zhukova M, Widera D, Pan E, Pakhomova A, Krupin V, Ermakova N, Skurikhina V, Sandrikina L, Morozov S, Kubatiev A, Dygai A. Spiperone Stimulates Regeneration in Pulmonary Endothelium Damaged by Cigarette Smoke and Lipopolysaccharide. Int J Chron Obstruct Pulmon Dis. 2021 Dec 30;16:3575-3591. doi: 10.2147/COPD.S336410. PMID: 35002229; PMCID: PMC8722540.
4. Skurikhin EG, Khmelevskaya ES, Ermakova NN, Pershina OV, Reztsova AM, Krupin VA, Stepanova IE, Reztsova VM, Reikhart DV, Dygai AM. Effect of spiperone on mesenchymal multipotent stromal and hemopoietic stem cells under conditions of pulmonary fibrosis. Bull Exp Biol Med. 2014 May;157(1):132-7. doi: 10.1007/s10517-014-2508-y. Epub 2014 Jun 11. PMID: 24913578.
In vitro protocol:
1. Matsuo T, Izumi Y, Wakita S, Kume T, Takada-Takatori Y, Sawada H, Akaike A. Haloperidol, spiperone, pimozide and aripiprazole reduce intracellular dopamine content in PC12 cells and rat mesencephalic cultures: Implication of inhibition of vesicular transport. Eur J Pharmacol. 2010 Aug 25;640(1-3):68-74. doi: 10.1016/j.ejphar.2010.04.043. Epub 2010 May 9. PMID: 20460122.
2. Lu D, Carson DA. Spiperone enhances intracellular calcium level and inhibits the Wnt signaling pathway. BMC Pharmacol. 2009 Nov 30;9:13. doi: 10.1186/1471-2210-9-13. PMID: 19948059; PMCID: PMC2789054.
In vivo protocol:
1. Skurikhin E, Pershina O, Zhukova M, Widera D, Pan E, Pakhomova A, Krupin V, Ermakova N, Skurikhina V, Sandrikina L, Morozov S, Kubatiev A, Dygai A. Spiperone Stimulates Regeneration in Pulmonary Endothelium Damaged by Cigarette Smoke and Lipopolysaccharide. Int J Chron Obstruct Pulmon Dis. 2021 Dec 30;16:3575-3591. doi: 10.2147/COPD.S336410. PMID: 35002229; PMCID: PMC8722540.
2. Skurikhin EG, Khmelevskaya ES, Ermakova NN, Pershina OV, Reztsova AM, Krupin VA, Stepanova IE, Reztsova VM, Reikhart DV, Dygai AM. Effect of spiperone on mesenchymal multipotent stromal and hemopoietic stem cells under conditions of pulmonary fibrosis. Bull Exp Biol Med. 2014 May;157(1):132-7. doi: 10.1007/s10517-014-2508-y. Epub 2014 Jun 11. PMID: 24913578.
1: BOBON J, COLLARD J, DELREE C, GERNAY JM. LE SPIROP'ERIDOL [SPIROPERIDOL]. Acta Neurol Psychiatr Belg. 1963 Dec;63:991-1003. French. PMID: 14106849.
2: Weinstock M, Speiser Z. Modification by propranolol and related compounds of motor activity and stereotype behaviour induced in the rat by amphetamine. Eur J Pharmacol. 1974 Jan;25(1):29-35. doi: 10.1016/0014-2999(74)90090-9. PMID: 4279823.
3: Dow RC, Hill AG, McQueen JK. Proceedings: Effects of some dopamine receptor stimulants on cobalt-induced epilepsy in the rat. Br J Pharmacol. 1974 Sep;52(1):135P. PMID: 4451788; PMCID: PMC1776967.
4: Everitt BJ, Fuxe K, Hökfelt T. Inhibitory role of dopamine and 5-hydroxytryptamine in the sexual behaviour of female rats. Eur J Pharmacol. 1974 Nov;29(1):187-91. doi: 10.1016/0014-2999(74)90190-3. PMID: 4279825.
