Details of the Drug

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

Affected Organisms

Humans and other mammals

ATC Code

C09CA04: Irbesartan

C09CA: Angiotensin II receptor blockers (ARBs), plain

C09C: ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), PLAIN

C09: AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM

C: CARDIOVASCULAR SYSTEM

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL1513
CAS Number: 138402-11-6
UNII: J0E2756Z7N
DrugBank ID: DB01029
TTD ID: D00JAU
VARIDT ID: DR00482
INTEDE ID: DR0879
ACDINA ID: D00330

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[15]
Endoplasmic reticulum aminopeptidase 1 (ERAP1)	OT72S99B	ERAP1_HUMAN	Drug Response	[16]
Natriuretic peptides A (NPPA)	OTMQNTNX	ANF_HUMAN	Gene/Protein Processing	[17]
Renin (REN)	OT52GZR2	RENI_HUMAN	Gene/Protein Processing	[18]
Transforming growth factor beta-1 proprotein (TGFB1)	OTV5XHVH	TGFB1_HUMAN	Drug Response	[19]

Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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]	[20]
Captopril	DM458UM	Major	Increased risk of hyperkalemia by the combination of Irbesartan and Captopril.	Hypertension [BA00-BA04]	[21]

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]	[22]
Insulin-aspart	DMX7V28	Moderate	Increased risk of hypoglycemia by the combination of Irbesartan and Insulin-aspart.	Acute diabete complication [5A2Y]	[23]
Cariprazine	DMJYDVK	Moderate	Additive hypotensive effects by the combination of Irbesartan and Cariprazine.	Bipolar disorder [6A60]	[24]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Irbesartan caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[25]
Drospirenone	DM1A9W3	Moderate	Increased risk of hyperkalemia by the combination of Irbesartan and Drospirenone.	Contraceptive management [QA21]	[26]
Ardeparin	DMYRX8B	Moderate	Increased risk of hyperkalemia by the combination of Irbesartan and Ardeparin.	Coronary thrombosis [BA43]	[21]
Lumacaftor	DMCLWDJ	Moderate	Increased metabolism of Irbesartan caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[27]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Irbesartan caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[28]
MK-8228	DMOB58Q	Moderate	Increased metabolism of Irbesartan caused by MK-8228 mediated induction of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[29]
Selegiline	DM6034S	Moderate	Additive hypotensive effects by the combination of Irbesartan and Selegiline.	Depression [6A70-6A7Z]	[30]
Isocarboxazid	DMAF1NB	Moderate	Additive hypotensive effects by the combination of Irbesartan and Isocarboxazid.	Depression [6A70-6A7Z]	[30]
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Irbesartan and OPC-34712.	Depression [6A70-6A7Z]	[24]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Irbesartan caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[31]
Procarbazine	DMIK367	Moderate	Additive hypotensive effects by the combination of Irbesartan and Procarbazine.	Hodgkin lymphoma [2B30]	[30]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Irbesartan caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[32]
Fenofibrate	DMFKXDY	Moderate	Decreased metabolism of Irbesartan caused by Fenofibrate mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[33]
Tolvaptan	DMIWFRL	Moderate	Increased risk of hyperkalemia by the combination of Irbesartan and Tolvaptan.	Hypo-osmolality/hyponatraemia [5C72]	[34]
ITI-007	DMUQ1DO	Moderate	Additive hypotensive effects by the combination of Irbesartan and ITI-007.	Insomnia [7A00-7A0Z]	[24]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Irbesartan caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[33]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Irbesartan caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[35]
Ozanimod	DMT6AM2	Moderate	Additive hypotensive effects by the combination of Irbesartan and Ozanimod.	Multiple sclerosis [8A40]	[30]
Promethazine	DM6I5GR	Moderate	Additive hypotensive effects by the combination of Irbesartan and Promethazine.	Nausea/vomiting [MD90]	[24]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Irbesartan caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[36]
Safinamide	DM0YWJC	Moderate	Additive hypotensive effects by the combination of Irbesartan and Safinamide.	Parkinsonism [8A00]	[30]
Rasagiline	DM3WKQ4	Moderate	Additive hypotensive effects by the combination of Irbesartan and Rasagiline.	Parkinsonism [8A00]	[30]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Irbesartan caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[37]
Quetiapine	DM1N62C	Moderate	Additive hypotensive effects by the combination of Irbesartan and Quetiapine.	Schizophrenia [6A20]	[24]
Aripiprazole	DM3NUMH	Moderate	Additive hypotensive effects by the combination of Irbesartan and Aripiprazole.	Schizophrenia [6A20]	[24]
Paliperidone	DM7NPJS	Moderate	Additive hypotensive effects by the combination of Irbesartan and Paliperidone.	Schizophrenia [6A20]	[24]
Molindone	DMAH70G	Moderate	Additive hypotensive effects by the combination of Irbesartan and Molindone.	Schizophrenia [6A20]	[24]
Thiothixene	DMDINC4	Moderate	Additive hypotensive effects by the combination of Irbesartan and Thiothixene.	Schizophrenia [6A20]	[24]
Amisulpride	DMSJVAM	Moderate	Additive hypotensive effects by the combination of Irbesartan and Amisulpride.	Schizophrenia [6A20]	[24]
Asenapine	DMSQZE2	Moderate	Additive hypotensive effects by the combination of Irbesartan and Asenapine.	Schizophrenia [6A20]	[24]
Insulin-detemir	DMOA4VW	Moderate	Increased risk of hypoglycemia by the combination of Irbesartan and Insulin-detemir.	Type-1/2 diabete [5A10-5A11]	[22]
Insulin degludec	DMPL395	Moderate	Increased risk of hypoglycemia by the combination of Irbesartan and Insulin degludec.	Type-1/2 diabete [5A10-5A11]	[22]
Trimeprazine	DMEMV9D	Moderate	Additive hypotensive effects by the combination of Irbesartan and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[38]


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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


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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

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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
5	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
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.
11	Drug interactions with irbesartan. Clin Pharmacokinet. 2001;40(8):605-14.
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	A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.
16	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.
17	Plasma atrial natriuretic peptide in essential hypertension after treatment with irbesartan. Blood Press. 2002;11(2):91-4. doi: 10.1080/08037050211263.
18	Long-term effects of irbesartan and atenolol on the renin-angiotensin-aldosterone system in human primary hypertension: the Swedish Irbesartan Left Ventricular Hypertrophy Investigation versus Atenolol (SILVHIA). J Cardiovasc Pharmacol. 2003 Dec;42(6):719-26. doi: 10.1097/00005344-200312000-00005.
19	Transforming growth factor beta1 genotype and change in left ventricular mass during antihypertensive treatment--results from the Swedish Irbesartan Left Ventricular Hypertrophy Investigation versus Atenolol (SILVHIA). Clin Cardiol. 2004 Mar;27(3):169-73. doi: 10.1002/clc.4960270315.
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