Piperazine: Difference between revisions

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|alcohol=Alcohol-Piperazine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
|alcohol=Alcohol-Piperazine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.
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{{chembox new
| ImageFileL1 = Piperazine structure.jpg
| ImageSizeL1 = 70px
| ImageFileR1 = Piperazine3d.png
| ImageFileR2 = 80px
| IUPACName = piperazine
| SystematicName =
| OtherNames = Hexahydropyrazine<br>Piperazidine<br>Diethylenediamine
| Section1 = {{Chembox Identifiers
| CASNo = 110-85-0
| PubChem = 4837
| SMILES = C1CNCCN1
| ATCCode_prefix = P02
| ATCCode_suffix = CB01
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = | C=4 | H=10 | N=2
| MolarMass = 86.136 g/mol
| Appearance =
| Density =
| MeltingPt = 106°C
| Melting_notes =
| BoilingPt = 146°C
| Boiling_notes =
| pKa = 5.68, 9.82
| pKb = }}
| Section5 = {{Chembox Pharmacology
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound = 60-70%
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| PregCat =
| PregCat_AU =
| PregCat_US = }}
}}
{{CMG}}
{{EH}}
==Overview==
'''Piperazine''' is an [[organic compound]] that consists of a six-membered ring containing two opposing nitrogen atoms.  Piperazine exists as small [[alkaline]] [[deliquescent]] [[crystal]]s with a [[salt|saline]] taste.
The '''piperazines''' are a broad class of chemical compounds, many with important pharmacological properties, which contain a core piperazine [[functional group]].
==Origin and naming==
Piperazines were originally named because of their chemical similarity with [[piperidine]], a constituent of [[piperine]] in the [[black pepper]] plant (''Piper nigrum''). Piperidine itself is found in [[fireant]] venom and is the cause of the burning sensations from the bites of these insects.
==Chemistry==
Piperazine is freely soluble in water and [[ethylene glycol]], but insoluble in [[diethyl ether]].  It is a weak [[base (chemistry)|base]] with a [[pKb|pK<sub>b</sub>]] of 4.19; the [[pH]] of a 10% aqueous solution is 10.8-11.8.  Piperazine readily absorbs water and [[carbon dioxide]] from the air.  Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic [[ammonia]] with [[1,2-Dichloroethane|1,2-dichloroethane]]; by the action of [[sodium]] and [[ethylene glycol]] on [[ethylene diamine]] [[hydrochloride]]; or by reduction of [[pyrazine]] with sodium in [[ethanol]].
==Piperazine Derivatives as Drugs==
Piperazine was introduced to [[medicine]] as a solvent for [[uric acid]]. When taken into the body the drug is partly [[redox|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. [[Lycetol]], [[lysidine]] and [[sidonal]] are compounds having similar action. Many piperazine derivatives are notable successful drugs, including:
*Piperazine [[citrate]] (antiparasitic)
*[[Fluphenazine]] ([[phenothiazine]] [[antipsychotic]] drug)
*[[Perphenazine]] ([[phenothiazine]] [[antipsychotic]] drug)
*[[Prochlorperazine]] ([[phenothiazine]] [[antipsychotic]] drug)
*[[Trifluoperazine]] ([[phenothiazine]] [[antipsychotic]] drug)
*[[Flupentixol]] ([[thioxanthene]] [[antipsychotic]] drug)
*[[Thiothixene]] ([[thioxanthene]] [[antipsychotic]] drug)
*[[Zuclopenthixol]] ([[thioxanthene]] [[antipsychotic]] drug)
*[[Clozapine]] ([[antipsychotic]] drug)
*[[Olanzapine]] ([[antipsychotic]] drug)
*[[Aripiprazole]] ([[antipsychotic]] drug)
*[[Ziprasidone]]  ([[antipsychotic]] drug
*[[Sildenafil]] (impotence drug)
*[[Vardenafil]] (impotence drug)
*[[Imatinib]] (leukemia drug)
*[[Meclizine]] (motion sickness drug)
*[[Cyclizine]] (antiemetic antihistamine)
*[[Niaprazine]] (sedating antihistamine)
*[[Trazodone]] (sedating antidepressant)
*[[Nefazodone]] (analgesic antidepressant)
*[[Antrafenine]] (analgesic)
*[[Befuraline]] (stimulant antidepressant)
*[[Trelibet]] (stimulant antidepressant)
*[[Fipexide]] (nootropic)
*[[Trimetazidine]] (anti-angina drug)
*[[Ranolazine]] (anti-angina drug)
*[[Benzylpiperazine|BZP]] (recreational stimulant)
*[[TFMPP]] (hallucinogen)
*[[1-(3-Chlorophenyl)piperazine|mCPP]] (stimulant)
*[[MeOPP]] (stimulant)
*[[pFPP]] (hallucinogen)
*[[Hydrocathitryptozine]] (synthetic stimulant/hallucinogen)
==As an anthelmintic==
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 [[paralysis|paralysing]] parasites, which allows the host body to easily remove or expel the invading organism. This action is mediated by its [[agonist]] effects upon the inhibitory [[GABA]] (γ-aminobutyric acid) receptor. Its selectivity for [[helminths]] is because vertebrates only use GABA in the [[CNS]] and the helminths' GABA receptor is a different isoform to the vertebrate's one. ''Piperazine hydrate'' and ''piperazine citrate'' are the main anthelminthic piperazines. These drugs are often referred to simply as "piperazine" which may cause confusion between the specific anthelmintic drugs and the entire class of piperazine-containing compounds.
==Other uses==
Piperazines are also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials.
Piperazine ferulate tablets are used as a Chinese herb and in one patient resulted in elevated liver enzymes when taken during treatment for latent tuberculosis infection with isoniazid (INH). Stopping both Chinese herb and INH brought liver enzymes back to normal range within 1 month.
==References==
*''Merck Index'', 11th Edition, '''7431'''.
==See also==
* [[Piperidine]]
==External links==
*[http://www.erowid.org/chemicals/piperazines/piperazines.shtml Erowid piperazine vault]
* [http://www.tripme.co.nz Piperazine Reviews and Information]
<br>
{{1911}}
{{Anthelmintics}}
[[Category:Amines]]
[[Category:Piperazines|*]]
[[de:Piperazin]]
[[fr:Pipérazine]]
[[it:Piperazina]]
[[lt:Piperazinas]]
[[ja:ピペラジン]]
[[pl:Piperazyna]]
[[fi:Piperatsiini]]
{{jb1}}
{{WH}}
{{WS}}

