Details
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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20852674Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/veralipride.html | https://www.ncbi.nlm.nih.gov/pubmed/2864641 | https://www.ncbi.nlm.nih.gov/pubmed/20082603
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20852674
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/veralipride.html | https://www.ncbi.nlm.nih.gov/pubmed/2864641 | https://www.ncbi.nlm.nih.gov/pubmed/20082603
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20082603
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/2864641
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2549113 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Aclimafel Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Veralipride-induced tardive dystonia in a patient with bipolar psychosis. | 1992 Oct |
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[Parkinson syndrome induced by veralipride]. | 1995 Jun |
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[Extrapyramidal disorders induced by veralipride (Agreal). Apropos of 5 cases]. | 1995 Sep-Oct |
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Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs. | 1999 Mar |
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Worsening of Parkinsonism after the use of veralipride for treatment of menopause: case report. | 2001 Mar |
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Modification of vasomotor symptoms after various treatment modalities in the postmenopause. | 2001 May |
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Cimicifuga extract BNO 1055: reduction of hot flushes and hints on antidepressant activity. | 2003 Mar 14 |
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[Drug-induced hyperprolactinemia: a case-non-case study from the national pharmacovigilance database]. | 2003 Mar-Apr |
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Alternatives to estrogen. | 2003 Sep |
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The Women's Health Questionnaire (WHQ): Frequently Asked Questions (FAQ). | 2003 Sep 10 |
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Veralipride administered in combination with raloxifene decreases hot flushes and improves bone density in early postmenopausal women. | 2004 Apr |
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Predictors of hot flushes in postmenopausal women who receive raloxifene therapy. | 2004 Dec |
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[Post-menopausal hot flushes and parkinsonism]. | 2004 Nov 1-15 |
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The use of a sum of inverse Gaussian functions to describe the absorption profile of drugs exhibiting complex absorption. | 2005 Aug |
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[Extrapyramidal adverse effects of veralipride (Agreal), a drug used to treat hot flushes: a propos of 17 cases]. | 2005 Jun |
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[Clinical guide to the menopause and post-menopause]. | 2005 Sep 30 |
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Tardive dyskinesia after long-term veralipride treatment. | 2005 Spring |
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Tardive blepharospasm beginning after withdrawal of veralipride. | 2006 Nov |
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The safety of veralipride. | 2006 Sep |
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Reversible jump Markov chain Monte Carlo for deconvolution. | 2007 Jun |
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Management of menopause-associated vasomotor symptoms: Current treatment options, challenges and future directions. | 2010 Aug 9 |
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Bioactivity of isoflavones: assessment through a theoretical model as a way to obtain a "Theoretical Efficacy Related to Estradiol (TERE)". | 2010 Feb 2 |
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Actual status of veralipride use. | 2010 Sep 7 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20852674
100 mg/day for 20 days, with 10 days drug free.
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66883
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WHO-VATC |
QN05AL06
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WHO-ATC |
N05AL06
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66644-81-3
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SUB00037MIG
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47979
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266-435-5
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VERALIPRIDE
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2814
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DTXSID6046268
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C027429
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C152857
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100000079079
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39468
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CHEMBL2105581
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m11412
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4781
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S7064109UD
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DB13523
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ACTIVE MOIETY