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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:bupivacaine
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Accession:CHEBI:3215 term browser browse the term
Definition:A racemate composed of equimolar amounts of dextrobupivacaine and levobupivacaine. Used (in the form of its hydrochloride hydrate) as a local anaesthetic.
Synonyms:exact_synonym: rac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
 related_synonym: (RS)-bupivacaine;   1-Butyl-2',6'-pipecoloxylidide;   1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide;   Carbostesin;   DL-Bupivacaine;   Formula=C18H28N2O;   bupivacaina;   bupivacainum;   dl-1-Butyl-2',6'-pipecoloxylidide;   racemic bupivacaine
 alt_id: CHEBI:250882
 xref: CAS:2180-92-9;   CAS:38396-39-3;   DrugBank:DB00297;   HMDB:HMDB0014442;   KEGG:C07529;   KEGG:D07552
 xref_mesh: MESH:D002045
 xref: PMID:10211016;   PMID:10499757;   PMID:11018648;   PMID:11020763;   PMID:11412729;   PMID:11529341;   PMID:11759364;   PMID:11778087;   PMID:11801199;   PMID:11812691;   PMID:14980918;   PMID:15321223;   PMID:16037174;   PMID:16418020;   PMID:17134470;   PMID:18299091;   PMID:18420860;   PMID:18451389;   PMID:18940244;   PMID:19468619;   PMID:19800297;   PMID:20164497;   PMID:23446090;   PMID:23807278;   PMID:23925646;   PMID:23978626;   PMID:24117122;   PMID:24117225;   PMID:24200700;   PMID:24317184;   PMID:24393760;   PMID:24398818;   PMID:24445889;   PMID:24450503;   PMID:24476569;   PMID:24513957;   PMID:24532522;   PMID:24535791;   PMID:8368547;   PMID:8489063;   PMID:9209608;   PMID:9989796;   Patent:US2955111;   Reaxys:280794;   Wikipedia:Bupivacaine
 cyclic_relationship: is_conjugate_base_of CHEBI:77455


show annotations for term's descendants           Sort by:
bupivacaine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bax BCL2 associated X, apoptosis regulator increases expression
multiple interactions		 ISO Bupivacaine results in increased expression of BAX protein
8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one promotes the reaction [[Glucose co-treated with Bupivacaine] results in increased expression of BAX protein]; [Glucose co-treated with Bupivacaine] results in increased expression of BAX protein		 CTD PMID:31672611 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of BCL2 protein
8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one promotes the reaction [[Glucose co-treated with Bupivacaine] results in decreased expression of BCL2 protein]; [Glucose co-treated with Bupivacaine] results in decreased expression of BCL2 protein; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of BCL2 protein]		 CTD PMID:31672611 PMID:34793778 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Bdnf brain-derived neurotrophic factor multiple interactions
decreases expression		 ISO MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]; MIR497 mRNA inhibits the reaction [SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; NLRX1 protein affects the reaction [MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of BDNF mRNA] CTD PMID:35410500 NCBI chr 3:96,165,042...96,215,621
Ensembl chr 3:96,165,042...96,215,615 		JBrowse link
G Casp3 caspase 3 decreases expression
increases cleavage
multiple interactions
increases activity		 ISO
EXP		 Bupivacaine results in decreased expression of CASP3 protein
Bupivacaine results in increased cleavage of CASP3 protein
MCL1 protein promotes the reaction [notoginsenoside R1 inhibits the reaction [Bupivacaine results in increased cleavage of CASP3 protein]]; notoginsenoside R1 inhibits the reaction [Bupivacaine results in increased cleavage of CASP3 protein]
Bupivacaine results in increased activity of CASP3 protein		 CTD PMID:16109997 PMID:20194319 PMID:38316350 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp9 caspase 9 decreases expression
multiple interactions
increases cleavage		 ISO Bupivacaine results in decreased expression of CASP9 protein
MCL1 protein promotes the reaction [notoginsenoside R1 inhibits the reaction [Bupivacaine results in increased cleavage of CASP9 protein]]; notoginsenoside R1 inhibits the reaction [Bupivacaine results in increased cleavage of CASP9 protein]		 CTD PMID:20194319 PMID:38316350 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Cs citrate synthase decreases activity EXP Bupivacaine results in decreased activity of CS protein CTD PMID:20645041 NCBI chr 7:758,074...791,421
Ensembl chr 7:758,345...791,421 		JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of CYP3A9 mRNA CTD PMID:22341215 NCBI chr12:16,806,222...16,846,428
Ensembl chr12:16,806,207...16,846,422 		JBrowse link
G Dnm1l dynamin 1-like decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of DNM1L protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of DNM1L protein]		 CTD PMID:34793778 NCBI chr11:84,581,216...84,632,382
Ensembl chr11:84,581,216...84,631,482 		JBrowse link
G Entpd4 ectonucleoside triphosphate diphosphohydrolase 4 multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of ENTPD4 mRNA CTD PMID:22341215 NCBI chr15:44,630,878...44,658,654
Ensembl chr15:44,630,873...44,658,706 		JBrowse link
G H2ax H2A.X variant histone multiple interactions
increases expression		 ISO Glucose promotes the reaction [Bupivacaine results in increased expression of H2AX protein] CTD PMID:31672611 NCBI chr 8:44,671,907...44,673,262
Ensembl chr 8:44,671,786...44,673,239 		JBrowse link
G Hpgds hematopoietic prostaglandin D synthase increases expression ISO Bupivacaine results in increased expression of HPGDS mRNA; Bupivacaine results in increased expression of HPGDS protein CTD PMID:19359520 NCBI chr 4:94,368,426...94,397,931
Ensembl chr 4:94,373,342...94,397,883 		JBrowse link
G Hrh1 histamine receptor H 1 affects binding ISO HRH1 protein binds to Bupivacaine CTD PMID:32061592 NCBI chr 4:147,564,963...147,649,353
Ensembl chr 4:147,645,995...147,647,455 		JBrowse link
G Hspa12a heat shock protein family A (Hsp70) member 12A decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of HSPA12A protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of BCL2 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of DNM1L protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of MFN1 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PINK1 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PPARGC1A protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PRKN protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A1 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A4 protein]; HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of TOMM20 protein]		 CTD PMID:34793778 NCBI chr 1:257,935,642...258,096,602
Ensembl chr 1:257,935,644...258,096,846 		JBrowse link
G Itgam integrin subunit alpha M increases expression
multiple interactions		 ISO Bupivacaine results in increased expression of ITGAM mRNA
4-benzhydryloxy-1-(3-(1H-tetrazol-5-yl-)-propyl)piperidine inhibits the reaction [Bupivacaine results in increased expression of ITGAM mRNA]		 CTD PMID:19359520 NCBI chr 1:182,659,047...182,709,501
Ensembl chr 1:182,659,000...182,709,503 		JBrowse link
G Kcne1 potassium voltage-gated channel subfamily E regulatory subunit 1 multiple interactions ISO Bupivacaine results in decreased activity of [KCNQ1 protein binds to KCNE1 protein]; KCNE1 protein inhibits the reaction [KCNQ1 protein mutant form results in increased susceptibility to Bupivacaine] CTD PMID:16931984 NCBI chr11:31,580,951...31,594,116
Ensembl chr11:31,580,742...31,593,901 		JBrowse link
G Kcnk9 potassium two pore domain channel subfamily K member 9 multiple interactions ISO Bupivacaine inhibits the reaction [KCNK9 protein results in increased transport of Potassium] CTD PMID:11249964 NCBI chr 7:104,429,186...104,473,924
Ensembl chr 7:104,437,934...104,473,175 		JBrowse link
G Kcnn2 potassium calcium-activated channel subfamily N member 2 affects response to substance ISO KCNN2 protein affects the susceptibility to Bupivacaine CTD PMID:33887967 NCBI chr18:37,817,966...38,258,347
Ensembl chr18:37,817,957...38,258,347 		JBrowse link
G Kcnq1 potassium voltage-gated channel subfamily Q member 1 multiple interactions
decreases activity
increases response to substance		 ISO Bupivacaine results in decreased activity of [KCNQ1 protein binds to KCNE1 protein]; KCNE1 protein inhibits the reaction [KCNQ1 protein mutant form results in increased susceptibility to Bupivacaine]
Bupivacaine results in decreased activity of KCNQ1 protein		 CTD PMID:16931984 NCBI chr 1:198,291,711...198,624,683
Ensembl chr 1:198,291,766...198,624,669 		JBrowse link
G Ldha lactate dehydrogenase A increases secretion
multiple interactions		 ISO Bupivacaine results in increased secretion of LDHA protein
notoginsenoside R1 inhibits the reaction [Bupivacaine results in increased secretion of LDHA protein]		 CTD PMID:38316350 NCBI chr 1:97,371,823...97,381,247
Ensembl chr 1:97,366,021...97,433,472 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation
multiple interactions		 ISO Bupivacaine results in increased phosphorylation of MAPK1 protein
Glucose promotes the reaction [Bupivacaine results in increased phosphorylation of MAPK1 protein]		 CTD PMID:34060177 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions		 ISO Bupivacaine results in increased phosphorylation of MAPK3 protein
Glucose promotes the reaction [Bupivacaine results in increased phosphorylation of MAPK3 protein]		 CTD PMID:34060177 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of MCL1 protein
MCL1 protein promotes the reaction [notoginsenoside R1 inhibits the reaction [Bupivacaine results in increased cleavage of CASP3 protein]]; MCL1 protein promotes the reaction [notoginsenoside R1 inhibits the reaction [Bupivacaine results in increased cleavage of CASP9 protein]]		 CTD PMID:38316350 NCBI chr 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303 		JBrowse link
G Mfn1 mitofusin 1 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of MFN1 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of MFN1 protein]		 CTD PMID:34793778 NCBI chr 2:115,313,380...115,359,651
Ensembl chr 2:115,313,401...115,359,640 		JBrowse link
G Mir497 microRNA 497 multiple interactions
increases expression		 ISO MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]; MIR497 mRNA inhibits the reaction [SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; MIR497 mRNA promotes the reaction [Bupivacaine results in decreased expression of NLRX1 mRNA]; NLRX1 protein affects the reaction [MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; SNHG12 inhibits the reaction [Bupivacaine results in increased expression of MIR497 mRNA] CTD PMID:35410500 NCBI chr10:54,951,514...54,951,582
Ensembl chr10:54,951,505...54,951,584 		JBrowse link
G Myf5 myogenic factor 5 decreases expression EXP Bupivacaine results in decreased expression of MYF5 protein CTD PMID:10434046 NCBI chr 7:42,802,946...42,806,177
Ensembl chr 7:42,802,946...42,806,177 		JBrowse link
G Myod1 myogenic differentiation 1 decreases expression EXP Bupivacaine results in decreased expression of MYOD1 protein CTD PMID:10434046 NCBI chr 1:96,884,864...96,887,574
Ensembl chr 1:96,884,948...96,887,554 		JBrowse link
G Myog myogenin decreases expression EXP Bupivacaine results in decreased expression of MYOG protein CTD PMID:10434046 NCBI chr13:45,745,455...45,748,044
Ensembl chr13:45,745,436...45,748,039 		JBrowse link
G Nlrx1 NLR family member X1 multiple interactions
decreases expression		 ISO MIR497 mRNA promotes the reaction [Bupivacaine results in decreased expression of NLRX1 mRNA]; NLRX1 protein affects the reaction [MIR497 mRNA affects the reaction [Bupivacaine results in decreased expression of BDNF mRNA]]; SNHG12 inhibits the reaction [Bupivacaine results in decreased expression of NLRX1 mRNA] CTD PMID:35410500 NCBI chr 8:44,588,476...44,606,678
Ensembl chr 8:44,590,048...44,606,484 		JBrowse link
G Pink1 PTEN induced kinase 1 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of PINK1 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PINK1 protein]		 CTD PMID:34793778 NCBI chr 5:150,530,523...150,542,635
Ensembl chr 5:150,530,523...150,542,635 		JBrowse link
G Ppargc1a PPARG coactivator 1 alpha increases expression
multiple interactions
decreases expression		 ISO Bupivacaine results in increased expression of PPARGC1A mRNA
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PPARGC1A protein]		 CTD PMID:34793778 NCBI chr14:58,860,752...59,516,525
Ensembl chr14:58,861,144...59,512,656 		JBrowse link
G Prkcb protein kinase C, beta multiple interactions EXP [Bupivacaine co-treated with Tetrodotoxin co-treated with Dexamethasone] results in decreased expression of PRKCB mRNA CTD PMID:22341215 NCBI chr 1:176,832,173...177,163,539
Ensembl chr 1:176,832,226...177,163,536 		JBrowse link
G Prkn parkin RBR E3 ubiquitin protein ligase decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of PRKN protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of PRKN protein]		 CTD PMID:34793778 NCBI chr 1:48,688,651...49,882,520
Ensembl chr 1:48,690,556...49,882,555 		JBrowse link
G Ptgdr prostaglandin D2 receptor affects expression ISO Bupivacaine affects the expression of PTGDR mRNA CTD PMID:19359520 NCBI chr15:17,360,304...17,367,679
Ensembl chr15:17,360,304...17,367,679 		JBrowse link
G Ptgs1 prostaglandin-endoperoxide synthase 1 increases expression ISO Bupivacaine results in increased expression of PTGS1 mRNA CTD PMID:18165598 NCBI chr 3:19,584,015...19,605,589
Ensembl chr 3:19,584,015...19,605,586 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 increases expression
multiple interactions		 ISO Bupivacaine results in increased expression of PTGS2 mRNA
[Bupivacaine results in increased expression of PTGS2] which results in increased abundance of Dinoprostone		 CTD PMID:18165598 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Slc25a29 solute carrier family 25 member 29 multiple interactions
decreases activity		 EXP Emulsions inhibits the reaction [Bupivacaine results in decreased activity of SLC25A29 protein] CTD PMID:35135371 NCBI chr 6:127,742,027...127,752,915
Ensembl chr 6:127,742,033...127,752,940 		JBrowse link
G Slc2a1 solute carrier family 2 member 1 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of SLC2A1 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A1 protein]		 CTD PMID:34793778 NCBI chr 5:132,717,196...132,745,416
Ensembl chr 5:132,717,196...132,745,416 		JBrowse link
G Slc2a4 solute carrier family 2 member 4 multiple interactions
decreases expression		 ISO HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of SLC2A4 protein] CTD PMID:34793778 NCBI chr10:54,666,015...54,671,581
Ensembl chr10:54,666,015...54,671,565 		JBrowse link
G Slc6a2 solute carrier family 6 member 2 multiple interactions ISO Bupivacaine inhibits the reaction [[Desipramine results in decreased activity of SLC6A2 protein] which results in decreased abundance of Norepinephrine] CTD PMID:16725121 NCBI chr19:14,010,292...14,055,317
Ensembl chr19:14,010,386...14,050,357 		JBrowse link
G Tomm20 translocase of outer mitochondrial membrane 20 decreases expression
multiple interactions		 ISO Bupivacaine results in decreased expression of TOMM20 protein
HSPA12A protein inhibits the reaction [Bupivacaine results in decreased expression of TOMM20 protein]		 CTD PMID:34793778 NCBI chr19:54,925,197...54,935,188
Ensembl chr19:54,923,402...54,935,198 		JBrowse link
G Trpv1 transient receptor potential cation channel, subfamily V, member 1 increases activity
multiple interactions		 EXP Bupivacaine results in increased activity of TRPV1 protein
Bupivacaine affects the reaction [Capsaicin results in increased activity of TRPV1 protein]		 CTD PMID:15854744 PMID:18172555 NCBI chr10:57,851,428...57,876,513
Ensembl chr10:57,851,428...57,876,513 		JBrowse link
G Xrcc6 X-ray repair cross complementing 6 increases expression
multiple interactions		 ISO Bupivacaine results in increased expression of XRCC6 protein
8-dibenzothiophen-4-yl-2-morpholin-4-yl-chromen-4-one inhibits the reaction [[Glucose co-treated with Bupivacaine] results in increased expression of XRCC6 protein]; [Glucose co-treated with Bupivacaine] results in increased expression of XRCC6 protein; Glucose inhibits the reaction [Bupivacaine results in increased expression of XRCC6 protein]		 CTD PMID:31672611 NCBI chr 7:113,542,992...113,563,762
Ensembl chr 7:113,543,057...113,563,762 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19917
    chemical entity 19915
      chemical substance 14411
        mixture 13729
          racemate 12106
            bupivacaine 42
Path 2
Term Annotations click to browse term
  CHEBI ontology 19917
    subatomic particle 19915
      composite particle 19915
        hadron 19915
          baryon 19915
            nucleon 19915
              atomic nucleus 19915
                atom 19915
                  main group element atom 19855
                    p-block element atom 19855
                      carbon group element atom 19794
                        carbon atom 19790
                          organic molecular entity 19790
                            heteroorganic entity 19548
                              organochalcogen compound 19307
                                organooxygen compound 19223
                                  carbon oxoacid 18687
                                    carboxylic acid 18684
                                      carboacyl group 17720
                                        univalent carboacyl group 17720
                                          carbamoyl group 17571
                                            carboxamide 17571
                                              monocarboxylic acid amide 15747
                                                piperidinecarboxamide 80
                                                  1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide 42
                                                    dextrobupivacaine 42
                                                      bupivacaine 42
paths to the root