Synonym
Perospirone HCl Dihydrate; SM-9018; SM9018; SM 9018; Lullan
IUPAC/Chemical Name
(3aR,7aS)-2-(4-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)butyl)hexahydro-1H-isoindole-1,3(2H)-dione hydrochloride
InChi Key
HIZFAPMOZFYELI-GNXQHMNLSA-N
InChi Code
InChI=1S/C23H30N4O2S.ClH/c28-22-17-7-1-2-8-18(17)23(29)27(22)12-6-5-11-25-13-15-26(16-14-25)21-19-9-3-4-10-20(19)30-24-21;/h3-4,9-10,17-18H,1-2,5-8,11-16H2;1H/t17-,18+;
SMILES Code
O=C1N(CCCCN2CCN(C3=NSC4=C3C=CC=C4)CC2)C([C@]5([H])CCCC[C@]15[H])=O.[H]Cl
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
>2 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
2934.99.9001
More Info
Related CAS#
150915-41-6(Perospirone )
192052-81-6(Perospirone HCl Dihydrate)
Biological target:
Perospirone hydrochloride (SM-9018) is an orally active antagonist of 5-HT2A receptor (Ki of 0.6 nM) and dopamine D2 receptor (Ki of 1.4 nM).
In vitro activity:
SM-9018 possessed very high affinity for 5-HT2, D2 and 5-HT1A receptors (Ki = 0.61, 1.4 and 2.9 nM, respectively), and it had moderate affinity for alpha 1 and D1 receptors (Ki = 17 and 41 nM, respectively). However, SM-9018 had only negligible affinity for alpha 2, opiate, glutamate, phencyclidine, benzodiazepine and GABAA receptors. These results suggest that SM-9018 may be a novel antipsychotic agent with binding affinity for 5-HT2 and 5-HT1A receptors.
Reference: Jpn J Pharmacol. 1990 Dec;54(4):478-81. https://pubmed.ncbi.nlm.nih.gov/1982326/
In vivo activity:
The present study was undertaken to examine the effects of perospirone, an atypical antipsychotic drug with 5-HT(1A) receptor agonism, on cognitive deficits in mice after repeated administration of the NMDA receptor antagonist phencyclidine (PCP). Subsequent subchronic (14 days) administration of perospirone (1.0, 3.0, or 10 mg/kg) significantly attenuated PCP (10 mg/kg)-induced cognitive deficits in mice, in a dose-dependent manner. These findings suggest that repeated PCP administration alters 5-HT(1A) receptor function in the mouse brain, and that subsequent subchronic administration of perospirone ameliorates PCP-induced cognitive deficits via 5-HT(1A) receptors.
Reference: Eur Neuropsychopharmacol. 2008 Jun;18(6):448-54. https://pubmed.ncbi.nlm.nih.gov/18164909/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
92.5 |
199.77 |
|
| Water |
5.0 |
10.80 |
|
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
463.04
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. Zhou YG, Li KY, Li HD. Effect of the novel antipsychotic drug perospirone on P-glycoprotein function and expression in Caco-2 cells. Eur J Clin Pharmacol. 2008 Jul;64(7):697-703. doi: 10.1007/s00228-008-0487-5. Epub 2008 May 14. PMID: 18478216.
2. Kato T, Hirose A, Ohno Y, Shimizu H, Tanaka H, Nakamura M. Binding profile of SM-9018, a novel antipsychotic candidate. Jpn J Pharmacol. 1990 Dec;54(4):478-81. doi: 10.1254/jjp.54.478. PMID: 1982326.
3. Hagiwara H, Fujita Y, Ishima T, Kunitachi S, Shirayama Y, Iyo M, Hashimoto K. Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of the antipsychotic drug perospirone: role of serotonin 5-HT1A receptors. Eur Neuropsychopharmacol. 2008 Jun;18(6):448-54. doi: 10.1016/j.euroneuro.2007.11.005. Epub 2007 Dec 31. PMID: 18164909.
4. Matsushita M, Egashira N, Harada S, Okuno R, Mishima K, Iwasaki K, Nishimura R, Fujiwara M. Perospirone, a novel antipsychotic drug, inhibits marble-burying behavior via 5-HT1A receptor in mice: implications for obsessive-compulsive disorder. J Pharmacol Sci. 2005 Oct;99(2):154-9. doi: 10.1254/jphs.fp0050144. Epub 2005 Oct 6. PMID: 16210777.
