Page last updated: 2024-12-08
bifeprunox
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
bifeprunox: an antipsychotic agent [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 208951 |
| CHEMBL ID | 218166 |
| CHEBI ID | 177517 |
| SCHEMBL ID | 114371 |
| MeSH ID | M0497678 |
Synonyms (36)
| Synonym |
|---|
| 7-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]-3h-1,3-benzoxazol-2-one |
| bifeprunox |
| CHEBI:177517 |
| D06566 |
| bifeprunox (usan/inn) |
| 350992-10-8 |
| bifeprunox [inn] |
| bdbm50241119 |
| 7-(4-biphenyl-3-ylmethyl-piperazin-1-yl)-3h-benzooxazol-2-one |
| CHEMBL218166 , |
| L001659 |
| 2(3h)-benzoxazolone, 7-(4-((1,1'-biphenyl)-3-ylmethyl)-1-piperazinyl)- |
| ap69e83z79 , |
| du 127090 |
| 7-(4-(biphenyl-3-ylmethyl)piperazin-1-yl)benzoxazol-2(3h)-one |
| bifeprunoxum |
| bifeprunox [usan:inn] |
| bifeprunoxum [inn-latin] |
| unii-ap69e83z79 |
| 7-[4-[(3-phenylphenyl)methyl]-1-piperazinyl]-3h-1,3-benzoxazol-2-one |
| A822533 |
| AKOS015904572 |
| 7-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]-3h-benzo[d]oxazol-2-one |
| bifeprunox [mi] |
| 7-[4-(biphenyl-3-ylmethyl)piperazin-1-yl]benzoxazol-2(3h)-one |
| bifeprunox [who-dd] |
| bifeprunox [usan] |
| DB04888 |
| SCHEMBL114371 |
| CYGODHVAJQTCBG-UHFFFAOYSA-N |
| 7-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]-3h-benzooxazol-2-one |
| DTXSID80188592 |
| 7-[4-([1,1'-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3h)-benzoxazolone |
| Q4904729 |
| HY-14547 |
| CS-0003435 |
Research Excerpts
Overview
Bifeprunox is a novel antipsychotic drug designed to treat schizophrenia. It is a partial dopamine agonist with a unique receptor-binding profile.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Bifeprunox is a novel antipsychotic drug designed to treat schizophrenia. " | ( Bifeprunox versus placebo for schizophrenia. Chattopadhyay, A; Frey, S; Green, G, 2016) | 3.32 |
| "Bifeprunox is a partial dopamine agonist with a unique receptor-binding profile and potential antipsychotic properties." | ( Efficacy and safety of bifeprunox in patients with an acute exacerbation of schizophrenia: results from a randomized, double-blind, placebo-controlled, multicenter, dose-finding study. Casey, DE; Heisterberg, J; Sands, EE; Yang, HM, 2008) | 2.1 |
Treatment
| Excerpt | Reference | Relevance |
|---|---|---|
| "Treatment with Bifeprunox was found to significantly reduce all of the measured parameters except white fat mass compared to the control group." | ( Different effects of bifeprunox, aripiprazole, and haloperidol on body weight gain, food and water intake, and locomotor activity in rats. De Santis, M; Deng, C; Huang, XF; Lian, J; Pan, B, 2014) | 1.06 |
Toxicity
The most common treatment-emergent adverse events (TEAEs) noted with bifeprunox were gastrointestinal. No clear dose-related trend in the incidence of any TEAE was observed.
