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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 chr13:85,135,384...85,175,178
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 Mir221 microRNA 221 decreases expression ISO Ezetimibe results in decreased expression of MIR221 CTD PMID:25517390 NCBI chr  X:3,429,465...3,429,573
Ensembl chr  X:3,429,465...3,429,573
JBrowse link
G Npc1l1 NPC1 like intracellular cholesterol transporter 1 decreases expression
decreases response to substance
decreases activity
ISO Ezetimibe results in decreased expression of NPC1L1 mRNA
NPC1L1 exon SNP results in decreased susceptibility to Ezetimibe
Ezetimibe results in decreased activity of NPC1L1 protein
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...95,047,358
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 8:6,072,673...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
Ensembl chr 9:88,713,184...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
Ensembl chr 9:88,713,184...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 19932
    role 19904
      biological role 19902
        biochemical role 19598
          antimetabolite 10307
            ezetimibe 20
Path 2
Term Annotations click to browse term
  CHEBI ontology 19932
    subatomic particle 19930
      composite particle 19930
        hadron 19930
          baryon 19930
            nucleon 19930
              atomic nucleus 19930
                atom 19930
                  main group element atom 19876
                    p-block element atom 19876
                      carbon group element atom 19816
                        carbon atom 19812
                          organic molecular entity 19812
                            heteroorganic entity 19559
                              organochalcogen compound 19317
                                organooxygen compound 19231
                                  carbon oxoacid 18687
                                    carboxylic acid 18684
                                      carboacyl group 17725
                                        univalent carboacyl group 17725
                                          carbamoyl group 17579
                                            carboxamide 17579
                                              lactam 8391
                                                beta-lactam 831
                                                  ezetimibe 20
paths to the root