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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
Structure of VERALIPRIDE

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)

HIDE SMILES / InChI

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 ( + / - )

Description
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

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/2864641

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Aclimafel

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.3381 mg/L
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1.927 mg × h/L
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4.14 h
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
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
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
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

Doses

DosePopulationAdverse 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)
Breast tension (22 patients)
Gastrointestinal disorders (6 patients)
Asthenia (4 patients)
Tachypnea (2 patients)
Dyspnea (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

100 mg/day for 20 days, with 10 days drug free.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:38:41 GMT 2025
Edited
by admin
on Mon Mar 31 18:38:41 GMT 2025
Record UNII
S7064109UD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AGRADIL
Preferred Name English
VERALIPRIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
VERALIPRIDE [MART.]
Common Name English
veralipride [INN]
Common Name English
AGREAL
Brand Name English
Veralipride [WHO-DD]
Common Name English
VERALIPRIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
WHO-VATC QN05AL06
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
WHO-ATC N05AL06
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
Code System Code Type Description
CAS
66644-81-3
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
EVMPD
SUB00037MIG
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
PUBCHEM
47979
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
ECHA (EC/EINECS)
266-435-5
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
WIKIPEDIA
VERALIPRIDE
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
DRUG CENTRAL
2814
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID6046268
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
MESH
C027429
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
NCI_THESAURUS
C152857
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
SMS_ID
100000079079
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
RXCUI
39468
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL2105581
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
MERCK INDEX
m11412
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY Merck Index
INN
4781
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
FDA UNII
S7064109UD
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
DRUG BANK
DB13523
Created by admin on Mon Mar 31 18:38:42 GMT 2025 , Edited by admin on Mon Mar 31 18:38:42 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY