General Information of Drug (ID: DMTP1DC)

Drug Name
Irbesartan
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
Indication
Disease Entry ICD 11 Status REF
Diabetic kidney disease GB61.Z Approved [1]
Hypertension BA00-BA04 Approved [2]
Coronavirus Disease 2019 (COVID-19) 1D6Y Investigative [3]
High blood pressure BA00 Investigative [1]
Therapeutic Class
Antihypertensive Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 428.5
Logarithm of the Partition Coefficient (xlogp) 4.1
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability
70% of drug becomes completely available to its intended biological destination(s) [5]
Clearance
The drug present in the plasma can be removed from the body at the rate of 2.3 mL/min/kg [6]
Elimination
2.5% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 14 hours [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 10 micromolar/kg/day [7]
Unbound Fraction
The unbound fraction of drug in plasma is 0.1% [6]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.94 L/kg [6]
Water Solubility
The ability of drug to dissolve in water is measured as 0.08 mg/mL [4]
Chemical Identifiers
Formula
C25H28N6O
IUPAC Name
2-butyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one
Canonical SMILES
CCCCC1=NC2(CCCC2)C(=O)N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5
InChI
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)
InChIKey
YOSHYTLCDANDAN-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3749
ChEBI ID
CHEBI:5959
CAS Number
138402-11-6
DrugBank ID
DB01029
TTD ID
D00JAU
VARIDT ID
DR00482
INTEDE ID
DR0879
ACDINA ID
D00330
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Angiotensin II receptor type-1 (AGTR1) TT8DBY3 AGTR1_HUMAN Antagonist [8]
HUMAN type-1 angiotensin II receptor (AGTR1) TTPKMXQ AGTR1_HUMAN Antagonist [9]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [10]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [11]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [12]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [13]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [14]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DEF2WXN UD13_HUMAN Substrate [14]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Angiotensin-converting enzyme 2 (ACE2) OTTRZGU7 ACE2_HUMAN Drug Response [15]
Angiotensinogen (AGT) OTBZLYR3 ANGT_HUMAN Gene/Protein Processing [16]
Apolipoprotein B-100 (APOB) OTH0UOCZ APOB_HUMAN Drug Response [17]
B2 bradykinin receptor (BDKRB2) OTOA9D3W BKRB2_HUMAN Drug Response [18]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [19]
Carbonic anhydrase 1 (CA1) OTNFBVVQ CAH1_HUMAN Gene/Protein Processing [20]
Cytochrome P450 11B2, mitochondrial (CYP11B2) OTIOLWYN C11B2_HUMAN Drug Response [21]
Cytochrome P450 2C8 (CYP2C8) OTHCWT42 CP2C8_HUMAN Gene/Protein Processing [13]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Drug Response [22]
Endoplasmic reticulum aminopeptidase 1 (ERAP1) OT72S99B ERAP1_HUMAN Drug Response [23]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Diabetic kidney disease
ICD Disease Classification GB61.Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Angiotensin II receptor type-1 (AGTR1) DTT AGTR1 8.95E-01 1.34E-02 0.07
Peptide transporter 1 (SLC15A1) DTP PEPT1 4.57E-01 2.15E-02 1.72E-01
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 1.82E-04 -1.35E-01 -5.84E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 1.90E-01 -9.81E-03 -5.96E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.04E-02 6.29E-02 3.54E-01
Prostaglandin G/H synthase 1 (COX-1) DME PTGS1 3.97E-03 1.56E-01 4.33E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Irbesartan
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Aliskiren DM1BV7W Major Increased risk of hyperkalemia by the combination of Irbesartan and Aliskiren. Hypertension [BA00-BA04] [24]
Captopril DM458UM Major Increased risk of hyperkalemia by the combination of Irbesartan and Captopril. Hypertension [BA00-BA04] [25]
Coadministration of a Drug Treating the Disease Different from Irbesartan (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Insulin-glulisine DMQI0FU Moderate Increased risk of hypoglycemia by the combination of Irbesartan and Insulin-glulisine. Acute diabete complication [5A2Y] [26]
