Page last updated: 2024-12-07

kampirone

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Description

1-(2-pyrimidinyl)piperazine: metabolite of buspirone; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID88747
CHEMBL ID724
CHEBI ID166562
SCHEMBL ID169214
MeSH IDM0220146

Synonyms (82)

Synonym
AC-1840
1-(2-pyrimidyl)piperazine
n-(2-pyrimidinyl)piperazine
einecs 244-135-5
pyrimidine, 2-(1-piperazinyl)-
2-(1-piperazinyl)pyrimidine
1-pp
4-(2-pyrimidinyl)piperazine
1-(2-pyrimidinyl)piperazine
2-(piperazin-1-yl)pyrimidine
brn 0151178
mj 13653
EN300-33983
BB 0248124
CHEBI:166562
2-piperazin-1-ylpyrimidine
SDCCGMLS-0065816.P001
kampirone
campiron
campirone
2-piperazino-pyrimidine
PDSP2_000481
PDSP1_000483
STK088200
1-(2-pyrimidyl)piperazine, 98%
1-pyrimidin-2-yl-piperazine
20980-22-7
MAYBRIDGE1_004282
2-piperazin-1-yl-pyrimidine
CHEMBL724 ,
AKOS000264519
2-piperazinopyrimidine
inchi=1/c8h12n4/c1-2-10-8(11-3-1)12-6-4-9-5-7-12/h1-3,9h,4-7h2
mrbfgehilmyptf-uhfffaoysa-
P1110
bdbm50007403
NCGC00247000-01
h3b5b38f56 ,
unii-h3b5b38f56
4-25-00-02083 (beilstein handbook reference)
1-(2-pyrimidyl)-piperazine
125523-53-7
FT-0673928
BP-13017
FT-0605569
buspirone hydrochloride impurity a [ep impurity]
1-pyrimidinylpiperazine
1-(2-pyrimidinyl)-piperazine
AM62510
1-(pyrimidin-2-yl)piperazine
pyrimidinylpiperazine
SCHEMBL169214
FS-1244
2-(piperazinyl)pyrimidine
n-(2-pyrimidyl)piperazine
2-(1-piperazinyl)-pyrimidine
1-(2pyrimidinyl)piperazine
2-piperazin-1-yl pyrimidine
1-pyrimidin-2-ylpiperazine
1-(pyrimidine-2-yl)piperazine
1-(2-pyrimidyl)piperizine
1-(2-pyrimidinyl) piperzine
1-pyrimidin-2-yl-piperazin
1-(2-pyrimidinyl) piperazine
2- (1-piperazinyl)pyrimidine
n-(pyrimidin-2-yl)piperazine
4-(2-pyrimidinyl) piperazine
1-(2-pyrimidyl) piperazine
W-107583
2-(1-piperazinyl)pyrimidine #
mfcd00040742
buspirone ep impurity a
CS-W004464
DTXSID00864967
buspirone usp rc a; 2-(piperazin-1-yl)pyrimidine; 2-(1-piperazinyl)pyrimidine; 1-(2-pyrimidinyl)piperazine; 2-piperazinopyrimidine; 4-(2-pyrimidinyl)piperazine
Q7263602
(s)-homoserinehydrochloride
buspirone metabolite (1-(2-pyrimidyl)-piperazine)
F11219
PD014414
HY-W004464
Z262221634

