Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H10N2 |
Molecular Weight | 86.1356 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CNCCN1
InChI
InChIKey=GLUUGHFHXGJENI-UHFFFAOYSA-N
InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
Molecular Formula | C4H10N2 |
Molecular Weight | 86.1356 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.mayoclinic.org/drugs-supplements/piperazine-oral-route/proper-use/drg-20065522Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27177234 |
Sources: http://www.mayoclinic.org/drugs-supplements/piperazine-oral-route/proper-use/drg-20065522
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27177234 |
Piperazine, a six membered nitrogen containing heterocycle, is of great significance to the rational design of drugs. This moiety can be found in a plethora of well-known drugs with various therapeutic uses, such as antipsychotic, antihistamine, antianginal, antidepressant, anticancer, antiviral, cardio protectors, anti-inflammatory, and imaging agents. Slight modification to the substitution pattern on the piperazine nucleus facilitates a recognizable difference in the medicinal potential of the resultant molecules. Piperazine has been used as an antihelmintic drug. Piperazine works by paralyzing the worms. They are then passed in the stool.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5099003 | https://www.ncbi.nlm.nih.gov/pubmed/7673626
Curator's Comment: Piperazine is neurotoxic.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: UniProtKB: D6BK80_HAECO | D6BJF3_HAECO (GABA receptor subunit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22075040 |
6.23 mM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | MULTIFUGE Approved UsePiperazine belongs to the family of medicines called anthelmintics. Anthelmintics are used in the treatment of worm infections. Piperazine is used to treat: common roundworms (ascariasis) and pinworms (enterobiasis; oxyuriasis). Launch Date1954 |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg/m3/h single, respiratory Studied dose Dose: 10 mg/m3/h Route: respiratory Route: single Dose: 10 mg/m3/h Sources: |
unhealthy, 42 years |
Other AEs: Asthma late onset... |
115 mg/kg 1 times / day steady, oral Highest studied dose Dose: 115 mg/kg, 1 times / day Route: oral Route: steady Dose: 115 mg/kg, 1 times / day Sources: |
unhealthy, 6 years |
Disc. AE: Myoclonus... AEs leading to discontinuation/dose reduction: Myoclonus (1 patient) Sources: |
65 mg/kg 1 times / day steady, oral Recommended Dose: 65 mg/kg, 1 times / day Route: oral Route: steady Dose: 65 mg/kg, 1 times / day Sources: |
unhealthy, 9 years |
Disc. AE: Ataxia... AEs leading to discontinuation/dose reduction: Ataxia (1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Asthma late onset | 1 patient | 10 mg/m3/h single, respiratory Studied dose Dose: 10 mg/m3/h Route: respiratory Route: single Dose: 10 mg/m3/h Sources: |
unhealthy, 42 years |
Myoclonus | 1 patient Disc. AE |
115 mg/kg 1 times / day steady, oral Highest studied dose Dose: 115 mg/kg, 1 times / day Route: oral Route: steady Dose: 115 mg/kg, 1 times / day Sources: |
unhealthy, 6 years |
Ataxia | 1 patient Disc. AE |
65 mg/kg 1 times / day steady, oral Recommended Dose: 65 mg/kg, 1 times / day Route: oral Route: steady Dose: 65 mg/kg, 1 times / day Sources: |
unhealthy, 9 years |
PubMed
Title | Date | PubMed |
---|---|---|
Gonadotrophin-releasing hormone antagonists for assisted conception. | 2001 |
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Investigation of synthetic peptide hormones by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry: analysis of a synthesis crude of peptide triptorelin. | 2001 |
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Dose-dense sequential adjuvant chemotherapy with epirubicin, paclitaxel and CMF in high-risk breast cancer. | 2001 |
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Biliary Ascariasis in children. | 2001 Apr-Jun |
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A practical GnRH analogue (triptorelin) stimulation test to distinguish constitutional delay of puberty from hypogonadotropic hypogonadism in prepubertal boys. | 2001 Apr-Jun |
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Diketopiperazine receptors: a novel class of highly selective receptors for binding small peptides. | 2001 Aug 3 |
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Pharmacokinetics and metabolism of a selective PDE5 inhibitor (UK-343,664) in rat and dog. | 2001 Aug-Sep |
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A combination therapy of dexamethasone and somatostatin analog reintroduces objective clinical responses to LHRH analog in androgen ablation-refractory prostate cancer patients. | 2001 Dec |
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Effects of androgen manipulation on postprandial triglyceridaemia, low-density lipoprotein particle size and lipoprotein(a) in men. | 2001 Dec |
|
Asymmetric transformation of N-nitrosamines by inclusion crystallization with optically active hosts. | 2001 Jan 26 |
|
[Inactivation of Trypanosoma cruzi trypanothione reductase by phenothiazine cationic free radicals]. | 2001 Jan-Mar |
|
Estrogen 'add-back' and lipid profile during GnRH agonist (triptorelin) therapy. | 2001 Jul |
|
