Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D00JAU
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| Former ID |
DAP000364
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| Drug Name |
Irbesartan
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| Synonyms |
irbesartan; 138402-11-6; Aprovel; Avapro; Karvea; SR-47436; BMS-186295; BMS 186295; Irbesartan [USAN:INN]; SR 47436; UNII-J0E2756Z7N; CHEMBL1513; 8-butyl-7-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-7,9-diazaspiro[44]non-8-en-6-one; CHEBI:5959; C25H28N6O; YOSHYTLCDANDAN-UHFFFAOYSA-N; J0E2756Z7N; 2-butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[44]non-1-en-4-one; 3-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-1,3-diazaspiro[44]non-1-en-4-one; NCGC00095122-01; AK-57149; DSSTox_CID_3169; Aprovel; Irbesarran; Irbetan; Lrbesartan; BMS Brand of Irbesartan; Bristol Myers Brand of Irbesartan; SanofiWinthrop Brand of Irbesartan; Aprovel (TN); Avalide (TN); Avapro (TN); Karvea (TN); Irbesartan (JAN/USAN/INN); BMS-186295, SR-47436,Aprovel, Karvea, Irbesartan; 2-Butyl-3-(p-(o-1H-tetrazol-5-ylphenyl)benzyl)-1,3-diazaspiro(44)non-1-en-4-one; 2-Butyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]1,3-diaza-spiro[44]non-1-en-4-one; 2-butyl-3-[ p-(o-1 H-tetrazol-5-ylphenyl)benzyl]-1,3-diazaspiro[4,4]non-1-en-4-one; 2-butyl-3-[p-(o-1H-tetrazol-5-ylphenyl)benzyl]-1,3-diazaspiro[44]non-1-en-4-one; 2-butyl-3-{[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl}-1,3-diazaspiro[44]non-1-en-4-one; 2-n-butyl-3-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,3-diazaspiro(4,4)non-1-en-4-one; [3H]irbesartan
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| Drug Type |
Small molecular drug
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| Indication | Hypertension [ICD-11: BA00-BA04; ICD-9: 401] | Approved | [1], [2] | |
| Therapeutic Class |
Antihypertensive Agents
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| Company |
Bristol-Myers Squibb
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| Structure |
 |
Download2D MOL |
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| Formula |
C25H28N6O
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| Canonical SMILES |
CCCCC1=NC2(CCCC2)C(=O)N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5
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| InChI |
1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)
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| InChIKey |
YOSHYTLCDANDAN-UHFFFAOYSA-N
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| CAS Number |
CAS 138402-11-6
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| PubChem Compound ID | ||||
| PubChem Substance ID |
9672, 5243560, 7847589, 8152372, 11364645, 11367207, 11369769, 11372006, 11374741, 11377931, 11485625, 11489491, 11490809, 11492936, 11495565, 11528645, 12014641, 14758693, 14905264, 26612692, 26680708, 26719813, 26748950, 26748951, 29222869, 46386566, 46506575, 46530573, 47365300, 48035232, 48416128, 49681744, 49830881, 50107493, 53787775, 56312044, 56313979, 57321974, 77118987, 81092816, 85174437, 85209120, 85789259, 91011661, 92124749, 92307926, 92308458, 92713301, 93166505, 93621098
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| ChEBI ID |
CHEBI:5959
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| ADReCS Drug ID | BADD_D01194 | |||
| SuperDrug ATC ID |
C09CA04
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| SuperDrug CAS ID |
cas=138402116
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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 dorei DSM 17855
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides dorei DSM 17855 (log2FC = -0.724; p = 0.035). | |||
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Studied Microbe: Bacteroides fragilis ATCC43859
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides fragilis ATCC43859 (log2FC = -0.706; p = 0.021). | |||
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Studied Microbe: Bacteroides fragilis HMW 610
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides fragilis HMW 610 (log2FC = -0.658; p = 0.015). | |||
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Studied Microbe: Bacteroides fragilis HMW 615
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides fragilis HMW 615 (log2FC = -0.606; p = 0.032). | |||
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Studied Microbe: Bacteroides fragilis str. DS-208
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides fragilis str. DS-208 (log2FC = -0.513; p = 0.001). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 7330
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides thetaiotaomicron 7330 (log2FC = -0.404; p = 0.032). | |||
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Studied Microbe: Bacteroides thetaiotaomicron VPI-5482
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides thetaiotaomicron VPI-5482 (log2FC = -0.452; p = 0.009). | |||
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Studied Microbe: Bacteroides uniformis ATCC 8492
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides uniformis ATCC 8492 (log2FC = -0.599; p = 0.004). | |||
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Studied Microbe: Bacteroides vulgatus ATCC 8482
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides vulgatus ATCC 8482 (log2FC = -0.494; p = 0.004). | |||
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Studied Microbe: Bacteroides xylanisolvens DSM18836
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bacteroides xylanisolvens DSM18836 (log2FC = -0.515; p = 0.004). | |||
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Studied Microbe: Odoribacter splanchnicus
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Odoribacter splanchnicus (log2FC = -0.478; p = 0.008). | |||
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Studied Microbe: Parabacteroides johnsonii DSM 18315
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Parabacteroides johnsonii DSM 18315 (log2FC = -0.428; p = 0.016). | |||
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Studied Microbe: Parabacteroides merdae ATCC 43184
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Parabacteroides merdae ATCC 43184 (log2FC = -0.391; p = 0.012). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium ruminantium
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|
[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Bifidobacterium ruminantium (log2FC = -0.365; p = 0.012). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia hansenii DSM20583
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[3] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Irbesartan can be metabolized by Blautia hansenii DSM20583 (log2FC = -0.341; p = 0.033). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Angiotensin II receptor type-1 (AGTR1) | Target Info | Antagonist | [4], [5] |
| KEGG Pathway | Calcium signaling pathway | |||
| cGMP-PKG signaling pathway | ||||
| Neuroactive ligand-receptor interaction | ||||
| Adrenergic signaling in cardiomyocytes | ||||
| Vascular smooth muscle contraction | ||||
| Renin-angiotensin system | ||||
| Renin secretion | ||||
| Pathways in cancer | ||||
| NetPath Pathway | TGF_beta_Receptor Signaling Pathway | |||
| Panther Pathway | Angiotensin II-stimulated signaling through G proteins and beta-arrestin | |||
| Pathwhiz Pathway | Angiotensin Metabolism | |||
| Muscle/Heart Contraction | ||||
| Pathway Interaction Database | Arf6 trafficking events | |||
| Arf6 signaling events | ||||
| Angiopoietin receptor Tie2-mediated signaling | ||||
| Reactome | Peptide ligand-binding receptors | |||
| G alpha (q) signalling events | ||||
| WikiPathways | ACE Inhibitor Pathway | |||
| GPCRs, Class A Rhodopsin-like | ||||
| Gastrin-CREB signalling pathway via PKC and MAPK | ||||
| Peptide GPCRs | ||||
| Allograft Rejection | ||||
| GPCR ligand binding | ||||
| GPCR downstream signaling | ||||
| 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: 589). | |||
| REF 2 | New antiarrhythmic agents for atrial fibrillation and atrial flutter. Expert Opin Emerg Drugs. 2005 May;10(2):311-22. | |||
| REF 3 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 4 | Radioligand binding assays: application of [(125)I]angiotensin II receptor binding. Methods Mol Biol. 2009;552:131-41. | |||
| REF 5 | Binding characteristics of [(3)H]-irbesartan to human recombinant angiotensin type 1 receptors. J Renin Angiotensin Aldosterone Syst. 2000 Jun;1(2):159-65. | |||
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