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The differences between the median pharmacokinetic values of buspirone for healthy subjects, patients with mild to moderate renal impairment, and anuric patients were not statistically significant."( Clinical pharmacokinetics of oral buspirone in patients with impaired renal function.
Caccia, S; Gammans, RE; Garattini, S; Mayol, RF; Mingardi, G; Pfeffer, M; Placchi, M; Vigano, GL, 1988
)
0.27
"05) and the Cmax by 57% (P<0."( Interactions of buspirone with itraconazole and rifampicin: effects on the pharmacokinetics of the active 1-(2-pyrimidinyl)-piperazine metabolite of buspirone.
Kivistö, KT; Lamberg, TS; Neuvonen, PJ, 1999
)
0.3
" Examination of Cmin vs time plots revealed that the steady state was attained by day 7 except for one monkey who demonstrated much higher Cmin values."( Pharmacokinetics of buspirone following oral administration to rhesus monkeys.
Greene, DS; Marathe, PH; Markham, P; Shen, F, 1999
)
0.3
"2 ml/min and for terminal elimination half-life of 25 and 79 min, respectively."( Pharmacokinetic-pharmacodynamic modeling of buspirone and its metabolite 1-(2-pyrimidinyl)-piperazine in rats.
Danhof, M; Maas, HJ; Peletier, LA; Rusiç-Pavletiç, J; Van der Graaf, PH; Zuideveld, KP, 2002
)
0.31
" The secondary objective was to study the possible pharmacodynamic interaction between these two anxiolytic drugs."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
0.32
" Pharmacodynamic testing and measurement of plasma prolactin concentrations were carried out on day 7 and day 8 to assess the pharmacodynamic consequences of deramciclane and buspirone co-administration."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
0.32
"001) and 20% increase in the elimination half-life ( P=0."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
0.32
"Deramciclane does not inhibit CYP3A4 activity as measured by buspirone pharmacokinetics, and there were no indications of relevant pharmacodynamic interaction after multiple doses of deramciclane and a single dose of buspirone."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
0.32

Bioavailability

ExcerptReferenceRelevance
" The absolute bioavailability of buspirone is approximately 4%."( Clinical pharmacokinetics and pharmacodynamics of buspirone, an anxiolytic drug.
Mahmood, I; Sahajwalla, C, 1999
)
0.3
" No significant differences in bioavailability were observed between the IR and the three gepirone-ER formulations, indicating that any of the once-daily gepirone-ER formulations could be substituted for gepirone-IR."( Pharmacokinetic evaluation of gepirone immediate-release capsules and gepirone extended-release tablets in healthy volunteers.
Sitsen, JM; Timmer, CJ, 2003
)
0.32

