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Chemistry

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Also known as: Lurasidone hcl, 367514-88-3, Latuda, Sm-13496, Lurasidone hydrochloride [usan], Sm 13496
Molecular Formula
C28H37ClN4O2S
Molecular Weight
529.1  g/mol
InChI Key
NEKCRUIRPWNMLK-SCIYSFAVSA-N
FDA UNII
O0P4I5851I

Lurasidone Hydrochloride
A thiazole derivative and atypical ANTIPSYCHOTIC AGENT that functions as a DOPAMINE D2 RECEPTOR ANTAGONIST; SEROTONIN 5-HT2 RECEPTOR ANTAGONIST, serotonin 5-HT7 receptor antagonist, and antagonist of the adrenergic 2A and 2C receptors, as well as a partial SEROTONIN 5-HT1A RECEPTOR AGONIST. It is used in the treatment of SCHIZOPHRENIA and BIPOLAR DISORDER.
1 2D Structure

Lurasidone Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2R,6S,7R)-4-[[(1R,2R)-2-[[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]methyl]cyclohexyl]methyl]-4-azatricyclo[5.2.1.02,6]decane-3,5-dione;hydrochloride
2.1.2 InChI
InChI=1S/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-;/m0./s1
2.1.3 InChI Key
NEKCRUIRPWNMLK-SCIYSFAVSA-N
2.1.4 Canonical SMILES
C1CCC(C(C1)CN2CCN(CC2)C3=NSC4=CC=CC=C43)CN5C(=O)C6C7CCC(C7)C6C5=O.Cl
2.1.5 Isomeric SMILES
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.Cl
2.2 Other Identifiers
2.2.1 UNII
O0P4I5851I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 13496, Sm

2. Hcl, Lurasidone

3. Hydrochloride, Lurasidone

4. Latuda

5. Lurasidone

6. Lurasidone Hcl

7. N-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinylmethyl)-1-cyclohexylmethyl)-2,3-bicyclo(2.2.1)heptanedicarboximide

8. Sm 13,496

9. Sm 13496

10. Sm-13,496

11. Sm-13496

12. Sm13,496

13. Sm13496

2.3.2 Depositor-Supplied Synonyms

1. Lurasidone Hcl

2. 367514-88-3

3. Latuda

4. Sm-13496

5. Lurasidone Hydrochloride [usan]

6. Sm 13496

7. Chebi:70732

8. O0p4i5851i

9. Lurasidonhydrochloride

10. (1s,2r,6s,7r)-4-[[(1r,2r)-2-[[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]methyl]cyclohexyl]methyl]-4-azatricyclo[5.2.1.02,6]decane-3,5-dione;hydrochloride

11. (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

12. (1r,2s,6r,7s)-4-{[(1r,2r)-2-{[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl]methyl}-4-azatricyclo[5.2.1.0^{2,6}]decane-3,5-dione Hydrochloride

13. 4,7-methano-1h-isoindole-1,3(2h)-dione, 2-(((1r,2r)-2-((4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)methyl)cyclohexyl)methyl)hexahydro-, Monohydrochloride, (3ar,4s,7r,7as)-

14. Unii-o0p4i5851i

15. Latuda (tn)

16. Lurasidone Monohydrochloride

17. Lurasidone-d8 Hydrochloride

18. Sm-13496 (hydrochloride)

19. Schembl1534132

20. Chembl1615372

21. Dtxsid401027714

22. Lurasidone Hydrochloride (jan/usan)

23. Lurasidone Hydrochloride [mi]

24. S3044

25. Smp-13496

26. Lurasidone Hydrochloride [jan]

27. Akos022185856

28. Ex-3125

29. Mk-3756

30. Lurasidone Hydrochloride [mart.]

31. Lurasidone Hydrochloride [vandf]

32. Lurasidone Hydrochloride [who-dd]

33. As-35074

34. Lurasidone Hydrochloride, >=98% (hplc)

35. Lurasidone Hydrochloride [orange Book]

36. D04820

37. Q27882070

38. (3ar,4s,7r,7as)-2-((1r,2r)-2-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl)cyclohexylmethyl)hexahydro-4,7-methano-2h-isoindole-1,3-dione, Hydrochloride

39. (3ar,4s,7r,7as)-2-{(1r,2r)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-4,7-methano-2h-isoindole-1,3-dione Hydrochloride

40. (3ar,4s,7r,7as)-2-{[(1r,2r)-2-{[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl]methyl}hexahydro-1h-4,7-methanoisoindole-1,3(2h)-dione Hydrochloride

41. 4-(1,2-benzothiazol-3-yl)-1-{[(1r,2r)-2-{[(3ar,4s,7r,7as)-1,3-dioxooctahydro-2h-4,7-methanoisoindol-2-yl]methyl}cyclohexyl]methyl}piperazin-1-ium Chloride

42. Lurasidone Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2006-10-26
3 Chemical and Physical Properties
Molecular Weight 529.1 g/mol
Molecular Formula C28H37ClN4O2S
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass528.2325753 g/mol
Monoisotopic Mass528.2325753 g/mol
Topological Polar Surface Area85 Ų
Heavy Atom Count36
Formal Charge0
Complexity804
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameLatuda
PubMed HealthLurasidone (By mouth)
Drug ClassesAntipsychotic, Central Nervous System Agent
Drug LabelLATUDA is a psychotropic agent belonging to the chemical class of benzoisothiazol derivatives. Its chemical name is (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl] cyclohexylmethyl}hexahydro-4,7-methano-2H-isoindole-1,3...
Active IngredientLurasidone hydrochloride
Dosage FormTablet
RouteOral
Strength120mg; 60mg; 80mg; 40mg; 20mg
Market StatusPrescription
CompanySunovion Pharms

2 of 2  
Drug NameLatuda
PubMed HealthLurasidone (By mouth)
Drug ClassesAntipsychotic, Central Nervous System Agent
Drug LabelLATUDA is a psychotropic agent belonging to the chemical class of benzoisothiazol derivatives. Its chemical name is (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl] cyclohexylmethyl}hexahydro-4,7-methano-2H-isoindole-1,3...
Active IngredientLurasidone hydrochloride
Dosage FormTablet
RouteOral
Strength120mg; 60mg; 80mg; 40mg; 20mg
Market StatusPrescription
CompanySunovion Pharms

4.2 Drug Indication

Treatment of schizophrenia in adults aged 18 years and over.


Treatment of schizophrenia


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adrenergic alpha-2 Receptor Antagonists

Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Antagonists.)


Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)


Dopamine D2 Receptor Antagonists

Compounds and drugs that bind to and inhibit or block the activation of DOPAMINE D2 RECEPTORS. (See all compounds classified as Dopamine D2 Receptor Antagonists.)


Serotonin 5-HT2 Receptor Antagonists

Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes. (See all compounds classified as Serotonin 5-HT2 Receptor Antagonists.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Atypical Antipsychotic [EPC]
5.3 ATC Code

N05AE05


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07-Jan-2021
27-Sep-2024
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DOSAGE - TABLET;ORAL - 120MG

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