|Accession Number||DB00592 (APRD00225)|
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.
|Brand mixtures||Not Available|
|Mass Spec||show(8 KB)|
|Alternative parents||Piperazines; Polyamines; Dialkylamines|
|Substituents||polyamine; secondary aliphatic amine; secondary amine; amine; organonitrogen compound|
|Classification description||This compound belongs to the diazinanes. These are organic compounds containing diazinane, a six-membered saturated heterocycle containing four carbon atoms and two nitrogen atoms.|
|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|
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|
|Toxicity||LD50 = 5 g/kg (Human, oral). Symptoms of overdose include muscle fatigue, seizures, and difficulty breathing.|
|SNP Mediated Effects||Not Available|
|SNP Mediated Adverse Drug Reactions||Not Available|
|Predicted ADMET features|
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Hong-Xin Li, Jose Guadalupe Santiesteban, Lenore Ann Emig, John Nelson Armor, “Triethylenediamine and piperazine synthesis using zeolite catalysts modified with a silicon-containing compound.” U.S. Patent US6084096, issued 0000.US6084096
|General Reference||Not Available|
|PDB Entries||Not Available|
|FDA label||Not Available|
|Drug Interactions||Not Available|
|Food Interactions||Not Available|
Pharmacological action: yes
|Gamma-aminobutyric acid receptor subunit beta-3||P28472||Details|
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Pharmacological action: unknown
|Cytochrome P450 2D6||P10635||Details|
- 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