Piperazine
Identification
- Summary
Piperazine is a medication used to treat roundworm and pinworm.
- Generic Name
- Piperazine
- DrugBank Accession Number
- DB00592
- Background
Piperazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms. First used as a solvent for uric acid, the use of piperazine as an anthelmintic agent was first introduced in 1953. Upon entry into the systemic circulation, the drug is partly oxidized and partly eliminated as an unchanged compound. 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. Piperazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Piperazine (DB00592)
- Weight
- Average: 86.1356
Monoisotopic: 86.08439833 - Chemical Formula
- C4H10N2
- Synonyms
- Diethylenediamine
- Piperazidine
- Piperazin
- Piperazina
- Piperazine
- External IDs
- FEMA NO. 4250
- P02CB01
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.
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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.
Target Actions Organism AGamma-aminobutyric acid receptor subunit beta-3 agonistHumans - 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).
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- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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LD50 = 5 g/kg (Human, oral). Symptoms of overdose include muscle fatigue, seizures, and difficulty breathing.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Piperazine can be increased when combined with Abatacept. Abiraterone The metabolism of Piperazine can be decreased when combined with Abiraterone. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Piperazine. Acebutolol The metabolism of Piperazine can be decreased when combined with Acebutolol. Acetaminophen The metabolism of Piperazine can be decreased when combined with Acetaminophen. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Piperazine. Adalimumab The metabolism of Piperazine can be increased when combined with Adalimumab. Albiglutide The therapeutic efficacy of Albiglutide can be decreased when used in combination with Piperazine. Almotriptan The metabolism of Almotriptan can be decreased when combined with Piperazine. Alogliptin The therapeutic efficacy of Alogliptin can be decreased when used in combination with Piperazine. 
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- Take with or without food. The absorption is unaffected by food.
Products
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Ingredient UNII CAS InChI Key Piperazine adipate V7P5P122LB 142-88-1 BVEGEKOBSPXUJS-UHFFFAOYSA-N Piperazine citrate 63KP7FXF2I 41372-10-5 SWDXALWLRYIJHK-UHFFFAOYSA-N Piperazine hexahydrate P3M07B8U64 142-63-2 AVRVZRUEXIEGMP-UHFFFAOYSA-N Piperazine hydrate 5O5QWX2S2D 16832-43-2 JRRBJSPQEVZLPI-UHFFFAOYSA-N Piperazine hydrochloride 17VU4Z4W88 142-64-3 CVVIJWRCGSYCMB-UHFFFAOYSA-N Piperazine monohydrochloride 7N36JHA4P6 7542-23-6 MSQACBWWAIBWIC-UHFFFAOYSA-N Piperazine phosphate 8TIF7T48FP 18534-18-4 PMGABIJVFLPSLS-UHFFFAOYSA-N Piperazine sulfate C8493J9B36 3597-26-0 MYNIYCGOBKAQAO-UHFFFAOYSA-N - International/Other Brands
- Antepar / Uvilon / Vermidol / Vermizine
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Versol 100mg Liquid 100 mg / mL Oral Les Produits Gerbex Inc. 1970-12-31 1998-07-02 Canada 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Entacyl Granules Powder, for solution 2 g / pck Oral Shire Pharma Canada Ulc 1995-12-31 2001-09-17 Canada Entacyl Granules 2.0gm Powder 2 g / 4 g Oral Allen & Hanburys A Glaxo Canada Ltd. Co. 1951-12-31 1996-09-10 Canada Entacyl Susp 0.6gm/5ml Suspension 600 mg / 5 mL Oral Allen & Hanburys A Glaxo Canada Ltd. Co. 1951-12-31 1998-07-29 Canada Entacyl Suspension-600mg/5ml Suspension 600 mg / 5 mL Oral Roberts Pharmaceutical 1997-04-01 2000-07-31 Canada Formule C34 Liquid 100 mg / mL Oral Herbages Naturbec LtÉe. 1979-12-31 2020-10-06 Canada Veriga 125 Liquid 110 mg / mL Oral Frega Inc. 1979-12-31 1996-09-09 Canada Vermirex Syr Syrup 110 mg / mL Oral Les Laboratoires Vachon Inc. 1968-12-31 2008-07-09 Canada
Categories
- ATC Codes
