Veralipride

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); 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 ;
PubChem CID	47979;
ChemSpider	43638 ;
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) ; Key:RYJXBGGBZJGVQF-UHFFFAOYSA-N ;
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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.

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In September 2006, veralipride was withdrawn from the Spanish market.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]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Carranza-Lira S (September 2010). "Actual status of veralipride use". Clinical Interventions in Aging. 5: 271–6. doi:10.2147/cia.s12640. PMC 2938034. PMID 20852674.
^ "Overall Summary of the Scientific Evaluation of Medicinal Products Containing Veralipride" (PDF). EMEA.

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[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[pmid20852674-2] Carranza-Lira S (September 2010). "Actual status of veralipride use". Clinical Interventions in Aging. 5: 271–6. doi:10.2147/cia.s12640. PMC 2938034. PMID 20852674.

[3] "Overall Summary of the Scientific Evaluation of Medicinal Products Containing Veralipride" (PDF). EMEA.

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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

See also

References