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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:fentanyl
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Accession:CHEBI:119915 term browser browse the term
Definition:A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.
Synonyms:exact_synonym: N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
 related_synonym: 1-phenethyl-4-(N-phenylpropionamido)piperidine;   1-phenethyl-4-N-propionylanilinopiperidine;   Duragesic;   Formula=C22H28N2O;   InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3;   InChIKey=PJMPHNIQZUBGLI-UHFFFAOYSA-N;   N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide;   N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide;   N-(1-phenethyl-4-piperidyl)propionanilide;   N-(1-phenethylpiperidin-4-yl)-N-phenylpropionamide;   N-phenethyl-4-(N-propionylanilino)piperidine;   N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide;   SMILES=CCC(=O)N(C1CCN(CC1)CCc1ccccc1)c1ccccc1;   fentanilo;   fentanylum;   phentanyl
 alt_id: CHEBI:310077;   CHEBI:5012
 xref: CAS:437-38-7;   DrugBank:DB00813;   Drug_Central:1164;   KEGG:D00320
 xref_mesh: MESH:D005283
 xref: PMID:10669565;   PMID:10987438;   PMID:11585443;   PMID:14698188;   PMID:16621415;   PMID:18462178;   PMID:18728103;   PMID:30176422;   PMID:30305277;   Patent:FR1344366;   Patent:US3164600;   Reaxys:494484;   VSDB:1864;   Wikipedia:Fentanyl


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fentanyl term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A increases transport
multiple interactions
increases response to substance		 ISO
EXP		 ABCB1 protein results in increased transport of Fentanyl
tariquidar inhibits the reaction [ABCB1 protein results in increased transport of Fentanyl]
ABCB1 protein results in increased susceptibility to Fentanyl		 CTD PMID:29669042 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Arrb2 arrestin, beta 2 affects localization ISO Fentanyl affects the localization of ARRB2 protein CTD PMID:27030709 NCBI chr10:55,146,887...55,154,854
Ensembl chr10:55,146,818...55,154,850 		JBrowse link
G Calca calcitonin-related polypeptide alpha multiple interactions EXP Fentanyl inhibits the reaction [Potassium Chloride results in increased secretion of CALCA protein]; Naloxone inhibits the reaction [Fentanyl inhibits the reaction [Potassium Chloride results in increased secretion of CALCA protein]] CTD PMID:27030709 NCBI chr 1:168,878,212...168,883,176
Ensembl chr 1:168,878,214...168,883,105 		JBrowse link
G Crh corticotropin releasing hormone affects expression EXP Fentanyl affects the expression of CRH mRNA CTD PMID:18819432 NCBI chr 2:102,143,055...102,144,919
Ensembl chr 2:102,143,055...102,144,919 		JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 increases metabolic processing ISO CYP3A4 protein results in increased metabolism of Fentanyl CTD PMID:11811955 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008 		JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit increases expression EXP Fentanyl results in increased expression of FOS protein CTD PMID:7970238 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036 		JBrowse link
G Gast gastrin multiple interactions EXP [fluanisone co-treated with Fentanyl co-treated with Midazolam] inhibits the reaction [GAST protein results in increased secretion of Histamine] CTD PMID:10864877 NCBI chr10:85,264,832...85,269,393
Ensembl chr10:85,264,832...85,267,496 		JBrowse link
G Il2 interleukin 2 decreases expression ISO Fentanyl results in decreased expression of IL2 mRNA CTD PMID:23965172 NCBI chr 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566 		JBrowse link
G Il4 interleukin 4 increases expression ISO Fentanyl results in increased expression of IL4 mRNA CTD PMID:23965172 NCBI chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750 		JBrowse link
G Kcnh2 potassium voltage-gated channel subfamily H member 2 decreases activity ISO Fentanyl results in decreased activity of KCNH2 protein CTD PMID:28551711 NCBI chr 4:10,826,834...10,859,009
Ensembl chr 4:10,826,928...10,859,008 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 increases phosphorylation ISO Fentanyl results in increased phosphorylation of MAPK1 protein CTD PMID:23965172 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 ISO Fentanyl results in increased phosphorylation of MAPK3 protein CTD PMID:23965172 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Nfkbia NFKB inhibitor alpha increases expression ISO Fentanyl results in increased expression of NFKBIA protein CTD PMID:22258905 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941 		JBrowse link
G Oprm1 opioid receptor, mu 1 increases phosphorylation ISO Fentanyl results in increased phosphorylation of OPRM1 protein CTD PMID:17240843 PMID:21957251 PMID:23300227 NCBI chr 1:43,160,057...43,413,409
Ensembl chr 1:43,160,057...43,413,409 		JBrowse link
G Pdyn prodynorphin increases expression EXP Fentanyl results in increased expression of PDYN protein CTD PMID:19200067 NCBI chr 3:116,900,990...116,913,334
Ensembl chr 3:116,900,992...116,913,334 		JBrowse link
G Pld2 phospholipase D2 increases activity ISO Fentanyl results in increased activity of PLD2 protein CTD PMID:23965172 NCBI chr10:55,256,326...55,274,192
Ensembl chr10:55,256,359...55,272,808 		JBrowse link
G Pomc proopiomelanocortin decreases expression
multiple interactions		 ISO Fentanyl results in decreased expression of POMC protein alternative form
[Fentanyl co-treated with Morphine] results in decreased expression of POMC protein alternative form		 CTD PMID:20084599 NCBI chr 6:26,939,844...26,945,666
Ensembl chr 6:26,939,837...26,945,664 		JBrowse link
G Ren renin multiple interactions ISO [Fentanyl co-treated with Isoflurane] results in decreased expression of REN protein CTD PMID:3284271 NCBI chr13:44,796,260...44,807,491
Ensembl chr13:44,796,091...44,807,489 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19808
    role 19757
      application 19467
        pharmaceutical 19315
          adjuvant 1777
            fentanyl 18
              fentanyl citrate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19808
    subatomic particle 19807
      composite particle 19807
        hadron 19807
          baryon 19807
            nucleon 19807
              atomic nucleus 19807
                atom 19807
                  main group element atom 19704
                    main group molecular entity 19704
                      s-block molecular entity 19489
                        hydrogen molecular entity 19484
                          hydrides 18841
                            inorganic hydride 17688
                              pnictogen hydride 17669
                                nitrogen hydride 17542
                                  azane 17278
                                    ammonia 17277
                                      organic amino compound 17277
                                        amine 7820
                                          primary amine 5725
                                            primary arylamine 2986
                                              aniline 2824
                                                anilide 272
                                                  fentanyl 18
                                                    fentanyl citrate 0
paths to the root