Drug/Small Molecule:
piperazine

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PharmGKB contains no Clinical Variants that meet the highest level of criteria.

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This is a non-comprehensive list of genetic tests with pharmacogenetics relevance, typically submitted by the manufacturer and manually curated by PharmGKB. The information listed is provided for educational purposes only and does not constitute an endorsement of any listed test or manufacturer.

A more complete listing of genetic tests is found at the Genetic Testing Registry (GTR).

PGx Test Variants Assayed Gene?
2D structure from PubChem
provided by PubChem

Overview

Generic Names
  • Diethylenediamine
  • Diethyleneimine
  • Diketopiperazine
  • Glycine anhydride
  • Hexahydropyrazine
  • Piperazin
  • Piperazin [Germany]
  • Piperazine Citrate
  • Piperazine hexahydrate
  • Piperazine hydrate
  • Prolixin Decanoate
  • fluphenazine dihydrochloride
Trade Names
  • Anatensol
  • Antepan
  • Antepar
  • Antiren
  • Asca-Trol No. 3
  • Bryrel
  • Dapotum
  • Dispermine
  • Entacyl
  • Eraverm
  • Lumbrical
  • Lyogen
  • Moditen
  • Multifuge
  • Omca
  • Pacinol
  • Permitil
  • Piperazidine
  • Pipersol
  • Siqualone
  • Tasnon
  • Tensofin
  • Upixon
  • Uvilon
  • Valamina
  • Vermex
  • Vermidol
  • Vermizine
  • Worm-A-Ton
  • Worm-away
  • Wurmirazin
Brand Mixture Names
  • Canoids Cap (Aloin + Areca Catechu + Arecoline HBr + Benzocaine + Piperazine Citrate + Santonin)
  • Dyrex T F (Phenothiazine + Piperazine + Trichlorfon)
  • Feloids Tab (Aloin + Areca Catechu + Arecoline HBr + Benzocaine + Piperazine Citrate + Santonin)
  • Multi Wormer for Cats (Dichlorophene + Piperazine (Piperazine Citrate))
  • Multi Wormer for Dogs (Dichlorophene + Piperazine (Piperazine Citrate))
  • Ripercol Horse Wormer (Piperazine (Piperazine Hydrochloride) + Tetramisole HCl)

PharmGKB Accession Id:
PA450977

Description

Piperazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystals with a saline taste.

Piperazine was introduced to medicine as a solvent for uric acid. When taken into the body the drug is partly oxidized and partly eliminated unchanged. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful.

Piperazine was first introduced as an anthelmintic in 1953. A large number of piperazine compounds have anthelmintic action. Their mode of action is generally by paralysing parasites, which allows the host body to easily remove or expel the invading organism.

Source: Drug Bank

Indication

Used as alternative treatment for ascariasis caused by Ascaris lumbricoides (roundworm) and enterobiasis (oxyuriasis) caused by Enterobius vermicularis (pinworm). It is also used to treat partial intestinal obstruction by the common roundworm, a condition primarily occurring in children.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

Piperazine is a GABA receptor agonist. Piperzine binds directly and selectively to muscle membrane GABA receptors, presumably causing hyperpolarization of nerve endings, resulting in flaccid paralysis of the worm. While the worm is paralyzed, it is dislodged from the intestinal lumen and expelled live from the body by normal intestinal peristalsis.

Source: Drug Bank

Pharmacology

Piperazine is an anthelminthic especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine hydrate and piperazine citrate are the main anthelminthic piperazines.

Source: Drug Bank

Food Interaction

Take without regard to meals.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

About 25% is metabolized in the liver. Piperazine is nitrosated to form N -mononitrosopiperazine (MNPz) in gastric juice, which is then metabolized to N-nitroso-3-hydroxypyrrolidine (NHPYR).

Source: Drug Bank

Protein Binding

60-70%

Source: Drug Bank

Absorption

Rapidly absorbed from the gastrointestinal tract

Source: Drug Bank

Toxicity

LD 50 = 5 g/kg (Human, oral). Symptoms of overdose include muscle fatigue, seizures, and difficulty breathing.

Source: Drug Bank

Chemical Properties

Chemical Formula

C4H10N2

Source: Drug Bank

Isomeric SMILES

C1CNCCN1

Source: OpenEye

Canonical SMILES

C1CNCCN1

Source: Drug Bank

Average Molecular Weight

86.1356

Source: Drug Bank

Monoisotopic Molecular Weight

86.08439833

Source: Drug Bank

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00592
PDB:
169
ChEBI:
28568
KEGG Compound:
C07973
KEGG Drug:
D00807
PubChem Compound:
4837
PubChem Substance:
46507642
7847872
Drugs Product Database (DPD):
97128
ChemSpider:
13835459
HET:
169
Therapeutic Targets Database:
DAP001418

Clinical Trials

These are trials that mention piperazine and are related to either pharmacogenetics or pharmacogenomics.

Common Searches

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Sources for PharmGKB drug information: DrugBank, Open Eye Scientific Software.