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Details

Stereochemistry ACHIRAL
Molecular Formula 2C6H8O7.3C4H10N2
Molecular Weight 642.6548
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPERAZINE CITRATE ANHYDROUS

SMILES

C(C(=O)O)C(CC(=O)O)(C(=O)O)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O.C1CNCCN1.C1CNCCN1.C1CNCCN1

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

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H10N2
Molecular Weight 86.1358
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: UniProtKB: D6BK80_HAECO | D6BJF3_HAECO (GABA receptor subunit)
6.23 mM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MULTIFUGE

Approved Use

Piperazine 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 Date

-4.88332788E11
Doses

Doses

DosePopulationAdverse 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
n = 1
Health Status: unhealthy
Condition: Occupational asthma
Age Group: 42 years
Sex: F
Population Size: 1
Sources:
Other AEs: Asthma late onset...
Other AEs:
Asthma late onset (1 patient)
Sources:
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
n = 1
Health Status: unhealthy
Condition: abdominal pain due to probable worm infestation
Age Group: 6 years
Sex: F
Population Size: 1
Sources:
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
n = 1
Health Status: unhealthy
Condition: pinworm or roundworm infections
Age Group: 9 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Ataxia...
AEs leading to
discontinuation/dose reduction:
Ataxia (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
n = 1
Health Status: unhealthy
Condition: Occupational asthma
Age Group: 42 years
Sex: F
Population Size: 1
Sources:
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
n = 1
Health Status: unhealthy
Condition: abdominal pain due to probable worm infestation
Age Group: 6 years
Sex: F
Population Size: 1
Sources:
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
n = 1
Health Status: unhealthy
Condition: pinworm or roundworm infections
Age Group: 9 years
Sex: M
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Return to fertility after extended chemical castration with a GnRH antagonist.
2001
Gonadotrophin-releasing hormone antagonists for assisted conception.
2001
Biliary Ascariasis in children.
2001 Apr-Jun
Mass spectrometric studies on small open-chain piperazine-containing ligands and their transition metal complexes.
2001 Aug
Prospective evaluation of hot flashes during treatment with parenteral estrogen or complete androgen ablation for metastatic carcinoma of the prostate.
2001 Aug
Intracellular PO(2) decreases with increasing stimulation frequency in contracting single Xenopus muscle fibers.
2001 Aug
Diketopiperazine receptors: a novel class of highly selective receptors for binding small peptides.
2001 Aug 3
Pharmacokinetics and metabolism of a selective PDE5 inhibitor (UK-343,664) in rat and dog.
2001 Aug-Sep
A combination therapy of dexamethasone and somatostatin analog reintroduces objective clinical responses to LHRH analog in androgen ablation-refractory prostate cancer patients.
2001 Dec
Effects of androgen manipulation on postprandial triglyceridaemia, low-density lipoprotein particle size and lipoprotein(a) in men.
2001 Dec
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 Feb 1
The lumbrical provocation test in subjects with median inclusive paresthesia.
2001 Jul
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 Jul 13
Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism.
2001 Jul-Aug
Leuprorelin and triptorelin: new indication. Preoperative treatment of uterine leiomyoma: no proven value.
2001 Jun
[Study on the latency difference between compound muscle and sensory nerve action potentials].
2001 Jun
Investigation of solid-state reactions using variable temperature X-ray powder diffractrometry. I. Aspartame hemihydrate.
2001 Mar
Antianaphylactic and antiasthmatic properties of new piperazinyl 7-(beta-hydroxypropyl)-theophylline derivatives in guinea pigs.
2001 Mar-Apr
[Decapeptyl (triptorelin) in the treatment of endometriosis genitalis externa].
2001 May
[The results of GnRH analog treatment of endometriosis].
2001 May
Tubular aggregates observed in spindle muscle fiber of horse lumbrical muscle.
2001 May
[Rugulosuvines A and B--diketopiperazine alkaloids from Penicillium rugulosum and Penicillium piscarium fungi].
2001 May-Jun
N1-phenyl substituted 4-quinolones of tuberculostatic activity.
2001 Nov
Evaluation of the absorption, excretion and metabolism of [14C] etoperidone in man.
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
New mu-opioid receptor agonists with piperazine moiety.
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
Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors.
2001 Sep
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
Monocharged inhibitors of mast cell tryptase derived from potent and selective dibasic inhibitors.
2001 Sep 3
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:35:43 UTC 2021
Edited
by admin
on Sat Jun 26 10:35:43 UTC 2021
Record UNII
RI85381D5G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPERAZINE CITRATE ANHYDROUS
WHO-IP  
Common Name English
NSC-86779
Code English
ADIPRAZINE
Common Name English
PIPERAZINE CITRATE [MI]
Common Name English
PIPERAZINI CITRAS ANHYDROUS [WHO-IP LATIN]
Common Name English
ADIPIC ACID, COMPD. WITH PIPERAZINE (1:1)
Common Name English
PIPERAZINE, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (3:2)
Systematic Name English
PIPERAZINE CITRATE ANHYDROUS [WHO-IP]
Common Name English
Code System Code Type Description
PUBCHEM
15595021
Created by admin on Sat Jun 26 10:35:44 UTC 2021 , Edited by admin on Sat Jun 26 10:35:44 UTC 2021
PRIMARY
CAS
144-29-6
Created by admin on Sat Jun 26 10:35:44 UTC 2021 , Edited by admin on Sat Jun 26 10:35:44 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PIPERAZINE CITRATE ANHYDROUS
Created by admin on Sat Jun 26 10:35:44 UTC 2021 , Edited by admin on Sat Jun 26 10:35:44 UTC 2021
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.
FDA UNII
RI85381D5G
Created by admin on Sat Jun 26 10:35:44 UTC 2021 , Edited by admin on Sat Jun 26 10:35:44 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-622-8
Created by admin on Sat Jun 26 10:35:44 UTC 2021 , Edited by admin on Sat Jun 26 10:35:44 UTC 2021
PRIMARY
MERCK INDEX
M8846
Created by admin on Sat Jun 26 10:35:44 UTC 2021 , Edited by admin on Sat Jun 26 10:35:44 UTC 2021
PRIMARY Merck Index
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