Veralipride

Veralipride (Agreal, Agradil) is an atypical antipsychotic of the benzamide class. It is used for the treatment of vasomotor symptoms associated with menopause. It is a D₂ receptor antagonist and it induces prolactin secretion without any estrogenic or progestagenic effects.^[2] It was first authorised for use in 1979. However, Veralipride has never gained approval in the United States.

Veralipride

Clinical data
Trade names	Agreal, Agradil
Routes of administration	Oral
ATC code	N05AL06 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1] In general: ℞ (Prescription only)
Identifiers
IUPAC name 2,3-dimethoxy-N-[(1-prop-2-enylpyrrolidin-2-yl)methyl]-5-sulfamoylbenzamide
CAS Number	66644-81-3 Y
PubChem CID	47979
ChemSpider	43638 N
UNII	S7064109UD
KEGG	D07311
ChEBI	CHEBI:135600
ChEMBL	ChEMBL2105581
CompTox Dashboard (EPA)	DTXSID6046268
ECHA InfoCard	100.060.376
Chemical and physical data
Formula	C17H25N3O5S
Molar mass	383.46 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=CC(=C1OC)C(=O)NCC2CCCN2CC=C)S(=O)(=O)N
InChI InChI=1S/C17H25N3O5S/c1-4-7-20-8-5-6-12(20)11-19-17(21)14-9-13(26(18,22)23)10-15(24-2)16(14)25-3/h4,9-10,12H,1,5-8,11H2,2-3H3,(H,19,21)(H2,18,22,23) N Key:RYJXBGGBZJGVQF-UHFFFAOYSA-N N
NY (what is this?)  (verify)

The women who took it, in addition to extra-pyramidal effects, experienced an aggressive form of depression that resulted in death by suicide for some. The Sanofi laboratory, despite knowing its side effects, allowed women to continue taking it for a considerable amount of time. For this reason, its sale was banned in all countries except Mexico, which allowed its sale to continue for at least 15 years.

In September 2006, veralipride was withdrawn from the Spanish market. As a result, the European Commission referred the matter to the European Medicines Agency (EMA). In July 2007, the EMA recommended the withdrawal of marketing authorisations for veralipride.^[3]