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Drug Classes (1)
| Class | Description |
|---|---|
| biphenyls | Benzenoid aromatic compounds containing two phenyl or substituted-phenyl groups which are joined together by a single bond. |
| [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 (6)
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| 5-hydroxytryptamine receptor 1A | Homo sapiens (human) | Ki | 0.0086 | 0.0001 | 0.5326 | 10.0000 | AID1803435; AID4442; AID457695 |
| D(2) dopamine receptor | Homo sapiens (human) | IC50 (µMol) | 0.0029 | 0.0000 | 0.7472 | 8.0000 | AID727074 |
| D(2) dopamine receptor | Homo sapiens (human) | Ki | 0.0023 | 0.0000 | 0.6518 | 10.0000 | AID1154611; AID1803434; AID457694; AID458632; AID458633; AID63971; AID727075 |
| 5-hydroxytryptamine receptor 2A | Rattus norvegicus (Norway rat) | Ki | 3.3113 | 0.0001 | 0.6017 | 10.0000 | AID277974 |
| 5-hydroxytryptamine receptor 1A | Rattus norvegicus (Norway rat) | Ki | 0.0646 | 0.0001 | 0.7396 | 10.0000 | AID277973 |
| D(2) dopamine receptor | Rattus norvegicus (Norway rat) | Ki | 0.0015 | 0.0000 | 0.4375 | 10.0000 | AID277975 |
| Transporter | Rattus norvegicus (Norway rat) | Ki | 0.0093 | 0.0001 | 0.7629 | 5.5000 | AID457695 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Activation Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| 5-hydroxytryptamine receptor 1A | Homo sapiens (human) | EC50 (µMol) | 0.3236 | 0.0001 | 0.2571 | 8.0000 | AID277976 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (112)
Molecular Functions (13)
Ceullar Components (22)
Bioassays (33)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1803435 | Binding Affinity Assay from Article 10.3109/14756366.2013.776556: \\Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones.\\ | 2014 | Journal of enzyme inhibition and medicinal chemistry, Apr, Volume: 29, Issue:2 | Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. |
| AID1803434 | Binding Affinity Assay from Article 10.3109/14756366.2013.776556: \\Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones.\\ | 2014 | Journal of enzyme inhibition and medicinal chemistry, Apr, Volume: 29, Issue:2 | Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. |
| AID1474758 | Agonist activity at D2 long receptor (unknown origin) expressed in Flp-In-CHO cells assessed as change in transduction coefficient by measuring induction of ERK1/2 phosphorylation after 5 mins by Alphascreen assay | 2017 | Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11 | Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. |
| AID727075 | Displacement of [3H]raclopride from human D2 dopamine receptor expressed in CHO cell membranes | 2013 | Bioorganic & medicinal chemistry letters, Jan-15, Volume: 23, Issue:2 | Synthesis and SAR of aminothiazole fused benzazepines as selective dopamine D2 partial agonists. |
| AID457694 | Agonist activity at dopamine D2 receptor | 2010 | Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5 | Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors. |
| AID458634 | Selectivity ratio of Ki for human dopamine D2 receptor at low affinity state to Ki for human dopamine D2 receptor at high affinity state | 2010 | Journal of medicinal chemistry, Mar-25, Volume: 53, Issue:6 | Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16). |
| AID1474757 | Agonist activity at D2 long receptor (unknown origin) expressed in Flp-In-CHO cells co-expressing Rluc8-tagged Galphai1 assessed as change in transduction coefficient by measuring Galphai1 activation after 5 mins in presence of coelenterazine by BRET assa | 2017 | Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11 | Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. |
| AID277975 | Displacement of [3H]YM-09151-2 from rat striatum D2 receptor | 2007 | Journal of medicinal chemistry, Feb-22, Volume: 50, Issue:4 | Towards a new generation of potential antipsychotic agents combining D2 and 5-HT1A receptor activities. |
| AID63971 | Binding affinity for dopamine receptor D2 determined using [3H]spiperone | 2001 | Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17 | New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D(2)-receptor and serotonin 5-HT(1A)-receptor affinities. |
| AID177715 | In vivo suppression of the conditioned avoidance response (CAR) in rats after po administration of the compound | 2001 | Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17 | New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D(2)-receptor and serotonin 5-HT(1A)-receptor affinities. |
| AID458635 | Activity at dopamine D2L receptor expressed in HEK293 cells coexpressing Galphaqi5 assessed as maximal efficacy relative to control | 2010 | Journal of medicinal chemistry, Mar-25, Volume: 53, Issue:6 | Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16). |
| AID1154611 | Displacement of [3H]nemonapride from dopamine D2L receptor (unknown origin) expressed in African green monkey COS7 cells | 2014 | Journal of medicinal chemistry, Jul-10, Volume: 57, Issue:13 | Novel aza-analogous ergoline derived scaffolds as potent serotonin 5-HT₆ and dopamine D₂ receptor ligands. |
| AID458652 | Reduction in amphetamine-induced locomotor activity in Sprague-Dawley rat striatum at 7.68 umol/kg, sc relative to control | 2010 | Journal of medicinal chemistry, Mar-25, Volume: 53, Issue:6 | Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16). |
| AID4442 | Binding affinity for 5-hydroxytryptamine 1A receptor determined using [3H]8-OH-DPAT as radioligand | 2001 | Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17 | New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D(2)-receptor and serotonin 5-HT(1A)-receptor affinities. |
| AID458633 | Displacement of [3H]spiperone from human dopamine D2 receptor at high affinity state expressed in HEK293 cells | 2010 | Journal of medicinal chemistry, Mar-25, Volume: 53, Issue:6 | Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16). |
