Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | 2C6H8O7.3C4H10N2 |
| Molecular Weight | 642.6538 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CNCCN1.C2CNCCN2.C3CNCCN3.OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O
InChI
InChIKey=JDDHUROHDHPVIO-UHFFFAOYSA-N
InChI=1S/2C6H8O7.3C4H10N2/c2*7-3(8)1-6(13,5(11)12)2-4(9)10;3*1-2-6-4-3-5-1/h2*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);3*5-6H,1-4H2
| Molecular Formula | C6H8O7 |
| Molecular Weight | 192.1235 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
|---|---|---|
| Synthesis and antibacterial activity of some novel N-substituted piperazinyl-quinolones. | 2002-02-02 |
|
| A post-Amadori inhibitor pyridoxamine also inhibits chemical modification of proteins by scavenging carbonyl intermediates of carbohydrate and lipid degradation. | 2002-02-01 |
|
| Orally-effective, long-acting sorbitol dehydrogenase inhibitors: synthesis, structure-activity relationships, and in vivo evaluations of novel heterocycle-substituted piperazino-pyrimidines. | 2002-01-17 |
|
| Antianaphylactic and antiasthmatic properties of new piperazinyl 7-(beta-hydroxypropyl)-theophylline derivatives in guinea pigs. | 2002-01-15 |
|
| 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. | 2002-01-03 |
|
| Lumbrical and interossei recording in severe carpal tunnel syndrome. | 2002-01 |
|
| Biliary Ascariasis in children. | 2001-12-06 |
|
| A combination therapy of dexamethasone and somatostatin analog reintroduces objective clinical responses to LHRH analog in androgen ablation-refractory prostate cancer patients. | 2001-12 |
|
| Effects of androgen manipulation on postprandial triglyceridaemia, low-density lipoprotein particle size and lipoprotein(a) in men. | 2001-12 |
|
| The discovery of anthranilic acid-based MMP inhibitors. Part 3: incorporation of basic amines. | 2001-11-19 |
|
| Solid-phase synthesis of libraries generated from a 4-phenyl-2-carboxy-piperazine scaffold. | 2001-11-13 |
|
| 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. | 2001-11-08 |
|
| N1-phenyl substituted 4-quinolones of tuberculostatic activity. | 2001-11 |
|
| Evaluation of the absorption, excretion and metabolism of [14C] etoperidone in man. | 2001-11 |
|
| Physical and chemical enhancement of transdermal delivery of triptorelin. | 2001-11 |
|
| Intracellular signaling pathway of FGF-2-modulated corneal endothelial cell migration during wound healing in vitro. | 2001-11 |
|
| 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. | 2001-11 |
|
| Intermetatarsal spaces: analysis with MR bursography, anatomic correlation, and histopathology in cadavers. | 2001-11 |
|
| Comparative study of new benzenesulphonamide fluoroquinolones structurally related to ciprofloxacin against selected ciprofloxacin-susceptible and -resistant Gram-positive cocci. | 2001-11 |
|
| Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether beta-cyclodextrin. | 2001-10-23 |
|
| Synthesis and in vitro evaluation of a series of diketopiperazine inhibitors of plasminogen activator inhibitor-1. | 2001-10-08 |
|
| 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. | 2001-10 |
|
| New mu-opioid receptor agonists with piperazine moiety. | 2001-10 |
|
| Lumpidin, a novel biomarker of some ochratoxin a producing penicillia. | 2001-10 |
|
| Polar nitrogen compounds and their behaviour in the drinking water treatment process. | 2001-10 |
|
| Pharmacokinetics and metabolism of a selective PDE5 inhibitor (UK-343,664) in rat and dog. | 2001-09-25 |
|
| Kinetics and mechanisms of the reactions of 3-methoxyphenyl, 3-chlorophenyl, and 4-cyanophenyl 4-nitrophenyl thionocarbonates with alicyclic amines. | 2001-09-07 |
|
| Monocharged inhibitors of mast cell tryptase derived from potent and selective dibasic inhibitors. | 2001-09-03 |
|
| Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors. | 2001-09 |
|
| Continuous beds with vancomycin as chiral stationary phase for capillary electrochromatography. | 2001-09 |
