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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:fenfluramine
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Accession:CHEBI:5000 term browser browse the term
Definition:A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.
Synonyms:related_synonym: 1-(m-trifluoromethyl-phenyl)-2-ethylaminopropane;   2-ethylamino-1-(3-trifluoromethylphenyl)propane;   3-(trifluoromethyl)-N-ethyl-alpha-methylphenethylamine;   Ethyl-[1-methyl-2-(3-trifluoromethyl-phenyl)-ethyl]-amine;   Formula=C12H16F3N;   InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3;   InChIKey=DBGIVFWFUFKIQN-UHFFFAOYSA-N;   N-ethyl-1-(3-(trifluoromethyl)phenyl)propan-2-amine;   N-ethyl-alpha-methyl-3-trifluoromethylphenethylamine;   SMILES=CCNC(C)Cc1cccc(c1)C(F)(F)F;   fenfluraminum
 alt_id: CHEBI:239434
 xref: Beilstein:2109374;   CAS:458-24-2;   DrugBank:DB00574;   Drug_Central:1150;   HMDB:HMDB0015322;   KEGG:C06996;   KEGG:D07945
 xref_mesh: MESH:D005277
 xref: PMID:11716826;   PMID:15637164;   PMID:15677429;   Patent:US3198833;   Reaxys:2109374;   Wikipedia:Fenfluramine



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fenfluramine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bmpr2 bone morphogenetic protein receptor type 2 increases response to substance ISO BMPR2 gene mutant form results in increased susceptibility to Fenfluramine CTD PMID:12358323 NCBI chr 9:61,192,718...61,307,280
Ensembl chr 9:61,190,566...61,301,809
JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit multiple interactions
increases expression
EXP Fluoxetine inhibits the reaction [Fenfluramine results in increased expression of FOS protein]; N-chlorophenylalanine inhibits the reaction [Fenfluramine results in increased expression of FOS protein] CTD PMID:9452197 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036
JBrowse link
G Htr2a 5-hydroxytryptamine receptor 2A affects binding ISO Fenfluramine binds to HTR2A protein CTD PMID:10617681 NCBI chr15:49,950,035...50,022,188
Ensembl chr15:49,950,804...50,020,928
JBrowse link
G Htr2b 5-hydroxytryptamine receptor 2B increases response to substance
affects binding
ISO HTR2B gene mutant form results in increased susceptibility to Fenfluramine
Fenfluramine binds to HTR2B protein
CTD PMID:10617681 PMID:14659797 NCBI chr 9:86,735,793...86,756,640
Ensembl chr 9:86,742,102...86,755,108
JBrowse link
G Htr2c 5-hydroxytryptamine receptor 2C affects binding ISO Fenfluramine binds to HTR2C protein CTD PMID:10617681 NCBI chr  X:110,640,777...110,870,288
Ensembl chr  X:110,641,153...110,870,287
JBrowse link
G Prl prolactin multiple interactions
increases expression
increases secretion
ISO
EXP
Cocaine affects the reaction [Fenfluramine results in increased expression of PRL protein]
Clonidine inhibits the reaction [Fenfluramine results in increased secretion of PRL protein]; talipexole inhibits the reaction [Fenfluramine results in increased secretion of PRL protein]
CTD PMID:1678730 PMID:9232209 PMID:9330023 PMID:9598218 PMID:10349036 NCBI chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062
JBrowse link
(S)-fenfluramine term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Slc22a2 solute carrier family 22 member 2 multiple interactions ISO Dexfenfluramine inhibits the reaction [SLC22A2 protein results in increased uptake of 4-(4-dimethylaminostyryl)-1-methylpyridinium] CTD PMID:21599003 NCBI chr 1:48,121,061...48,163,268
Ensembl chr 1:48,121,061...48,163,268
JBrowse link
G Slc6a4 solute carrier family 6 member 4 affects activity ISO Dexfenfluramine affects the activity of SLC6A4 protein CTD PMID:18506000 NCBI chr10:61,824,208...61,858,924
Ensembl chr10:61,826,123...61,858,384
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19659
    role 19634
      biological role 19633
        pharmacological role 18933
          neurotransmitter agent 16564
            serotonergic drug 4257
              serotonergic agonist 982
                fenfluramine 8
                  (R)-fenfluramine 0
                  (S)-fenfluramine + 2
                  fenfluramine hydrochloride + 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19659
    subatomic particle 19658
      composite particle 19658
        hadron 19658
          baryon 19658
            nucleon 19658
              atomic nucleus 19700
                atom 19658
                  main group element atom 19607
                    main group molecular entity 19649
                      s-block molecular entity 19457
                        hydrogen molecular entity 19450
                          hydrides 18928
                            organic hydride 18546
                              organic fundamental parent 18582
                                hydrocarbon 18313
                                  halohydrocarbon 15337
                                    haloalkane 12074
                                      fluoroalkane 7752
                                        fluoromethanes 6698
                                          tetrafluoromethane 6698
                                            trifluoromethyl group 6698
                                              (trifluoromethyl)benzenes 6705
                                                fenfluramine 8
                                                  (R)-fenfluramine 0
                                                  (S)-fenfluramine + 2
                                                  fenfluramine hydrochloride + 0
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