| AID1474756 | Agonist activity at D2 long receptor (unknown origin) expressed in Flp-In-CHO cells co-expressing Rluc8-tagged GalphaoB assessed as change in transduction coefficient by measuring GalphaoB activation in presence of coelenterazine by BRET assay | 2017 | Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11 | Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. |
| AID457695 | Agonist activity at 5HT1A receptor | 2010 | Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5 | Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors. |
| AID277973 | Displacement of [3H]OH-DPAT from rat cortex 5HT1A receptor | 2007 | Journal of medicinal chemistry, Feb-22, Volume: 50, Issue:4 | Towards a new generation of potential antipsychotic agents combining D2 and 5-HT1A receptor activities. |
| AID1474755 | Agonist activity at Rluc8-tagged D2 long receptor (unknown origin) expressed in Flp-In-CHO cells co-expressing YFP-tagged beta-arrestin2 assessed as change in transduction coefficient by measuring beta-arrestin2 recruitment measured after 5 mins by BRET a | 2017 | Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11 | Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. |
| AID277976 | Agonist activity at human 5HT1A receptor in HeLa cells assessed as stimulation of [35S]GTP-gamma-S binding | 2007 | Journal of medicinal chemistry, Feb-22, Volume: 50, Issue:4 | Towards a new generation of potential antipsychotic agents combining D2 and 5-HT1A receptor activities. |
| AID277974 | Displacement of [3H]ketanserin from rat cortex 5HT2A receptor | 2007 | Journal of medicinal chemistry, Feb-22, Volume: 50, Issue:4 | Towards a new generation of potential antipsychotic agents combining D2 and 5-HT1A receptor activities. |
| AID1474754 | Displacement of [3H]spiperone from D2 long receptor (unknown origin) expressed in Flp-In-CHO cell membranes assessed as transduction coefficient by measuring dissociation half life after 5 mins by liquid scintillation counter method | 2017 | Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11 | Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. |
| AID727076 | Intrinsic agonist activity at human D2 dopamine receptor expressed in CHO cell membrane using cellular CD spectroscopy by Cell-Key assay | 2013 | Bioorganic & medicinal chemistry letters, Jan-15, Volume: 23, Issue:2 | Synthesis and SAR of aminothiazole fused benzazepines as selective dopamine D2 partial agonists. |
| AID458632 | Displacement of [3H]spiperone from human dopamine D2 receptor at low affinity state expressed in HEK293 cells | 2010 | Journal of medicinal chemistry, Mar-25, Volume: 53, Issue:6 | Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16). |
| AID130711 | In vivo inhibition of the apomorphine-induced climbing behavior in mice | 2001 | Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17 | New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D(2)-receptor and serotonin 5-HT(1A)-receptor affinities. |
| AID458647 | Reduction in spontaneous locomotor activity in Sprague-Dawley rat striatum at 7.68 umol/kg, sc relative to control | 2010 | Journal of medicinal chemistry, Mar-25, Volume: 53, Issue:6 | Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16). |
| AID1474759 | Agonist activity at D2 long receptor (unknown origin) expressed in Flp-In-CHO cells assessed as change in transduction coefficient by measuring inhibition of forskolin-induced cAMP production measured after 5 mins in presence of coelenterazine by BRET ass | 2017 | Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11 | Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. |
| AID727074 | Antagonist activity at human D2 dopamine receptor expressed in CHO cell membrane by GTPgammaS-binding assay | 2013 | Bioorganic & medicinal chemistry letters, Jan-15, Volume: 23, Issue:2 | Synthesis and SAR of aminothiazole fused benzazepines as selective dopamine D2 partial agonists. |
| AID277977 | Agonist activity at human 5HT1A receptor in HeLa cells assessed as stimulation of [35S]GTPgammaS binding relative to serotonin | 2007 | Journal of medicinal chemistry, Feb-22, Volume: 50, Issue:4 | Towards a new generation of potential antipsychotic agents combining D2 and 5-HT1A receptor activities. |
| AID179817 | Tested for occurrence of lower lip retraction in rat after po administration of the compound | 2001 | Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17 | New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D(2)-receptor and serotonin 5-HT(1A)-receptor affinities. |
| AID1474767 | Agonist activity at D2 long receptor (unknown origin) expressed in Flp-In-CHO cells assessed as change in transduction coefficient by measuring cellular impedance measured immediately at 15 secs interval for 90 mins by xCELLigence assay | 2017 | Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11 | Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. |
| AID1154614 | Intrinsic activity at human dopamine D2L receptor expressed in Sf9 cell membrane by [35S]GTPgammaS binding assay | 2014 | Journal of medicinal chemistry, Jul-10, Volume: 57, Issue:13 | Novel aza-analogous ergoline derived scaffolds as potent serotonin 5-HT₆ and dopamine D₂ receptor ligands. |
| AID458630 | Reduction in 3,4-dihydroxyphenylacetic acid level in Sprague-Dawley rat striatum at 7.68 umol/kg, sc relative to saline treated control | 2010 | Journal of medicinal chemistry, Mar-25, Volume: 53, Issue:6 | Synthesis and evaluation of a set of 4-phenylpiperidines and 4-phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(methylsulfonyl)phenyl]-1-propylpiperidine (huntexil, pridopidine, ACR16). |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (30)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 16 (53.33) | 29.6817 |
| 2010's | 14 (46.67) | 24.3611 |
| 2020's | 0 (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: 28.80
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 moderate demand-to-supply ratio for research on this compound.
| This Compound (28.80) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 1 (3.33%) | 5.53% |
| Reviews | 4 (13.33%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 25 (83.33%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||