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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:ezetimibe
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Accession:CHEBI:49040 term browser browse the term
Definition:A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).
Synonyms:exact_synonym: (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
 related_synonym: Ezedoc;   Ezetrol;   Formula=C24H21F2NO3;   InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1;   InChIKey=OLNTVTPDXPETLC-XPWALMASSA-N;   SMILES=[H][C@]1(CC[C@H](O)c2ccc(F)cc2)C(=O)N(c2ccc(F)cc2)[C@]1([H])c1ccc(O)cc1;   Zetia;   ezetimiba;   ezetimibum
 alt_id: MESH:D000069438
 xref: Beilstein:7981967;   CAS:163222-33-1;   DrugBank:DB00973;   Drug_Central:1125;   HMDB:HMDB0015108;   KEGG:D01966;   LINCS:LSM-5536
 xref_mesh: MESH:D000069438
 xref: PMID:17587760;   PMID:18585981;   PMID:23219178;   PMID:23266293;   PMID:23317398;   PMID:23471229;   PMID:23510093;   PMID:23538020;   Reaxys:7981967;   Wikipedia:Ezetimibe


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ezetimibe term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abca1 ATP binding cassette subfamily A member 1 decreases expression ISO Ezetimibe results in decreased expression of ABCA1 mRNA CTD PMID:16177187 NCBI chr 5:67,678,267...67,801,162
Ensembl chr 5:67,681,297...67,801,170
JBrowse link
G Abcb11 ATP binding cassette subfamily B member 11 decreases activity
multiple interactions
ISO Ezetimibe results in decreased activity of ABCB11 protein
Ezetimibe inhibits the reaction [ABCB11 protein results in increased transport of Taurocholic Acid]
CTD PMID:24014644 NCBI chr 3:54,016,854...54,112,797
Ensembl chr 3:54,017,127...54,112,730
JBrowse link
G Apoa1 apolipoprotein A1 multiple interactions ISO [Niacin co-treated with Ezetimibe co-treated with Simvastatin] results in increased expression of APOA1 protein; [Simvastatin co-treated with Ezetimibe] results in increased expression of APOA1 protein; Niacin promotes the reaction [[Simvastatin co-treated with Ezetimibe] results in increased expression of APOA1 protein] CTD PMID:18420099 PMID:20152243 NCBI chr 8:46,527,251...46,529,035
Ensembl chr 8:46,527,144...46,529,035
JBrowse link
G Crp C-reactive protein multiple interactions ISO [Ezetimibe co-treated with Simvastatin] results in decreased expression of CRP protein; [Simvastatin co-treated with Ezetimibe] promotes the reaction [Niacin results in decreased expression of CRP protein] CTD PMID:18420099 PMID:20152243 NCBI chr13:85,131,635...85,175,179
Ensembl chr13:85,124,977...85,175,178
JBrowse link
G Hmgcr 3-hydroxy-3-methylglutaryl-CoA reductase multiple interactions
increases activity
ISO [Simvastatin co-treated with Ezetimibe] results in increased expression of HMGCR mRNA
Ezetimibe results in increased activity of HMGCR protein
CTD PMID:17980884 NCBI chr 2:27,997,523...28,018,983
Ensembl chr 2:27,997,525...28,019,703
JBrowse link
G Ldlr low density lipoprotein receptor multiple interactions ISO [Simvastatin co-treated with Ezetimibe] results in increased expression of LDLR mRNA CTD PMID:17980884 NCBI chr 8:20,270,020...20,292,981
Ensembl chr 8:20,270,041...20,294,580
JBrowse link
G Npc1l1 NPC1 like intracellular cholesterol transporter 1 decreases expression
decreases activity
decreases response to substance
ISO Ezetimibe results in decreased expression of NPC1L1 mRNA
Ezetimibe results in decreased activity of NPC1L1 protein
NPC1L1 exon SNP results in decreased susceptibility to Ezetimibe
CTD PMID:15679830 PMID:16177187 PMID:28057006 NCBI chr14:81,071,448...81,091,113
Ensembl chr14:81,071,451...81,091,113
JBrowse link
G Nr1h2 nuclear receptor subfamily 1, group H, member 2 decreases expression ISO Ezetimibe results in decreased expression of NR1H2 mRNA CTD PMID:16177187 NCBI chr 1:95,041,967...95,047,377
Ensembl chr 1:95,041,967...95,047,377
JBrowse link
G Pcsk9 proprotein convertase subtilisin/kexin type 9 multiple interactions ISO [Simvastatin co-treated with Ezetimibe] results in increased expression of PCSK9 mRNA CTD PMID:17980884 NCBI chr 5:121,211,278...121,233,688