- P02CB01 — Piperazine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as piperazines. These are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- Piperazines
- Alternative Parents
- Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aliphatic heteromonocyclic compound / Amine / Azacycle / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Piperazine / Secondary aliphatic amine / Secondary amine
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- azacycloalkane, saturated organic heteromonocyclic parent, piperazines (CHEBI:28568)
- Affected organisms
- Parasitic nematodes and other roundworms
Chemical Identifiers
- UNII
- 1RTM4PAL0V
- CAS number
- 110-85-0
- InChI Key
- GLUUGHFHXGJENI-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
- IUPAC Name
- piperazine
- SMILES
- C1CNCCN1
References
- Synthesis Reference
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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014730
- KEGG Drug
- D00807
- KEGG Compound
- C07973
- PubChem Compound
- 4837
- PubChem Substance
- 46507642
- ChemSpider
- 13835459
- 8340
- ChEBI
- 28568
- ChEMBL
- CHEMBL1412
- ZINC
- ZINC000005850277
- Therapeutic Targets Database
- DAP001418
- PharmGKB
- PA450977
- PDBe Ligand
- PZE
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Piperazine
- AHFS Codes
- 08:08.00 — Anthelmintics
- PDB Entries
- 3qf1 / 5g4b / 6esm
- MSDS
- Download (71.9 KB)
Clinical Trials
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 Syrup Oral Powder, for solution Oral 2 g / pck Powder Oral 2 g / 4 g Suspension Oral 600 mg / 5 mL Liquid Oral 100 mg / mL Solution Oral Lozenge Oral Powder Oral Capsule Liquid Oral 110 mg / mL Syrup Oral 110 mg / mL Solution Oral 500 mg/5ml Syrup Oral 750 mg/5ml Syrup Oral 500 mg/5ml - Prices
Unit description Cost Unit Desipramine HCl 150 mg tablet 4.67USD tablet Desipramine HCl 100 mg tablet 2.81USD tablet Desipramine HCl 75 mg tablet 2.63USD tablet Desipramine HCl 50 mg tablet 1.64USD tablet Desipramine HCl 10 mg tablet 0.87USD tablet Desipramine HCl 25 mg tablet 0.83USD tablet Piperazine citrate crystals 0.05USD 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 (°C) 106 °C PhysProp boiling point (°C) 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 371.0 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 25.45 m3·mol-1 ChemAxon Polarizability 9.97 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7652 Blood Brain Barrier + 0.8549 Caco-2 permeable + 0.6029 P-glycoprotein substrate Substrate 0.7537 P-glycoprotein inhibitor I Non-inhibitor 0.9851 P-glycoprotein inhibitor II Non-inhibitor 0.996 Renal organic cation transporter Non-inhibitor 0.562 CYP450 2C9 substrate Non-substrate 0.9243 CYP450 2D6 substrate Non-substrate 0.5478 CYP450 3A4 substrate Non-substrate 0.8425 CYP450 1A2 substrate Non-inhibitor 0.9165 CYP450 2C9 inhibitor Non-inhibitor 0.9681 CYP450 2D6 inhibitor Non-inhibitor 0.9632 CYP450 2C19 inhibitor Non-inhibitor 0.9805 CYP450 3A4 inhibitor Non-inhibitor 0.9928 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.99 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9171 Biodegradation Not ready biodegradable 0.9436 Rat acute toxicity 1.6247 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5571 hERG inhibition (predictor II) Non-inhibitor 0.7868
Spectra
- Mass Spec (NIST)
- Download (8 KB)
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Gaba-gated chloride ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRB3
- Uniprot ID
- P28472
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-3
- Molecular Weight
- 54115.04 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Maskell PD, Wafford KA, Bermudez I: Effects of gamma-HCH and delta-HCH on human recombinant GABA(A) receptors: dependence on GABA(A) receptor subunit combination. Br J Pharmacol. 2001 Jan;132(1):205-12. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- 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...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Maurer HH, Kraemer T, Springer D, Staack RF: Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Ther Drug Monit. 2004 Apr;26(2):127-31. [Article]
Drug created on June 13, 2005 13:24 / Updated on May 14, 2021 11:41