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2D Structure
Also known as: 199739-10-1, Invega sustenna, Xeplion, Invega trinza, Ro92670, Ro 92670
Molecular Formula
C39H57FN4O4
Molecular Weight
664.9  g/mol
InChI Key
VOMKSBFLAZZBOW-UHFFFAOYSA-N
FDA UNII
R8P8USM8FR

A benzisoxazole derivative and active metabolite of RISPERIDONE that functions as a DOPAMINE D2 RECEPTOR ANTAGONIST and SEROTONIN 5-HT2 RECEPTOR ANTAGONIST. It is an ANTIPSYCHOTIC AGENT used in the treatment of SCHIZOPHRENIA.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-2-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl] hexadecanoate
2.1.2 InChI
InChI=1S/C39H57FN4O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-36(45)47-34-17-16-24-44-38(34)41-29(2)32(39(44)46)23-27-43-25-21-30(22-26-43)37-33-20-19-31(40)28-35(33)48-42-37/h19-20,28,30,34H,3-18,21-27H2,1-2H3
2.1.3 InChI Key
VOMKSBFLAZZBOW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCCCCC(=O)OC1CCCN2C1=NC(=C(C2=O)CCN3CCC(CC3)C4=NOC5=C4C=CC(=C5)F)C
2.2 Other Identifiers
2.2.1 UNII
R8P8USM8FR
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(2-(4-(6-fluoro-3-(1,2-benzisoxazolyl))-1-piperidinyl)ethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4h-pyrido(1,2-a)pyrimidin-4-one

2. 9 Hydroxy Risperidone

3. 9 Hydroxyrisperidone

4. 9 Oh Risperidone

5. 9-hydroxy-risperidone

6. 9-hydroxyrisperidone

7. 9-oh-risperidone

8. Invega

9. Invega Sustenna

10. Paliperidone

11. Palmitate, Paliperidone

12. R 76477

13. R-76477

14. R76477

15. Sustenna, Invega

2.3.2 Depositor-Supplied Synonyms

1. 199739-10-1

2. Invega Sustenna

3. Xeplion

4. Invega Trinza

5. Ro92670

6. Ro 92670

7. Paliperidone Palmitate [usan]

8. R8p8usm8fr

9. 3-(2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)-2-methyl-4-oxo-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-9-yl Palmitate

10. Jns010

11. Hexadecanoic Acid, 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl)ethyl)-6,7,8,9-tetrahydro-2-methyl-4-oxo-4h-pyrido(1,2-a)pyrimidin-9-yl Ester

12. Chebi:83808

13. Jns-010

14. Ro-92670

15. R092670

16. (9rs)-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-2-methyl-4-oxo-6,7,8,9-tetrahydro-4h-pyrido(1,2-a)pyrimidin-9-yl Hexadecanoate

17. 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-4-oxo-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-9-yl Hexadecanoate

18. R-092670

19. Trinza

20. [3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-2-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl] Hexadecanoate

21. Hexadecanoic Acid, 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4-oxo-4h-pyrido[1,2-a]pyrimidin-9-yl Ester

22. Unii-r8p8usm8fr

23. 9-hydroxyrisperidone Palmitate

24. Jns 010

25. Pp3m

26. Paliperidone Janssen

27. Palperidone Palmitate

28. Paliperidone Palmitate-[d4]

29. Schembl1871384

30. Chembl2107360

31. Schembl12415674

32. Hy-a0019a

33. Dtxsid70870217

34. Paliperidone Palmitate [mi]

35. Bcp08473

36. Paliperidone Palmitate [jan]

37. Mfcd24386477

38. S5624

39. Paliperidone Palmitate [vandf]

40. Paliperidone Palmitate [mart.]

41. Paliperidone Palmitate [who-dd]

42. Sb17398

43. Ncgc00522023-01

44. Paliperidone Palmitate [ema Epar]

45. Ac-32485

46. As-77089

47. Paliperidone Palmitate [orange Book]

48. Cs-0016387

49. Ft-0673476

50. D83646

51. Q27157250

52. 3-(2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)-2-methyl-4-oxo-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-9-ylpalmitate

53. 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl Hexadecanoate

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 664.9 g/mol
Molecular Formula C39H57FN4O4
XLogP310.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count20
Exact Mass664.43638447 g/mol
Monoisotopic Mass664.43638447 g/mol
Topological Polar Surface Area88.2 Ų
Heavy Atom Count48
Formal Charge0
Complexity1090
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Xeplion is indicated for maintenance treatment of schizophrenia in adult patients stabilised with paliperidone or risperidone.

In selected adult patients with schizophrenia and previous responsiveness to oral paliperidone or risperidone, Xeplion may be used without prior stabilisation with oral treatment if psychotic symptoms are mild to moderate and a long-acting injectable treatment is needed.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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

N05AX13