Identification

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Name
Irbesartan
Accession Number
DB01029  (APRD00413)
Type
Small Molecule
Groups
Approved, Investigational
Description

Irbesartan is an angiotensin receptor blocker (ARB) indicated to treat hypertension or diabetic nephropathy.7,8 It can also be used as part of a combination product with hydrochlorothiazide for patients not well controlled or not expected to be well controlled on monotherapy.8 Unlike angiotensin converting enzyme inhibitors, ARBs are not associated with a dry cough.7,8

Irbesartan was granted FDA approval on 30 September 1997.7,8

Structure
Thumb
Synonyms
  • 2-butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[4.4]non-1-en-4-one
  • Irbesartan
External IDs
BMS 186295 / BMS-186295 / SR 47436 / SR-47436
Product Ingredients
IngredientUNIICASInChI Key
Irbesartan hydrochloride3OGC31WUMZ329055-23-4ZUYFSRQJPNUOQU-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act IrbesartanTabletOralActavis Pharma Company2011-03-212018-06-12Canada
Act IrbesartanTabletOralActavis Pharma Company2011-03-212018-06-12Canada
Act IrbesartanTabletOralActavis Pharma Company2011-03-212018-06-12Canada
AprovelTablet75 mgOralSanofi Clir Snc1997-08-27Not applicableEu
AprovelTablet, film coated150 mgOralSanofi Clir Snc1997-08-27Not applicableEu
AprovelTablet, film coated75 mgOralSanofi Clir Snc1997-08-27Not applicableEu
AprovelTablet300 mgOralSanofi Clir Snc1997-08-27Not applicableEu
AprovelTablet, film coated300 mgOralSanofi Clir Snc1997-08-27Not applicableEu
AprovelTablet75 mgOralSanofi Clir Snc1997-08-27Not applicableEu
AprovelTablet, film coated75 mgOralSanofi Clir Snc1997-08-27Not applicableEu
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ag-irbesartanTabletOralAngita Pharma Inc.2018-06-07Not applicableCanada
Ag-irbesartanTabletOralAngita Pharma Inc.2018-06-07Not applicableCanada
Ag-irbesartanTabletOralAngita Pharma Inc.2018-06-07Not applicableCanada
Apo-irbesartanTabletOralApotex Corporation2012-09-25Not applicableCanada
Apo-irbesartanTabletOralApotex Corporation2012-09-25Not applicableCanada
Apo-irbesartanTabletOralApotex Corporation2012-09-25Not applicableCanada
Auro-irbesartanTabletOralAuro Pharma Inc2013-07-08Not applicableCanada
Auro-irbesartanTabletOralAuro Pharma Inc2013-07-08Not applicableCanada
Auro-irbesartanTabletOralAuro Pharma Inc2013-07-08Not applicableCanada
Ava-irbesartanTabletOralAvanstra Inc2011-11-232014-08-21Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act Irbesartan/hctIrbesartan (300 mg) + Hydrochlorothiazide (25 mg)TabletOralActavis Pharma Company2011-03-212018-06-12Canada
Act Irbesartan/hctIrbesartan (300 mg) + Hydrochlorothiazide (12.5 mg)TabletOralActavis Pharma Company2011-03-212018-06-12Canada
Act Irbesartan/hctIrbesartan (150 mg) + Hydrochlorothiazide (12.5 mg)TabletOralActavis Pharma Company2011-03-212018-06-12Canada
Ag-irbesartan HctzIrbesartan (300 mg) + Hydrochlorothiazide (25 mg)TabletOralAngita Pharma Inc.2018-09-06Not applicableCanada
Ag-irbesartan HctzIrbesartan (300 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAngita Pharma Inc.2018-09-06Not applicableCanada
Ag-irbesartan HctzIrbesartan (150 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAngita Pharma Inc.2018-09-06Not applicableCanada
Apo-irbesartan/hctzIrbesartan (300 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2013-03-26Not applicableCanada
Apo-irbesartan/hctzIrbesartan (300 mg) + Hydrochlorothiazide (25 mg)TabletOralApotex Corporation2013-02-26Not applicableCanada
Apo-irbesartan/hctzIrbesartan (150 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2013-02-26Not applicableCanada
Auro-irbesartan HCTIrbesartan (300 mg) + Hydrochlorothiazide (25 mg)TabletOralAuro Pharma Inc2015-12-02Not applicableCanada
Categories
UNII
J0E2756Z7N
CAS number
138402-11-6
Weight
Average: 428.5294
Monoisotopic: 428.232459548
Chemical Formula
C25H28N6O
InChI Key
YOSHYTLCDANDAN-UHFFFAOYSA-N
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)
IUPAC Name
2-butyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-diazaspiro[4.4]non-1-en-4-one
SMILES
CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1