Insulin-aspart DMX7V28 Moderate Increased risk of hypoglycemia by the combination of Irbesartan and Insulin-aspart. Acute diabete complication [5A2Y] [27]
Cariprazine DMJYDVK Moderate Additive hypotensive effects by the combination of Irbesartan and Cariprazine. Bipolar disorder [6A60] [28]
Alpelisib DMEXMYK Moderate Increased metabolism of Irbesartan caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [29]
Drospirenone DM1A9W3 Moderate Increased risk of hyperkalemia by the combination of Irbesartan and Drospirenone. Contraceptive management [QA21] [30]
Ardeparin DMYRX8B Moderate Increased risk of hyperkalemia by the combination of Irbesartan and Ardeparin. Coronary thrombosis [BA43] [25]
Lumacaftor DMCLWDJ Moderate Increased metabolism of Irbesartan caused by Lumacaftor mediated induction of CYP450 enzyme. Cystic fibrosis [CA25] [31]
Ivacaftor DMZC1HS Moderate Decreased metabolism of Irbesartan caused by Ivacaftor mediated inhibition of CYP450 enzyme. Cystic fibrosis [CA25] [32]
MK-8228 DMOB58Q Moderate Increased metabolism of Irbesartan caused by MK-8228 mediated induction of CYP450 enzyme. Cytomegaloviral disease [1D82] [33]
Selegiline DM6034S Moderate Additive hypotensive effects by the combination of Irbesartan and Selegiline. Depression [6A70-6A7Z] [34]
Isocarboxazid DMAF1NB Moderate Additive hypotensive effects by the combination of Irbesartan and Isocarboxazid. Depression [6A70-6A7Z] [34]
OPC-34712 DMHG57U Moderate Additive hypotensive effects by the combination of Irbesartan and OPC-34712. Depression [6A70-6A7Z] [28]
Rifapentine DMCHV4I Moderate Increased metabolism of Irbesartan caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [35]
Procarbazine DMIK367 Moderate Additive hypotensive effects by the combination of Irbesartan and Procarbazine. Hodgkin lymphoma [2B30] [34]
Etravirine DMGV8QU Moderate Decreased metabolism of Irbesartan caused by Etravirine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [36]
Fenofibrate DMFKXDY Moderate Decreased metabolism of Irbesartan caused by Fenofibrate mediated inhibition of CYP450 enzyme. Hyper-lipoproteinaemia [5C80] [37]
Tolvaptan DMIWFRL Moderate Increased risk of hyperkalemia by the combination of Irbesartan and Tolvaptan. Hypo-osmolality/hyponatraemia [5C72] [38]
ITI-007 DMUQ1DO Moderate Additive hypotensive effects by the combination of Irbesartan and ITI-007. Insomnia [7A00-7A0Z] [28]
PF-06463922 DMKM7EW Moderate Increased metabolism of Irbesartan caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [37]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Irbesartan caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [39]
Ozanimod DMT6AM2 Moderate Additive hypotensive effects by the combination of Irbesartan and Ozanimod. Multiple sclerosis [8A40] [34]
Promethazine DM6I5GR Moderate Additive hypotensive effects by the combination of Irbesartan and Promethazine. Nausea/vomiting [MD90] [28]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Irbesartan caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [40]
Safinamide DM0YWJC Moderate Additive hypotensive effects by the combination of Irbesartan and Safinamide. Parkinsonism [8A00] [34]
Rasagiline DM3WKQ4 Moderate Additive hypotensive effects by the combination of Irbesartan and Rasagiline. Parkinsonism [8A00] [34]
Enzalutamide DMGL19D Moderate Increased metabolism of Irbesartan caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [41]
Quetiapine DM1N62C Moderate Additive hypotensive effects by the combination of Irbesartan and Quetiapine. Schizophrenia [6A20] [28]
Aripiprazole DM3NUMH Moderate Additive hypotensive effects by the combination of Irbesartan and Aripiprazole. Schizophrenia [6A20] [28]
Paliperidone DM7NPJS Moderate Additive hypotensive effects by the combination of Irbesartan and Paliperidone. Schizophrenia [6A20] [28]
Molindone DMAH70G Moderate Additive hypotensive effects by the combination of Irbesartan and Molindone. Schizophrenia [6A20] [28]
Thiothixene DMDINC4 Moderate Additive hypotensive effects by the combination of Irbesartan and Thiothixene. Schizophrenia [6A20] [28]
Amisulpride DMSJVAM Moderate Additive hypotensive effects by the combination of Irbesartan and Amisulpride. Schizophrenia [6A20] [28]
Asenapine DMSQZE2 Moderate Additive hypotensive effects by the combination of Irbesartan and Asenapine. Schizophrenia [6A20] [28]