Effect of reduced dose of triptorelin at the start of ovarian stimulation on the outcome of IVF: a randomized study. | 2001 Jul |
|
Transcarpal motor conduction velocity in carpal tunnel syndrome. | 2001 Jul |
|
Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism. | 2001 Jul-Aug |
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Actions of gonadotropin-releasing hormone antagonists on steroidogenesis in human granulosa lutein cells. | 2001 Jun |
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Antiproliferative signaling of luteinizing hormone-releasing hormone in human endometrial and ovarian cancer cells through G protein alpha(I)-mediated activation of phosphotyrosine phosphatase. | 2001 Jun |
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Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1h)-pyrazinones. | 2001 Jun 1 |
|
Determination of the partition coefficients of a homologous series of ciprofloxacin: influence of the N-4 piperazinyl alkylation on the antimicrobial activity. | 2001 Jun 4 |
|
On the branching of motoneurons. | 2001 Mar |
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Antianaphylactic and antiasthmatic properties of new piperazinyl 7-(beta-hydroxypropyl)-theophylline derivatives in guinea pigs. | 2001 Mar-Apr |
|
[The results of GnRH analog treatment of endometriosis]. | 2001 May |
|
Tubular aggregates observed in spindle muscle fiber of horse lumbrical muscle. | 2001 May |
|
Requirements for the application of protein sodium dodecyl sulfate-polyacrylamide gel electrophoresis and randomly amplified polymorphic DNA analyses to product speciation. | 2001 May |
|
Double-stranded DNA binding characteristics and subcellular distribution of a minor groove binding diphenyl ether bisbenzimidazole. | 2001 May 29 |
|
Effect of column temperature on the behaviour of some angiotensin converting enzyme inhibitors during high-performance liquid chromatographic analysis. | 2001 May 5 |
|
N1-phenyl substituted 4-quinolones of tuberculostatic activity. | 2001 Nov |
|
Physical and chemical enhancement of transdermal delivery of triptorelin. | 2001 Nov |
|
Intracellular signaling pathway of FGF-2-modulated corneal endothelial cell migration during wound healing in vitro. | 2001 Nov |
|
Protein kinase C-independent stimulation of activator protein-1 and c-Jun N-terminal kinase activity in human endometrial cancer cells by the LHRH agonist triptorelin. | 2001 Nov |
|
Intermetatarsal spaces: analysis with MR bursography, anatomic correlation, and histopathology in cadavers. | 2001 Nov |
|
Comparative study of new benzenesulphonamide fluoroquinolones structurally related to ciprofloxacin against selected ciprofloxacin-susceptible and -resistant Gram-positive cocci. | 2001 Nov |
|
The discovery of anthranilic acid-based MMP inhibitors. Part 3: incorporation of basic amines. | 2001 Nov 19 |
|
Three-dimensional quantitative structure-activity relationship (3D-QSAR) models for a novel class of piperazine-based stromelysin-1 (MMP-3) inhibitors: applying a "divide and conquer" strategy. | 2001 Nov 8 |
|
Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones. | 2001 Nov-Dec |
|
Solid-phase synthesis of libraries generated from a 4-phenyl-2-carboxy-piperazine scaffold. | 2001 Nov-Dec |
|
Structure-activity relationships in platelet-activating factor (PAF). 11-From PAF-antagonism to phospholipase A(2) inhibition: syntheses and structure-activity relationships in 1-arylsulfamido-2-alkylpiperazines. | 2001 Oct |
|
Lumpidin, a novel biomarker of some ochratoxin a producing penicillia. | 2001 Oct |
|
Polar nitrogen compounds and their behaviour in the drinking water treatment process. | 2001 Oct |
|
Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether beta-cyclodextrin. | 2001 Oct 23 |
|
Synthesis and in vitro evaluation of a series of diketopiperazine inhibitors of plasminogen activator inhibitor-1. | 2001 Oct 8 |
|
Continuous beds with vancomycin as chiral stationary phase for capillary electrochromatography. | 2001 Sep |
|
Comparison of practical treatment methods to eradicate pinworm (Dentostomella translucida) infections from Mongolian gerbils (Meroines unguiculatus). | 2001 Sep |
|
Use of gonadotropin-releasing hormone analog with tibolone to prevent cyclic attacks of acute intermittent porphyria. | 2001 Sep |
|
Significance of ligand tails for interaction with the minor groove of B-DNA. | 2001 Sep |
|
Kinetics and mechanisms of the reactions of 3-methoxyphenyl, 3-chlorophenyl, and 4-cyanophenyl 4-nitrophenyl thionocarbonates with alicyclic amines. | 2001 Sep 7 |
|
A post-Amadori inhibitor pyridoxamine also inhibits chemical modification of proteins by scavenging carbonyl intermediates of carbohydrate and lipid degradation. | 2002 Feb 1 |
|
Lumbrical and interossei recording in severe carpal tunnel syndrome. | 2002 Jan |
|
Orally-effective, long-acting sorbitol dehydrogenase inhibitors: synthesis, structure-activity relationships, and in vivo evaluations of novel heterocycle-substituted piperazino-pyrimidines. | 2002 Jan 17 |
|
Improvement in the selectivity and metabolic stability of the serotonin 5-HT(1A) ligand, S 15535: a series of cis- and trans-2-(arylcycloalkylamine) 1-indanols. | 2002 Jan 3 |
Patents
Sample Use Guides
No special preparations or other steps (for example, special diet, fasting, other medicines, laxatives, or enemas) are necessary before, during, or immediately after you take piperazine.