5: Rolls ET, Kelly PH, Shaw SG. Noradrenaline, dopamine, and brain-stimulation reward. Pharmacol Biochem Behav. 1974 Nov-Dec;2(6):735-40. doi: 10.1016/0091-3057(74)90103-8. PMID: 4463371.
6: Grabowska M, Michaluk J, Antkiewicz L. Influence of NBTI on metabolism of brain-HT. Arch Immunol Ther Exp (Warsz). 1975;23(4):505-9. PMID: 1164152.
7: Maj J, Mogilnicka E, Przewlocka B. Antagonistic effect of cyproheptadine on neuroleptic-induced catalepsy. Pharmacol Biochem Behav. 1975 Jan-Feb;3(1):25-7. doi: 10.1016/0091-3057(75)90076-3. PMID: 1168927.
8: Sarnek J, Baran L. The effect of 5-hydroxytrytamine synthesis inhibitors on neuroleptic-induced catalepsy in rats. Arch Immunol Ther Exp (Warsz). 1975;23(4):511-6. PMID: 1172422.
9: Smialowska M. The effect of apomorphine on serotonin neurons in dorsal raphe nucleus and catecholamine nerve terminals in paraventricular hypothalamic nucleus. Histofluorescence studies. Pol J Pharmacol Pharm. 1975 Jul- Aug;27(4):419-28. PMID: 126447.
10: Grabowska M. Influence of apomorphine on brain serotonin turnover rate. Pharmacol Biochem Behav. 1975 Jul-Aug;3(4):589-91. doi: 10.1016/0091-3057(75)90178-1. PMID: 1187722.
11: Antelman SM, Szechtman H. Tail pinch induces eating in sated rats which appears to depend on nigrostriatal dopamine. Science. 1975 Aug 29;189(4204):731-3. doi: 10.1126/science.1154024. PMID: 1154024.
12: Lenard LG, Beer B. Modification of avoidance behavior in 6-hydroxydopamine- treated rats by stimulation of central noradrenergic and dopaminergic receptors. Pharmacol Biochem Behav. 1975 Sep-Oct;3(5):887-93. doi: 10.1016/0091-3057(75)90122-7. PMID: 1208631.
13: Carlson KR, Eibergen RD. Susceptibility to amphetamine-elicited dyskinesias following chronic methadone treatment in monkeys. Ann N Y Acad Sci. 1976;281:336-49. doi: 10.1111/j.1749-6632.1976.tb27944.x. PMID: 828468.
14: Smialowska M. The influence of 1,3-dimethyl-5-adamantanamine (D-145) on catecholaminergic neurons of the rat brain, Histofluorescence studies. Pol J Pharmacol Pharm. 1976;28(3):259-67. PMID: 951308.
15: Mora F, Rolls ET, Burton MJ, Shaw GS, Shaw GS. Effects of dopamine-receptor blockade on self-stimulation in the monkey. Pharmacol Biochem Behav. 1976 Feb;4(2):211-6. doi: 10.1016/0091-3057(76)90018-6. PMID: 817302.
16: Baez LA, Eskridge NK, Schein R. Postnatal development of dopaminergic and cholinergic catalepsy in the rat. Eur J Pharmacol. 1976 Mar;36(1):155-62. doi: 10.1016/0014-2999(76)90267-3. PMID: 944132.
17: Kafi S, Gaillard JM. Brain dopamine receptors and sleep in the rat: effects of stimulation and blockade. Eur J Pharmacol. 1976 Aug;38(2):357-63. doi: 10.1016/0014-2999(76)90340-x. PMID: 182510.
18: Eibergen RD, Carlson KR. Dyskinesias in monkeys: interaction of methamphetamine with prior methadone treatment. Pharmacol Biochem Behav. 1976 Aug;5(2):175-87. doi: 10.1016/0091-3057(76)90034-4. PMID: 825885.
19: Maj J, Sarnek J, Klimek V, Rawlów A. On the anticataleptic action of cyproheptadine. Pharmacol Biochem Behav. 1976 Aug;5(2):201-5. doi: 10.1016/0091-3057(76)90037-x. PMID: 1033567.
20: Pawlowski L. The influence of serotonergic agents on the body temperature. Pol J Pharmacol Pharm. 1976 Nov-Dec;28(6):615-23. PMID: 138132.
