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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
PubMed

PubMed

TitleDatePubMed
Veralipride-induced tardive dystonia in a patient with bipolar psychosis.
1992 Oct
[Parkinson syndrome induced by veralipride].
1995 Jun
[Extrapyramidal disorders induced by veralipride (Agreal). Apropos of 5 cases].
1995 Sep-Oct
Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs.
1999 Mar
Worsening of Parkinsonism after the use of veralipride for treatment of menopause: case report.
2001 Mar
Modification of vasomotor symptoms after various treatment modalities in the postmenopause.
2001 May
Cimicifuga extract BNO 1055: reduction of hot flushes and hints on antidepressant activity.
2003 Mar 14
[Drug-induced hyperprolactinemia: a case-non-case study from the national pharmacovigilance database].
2003 Mar-Apr
Alternatives to estrogen.
2003 Sep
The Women's Health Questionnaire (WHQ): Frequently Asked Questions (FAQ).
2003 Sep 10
Veralipride administered in combination with raloxifene decreases hot flushes and improves bone density in early postmenopausal women.
2004 Apr
Predictors of hot flushes in postmenopausal women who receive raloxifene therapy.
2004 Dec
[Post-menopausal hot flushes and parkinsonism].
2004 Nov 1-15
The use of a sum of inverse Gaussian functions to describe the absorption profile of drugs exhibiting complex absorption.
2005 Aug
[Extrapyramidal adverse effects of veralipride (Agreal), a drug used to treat hot flushes: a propos of 17 cases].
2005 Jun
[Clinical guide to the menopause and post-menopause].
2005 Sep 30
Tardive dyskinesia after long-term veralipride treatment.
2005 Spring
Veralipride-induced acute coronary syndrome unmasking a non-secreting pheochromocytoma.
2006 Jul-Aug
Tardive blepharospasm beginning after withdrawal of veralipride.
2006 Nov
The safety of veralipride.
2006 Sep
Adverse drug reactions in patients with phaeochromocytoma: incidence, prevention and management.
2007
Safety of alternative treatments for menopausal symptoms after breast cancer: a qualitative systematic review.
2007 Feb
Treatment of premature menopause in breast cancer patients.
2007 Jun
Reversible jump Markov chain Monte Carlo for deconvolution.
2007 Jun
Pharmacological causes of hyperprolactinemia.
2007 Oct
Reduction of serum serotonin precursors after veralipride treatment for postmenopausal hot flushes.
2010 Apr
Management of menopause-associated vasomotor symptoms: Current treatment options, challenges and future directions.
2010 Aug 9
Bioactivity of isoflavones: assessment through a theoretical model as a way to obtain a "Theoretical Efficacy Related to Estradiol (TERE)".
2010 Feb 2
Actual status of veralipride use.
2010 Sep 7
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 Fri Dec 15 16:58:46 GMT 2023
Edited
by admin
on Fri Dec 15 16:58:46 GMT 2023
Record UNII
S7064109UD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VERALIPRIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
VERALIPRIDE [MART.]
Common Name English
veralipride [INN]
Common Name English
AGRADIL
Brand 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 Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
WHO-VATC QN05AL06
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
WHO-ATC N05AL06
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
Code System Code Type Description
CAS
66644-81-3
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
EVMPD
SUB00037MIG
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
PUBCHEM
47979
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
266-435-5
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
WIKIPEDIA
VERALIPRIDE
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
DRUG CENTRAL
2814
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID6046268
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
MESH
C027429
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
NCI_THESAURUS
C152857
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
SMS_ID
100000079079
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
RXCUI
39468
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL2105581
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
MERCK INDEX
m11412
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY Merck Index
INN
4781
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
FDA UNII
S7064109UD
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
DRUG BANK
DB13523
Created by admin on Fri Dec 15 16:58:46 GMT 2023 , Edited by admin on Fri Dec 15 16:58:46 GMT 2023
PRIMARY
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ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY