Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D09LWS
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| Former ID |
DAP000717
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| Drug Name |
Ezetimibe
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| Synonyms |
Ezedoc; Ezetimib; Ezetrol; Zetia; Zient; Essex brand of ezetimibe; MSD brand of ezetimibe; Merck brand of ezetimibe; SCH58235; Sch 58235; Ezetimibe [USAN:INN]; Inegy (TN); MK-0653; SCH-58235; Schering-Plough brand of ezetimibe; Vytorin (TN); Zetia (TN); Zetia , Ezetrol, Ezetimibe; Ezetimibe (JAN/USAN/INN); (-)-Sch 58235; (1-(4-fluorophenyl)-(3R)-(3-(4-fluorophenyl)-(3S)-hydroxypropyl)-(4S)-(4-hydroxyphenyl)-2-azetidinone); (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one; (3R,4S)-1-(p-Fluorophenyl)-3-((3S)-3-(p-fluorophenyl)-3-hydroxypropyl)-4-(p-hydroxyphenyl)-2-azetidinone; 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-(4-hydroxyphenyl)-2-azetidione; 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone
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| Drug Type |
Small molecular drug
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| Indication | Hypercholesterolaemia [ICD-11: 5C80.0] | Approved | [1], [2] | |
| Therapeutic Class |
Anticholesteremic Agents
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| Company |
Schering-Plough
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| Structure |
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Download2D MOL |
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| Formula |
C24H21F2NO3
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| Canonical SMILES |
C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)O
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| 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
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| InChIKey |
OLNTVTPDXPETLC-XPWALMASSA-N
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| CAS Number |
CAS 163222-33-1
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| PubChem Compound ID | ||||
| PubChem Substance ID |
7849028, 10250673, 11528896, 12014979, 14879623, 14928749, 26719841, 46226990, 46386640, 46507625, 49681809, 49693660, 50539938, 53787196, 57347010, 71821424, 81146074, 92308446, 92718207, 103326446, 104179182, 104253290, 104428106, 117884262, 124658886, 124757411, 124801398, 125164215, 126592989, 126621626, 126653456, 126667079, 127315811, 127315812, 127315813, 127315814, 127315815, 127315816, 127315817, 127315818, 127315819, 127315820, 127315821, 127315822, 127315823, 127315824, 128826430, 131854738, 134338005, 135107180
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| ChEBI ID |
CHEBI:49040
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| ADReCS Drug ID | BADD_D00864 | |||
| SuperDrug ATC ID |
C10AX09
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| SuperDrug CAS ID |
cas=163222331
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides fragilis HMW 615
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides fragilis HMW 615 (log2FC = -0.513; p = 0.017). | |||
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Studied Microbe: Bacteroides fragilis str. 3397 T10
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides fragilis str. 3397 T10 (log2FC = -0.613; p = 0.038). | |||
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Studied Microbe: Bacteroides fragilis str. 3986 T(B)9
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides fragilis str. 3986 T(B)9 (log2FC = -0.742; p = 0.036). | |||
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Studied Microbe: Bacteroides fragilis str. DS-208
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides fragilis str. DS-208 (log2FC = -0.531; p = 0.04). | |||
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Studied Microbe: Bacteroides stercoris ATCC 43183
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides stercoris ATCC 43183 (log2FC = -0.541; p = 0.021). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 7330
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides thetaiotaomicron 7330 (log2FC = -0.417; p = 0.025). | |||
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Studied Microbe: Bacteroides uniformis ATCC 8492
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides uniformis ATCC 8492 (log2FC = -0.865; p = 0.003). | |||
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Studied Microbe: Bacteroides xylanisolvens DSM18836
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Bacteroides xylanisolvens DSM18836 (log2FC = -0.511; p = 0.03). | |||
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Studied Microbe: Odoribacter splanchnicus
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Odoribacter splanchnicus (log2FC = -0.644; p = 0.035). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium animalis subsp.lactis BI-07
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|
[4] | |||
| Hierarchy | ||||
| Description | Ezetimibe can be metabolized by Bifidobacterium animalis subsp.lactis BI-07. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Clostridium sp.
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Clostridium sp. (log2FC = -0.402; p = 0.02). | |||
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Studied Microbe: Clostridium sporogenes ATCC 15579
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Ezetimibe can be metabolized by Clostridium sporogenes ATCC 15579 (log2FC = -0.872; p = 0.006). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Niemann-Pick C1-like protein 1 (NPC1L1) | Target Info | Inhibitor | [5] |
| KEGG Pathway | Fat digestion and absorption | |||
| WikiPathways | Vitamin A and Carotenoid Metabolism | |||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6816). | |||
| REF 2 | Emerging antidyslipidemic drugs. Expert Opin Emerg Drugs. 2008 Jun;13(2):363-81. | |||
| REF 3 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 4 | Bioaccumulation of therapeutic drugs by human gut bacteria. Nature. 2021 Sep;597(7877):533-538. | |||
| REF 5 | Update on patented cholesterol absorption inhibitors. Expert Opin Ther Pat. 2009 Aug;19(8):1083-107. | |||
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