10209. Paliperidone

Nomenclature

CAS number: 144598-75-4
3-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; 9-hydroxyrisperidone; RO-76477; R-76477; Invega (J & J).
C23H27FN4O3; mol wt 426.48.
C 64.77%, H 6.38%, F 4.45%, N 13.14%, O 11.25%.

Description and references

Dual antagonist of central dopamine D2 and serotonin type 2 (5HT2a) receptors; also active as an antagonist at α1 and α2 adrenergic receptors and H1 histamine receptors. Major active metabolite of risperidone, q.v. Prepn: C. G. M. Janssen et al., EP 368388; eidem, US 5158952 (1990, 1992 both to Janssen). Simultaneous LC/MS/MS determn with risperidone in plasma: M. Aravagiri, S. R. Marder, J. Mass Spectrom. 35, 718 (2000) DOI PubMed. Clinical trial in schizophrenia: J. Kane et al., Schizophr. Res. 90, 147 (2007) DOI PubMed. Review of development and clinical experience: L. Citrome, Int. J. Clin. Pract. 61, 653-662 (2007) DOI PubMed.

Chemical structure

Properties

Crystals from 2-propanol, mp 179.8°. Slightly sol in DMF; sparingly sol in 0.1N HCl, methylene chloride. Practically insol in water, hexane, 0.1N NaOH.

Derivative

Palmitate.

Nomenclature

CAS number: 199739-10-1
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; 9-hydroxyrisperidone palmitate; RO-92670.
C39H57FN4O4; mol wt 664.89.
C 70.45%, H 8.64%, F 2.86%, N 8.43%, O 9.63%.

Description and references

Prepn: M. K. J. Franois et al., WO 9744039; eidem, US 6077843 (1997, 2000 both to Janssen).

Properties

Crystals from isopropanol.

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Benzisoxazoles; Serotonin-Dopamine Antagonist