Dosage Studied

ExcerptRelevanceReference
" However, at higher doses the magnitude of these effects decreased and overall the dose-response curves displayed inverted U-shapes."( Effects of 5-HT1A receptor agonists and L-5-HTP in Montgomery's conflict test.
Engel, JA; Hjorth, S; Söderpalm, B, 1989
)
0.28
" These results suggest that within the normal therapeutic dosage ranges for both drugs, it is unlikely that a clinically significant interaction between them will occur."( Lack of interaction between cimetidine and buspirone.
Faulkner, HC; Gammans, RE; Goodson, PJ; Pfeffer, M; Rehm, KD; Westrick, ML, 1987
)
0.27
" No firm recommendation for specific dosage can be made based on the present data."( Clinical pharmacokinetics of oral buspirone in patients with impaired renal function.
Caccia, S; Gammans, RE; Garattini, S; Mayol, RF; Mingardi, G; Pfeffer, M; Placchi, M; Vigano, GL, 1988
)
0.27
") showed an anticonflict activity with a bell-shaped dose-response relationship without any effect on spontaneous water consumption."( Comparison of the anticonflict effect of buspirone and its major metabolite 1-(2-pyrimidinyl)-piperazine (1-PP) in rats.
Achiha, M; Amano, M; Goto, A; Hara, C; Ogawa, N; Sakai, A; Takahashi, N, 1993
)
0.29
" Plasma samples were obtained predose and at specified time points after dosing and analyzed for gepirone and 1-PP content by a specific gas chromatographic-mass spectrometric method."( Effect of food on the bioavailability of gepirone in humans.
Farmen, RH; Pittman, KA; Sciacca, MA; Sostrin, MB; Tay, LK, 1993
)
0.29
" Plasma profiles of buspirone and 1-PP following oral dosing are presented."( Simultaneous quantitation of buspirone and its major metabolite 1-(2-pyrimidinyl)piperazine in human plasma by high-performance liquid chromatography with coulometric detection.
Franklin, M; Odontiadis, J, 1996
)
0.29
"Buspirone is an anxiolytic drug given at a dosage of 15 mg/day."( Clinical pharmacokinetics and pharmacodynamics of buspirone, an anxiolytic drug.
Mahmood, I; Sahajwalla, C, 1999
)
0.3
" Our results showed that buspirone exhibited an inverted-U-shaped dose-response curve in both the EPM and the VC tests."( Oral buspirone causes a shift in the dose-response curve between the elevated-plus maze and Vogel conflict tests in Long-Evans rats: relation of brain levels of buspirone and 1-PP to anxiolytic action.
Benjamin, D; Crooke, JJ; Ilyin, SE; Lang, W; Reitz, AB; Rosenthal, DI; Vaidya, AH, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-arylpiperazine
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki1.41250.00010.739610.0000AID4411
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID409882Cytotoxicity against human GBM cells at 50 uM after 48 hrs by neutral red uptake assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines.
AID1220323Drug level in Sprague-Dawley rat plasma treated with [14C]PF-00734200 at 5 mg/kg, po administered as single dose by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11
Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
AID226485Hill coefficient in rat brain 5-hydroxytryptamine 1A assay1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Arylpiperazine derivatives as high-affinity 5-HT1A serotonin ligands.
AID409883Cytotoxicity against human HCT116 cells at 50 uM after 48 hrs by neutral red uptake assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines.
AID1220335Total drug level in Sprague-Dawley rat treated with [14C]PF-00734200 assessed as total radio activity at 5 mg/kg, po administered as single dose by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11
Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
AID1220324Drug level in beagle dog plasma treated with [14C]PF-00734200 at 5 mg/kg, po administered as single dose by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11
Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
AID409876Cytotoxicity against human GBM cells at 50 uM after 24 hrs by neutral red uptake assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines.
AID4095Evaluated for binding affinity towards 5-hydroxytryptamine 1A receptor in rat brain1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Arylpiperazine derivatives as high-affinity 5-HT1A serotonin ligands.
AID4411Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) receptor assayed by radiolabeled [3H]-8-OH-DPAT ligand displacement1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Binding of arylpiperazines, (aryloxy)propanolamines, and tetrahydropyridylindoles to the 5-HT1A receptor: contribution of the molecular lipophilicity potential to three-dimensional quantitative structure-affinity relationship models.
AID1220319Total drug level in beagle dog treated with [14C]PF-00734200 assessed as total radio activity at 5 mg/kg, po administered as single dose by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11
Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
AID781327pKa (acid-base dissociation constant) as determined by Morgenthaler ref: ChemMedChem 20072014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID1220317Drug level in urine of beagle dog treated with [14C]PF-00734200 at 5 mg/kg, po administered as single dose by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11
Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
AID204444Binding affinity towards sigma receptor in guinea pig brain membranes using [3H]DTG as radioligand1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
AID1220297Drug level in urine of Sprague-Dawley rat treated with [14C]PF-00734200 at 5 mg/kg, po administered as single dose by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11
Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
AID409880Cytotoxicity against human HCT116 cells at 50 uM after 24 hrs by neutral red uptake assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines.
AID1220333Retention time of the compound by HPLC method2012Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11
Metabolism, excretion, and pharmacokinetics of ((3,3-difluoropyrrolidin-1-yl)((2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a dipeptidyl peptidase inhibitor, in rat, dog and human.
AID409884Cytotoxicity against human KMS11 cells at 50 uM after 48 hrs by neutral red uptake assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines.
AID409881Cytotoxicity against human KMS11 cells at 50 uM after 24 hrs by neutral red uptake assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (82)

TimeframeStudies, This Drug (%)All Drugs %
pre-199021 (25.61)18.7374
1990's40 (48.78)18.2507
2000's15 (18.29)29.6817
2010's6 (7.32)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.78

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index9.78 (24.57)
Research Supply Index4.62 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials13 (14.77%)5.53%
Reviews2 (2.27%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other73 (82.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]