Stereochemistry | RACEMIC |
Molecular Formula | C17H25N3O5S |
Molecular Weight | 383.463 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C(=CC(=C1)S(N)(=O)=O)C(=O)NCC2CCCN2CC=C
InChI
InChIKey=RYJXBGGBZJGVQF-UHFFFAOYSA-N
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)
Molecular Formula | C17H25N3O5S |
Molecular Weight | 383.463 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Veralipride (trade name Agreal, Agradil) is a benzamide neuroleptic medicine indicated in the treatment of vasomotor symptoms associated with the menopause when a contraindication or non-acceptance of hormone therapy (HT) exists. Veralipride is a dopaminergic antagonist of receptor D2, that induces prolactin secretion without any estrogenic or progestagenic effects. Veralipride is well absorbed when administered orally, achieving maximal concentrations at 2.5 hours. It is poorly metabolized and is eliminated in the urine and feces. After oral administration, the half-life is 4 hours, and 44% is excreted without any changes in urine in the first 120 hours. Most of the studies agree that the decrease of vasomotor symptoms associated with the menopause (hot flushes) with veralipride use is from 48.0% to 89.9% depending on the time of use and method of administration. One of the main secondary effects of veralipride use is hyperprolactinemia, which may or may not be accompanied by galactorrhea, and can disappear at 48 hours of treatment withdrawal. The most serious effects that have been reported with veralipride use are those extrapyramidal, such as acute dyskinesia, tardive dyskinesia, Parkinsonism, postural tremor, myoclonia, and dystonia. Many of these have been related to over-dosage and due to the lack of prescription instruction follow-up. The presentation of secondary adverse events is decreased using this medicament at a dose no greater than 100 mg/day, for short time spans, and leaving drug-free intervals between schedules. Veralipride has never gained approval in the United States. On July 2007, the EMA recommended the withdrawal of marketing authorizations for veralipride. The still in use Mexican Official Norm for the prevention and control of perimenopausal and postmenopausal diseases in women establishes that the drug can be useful in the control of vasomotor symptoms.