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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 It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.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 9:66,568,074...66,683,019
Ensembl chr 9:66,568,074...66,676,494
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 6:109,300,433...109,303,299
Ensembl chr 6:109,300,433...109,303,299
JBrowse link
G Htr2a 5-hydroxytryptamine receptor 2A affects binding ISO Fenfluramine binds to HTR2A protein CTD PMID:10617681 NCBI chr15:56,666,152...56,732,469
Ensembl chr15:56,666,012...56,735,382
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 9:93,112,781...93,130,135
Ensembl chr 9:93,112,805...93,125,014
JBrowse link
G Htr2c 5-hydroxytryptamine receptor 2C affects binding ISO Fenfluramine binds to HTR2C protein CTD PMID:10617681 NCBI chr  X:118,084,520...118,318,040
Ensembl chr  X:118,084,890...118,318,039
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 chr17:39,814,236...39,824,299
Ensembl chr17:39,814,244...39,824,299
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 1:48,318,025...48,360,219
Ensembl chr 1:48,317,995...48,360,261
JBrowse link
G Slc6a4 solute carrier family 6 member 4 affects activity ISO Dexfenfluramine affects the activity of SLC6A4 protein CTD PMID:18506000 NCBI chr10:63,153,656...63,188,377
Ensembl chr10:63,153,651...63,176,463
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      biological role 19734
        pharmacological role 18797
          neurotransmitter agent 16425
            serotonergic drug 3957
              serotonergic agonist 978
                fenfluramine 8
                  (R)-fenfluramine 0
                  (S)-fenfluramine + 2
                  fenfluramine hydrochloride + 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    main group molecular entity 19672
                      s-block molecular entity 19430
                        hydrogen molecular entity 19420
                          hydrides 18686
                            organic hydride 18249
                              organic fundamental parent 18249
                                hydrocarbon 17969
                                  halohydrocarbon 13937
                                    haloalkane 11657
                                      fluoroalkane 7110
                                        fluoromethanes 6330
                                          tetrafluoromethane 6330
                                            trifluoromethyl group 6330
                                              (trifluoromethyl)benzenes 6330
                                                fenfluramine 8
                                                  (R)-fenfluramine 0
                                                  (S)-fenfluramine + 2
                                                  fenfluramine hydrochloride + 0
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