U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of Piperazine

SMILES

C1CNCCN1

InChI

InChIKey=GLUUGHFHXGJENI-UHFFFAOYSA-N
InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2

HIDE SMILES / InChI

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

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
Gonadotrophin-releasing hormone antagonists for assisted conception.
2001
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
Dose-dense sequential adjuvant chemotherapy with epirubicin, paclitaxel and CMF in high-risk breast cancer.
2001
The state of the art of dynamic coatings.
2001
Endoscopic carpal tunnel release and nerve conduction studies.
2001
Enzyme immunoassay for 6-amino-5-chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)benzimidazole, a novel 5-HT3 receptor antagonist.
2001 Apr
Acrylamide-based monoliths as robust stationary phases for capillary electrochromatography.
2001 Apr 20
Biliary Ascariasis in children.
2001 Apr-Jun
A practical GnRH analogue (triptorelin) stimulation test to distinguish constitutional delay of puberty from hypogonadotropic hypogonadism in prepubertal boys.
2001 Apr-Jun
Effects of androgen manipulation on postprandial triglyceridaemia, low-density lipoprotein particle size and lipoprotein(a) in men.
2001 Dec
[Comparison of different protocols of ovulation induction, by GnRH agonists and chorionic gonadotropin].
2001 Feb
D-TRP-6-LHRH (Triptorelin) is not effective in ovarian carcinoma: an EORTC Gynaecological Cancer Co-operative Group Study.
2001 Feb
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
FK960, a novel potential anti-dementia drug, enhances high K(+)-evoked release of somatostatin from rat hippocampal slices.
2001 Feb 16
Synthesis and structure-activity relationships of a new model of arylpiperazines. 5. Study of the physicochemical influence of the pharmacophore on 5-HT(1a)/alpha(1)-adrenergic receptor affinity: synthesis of a new derivative with mixed 5-HT(1a)/d(2) antagonist properties.
2001 Jan 18
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
The lumbrical provocation test in subjects with median inclusive paresthesia.
2001 Jul
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
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
[Study on the latency difference between compound muscle and sensory nerve action potentials].
2001 Jun
Structural characterization of the oxidative degradation products of an antifungal agent SCH 56592 by LC-NMR and LC-MS.
2001 Jun
Isolation and identification of clozapine metabolites in patient urine.
2001 Jun
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
Investigation of solid-state reactions using variable temperature X-ray powder diffractrometry. I. Aspartame hemihydrate.
2001 Mar
Requirements for the application of protein sodium dodecyl sulfate-polyacrylamide gel electrophoresis and randomly amplified polymorphic DNA analyses to product speciation.
2001 May
Fall in intracellular PO(2) at the onset of contractions in Xenopus single skeletal muscle fibers.
2001 May
Direct effects of GnRH agonists in human hormone-sensitive endometrial cells.
2001 May 15
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
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
Comparative study of new benzenesulphonamide fluoroquinolones structurally related to ciprofloxacin against selected ciprofloxacin-susceptible and -resistant Gram-positive cocci.
2001 Nov
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
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
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
Comparison of practical treatment methods to eradicate pinworm (Dentostomella translucida) infections from Mongolian gerbils (Meroines unguiculatus).
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
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
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 Fri Dec 15 15:09:35 UTC 2023
Edited
by admin
on Fri Dec 15 15:09:35 UTC 2023
Record UNII
1RTM4PAL0V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Piperazine
FHFI   GREEN BOOK   HSDB   II   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
Systematic Name English
PIPERAZINE [GREEN BOOK]
Common Name English
PIPERAZINE [MI]
Common Name English
PIPERAZINE [II]
Common Name English
PIPERAZINUM [HPUS]
Common Name English
PIPERAZINE [USP MONOGRAPH]
Common Name English
PIPERAZINE [HSDB]
Common Name English
PIPERAZINE [VANDF]
Common Name English
PIPERAZINE [USP-RS]
Common Name English
NSC-474
Code English
PIPERAZINE [MART.]
Common Name English
PIPERAZINE ANHYDROUS
Common Name English
FEMA NO. 4250
Code English
PIPERAZINE [FHFI]
Common Name English
PIPERAZINUM
HPUS  
Common Name English
P02CB01
Code English
TRIMETAZIDINE DIHYDROCHLORIDE IMPURITY G [EP IMPURITY]
Common Name English
Piperazine [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.1242C
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
CFR 21 CFR 556.513
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
CFR 21 CFR 520.1806
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
WHO-ATC P02CB01
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
WHO-VATC QP52AH01
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
JECFA EVALUATION PIPERAZINE
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
CFR 21 CFR 520.1807
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1412
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
PUBCHEM
4837
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
HSDB
1093
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
FDA UNII
1RTM4PAL0V
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID1021164
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
WIKIPEDIA
PIPERAZINE
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
NCI_THESAURUS
C61892
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
CHEBI
28568
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
MESH
C034930
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
EVMPD
SUB03841MIG
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
RXCUI
8340
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY RxNorm
RS_ITEM_NUM
1541601
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
JECFA MONOGRAPH
1604
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
DRUG BANK
DB00592
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
MERCK INDEX
m8846
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
2188
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
DAILYMED
1RTM4PAL0V
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
CAS
110-85-0
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
NSC
474
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-808-3
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
SMS_ID
100000085288
Created by admin on Fri Dec 15 15:09:36 UTC 2023 , Edited by admin on Fri Dec 15 15:09:36 UTC 2023
PRIMARY
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