NAV

Mepiprazole

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

Identification

Generic Name
Mepiprazole
DrugBank Accession Number
DB09197
Background

Mepiprazole is a minor tranquilizer with a phenylpiperazine structure. It is a pyrazolyl-alkyl-piperazine derivative. Mepiprazole 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. Clinical studies of mepiprazole including patients with irritable bowel syndrome (IBS) were conducted and the results showed some beneficial effects of mepiprazole in relieving IBS symptoms in certain patients. Like other phenylpiperazine drugs, mepiprazole produces the active metabolite m-chlorophenylpiperazine(mCPP).

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 304.82
Monoisotopic: 304.1454744
Chemical Formula
C16H21ClN4
Synonyms
  • Mepiprazol
  • Mepiprazole
  • Mepiprazolum
External IDs
  • EMD-16923
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Pharmacology

Indication

For the treatment of anxiety neuroses.

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Mepiprazole dihydrochlorideTN5WJ92YGP20344-15-4FOZDCFRVHJVSIY-UHFFFAOYSA-N
International/Other Brands
Psigodal

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Amine / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Chlorobenzene
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
977BAL0NR7
CAS number
20326-12-9
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Maj J, Sypniewska M: Central action of mepiprazole. Pol J Pharmacol Pharm. 1980 Jul-Aug;32(4):475-84. [Article]
  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. [Article]
  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. [Article]
  8. Dotevall G, Groll E: Controlled clinical trial of mepiprazole in irritable bowel syndrome. Br Med J. 1974 Oct 5;4(5935):16-8. [Article]
  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. [Article]
PubChem Compound
71897
PubChem Substance
310265105
ChemSpider
64909
ChEBI
134701
ChEMBL
CHEMBL2106537
ZINC
ZINC000000001682
Wikipedia
Mepiprazole

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-0a4j-6940000000-eeaab2cfd461ef03fa36
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0019000000-91d5eda36c7dedee4447
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1009000000-199d465ecfe1d8731e5a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0129000000-77a33d4966ab99265074
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ugi-6469000000-73c83dde4367cba118ec
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-2920000000-4d38dce3c40fe3a90302
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9110000000-db5a2d829393bf86202d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-165.30638
predicted
DeepCCS 1.0 (2019)
[M+H]+167.66437
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.75752
predicted
DeepCCS 1.0 (2019)

Drug created at October 16, 2015 21:40 / Updated at February 02, 2024 22:52