Piperazine
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
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
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Package and Label Display Panel
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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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Overview
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.
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 with a pKb 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; 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 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)
- BZP (recreational stimulant)
- TFMPP (hallucinogen)
- 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 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
External links
Template:1911 Template:Anthelmintics