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Identification
Name Piperazine
Accession Number DB00592 (APRD00225)
Type small molecule
Groups approved
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Diethylenediamine
Diethyleneimine
fluphenazine dihydrochloride
Hexahydropyrazine
Piperazin
Piperazin [Germany]
Piperazine hexahydrate
Piperazine hydrate
Salts Not Available
Brand names
Name Company
Anatensol
Antepar
Antiren
Asca-Trol No. 3
Dapotum
Dispermine
Eraverm
Lumbrical
Moditen
Multifuge
Omca
Pacinol
Permitil
Piperazidine
Pipersol
Tasnon
Tensofin
Upixon
Uvilon
Vermex
Vermidol
Vermizine
Worm-A-Ton
Worm-away
Wurmirazin
First Prev Next Last
Brand mixtures
Brand Name Ingredients
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
Categories
  • Anthelmintics
  • Antinematodal Agents
CAS number 110-85-0
Weight Average: 86.1356
Monoisotopic: 86.08439833
Chemical Formula C4H10N2
InChI Key InChIKey=GLUUGHFHXGJENI-UHFFFAOYSA-N
InChI
InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
Plain Text
IUPAC Name
piperazine
SMILES
C1CNCCN1
Plain Text
Mass Spec show (8 KB)
Taxonomy
Kingdom Organic
Classes
  • Piperazines
Substructures
  • Aliphatic and Aryl Amines
  • Piperazines
  • Heterocyclic compounds
Pharmacology
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.
Pharmacodynamics 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.
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.
Absorption Rapidly absorbed from the gastrointestinal tract
Volume of distribution Not Available
Protein binding 60-70%
Metabolism 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).
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity LD50 = 5 g/kg (Human, oral). Symptoms of overdose include muscle fatigue, seizures, and difficulty breathing.
Affected organisms
  • Parasitic nematodes and other roundworms
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
  • Glaxosmithkline
  • Sanofi aventis us llc
  • Bluline laboratories inc
  • Alpharma us pharmaceuticals division
  • Lannett co inc
  • Luitpold pharmaceuticals inc
  • Solvay pharmaceuticals
  • Impax laboratories inc
Packagers
  • Amend
Dosage forms
Form Route Strength
Liquid Oral
Solution / drops Oral
Syrup Oral
Prices
Unit description Cost Unit
Desipramine HCl 150 mg tablet 4.67 USD tablet
Desipramine HCl 100 mg tablet 2.81 USD tablet
Desipramine HCl 75 mg tablet 2.63 USD tablet
Desipramine HCl 50 mg tablet 1.64 USD tablet
Desipramine HCl 10 mg tablet 0.87 USD tablet
Desipramine HCl 25 mg tablet 0.83 USD tablet
Piperazine citrate crystals 0.05 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 106 °C PhysProp
boiling point 146 °C PhysProp
water solubility 1E+006 mg/L (at 25 °C) MERCK INDEX (1996)
logP -1.50 HANSCH,C ET AL. (1995)
logS 1.07 ADME Research, USCD
pKa 9.73 PERRIN,DD (1972)
Predicted Properties
Property Value Source
water solubility 3.71e+02 g/l ALOGPS
logP -1.2 ALOGPS
logP -0.73 ChemAxon
logS 0.63 ALOGPS
pKa (strongest basic) 9.56 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 24.06 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 25.45 ChemAxon
polarizability 9.97 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00807 Link_out
KEGG Compound C07973 Link_out
PubChem Compound 4837 Link_out
PubChem Substance 46507642 Link_out
ChemSpider 13835459 Link_out
ChEBI 28568 Link_out
ChEMBL 28568 Link_out
Therapeutic Targets Database DAP001418 Link_out
PharmGKB PA450977 Link_out
HET 169 Link_out
Drug Product Database 97128 Link_out
Drugs.com http://www.drugs.com/cons/piperazine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Piperazine Link_out
ATC Codes
  • P02CB01
  • R03DA09
AHFS Codes
  • 08:08.00
  • 92:02.00*
PDB Entries Not Available
FDA label Not Available
MSDS show (71.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Gamma-aminobutyric-acid receptor subunit beta-3

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P28472 Link_out
Gene: GABRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Maskell PD, Wafford KA, Bermudez I: Effects of gamma-HCH and delta-HCH on human recombinant GABA receptors: dependence on GABA receptor subunit combination. Br J Pharmacol. 2001 Jan;132(1):205-12. Pubmed
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Enzymes

1. Cytochrome P450 2D6

Actions: substrate

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19