Pharmacology

Indication

Irbesartan is indicated to treat hypertension and diabetic nephropathy in hypertensive patients with type 2 diabetes, elevated serum creatinine, and proteinuria.7 A combination product with hydrochlorothiazide is indicated for hypertension in patients with uncontrolled hypertension with monotherapy or first line in patients not expected to be well controlled with monotherapy.8

Associated Conditions
Pharmacodynamics

Irbesartan is an angiotensin receptor blocker used to treat hypertension and diabetic nephropathy.7,8 It has a long duration of action as it is usually taken once daily and a wide therapeutic index as doses may be as low as 150mg daily but doses of 900mg/day were well tolerated in healthy human subjects.7,8,5

Mechanism of action

Irbesartan prevents angiotensin II binding to the AT1 receptor in tissues like vascular smooth muscle and the adrenal gland.7,8 Irbesartan and its active metabolite bind the AT1 receptor with 8500 times more affinity than they bind to the AT2 receptor.7,8 Irbesartan's prevention of angiotensin II binding causes vascular smooth muscle relaxation and prevents the secretion of aldosterone, lowering blood pressure.7,8

Angiotensin II would otherwise bind to the AT1 receptor, inducing vasoconstriction and aldosterone secretion, raising blood pressure.7,8

TargetActionsOrganism
AType-1 angiotensin II receptor
antagonist
Humans
UTranscription factor AP-1
other/unknown
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Irbesartan is 60-80% bioavailable with a Tmax of 1.5-2hours.7,8 Taking irbesartan with food does not affect the bioavailability.7,8

In one study, healthy subjects were given single or multiple oral doses of 150mg, 300mg, 600mg, and 900mg of irbesartan.5 A single 150mg dose resulted in an AUC of 9.7±3.0µg\•hr/mL, a Tmax of 1.5 hours, a half life of 16±7 hours, and a Cmax of 1.9±0.4µg/mL.5 A single 300mg dose resulted in an AUC of 20.0±5.2µg\•hr/mL, a Tmax of 1.5 hours, a half life of 14±7 hours, and a Cmax of 2.9±0.9µg/mL.5 A single 600mg dose resulted in an AUC of 32.6±11.9µg\•hr/mL, a Tmax of 1.5 hours, a half life of 14±8 hours, and a Cmax of 4.9±1.2µg/mL.5 A single 900mg dose resulted in an AUC of 44.8±20.0µg\•hr/mL, a Tmax of 1.5 hours, a half life of 17±7 hours, and a Cmax of 5.3±1.9µg/mL.5

Multiple 150mg doses resulted in an AUC of 9.3±3.0µg\•hr/mL, a Tmax of 1.5 hours, a half life of 11±4 hours, and a Cmax of 2.04±0.4µg/mL.5 Multiple 300mg doses resulted in an AUC of 19.8±5.8µg\•hr/mL, a Tmax of 2.0 hours, a half life of 11±5 hours, and a Cmax of 3.3±0.8µg/mL.5 Multiple 600mg doses resulted in an AUC of 31.9±9.7µg\•hr/mL, a Tmax of 1.5 hours, a half life of 15±7 hours, and a Cmax of 4.4±0.7µg/mL.5 Multiple 900mg doses resulted in an AUC of 34.2±9.3µg\•hr/mL, a Tmax of 1.8 hours, a half life of 14±6 hours, and a Cmax of 5.6±2.1µg/mL.5

Volume of distribution

The volume of distribution of irbesartan is 53-93L.7,8

Protein binding

Irbesartan is 90% protein bound in plasma, mainly to albumin and α1-acid glycoprotein.7,8

Metabolism

Irbesaran is largely metabolized by glucuronidation and oxidation in the liver.7,8 The majority of metabolism occurs through the action of CYP2C9 with a negligible contribution from CYP3A4.7,8 Some hydroxylation also occurs in irbesartan metabolism.3

