Lurasidone hydrochloride Chemical Properties

Melting point:

198-205°C

Flash point:

9℃

storage temp. 

Refrigerator

solubility 

DMSO : 10 mg/mL (18.90 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)

form 

Powder

color 

White to off-white

InChI

InChI=1/C28H36N4O2S.ClH/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;1H/t18-,19+,20-,21-,24+,25-;/s3

InChIKey

PQXKDMSYBGKCJA-CVTJIBDQSA-N

SMILES

O=C1N(C(=O)[C@@]2([H])[C@]3([H])CC[C@@]([H])(C3)[C@@]12[H])C[C@@H]1CCCC[C@H]1CN1CCN(C2=NSC3=CC=CC=C23)CC1.Cl |&1:5,7,11,14,17,22,r|

Safety Information

Hazard Codes 

F,T

Risk Statements 

11-23/24/25-39/23/24/25

Safety Statements 

7-16-36/37-45

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

1

Lurasidone hydrochloride Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

Lurasidone is an atypical antipsychotic, inhibits Dopamine D2, 5-HT2A, 5-HT7, 5-HT1A and noradrenaline α2C with IC50 of 1.68 nM, 2.03 nM, 0.495 nM, 6.75 nM and 10.8 nM, respectively

Uses

An antipsychotic used for treatment of schizophrenia.

Definition

ChEBI: A hydrochloride obtained by reaction of lurasidone with one equivalent of hydrochloric acid. An atypical antipsychotic agent used for the treatment of schizophrenia.

Biological Activity

Lurasidone is an atypical antipsychotic, used clinically for treatment of schizophrenia and bi-polar disorder. It has nanomolar activity as an antagonist at dopamine D2, serotonin 5-HT2A, 5-HT7, and α2C-adrenergic receptors and as an agonist at 5-HT1A receptors.

Synthesis

(3aR,7aR)-4'-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindol-2,1'-piperazin]-2-ium methanesulfonate (Intermediate 4, 28.8 kg, 66.2 mol) and (3aR,4S,7R,7aS)-rel-hexahydro-1H-4,7-bridged methylidene isoindole-1,3(2H)-dione (Intermediate 5. 12.0 kg, 72.8 mol) as raw material and potassium carbonate (11.0 kg, 79.7 mol) as base were suspended in toluene (270 L). The resulting suspension was heated and refluxed at 105 °C for 15 h. The reaction process was monitored by UPLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature and quenched by the addition of water (90 L). The organic and aqueous phases were separated and the organic phase was concentrated to a smaller volume. Subsequently, the concentrated organic phase was treated with hydrochloric acid in isopropanol to afford the target product (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 hydrochloride ( Lurasidone hydrochloride, 34.4 kg, yield 98.3%, HPLC purity 99.49%).

References

[1] Patent: WO2015/56205, 2015, A1. Location in patent: Page/Page column 14
[2] Patent: WO2013/121440, 2013, A1

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