Insulin-detemir DMOA4VW Moderate Increased risk of hypoglycemia by the combination of Irbesartan and Insulin-detemir. Type-1/2 diabete [5A10-5A11] [26]
Insulin degludec DMPL395 Moderate Increased risk of hypoglycemia by the combination of Irbesartan and Insulin degludec. Type-1/2 diabete [5A10-5A11] [26]
Trimeprazine DMEMV9D Moderate Additive hypotensive effects by the combination of Irbesartan and Trimeprazine. Vasomotor/allergic rhinitis [CA08] [42]
⏷ Show the Full List of 36 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium stearyl fumarate E00545 23665634 lubricant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite E00392 104805 Diluent
Calcium hydrogenphosphate E00294 24441 Diluent
Calcium stearate E00244 15324 lubricant
Carmellose sodium E00625 Not Available Disintegrant
Crospovidone E00626 Not Available Disintegrant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Poloxamer 188 E00645 Not Available Emulsifying agent; Solubilizing agent; Surfactant
Polyethylene glycol 300 E00651 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80 E00665 Not Available Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
⏷ Show the Full List of 20 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Irbesartan 150 mg tablet 150 mg Oral Tablet Oral
Irbesartan 300 mg tablet 300 mg Oral Tablet Oral
Irbesartan 75 mg tablet 75 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Irbesartan FDA Label
2 FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 203534.
3 Renoprotective effect of the angiotensin-receptor antagonist irbesartan in patients with nephropathy due to type 2 diabetes. N Engl J Med. 2001 Sep 20;345(12):851-60. Clinical Trial;
4 BDDCS applied to over 900 drugs
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6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8 Radioligand binding assays: application of [(125)I]angiotensin II receptor binding. Methods Mol Biol. 2009;552:131-41.
9 Angiotensin receptor blockers as tentative SARS-CoV-2 therapeutics. Drug Dev Res. 2020 Mar 4.
10 High-affinity interaction of sartans with H+/peptide transporters. Drug Metab Dispos. 2009 Jan;37(1):143-9.
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12 Rapid detection of the known SNPs of CYP2C9 using oligonucleotide microarray. World J Gastroenterol. 2003 Jun;9(6):1342-6.
13 Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78.
14 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
15 Angiotensin converting enzyme gene polymorphism predicts blood pressure response to angiotensin II receptor type 1 antagonist treatment in hypertensive patients. J Hypertens. 2001 Oct;19(10):1783-7. doi: 10.1097/00004872-200110000-00012.
16 Angiotensin II receptor blockade in normotensive subjects: A direct comparison of three AT1 receptor antagonists. Hypertension. 1999 Mar;33(3):850-5. doi: 10.1161/01.hyp.33.3.850.
17 Single nucleotide polymorphisms in the apolipoprotein B and low density lipoprotein receptor genes affect response to antihypertensive treatment. BMC Cardiovasc Disord. 2004 Sep 28;4(1):16. doi: 10.1186/1471-2261-4-16.
18 B2 bradykinin receptor (B2BKR) polymorphism and change in left ventricular mass in response to antihypertensive treatment: results from the Swedish Irbesartan Left Ventricular Hypertrophy Investigation versus Atenolol (SILVHIA) trial. J Hypertens. 2003 Mar;21(3):621-4. doi: 10.1097/00004872-200303000-00029.
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20 The mechanism of action of angiotensin II is dependent on direct activation of vascular smooth muscle carbonic anhydrase I. Int J Clin Lab Res. 2000;30(3):119-25. doi: 10.1007/s005990070010.
21 Aldosterone synthase (CYP11B2) -344 C/T polymorphism is related to antihypertensive response: result from the Swedish Irbesartan Left Ventricular Hypertrophy Investigation versus Atenolol (SILVHIA) trial. Am J Hypertens. 2002 May;15(5):389-93. doi: 10.1016/s0895-7061(02)02256-2.
22 The CYP2C9 genotype predicts the blood pressure response to irbesartan: results from the Swedish Irbesartan Left Ventricular Hypertrophy Investigation vs Atenolol (SILVHIA) trial. J Hypertens. 2002 Oct;20(10):2089-93.
23 Adipocyte-derived leucine aminopeptidase genotype and response to antihypertensive therapy. BMC Cardiovasc Disord. 2003 Sep 18;3:11. doi: 10.1186/1471-2261-3-11. Epub 2003 Sep 18.
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