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

Details

Stereochemistry ACHIRAL
Molecular Formula 3C6H8O7.2C4H10N2.3H2O
Molecular Weight 802.6876
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPERAZINE CITRATE

SMILES

O.O.O.C1CNCCN1.C2CNCCN2.OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(=O)CC(O)(CC(O)=O)C(O)=O

InChI

InChIKey=CMNBASWUQKIYLL-UHFFFAOYSA-N
InChI=1S/3C6H8O7.2C4H10N2.3H2O/c3*7-3(8)1-6(13,5(11)12)2-4(9)10;2*1-2-6-4-3-5-1;;;/h3*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);2*5-6H,1-4H2;3*1H2

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

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 H2O
Molecular Weight 18.0153
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
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
Prospective evaluation of hot flashes during treatment with parenteral estrogen or complete androgen ablation for metastatic carcinoma of the prostate.
2001 Aug
Pharmacokinetics and metabolism of a selective PDE5 inhibitor (UK-343,664) in rat and dog.
2001 Aug-Sep
Synthesis and stereoselective kappa-receptor binding of methylated analogues of GR-89.696.
2001 Feb
The dorsal aponeurosis, intrinsic, hypothenar, and thenar musculature of the hand.
2001 Feb
Design of triptorelin loaded nanospheres for transdermal iontophoretic administration.
2001 Feb 19
Long-term remission of ovarian hyperandrogenism after short-term treatment with a gonadotropin-releasing hormone agonist.
2001 Jan
Efficacy of nafarelin in assisted reproductive technology: a meta-analysis.
2001 Jan-Feb
The lumbrical provocation test in subjects with median inclusive paresthesia.
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
Effect of the drug-matrix on the stability of enalapril maleate in tablet formulations.
2001 Jul
Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism.
2001 Jul-Aug
[Study on the latency difference between compound muscle and sensory nerve action potentials].
2001 Jun
Actions of gonadotropin-releasing hormone antagonists on steroidogenesis in human granulosa lutein cells.
2001 Jun
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
Investigations of new lead structures for the design of selective estrogen receptor modulators.
2001 Jun 7
On the branching of motoneurons.
2001 Mar
Dose-finding study for the use of long-acting gonadotrophin-releasing hormone analogues prior to ovarian stimulation for IVF.
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
Double-stranded DNA binding characteristics and subcellular distribution of a minor groove binding diphenyl ether bisbenzimidazole.
2001 May 29
Intermetatarsal spaces: analysis with MR bursography, anatomic correlation, and histopathology in cadavers.
2001 Nov
New mu-opioid receptor agonists with piperazine moiety.
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
Monocharged inhibitors of mast cell tryptase derived from potent and selective dibasic inhibitors.
2001 Sep 3
Lumbrical and interossei recording in severe carpal tunnel syndrome.
2002 Jan
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 Thu Jul 06 19:17:34 UTC 2023
Edited
by admin
on Thu Jul 06 19:17:34 UTC 2023
Record UNII
63KP7FXF2I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPERAZINE CITRATE
EP   GREEN BOOK   MART.   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
HYDROUS TRIPIPERAZINE DICITRATE
Common Name English
BRYREL
Brand Name English
PIPERAZINE CITRATE HYDRATE
Common Name English
Piperazine citrate [WHO-DD]
Common Name English
PIPERAZINE, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (3:2), HYDRATE
Common Name English
VERMIDOL
Brand Name English
PIPERAZINE CITRATE [GREEN BOOK]
Common Name English
PIPERAZINE CITRATE [VANDF]
Common Name English
PIPERAZINE CITRATE [MART.]
Common Name English
PIPERAZINE CITRATE [EP MONOGRAPH]
Common Name English
PIPERAZINE, CITRATE (3:2), TRIHYDRATE
Systematic Name English
PIPERAZINE CITRATE [USP MONOGRAPH]
Common Name English
ANTEPAR
Brand Name English
MULTIFUGE
Brand Name English
Piperazine citrate (3:2) hydrate
Common Name English
PIPERAZINE CITRATE [USP-RS]
Common Name English
PIPERAZINE CITRATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
CFR 21 CFR 520.2380D
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
CFR 21 CFR 520.763C
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
CFR 21 CFR 520.1803
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
Code System Code Type Description
FDA UNII
63KP7FXF2I
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
EVMPD
SUB14884MIG
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
RXCUI
342992
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY RxNorm
MESH
C006589
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
PUBCHEM
131801040
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
CAS
41372-10-5
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
NON-SPECIFIC STOICHIOMETRY
DRUG BANK
DBSALT000775
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
RS_ITEM_NUM
1541805
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
SMS_ID
100000079473
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
NCI_THESAURUS
C47674
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
DAILYMED
63KP7FXF2I
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
CAS
7140-78-5
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200842
Created by admin on Thu Jul 06 19:17:34 UTC 2023 , Edited by admin on Thu Jul 06 19:17:34 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY