Mepiprazole

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Mepiprazole
Accession Number
DB09197
Type
Small Molecule
Groups
Experimental
Description

Mepiprazole is a minor tranquilizer with a phenylpiperazine structure. It is a pyrazolyl-alkyl-piperazine derivative belonging to a class of psychotropic drug. It mediates a weak inhibitory action on the uptake of 5-HT on hypothalamic neurons [7]. Mepiprazole is marketed in Spain for the treatment of anxiety neuroses.

It acts as a 5-HT2A and α1-adrenergic receptor antagonist, and has also been shown to inhibit the reuptake and induce the release of serotonin, dopamine, and norepinephrine to varying extents. Controlled clinical trials of mepiprazole in patients with irritable bowel syndrome (IBS) were also carried out and suggested some benefits of the drug in relieving symptoms of IBS in some patients. Similarly to other phenylpiperazines like trazodone, nefazodone, and etoperidone, mepiprazole produces mCPP as an active metabolite.

Structure
Thumb
Synonyms
Not Available
External IDs
EMD-16923
Product Ingredients
IngredientUNIICASInChI Key
Mepiprazole hydrochlorideTN5WJ92YGP20344-15-4FOZDCFRVHJVSIY-UHFFFAOYSA-N
International/Other Brands
Psigodal
Categories
Not Available
UNII
977BAL0NR7
CAS number
20326-12-9
Weight
Average: 304.82
Monoisotopic: 304.1454744
Chemical Formula
C16H21ClN4
InChI Key
DOTIMEKVTCOGED-UHFFFAOYSA-N
InChI
InChI=1S/C16H21ClN4/c1-13-11-15(19-18-13)5-6-20-7-9-21(10-8-20)16-4-2-3-14(17)12-16/h2-4,11-12H,5-10H2,1H3,(H,18,19)
IUPAC Name
1-(3-chlorophenyl)-4-[2-(5-methyl-1H-pyrazol-3-yl)ethyl]piperazine
SMILES
[H]N1N=C(CCN2CCN(CC2)C2=CC(Cl)=CC=C2)C=C1C

Pharmacology

Indication

For the treatment of anxiety neuroses.

Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Poldinger W: Clinical trial of 3-methyl-5-(beta-N'-(N-m-chlorophenylpiperazino)ethyl)-pyrazole dihydrochloride (Mepiprazol) in the therapy of psychovegetative disorders. Int Pharmacopsychiatry. 1975;10(1):1-8. [PubMed:1095510]
  2. De Buck R, Van Durme R, Pelc I: [A controlled double-blind crossover study of the efficacy of mepiprazol (EMD 16.923) and of diazepam in the treatment of neurotic disorders]. Acta Psychiatr Belg. 1975 May;75(3):320-33. [PubMed:769484]
  3. Saldana Hernandez OH, Hernandez Gonzalez J: [Psychopharmological research with EMD 16-923 in patients with different degrees of anxiety]. Neurol Neurocir Psiquiatr. 1976;17(1):29-33. [PubMed:1052713]
  4. Cohen ML, Fuller RW, Kurz KD: Evidence that blood pressure reduction by serotonin antagonists is related to alpha receptor blockade in spontaneously hypertensive rats. Hypertension. 1983 Sep-Oct;5(5):676-81. [PubMed:6311738]
  5. Maj J, Sypniewska M: Central action of mepiprazole. Pol J Pharmacol Pharm. 1980 Jul-Aug;32(4):475-84. [PubMed:7255266]
  6. Fuxe K, Agnati LF, Ungerstedt U: The effect of mepiprazole on central monoamine neurons. Evidence for increased 5-hydroxytryptamine and dopamine receptor activity. Eur J Pharmacol. 1976 Jan;35(1):93-108. [PubMed:943291]
  7. Placheta P, Singer E, Kriwanek W, Hertting G: Mepiprazole, a new psychotropic drug: effects on uptake and retention of monoamines in rat brain synaptosomes. Psychopharmacology (Berl). 1976 Aug 17;48(3):295-301. [PubMed:9660]
  8. Dotevall G, Groll E: Controlled clinical trial of mepiprazole in irritable bowel syndrome. Br Med J. 1974 Oct 5;4(5935):16-8. [PubMed:4609545]
  9. Fong MH, Garattini S, Caccia S: 1-m-Chlorophenylpiperazine is an active metabolite common to the psychotropic drugs trazodone, etoperidone and mepiprazole. J Pharm Pharmacol. 1982 Oct;34(10):674-5. [PubMed:6128394]
External Links
PubChem Compound
71897
PubChem Substance
310265105
ChemSpider
64909
ChEBI
134701
ChEMBL
CHEMBL2106537
Wikipedia
Mepiprazole

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.409 mg/mLALOGPS
logP3.31ALOGPS
logP3.08ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)15.24ChemAxon
pKa (Strongest Basic)7.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.16 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.97 m3·mol-1ChemAxon
Polarizability34.3 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
Phenylpiperazines
Alternative Parents
N-arylpiperazines / Dialkylarylamines / Aniline and substituted anilines / N-alkylpiperazines / Chlorobenzenes / Aralkylamines / Aryl chlorides / Pyrazoles / Heteroaromatic compounds / Trialkylamines
show 4 more
Substituents
Phenylpiperazine / N-arylpiperazine / Tertiary aliphatic/aromatic amine / Dialkylarylamine / Aniline or substituted anilines / Chlorobenzene / Halobenzene / N-alkylpiperazine / Aralkylamine / Aryl chloride
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on October 16, 2015 15:40 / Updated on November 02, 2018 08:49