Synonym
SM13496; SM-13496; SM 13496; SM13,496; SM-13,496; SM 13,496; Lurasidone, trade name: Latuda
IUPAC/Chemical Name
(3aR,4S,7R,7aS)-2-(((1R,2R)-2-((4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)methyl)cyclohexyl)methyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
InChi Key
PQXKDMSYBGKCJA-CVTJIBDQSA-N
InChi Code
InChI=1S/C28H36N4O2S/c33-27-24-18-9-10-19(15-18)25(24)28(34)32(27)17-21-6-2-1-5-20(21)16-30-11-13-31(14-12-30)26-22-7-3-4-8-23(22)35-29-26/h3-4,7-8,18-21,24-25H,1-2,5-6,9-17H2/t18-,19+,20-,21-,24+,25-/m0/s1
SMILES Code
C1CC[C@H]([C@@H](C1)CN2CCN(CC2)C3=NSC4=CC=CC=C43)CN5C(=O)[C@H]6[C@@H]7CC[C@@H](C7)[C@H]6C5=O
Appearance
White to off-white solid powder
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#
367514-87-2 (Lurasidone free base); 367514-87-2 (Lurasidone HCl salt)
Biological target:
Lurasidone (SM-13496) is an antagonist of both dopamine D2 and 5-HT7 with IC50s of 1.68 and 0.495 nM, respectively.
In vitro activity:
The inhibitory effect of the atypical neuroleptic lurasidone on the main human cytochrome P450 (CYP) enzymes in pooled human liver microsomes and cDNA-expressed CYP enzymes (supersomes) was examined. Lurasidone moderately inhibited CYP1A2 (Ki = 12.6 and 15.5 µM in microsomes and supersomes), CYP2C9 (Ki = 18 and 3.5 µM in microsomes and supersomes) and CYP2C19 via a mixed mechanism (Ki = 18 and 18.4 µM in microsomes and supersomes), and CYP3A4 via a competitive mechanism (Ki = 29.4 and 9.1 µM in microsomes and supersomes). Moreover, lurasidone competitively, though weakly diminished the CYP2D6 activity (Ki = 37.5 and 85 µM in microsomes and supersomes).
Reference: Pharmacol Rep. 2020 Dec;72(6):1685-1694. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7704495/
In vivo activity:
To investigate the beneficial preclinical outcomes of lurasidone, a rat model of cranial nerve involvement model was established. The results (Fig. 2A) indicated that the total PANSS (Positive and Negative Syndrome Scale) score was significantly reduced in the rats with cranial nerve involvement treated with lurasidone compared with those treated with placebo. In addition, neuron impairment was analyzed on day 30 following lurasidone or placebo treatment. The results (Fig. 2B) showed that neuron impairment was significantly reduced in the hippocampus of lurasidone-treated mice. In addition, the risks of relapse and re-treatment in a 180-day observation period were analyzed following treatment with lurasidone, compared with the placebo. P-values were 0.00063 and 0.00048 for relapse rate and re-treatment, respectively (Fig. 2C and D). Furthermore, as shown in Fig. 2E and F, the lurasidone-treated mice had significantly higher rates of remission and reduced anxiety, compared with the placebo (P=0.0075 and P=0.0086, vs. placebo, respectively).
Reference: Mol Med Rep. 2018 Apr;17(4):6002-6008. https://www.spandidos-publications.com/mmr/17/4/6002
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
19.3 |
39.13 |
| DMF |
30.0 |
60.89 |
| Ethanol |
30.0 |
60.89 |
| Ethanol:PBS (pH 7.2) (1:2) |
0.3 |
0.67 |
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
492.68
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. Danek PJ, Wójcikowski J, Daniel WA. The atypical neuroleptics iloperidone and lurasidone inhibit human cytochrome P450 enzymes in vitro. Evaluation of potential metabolic interactions. Pharmacol Rep. 2020 Dec;72(6):1685-1694. doi: 10.1007/s43440-020-00102-5. Epub 2020 Apr 11. PMID: 32279279; PMCID: PMC7704495.
2. He B, Yu L, Li S, Xu F, Yang L, Ma S, Guo Y. Neuroprotective effect of lurasidone via antagonist activities on histamine in a rat model of cranial nerve involvement. Mol Med Rep. 2018 Apr;17(4):6002-6008. doi: 10.3892/mmr.2018.8595. Epub 2018 Feb 13. PMID: 29436643.
In vitro protocol:
1. Danek PJ, Wójcikowski J, Daniel WA. The atypical neuroleptics iloperidone and lurasidone inhibit human cytochrome P450 enzymes in vitro. Evaluation of potential metabolic interactions. Pharmacol Rep. 2020 Dec;72(6):1685-1694. doi: 10.1007/s43440-020-00102-5. Epub 2020 Apr 11. PMID: 32279279; PMCID: PMC7704495.
In vivo protocol:
1. He B, Yu L, Li S, Xu F, Yang L, Ma S, Guo Y. Neuroprotective effect of lurasidone via antagonist activities on histamine in a rat model of cranial nerve involvement. Mol Med Rep. 2018 Apr;17(4):6002-6008. doi: 10.3892/mmr.2018.8595. Epub 2018 Feb 13. PMID: 29436643.
1: Woo YS, Wang HR, Bahk WM. Lurasidone as a potential therapy for bipolar disorder. Neuropsychiatr Dis Treat. 2013;9:1521-9. doi: 10.2147/NDT.S51910. Epub 2013 Oct 8. Review. PubMed PMID: 24143101; PubMed Central PMCID: PMC3797281.
2: Tarazi FI, Riva MA. The preclinical profile of lurasidone: clinical relevance for the treatment of schizophrenia. Expert Opin Drug Discov. 2013 Oct;8(10):1297-307. doi: 10.1517/17460441.2013.815163. Epub 2013 Jul 10. Review. PubMed PMID: 23837554.
3: Bobo WV. Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults. Expert Rev Clin Pharmacol. 2013 Jan;6(1):61-91. doi: 10.1586/ecp.12.70. Review. PubMed PMID: 23272794.
4: Sanford M. Lurasidone : in the treatment of schizophrenia. CNS Drugs. 2013 Jan;27(1):67-80. doi: 10.1007/s40263-012-0026-x. Review. PubMed PMID: 23264146.
5: Citrome L. Lurasidone in schizophrenia: new information about dosage and place in therapy. Adv Ther. 2012 Oct;29(10):815-25. doi: 10.1007/s12325-012-0052-6. Epub 2012 Sep 20. Review. PubMed PMID: 23001538.
6: De Hert M, Yu W, Detraux J, Sweers K, van Winkel R, Correll CU. Body weight and metabolic adverse effects of asenapine, iloperidone, lurasidone and paliperidone in the treatment of schizophrenia and bipolar disorder: a systematic review and exploratory meta-analysis. CNS Drugs. 2012 Sep 1;26(9):733-59. doi: 10.2165/11634500-000000000-00000. Review. PubMed PMID: 22900950.
7: Tarazi FI, Stahl SM. Iloperidone, asenapine and lurasidone: a primer on their current status. Expert Opin Pharmacother. 2012 Sep;13(13):1911-22. doi: 10.1517/14656566.2012.712114. Epub 2012 Jul 31. Review. PubMed PMID: 22849428.
8: Risbood V, Lee JR, Roche-Desilets J, Fuller MA. Lurasidone: an atypical antipsychotic for schizophrenia. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1033-46. doi: 10.1345/aph.1M721. Epub 2012 Jul 24. Review. PubMed PMID: 22828971.
9: Yasui-Furukori N. Update on the development of lurasidone as a treatment for patients with acute schizophrenia. Drug Des Devel Ther. 2012;6:107-15. doi: 10.2147/DDDT.S11180. Epub 2012 May 8. Review. PubMed PMID: 22675261; PubMed Central PMCID: PMC3367402.
10: McIntyre RS, Cha DS, Alsuwaidan M, McIntosh D, Powell AM, Jerrell JM. A review of published evidence reporting on the efficacy and pharmacology of lurasidone. Expert Opin Pharmacother. 2012 Aug;13(11):1653-9. doi: 10.1517/14656566.2012.683174. Epub 2012 May 5. Review. PubMed PMID: 22559286.