Piperazine may be taken with or without food or on a full or empty stomach. However, if your doctor tells you to take the medicine a certain way, take it exactly as directed.
For patients taking the granules for oral solution form of piperazine:
Dissolve the contents of 1 packet of granules in 57 mL (about 2 ounces) of water, milk, or fruit juice.
Be sure to drink all of the liquid to get the full dose of medicine.
Take this medicine only as directed. Do not take more of it and do not take it more often than your doctor ordered. To do so may increase the chance of serious side effects.
To help clear up your infection completely, take this medicine in regularly spaced doses as ordered by your doctor. In some infections, a second treatment with this medicine may be required to clear up the infection completely. Do not miss any doses.
For patients taking piperazine for pinworms:
Pinworms may be easily passed from one person to another, especially among persons in the same household. Therefore, all household members may have to be treated at the same time to prevent their infection or reinfection.
Dosing
The dose of this medicine will be different for different patients. Follow your doctor's orders or the directions on the label. The following information includes only the average doses of this medicine. If your dose is different, do not change it unless your doctor tells you to do so.
The amount of medicine that you take depends on the strength of the medicine. Also, the number of doses you take each day, the time allowed between doses, and the length of time you take the medicine depend on the medical problem for which you are using the medicine.
For granules for oral solution dosage form:
For common roundworms or pinworms:
Adults and teenagers—2 grams three times a day for one day. Treatment may need to be repeated in two weeks.
Children—Dose is based on age and/or body weight. Treatment may need to be repeated in two weeks.
Up to 2 years of age: Dose must be determined by your doctor.
2 to 8 years of age: 2 grams once a day for one day.
8 to 14 years of age: 2 grams two times a day for one day.
For oral suspension dosage form:
For common roundworms or pinworms:
Adults and teenagers—1.8 grams every four hours for a total of three doses in one day. Treatment may need to be repeated in two weeks.
Children—Dose is based on age. Treatment may need to be repeated in two weeks.
Up to 2 years of age: 600 milligrams (mg) every four hours for a total of three doses in one day.
2 to 8 years of age: 1.2 grams every six hours for a total of two doses in one day.
8 to 14 years of age: 1.2 grams every four hours for a total of three doses in one day.
For tablet dosage form:
For common roundworms:
Adults and teenagers—3.5 grams (piperazine hexahydrate) per day for two days in a row. Treatment may need to be repeated in one week.
Children—Dose is based on body weight and must be determined by your doctor. However, the usual dose is 75 mg (piperazine hexahydrate) per kilogram (34 mg per pound) of body weight per day for two days in a row. Treatment may need to be repeated in one week.
For pinworms:
Adults and children—Dose is based on body weight and must be determined by your doctor. However, the usual dose is 65 mg (piperazine hexahydrate) per kilogram (29.5 mg per pound) of body weight per day for seven days in a row. Treatment may need to be repeated in one week.
Missed Dose
If you miss a dose of this medicine, take it as soon as possible. However, if it is almost time for your next dose, skip the missed dose and go back to your regular dosing schedule. Do not double doses.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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Record UNII |
1RTM4PAL0V
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Validated (UNII)
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CFR |
21 CFR 520.1242C
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CFR |
21 CFR 556.513
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CFR |
21 CFR 520.1806
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NCI_THESAURUS |
C250
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WHO-ATC |
P02CB01
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WHO-VATC |
QP52AH01
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JECFA EVALUATION |
PIPERAZINE
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CFR |
21 CFR 520.1807
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DTXSID1021164
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PIPERAZINE
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C61892
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C034930
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SUB03841MIG
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8340
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1541601
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m8846
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2188
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110-85-0
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474
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203-808-3
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100000085288
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