Revision as of 19:00, 9 January 2015

Piperazine
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Alberto Plate [2]

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Overview

Piperazine is {{{aOrAn}}} {{{drugClass}}} that is FDA approved for the {{{indicationType}}} of {{{indication}}}. Common adverse reactions include {{{adverseReactions}}}.

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

There is limited information regarding Piperazine FDA-Labeled Indications and Dosage (Adult) in the drug label.

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Piperazine in adult patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Piperazine in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

There is limited information regarding Piperazine FDA-Labeled Indications and Dosage (Pediatric) in the drug label.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Piperazine in pediatric patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Piperazine in pediatric patients.

Contraindications

There is limited information regarding Piperazine Contraindications in the drug label.

Warnings

There is limited information regarding Piperazine Warnings' in the drug label.

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Piperazine Clinical Trials Experience in the drug label.

Postmarketing Experience

There is limited information regarding Piperazine Postmarketing Experience in the drug label.

Drug Interactions

There is limited information regarding Piperazine Drug Interactions in the drug label.

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA): There is no FDA guidance on usage of Piperazine in women who are pregnant.
Pregnancy Category (AUS): There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Piperazine in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Piperazine during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Piperazine in women who are nursing.

Pediatric Use

There is no FDA guidance on the use of Piperazine in pediatric settings.

Geriatic Use

There is no FDA guidance on the use of Piperazine in geriatric settings.

Gender

There is no FDA guidance on the use of Piperazine with respect to specific gender populations.

Race

There is no FDA guidance on the use of Piperazine with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Piperazine in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Piperazine in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Piperazine in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Piperazine in patients who are immunocompromised.

Administration and Monitoring

Administration

There is limited information regarding Piperazine Administration in the drug label.

Monitoring

There is limited information regarding Piperazine Monitoring in the drug label.

IV Compatibility

There is limited information regarding the compatibility of Piperazine and IV administrations.

Overdosage

There is limited information regarding Piperazine overdosage. If you suspect drug poisoning or overdose, please contact the National Poison Help hotline (1-800-222-1222) immediately.

Pharmacology

Template:Chembox new

Mechanism of Action

There is limited information regarding Piperazine Mechanism of Action in the drug label.

Structure

There is limited information regarding Piperazine Structure in the drug label.

Pharmacodynamics

There is limited information regarding Piperazine Pharmacodynamics in the drug label.

Pharmacokinetics

There is limited information regarding Piperazine Pharmacokinetics in the drug label.

Nonclinical Toxicology

There is limited information regarding Piperazine Nonclinical Toxicology in the drug label.

Clinical Studies

There is limited information regarding Piperazine Clinical Studies in the drug label.

How Supplied

There is limited information regarding Piperazine How Supplied in the drug label.

Storage

There is limited information regarding Piperazine Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Piperazine |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Piperazine |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Piperazine Patient Counseling Information in the drug label.

Precautions with Alcohol

Alcohol-Piperazine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

There is limited information regarding Piperazine Brand Names in the drug label.

Look-Alike Drug Names

There is limited information regarding Piperazine Look-Alike Drug Names in the drug label.

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

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