|
| Comparison of practical treatment methods to eradicate pinworm (Dentostomella translucida) infections from Mongolian gerbils (Meroines unguiculatus). | 2001-09 |
|
| Use of gonadotropin-releasing hormone analog with tibolone to prevent cyclic attacks of acute intermittent porphyria. | 2001-09 |
|
| Significance of ligand tails for interaction with the minor groove of B-DNA. | 2001-09 |
|
| Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism. | 2001-08-18 |
|
| Diketopiperazine receptors: a novel class of highly selective receptors for binding small peptides. | 2001-08-03 |
|
| Mass spectrometric studies on small open-chain piperazine-containing ligands and their transition metal complexes. | 2001-08 |
|
| Prospective evaluation of hot flashes during treatment with parenteral estrogen or complete androgen ablation for metastatic carcinoma of the prostate. | 2001-08 |
|
| Intracellular PO(2) decreases with increasing stimulation frequency in contracting single Xenopus muscle fibers. | 2001-08 |
|
| Solvent effect on the alpha-effect for the reactions of aryl acetates with butane-2,3-dione monoximate and p-chlorophenoxide in MeCN-H2O mixtures. | 2001-07-13 |
|
| [Rugulosuvines A and B--diketopiperazine alkaloids from Penicillium rugulosum and Penicillium piscarium fungi]. | 2001-07-11 |
|
| The lumbrical provocation test in subjects with median inclusive paresthesia. | 2001-07 |
|
| Leuprorelin and triptorelin: new indication. Preoperative treatment of uterine leiomyoma: no proven value. | 2001-06 |
|
| [Study on the latency difference between compound muscle and sensory nerve action potentials]. | 2001-06 |
|
| [Decapeptyl (triptorelin) in the treatment of endometriosis genitalis externa]. | 2001-05 |
|
| [The results of GnRH analog treatment of endometriosis]. | 2001-05 |
|
| Tubular aggregates observed in spindle muscle fiber of horse lumbrical muscle. | 2001-05 |
|
| Investigation of solid-state reactions using variable temperature X-ray powder diffractrometry. I. Aspartame hemihydrate. | 2001-03 |
|
| Design, synthesis, and modeling of novel cyclic thrombin receptor-derived peptide analogues of the Ser42-Phe-Leu-Leu-Arg46 motif sequence with fixed conformations of pharmacophoric groups: importance of a Phe/Arg/NH2 cluster for receptor activation and implications in the design of nonpeptide thrombin receptor mimetics. | 2001-02-01 |
|
| Return to fertility after extended chemical castration with a GnRH antagonist. | 2001 |
|
| Gonadotrophin-releasing hormone antagonists for assisted conception. | 2001 |
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
by
admin
on
Edited
Mon Mar 31 21:10:02 GMT 2025
by
admin
on
Mon Mar 31 21:10:02 GMT 2025
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| Record UNII |
RI85381D5G
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| Record Status |
Validated (UNII)
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DTXSID40883334
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PIPERAZINE CITRATE ANHYDROUS
Created by
admin on Mon Mar 31 21:10:03 GMT 2025 , Edited by admin on Mon Mar 31 21:10:03 GMT 2025
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PRIMARY | Description: A fine, white, granular powder; almost odourless. Solubility: Soluble in 1.5 parts of water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Anthelmintic. Storage: Piperazine citrate should be kept in a well-closed container, protected from light. Piperazine citrate contains a variable amount of water of crystallization. Definition: Piperazine citrate contains not less than 98.0% and not more than 101.0% of (C4H10N2)3,2C6H8O7, calculated with reference to the anhydrous substance. | ||
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m8846
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PRIMARY | Merck Index |
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS | |||
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |