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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:levobupivacaine
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Accession:CHEBI:6149 term browser browse the term
Definition:The (S)-(-)-enantiomer of bupivacaine.
Synonyms:exact_synonym: (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
 related_synonym: (-)-bupivacaine;   (S)-1-butyl-2',6'-pipecoloxylidide;   (S)-bupivacaine;   Formula=C18H28N2O;   InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1;   InChIKey=LEBVLXFERQHONN-INIZCTEOSA-N;   L-(-)-1-Butyl-2',6'-pipecoloxylidide;   L-(-)-bupivacaine;   SMILES=CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
 xref: CAS:27262-47-1;   DrugBank:DB01002;   Drug_Central:4;   HMDB:HMDB0015137;   KEGG:C07887;   KEGG:D08116;   Reaxys:5382240;   Wikipedia:Levobupivacaine
 cyclic_relationship: is_conjugate_base_of CHEBI:77458;   is_enantiomer_of CHEBI:60790


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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
CTD PMID:31672611 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Casp3 caspase 3 decreases expression
increases activity
ISO
EXP
Bupivacaine results in decreased expression of CASP3 protein
Bupivacaine results in increased activity of CASP3 protein
CTD PMID:16109997 PMID:20194319 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp9 caspase 9 decreases expression ISO Bupivacaine results in decreased expression of CASP9 protein CTD PMID:20194319 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
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 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 chr15:44,630,873...44,658,706
Ensembl chr15:44,630,873...44,658,706
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 4:147,564,781...147,649,353
Ensembl chr 4:147,645,995...147,647,455
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...182,709,495
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 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 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 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 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 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 chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
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 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 19821
    role 19769
      chemical role 19345
        emulsifier 4412
          surfactant 4412
            amphiphile 22
              levobupivacaine 22
                bupivacaine 22
Path 2
Term Annotations click to browse term
  CHEBI ontology 19821
    subatomic particle 19819
      composite particle 19819
        hadron 19819
          baryon 19819
            nucleon 19819
              atomic nucleus 19819
                atom 19819
                  main group element atom 19716
                    p-block element atom 19716
                      carbon group element atom 19640
                        carbon atom 19630
                          organic molecular entity 19630
                            organic group 18737
                              organic divalent group 18728
                                organodiyl group 18728
                                  carbonyl group 18675
                                    carbonyl compound 18675
                                      carboxylic acid 18373
                                        carboacyl group 17485
                                          univalent carboacyl group 17485
                                            carbamoyl group 17299
                                              carboxamide 17299
                                                monocarboxylic acid amide 15008
                                                  piperidinecarboxamide 30
                                                    1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide 22
                                                      levobupivacaine 22
                                                        bupivacaine 22
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