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)
| Molecular Formula | C17H25N3O5S |
| Molecular Weight | 383.463 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 |
|---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2549113 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Aclimafel Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.3381 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
0.539 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
0.876 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
0.994 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.927 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
3.097 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
4.53 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
6.25 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.14 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
3.51 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
4.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
4.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3981429/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
VERALIPRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
100 mg 1 times / day steady, oral Highest studied dose|Studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: Bilateral galactorrhea, Breast tension... Other AEs: Bilateral galactorrhea (14 patients) Sources: Breast tension (22 patients) Gastrointestinal disorders (6 patients) Asthenia (4 patients) Tachypnea (2 patients) Dyspnea (2 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Bilateral galactorrhea | 14 patients | 100 mg 1 times / day steady, oral Highest studied dose|Studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Dyspnea | 2 patients | 100 mg 1 times / day steady, oral Highest studied dose|Studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Tachypnea | 2 patients | 100 mg 1 times / day steady, oral Highest studied dose|Studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Breast tension | 22 patients | 100 mg 1 times / day steady, oral Highest studied dose|Studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Asthenia | 4 patients | 100 mg 1 times / day steady, oral Highest studied dose|Studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Gastrointestinal disorders | 6 patients | 100 mg 1 times / day steady, oral Highest studied dose|Studied dose Dose: 100 mg, 1 times / day Route: oral Route: steady Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 33.0 |
no | |||
Page: 1.0 |
yes [EC50 14.1254 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 35 | 36 |
no |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 2.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Actual status of veralipride use. | 2010-09-07 |
|
| Management of menopause-associated vasomotor symptoms: Current treatment options, challenges and future directions. | 2010-08-09 |
|
| Reduction of serum serotonin precursors after veralipride treatment for postmenopausal hot flushes. | 2010-04 |
|
| Bioactivity of isoflavones: assessment through a theoretical model as a way to obtain a "Theoretical Efficacy Related to Estradiol (TERE)". | 2010-02-02 |
|
| Pharmacological causes of hyperprolactinemia. | 2007-10 |
|
| Treatment of premature menopause in breast cancer patients. | 2007-06 |
|
| Reversible jump Markov chain Monte Carlo for deconvolution. | 2007-06 |
|
| Safety of alternative treatments for menopausal symptoms after breast cancer: a qualitative systematic review. | 2007-02 |
|
| Adverse drug reactions in patients with phaeochromocytoma: incidence, prevention and management. | 2007 |
|
| Tardive blepharospasm beginning after withdrawal of veralipride. | 2006-11 |
|
| Veralipride-induced acute coronary syndrome unmasking a non-secreting pheochromocytoma. | 2006-09-08 |
|
| The safety of veralipride. | 2006-09 |
|
| [Clinical guide to the menopause and post-menopause]. | 2005-09-30 |
|
| The use of a sum of inverse Gaussian functions to describe the absorption profile of drugs exhibiting complex absorption. | 2005-08 |
|
| [Extrapyramidal adverse effects of veralipride (Agreal), a drug used to treat hot flushes: a propos of 17 cases]. | 2005-06 |
|
| Tardive dyskinesia after long-term veralipride treatment. | 2005 |
|
| Predictors of hot flushes in postmenopausal women who receive raloxifene therapy. | 2004-12 |
|
| [Post-menopausal hot flushes and parkinsonism]. | 2004-11-16 |
|
| Veralipride administered in combination with raloxifene decreases hot flushes and improves bone density in early postmenopausal women. | 2004-04 |
|
| The Women's Health Questionnaire (WHQ): Frequently Asked Questions (FAQ). | 2003-09-10 |
|
| Alternatives to estrogen. | 2003-09 |
|
| [Drug-induced hyperprolactinemia: a case-non-case study from the national pharmacovigilance database]. | 2003-08-29 |
|
| Cimicifuga extract BNO 1055: reduction of hot flushes and hints on antidepressant activity. | 2003-03-14 |
|
| Modification of vasomotor symptoms after various treatment modalities in the postmenopause. | 2001-05 |
|
| Worsening of Parkinsonism after the use of veralipride for treatment of menopause: case report. | 2001-03 |
|
| Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs. | 1999-03 |
|
| [Extrapyramidal disorders induced by veralipride (Agreal). Apropos of 5 cases]. | 1995-09-01 |
|
| [Parkinson syndrome induced by veralipride]. | 1995-06 |
|
| Veralipride-induced tardive dystonia in a patient with bipolar psychosis. | 1992-10 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:38:41 GMT 2025
by
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on
Mon Mar 31 18:38:41 GMT 2025
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| Record UNII |
S7064109UD
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| Record Status |
Validated (UNII)
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| Record Version |
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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 |