In vitro protocol:
1. Zhou YG, Li KY, Li HD. Effect of the novel antipsychotic drug perospirone on P-glycoprotein function and expression in Caco-2 cells. Eur J Clin Pharmacol. 2008 Jul;64(7):697-703. doi: 10.1007/s00228-008-0487-5. Epub 2008 May 14. PMID: 18478216.
2. Kato T, Hirose A, Ohno Y, Shimizu H, Tanaka H, Nakamura M. Binding profile of SM-9018, a novel antipsychotic candidate. Jpn J Pharmacol. 1990 Dec;54(4):478-81. doi: 10.1254/jjp.54.478. PMID: 1982326.
In vivo protocol:
1. Hagiwara H, Fujita Y, Ishima T, Kunitachi S, Shirayama Y, Iyo M, Hashimoto K. Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of the antipsychotic drug perospirone: role of serotonin 5-HT1A receptors. Eur Neuropsychopharmacol. 2008 Jun;18(6):448-54. doi: 10.1016/j.euroneuro.2007.11.005. Epub 2007 Dec 31. PMID: 18164909.
2. Matsushita M, Egashira N, Harada S, Okuno R, Mishima K, Iwasaki K, Nishimura R, Fujiwara M. Perospirone, a novel antipsychotic drug, inhibits marble-burying behavior via 5-HT1A receptor in mice: implications for obsessive-compulsive disorder. J Pharmacol Sci. 2005 Oct;99(2):154-9. doi: 10.1254/jphs.fp0050144. Epub 2005 Oct 6. PMID: 16210777.
1: Kambayashi R, Hagiwara-Nagasawa M, Goto A, Chiba K, Izumi-Nakaseko H, Naito AT, Matsumoto A, Sugiyama A. Experimental analysis of the onset mechanism of TdP reported in an LQT3 patient during pharmacological treatment with serotonin- dopamine antagonists against insomnia and nocturnal delirium. Heart Vessels. 2020 Apr;35(4):593-602. doi: 10.1007/s00380-019-01521-y. Epub 2019 Oct 18. PMID: 31628538.
2: Takeuchi Y, Kajiyama K, Ishiguro C, Uyama Y. Atypical Antipsychotics and the Risk of Hyperlipidemia: A Sequence Symmetry Analysis. Drug Saf. 2015 Jul;38(7):641-50. doi: 10.1007/s40264-015-0298-4. PMID: 26001933.
3: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Jul-Aug;32(6):437-61. doi: 10.1358/mf.2010.32.6.1538165. PMID: 20852754.
4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Nov;31(9):597-633. PMID: 20094643.
5: Bayés M, Rabasseda X. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Jan-Feb;30(1):67-99. PMID: 18389098.
6: Ishii E, Otani N, Tsuchiya M, Kizu J, Ishimatsu S. [Pharmacokinetics of perospirone hydrochloride at an excessive dose and changes in the serum prolactin level]. Chudoku Kenkyu. 2007 Jan;20(1):55-8. Japanese. PMID: 17319502.
7: Hamanaka S, Kamijo Y. New-onset diabetic ketoacidosis induced by the addition of perospirone hydrochloride in a patient treated with risperidone. Intern Med. 2007;46(4):199-200. doi: 10.2169/internalmedicine.46.1889. Epub 2007 Feb 15. PMID: 17301517.
8: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Oct;28(8):533-91. PMID: 17136234.
9: Ma N, Liu WY, Li HD, Zhu YG, Zhang BK, Wang F, Zhu RH, Xiang DX. Determination of perospirone by liquid chromatography/electrospray mass spectrometry: application to a pharmacokinetic study in healthy Chinese volunteers. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Mar 1;847(2):210-6. doi: 10.1016/j.jchromb.2006.10.007. Epub 2006 Nov 20. PMID: 17116433.
10: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jul-Aug;27(6):411-61. PMID: 16179960.
11: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Jun;26(5):357-91. PMID: 15319815.
12: Ohno Y. [Pharmacological characteristics of perospirone hydrochloride, a novel antipsychotic agent]. Nihon Yakurigaku Zasshi. 2000 Oct;116(4):225-31. Japanese. doi: 10.1254/fpj.116.225. PMID: 11084919.
13: Takahashi Y, Kusumi I, Ishikane T, Koyama T. In vivo occupation of dopamine D1, D2 and serotonin2A receptors by novel antipsychotic drug, SM-9018 and its metabolite, in rat brain. J Neural Transm (Vienna). 1998;105(2-3):181-91. doi: 10.1007/s007020050047. PMID: 9660096.