Ensembl chr 5:121,211,278...121,233,688
JBrowse link
G Pgr progesterone receptor multiple interactions ISO Ezetimibe binds to and results in decreased activity of PGR protein CTD PMID:25752796 NCBI chr 8:6,073,216...6,131,552
Ensembl chr 8:6,072,673...6,131,344
JBrowse link
G Pla2g7 phospholipase A2 group VII multiple interactions ISO [orlistat co-treated with Ezetimibe] results in decreased activity of PLA2G7 protein CTD PMID:18513463 NCBI chr 9:17,362,214...17,404,476
Ensembl chr 9:17,362,225...17,404,476
JBrowse link
G Rarg retinoic acid receptor, gamma decreases expression ISO Ezetimibe results in decreased expression of RARG mRNA CTD PMID:16177187 NCBI chr 7:133,367,833...133,390,301
Ensembl chr 7:133,367,833...133,390,177
JBrowse link
G Scarb1 scavenger receptor class B, member 1 decreases expression ISO Ezetimibe results in decreased expression of SCARB1 mRNA CTD PMID:16177187 NCBI chr12:31,296,143...31,362,649
Ensembl chr12:31,296,156...31,362,647
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 decreases expression ISO Ezetimibe results in decreased expression of SREBF1 mRNA CTD PMID:16177187 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650
JBrowse link
G Srebf2 sterol regulatory element binding transcription factor 2 decreases expression ISO Ezetimibe results in decreased expression of SREBF2 mRNA CTD PMID:16177187 NCBI chr 7:113,663,202...113,720,850
Ensembl chr 7:113,663,202...113,720,848
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP [Metformin co-treated with rosiglitazone co-treated with Valsartan co-treated with Ezetimibe] inhibits the reaction [[Methionine deficiency co-treated with Choline deficiency] results in increased expression of TNF protein]; Ezetimibe inhibits the reaction [[Methionine deficiency co-treated with Choline deficiency] results in increased expression of TNF protein] CTD PMID:16865780 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 increases glucuronidation ISO UGT1A1 protein results in increased glucuronidation of Ezetimibe CTD PMID:14977865 NCBI chr 9:88,801,344...88,808,465 JBrowse link
G Ugt1a2 UDP glucuronosyltransferase 1 family, polypeptide A2 increases glucuronidation ISO UGT1A3 protein results in increased glucuronidation of Ezetimibe CTD PMID:14977865 NCBI chr 9:88,791,216...88,808,465 JBrowse link
G Ugt2b7 UDP glucuronosyltransferase family 2 member B7 increases glucuronidation ISO UGT2B7 protein results in increased glucuronidation of Ezetimibe CTD PMID:14977865 NCBI chr14:20,896,682...20,919,604
Ensembl chr14:20,896,682...20,919,604
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19812
    role 19761
      biological role 19761
        biochemical role 19381
          antimetabolite 8517
            ezetimibe 19
Path 2
Term Annotations click to browse term
  CHEBI ontology 19812
    subatomic particle 19811
      composite particle 19811
        hadron 19811
          baryon 19811
            nucleon 19811
              atomic nucleus 19811
                atom 19811
                  main group element atom 19708
                    p-block element atom 19708
                      carbon group element atom 19630
                        carbon atom 19620
                          organic molecular entity 19620
                            organic group 18728
                              organic divalent group 18719
                                organodiyl group 18719
                                  carbonyl group 18667
                                    carbonyl compound 18667
                                      carboxylic acid 18364
                                        carboacyl group 17482
                                          univalent carboacyl group 17482
                                            carbamoyl group 17298
                                              carboxamide 17298
                                                lactam 8302
                                                  beta-lactam 794
                                                    ezetimibe 19
paths to the root