Irbesartan can be glucuronidated by UGT1A3 to the M8 metabolite, oxidized to the M3 metabolite, or hydroxylated by CYP2C9 to one of the M4, M5, or M7 metabolites.4,3 The M4, M5, and M7 metabolites are all hydroxylated to become the M1 metabolite, which is then oxidized to the M2 metabolite.4,3 The M4 metabolite can also be oxidized to the M6 metabolite before hydroxylation to the M2 metabolite.4,3 Finally, the minor metabolite SR 49498 is generated from irbesartan by an unknown mechanism.4,3

Route of elimination

20% of a radiolabelled oral dose of irbesartan is recovered in urine, and the rest is recovered in the feces.10 <2% of the dose is recovered in urine as the unchanged drug.10

Half life

The terminal elimination half life of irbesartan is 11-15 hours.7,8

Clearance

Total plasma clearance of irbesartan is 157-176mL/min while renal clearance is 3.0-3.5mL/min.7,8

Toxicity

The oral TDLO in humans is 30mg/kg/6W.9

Symptoms of overdose include hypotension and tachycardia or bradycardia.7,8 Terlipressin may be given to treat hypotension and tachycardia if conventional vasopressors fail to control blood pressure.6

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Irbesartan Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Irbesartan.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Irbesartan.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Irbesartan.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Irbesartan.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Irbesartan.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Irbesartan.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Irbesartan.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Irbesartan.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Irbesartan.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Irbesartan.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Gennady Nisnevich, "Novel synthesis of irbesartan." U.S. Patent US20040192713, issued September 30, 2004.

US20040192713
General References
  1. Lewis EJ, Hunsicker LG, Clarke WR, Berl T, Pohl MA, Lewis JB, Ritz E, Atkins RC, Rohde R, Raz I: 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. [PubMed:11565517]
  2. Croom KF, Curran MP, Goa KL, Perry CM: Irbesartan: a review of its use in hypertension and in the management of diabetic nephropathy. Drugs. 2004;64(9):999-1028. [PubMed:15101793]
  3. Chando TJ, Everett DW, Kahle AD, Starrett AM, Vachharajani N, Shyu WC, Kripalani KJ, Barbhaiya RH: Biotransformation of irbesartan in man. Drug Metab Dispos. 1998 May;26(5):408-17. [PubMed:9571222]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
  5. Marino MR, Langenbacher K, Ford NF, Uderman HD: Pharmacokinetics and pharmacodynamics of irbesartan in healthy subjects. J Clin Pharmacol. 1998 Mar;38(3):246-55. [PubMed:9549663]
  6. McNamee JJ, Trainor D, Michalek P: Terlipressin for refractory hypotension following angiotensin-II receptor antagonist overdose. Anaesthesia. 2006 Apr;61(4):408-9. doi: 10.1111/j.1365-2044.2006.04599.x. [PubMed:16548975]
  7. FDA Approved Drug Products: Irbesartan Oral Tablets [Link]
  8. FDA Approved Drug Products: Irbesartan and Hydrochlorothiazide Oral Tablets [Link]
  9. Cayman Chemicals: Irbesartan MSDS [Link]
  10. Sandoz Canada: Irbesartan Product Monograph [Link]
External Links
Human Metabolome Database
HMDB0015163
KEGG Drug
D00523
KEGG Compound
C07469
PubChem Compound
3749
PubChem Substance
46506575
ChemSpider
3618
BindingDB
50042235
ChEBI
5959
ChEMBL
CHEMBL1513
Therapeutic Targets Database
DAP000364
PharmGKB
PA450084
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Irbesartan
ATC Codes
C09CA04 — IrbesartanC09DB05 — Irbesartan and amlodipineC09DA04 — Irbesartan and diuretics
AHFS Codes
  • 24:32.08 — Angiotensin Ii Receptor Antagonists
FDA label
Download (263 KB)
MSDS
Download (57.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentDiabetic Kidney Disease1
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers1
1RecruitingTreatmentHigh Blood Pressure (Hypertension)1
1, 2Not Yet RecruitingTreatmentEbola Virus Disease1
2Active Not RecruitingTreatmentGlomerulosclerosis, Focal Segmental1
2CompletedTreatmentChronic Kidney Disease (CKD)1
2CompletedTreatmentHigh Blood Pressure (Hypertension)2
2RecruitingTreatmentBlood Pressures / BMI >30 kg/m2 / High Blood Pressure (Hypertension) / Stress, Psychological1
2RecruitingTreatmentMarfan Syndrome1
2, 3CompletedPreventionDiabetic Nephropathies / Glomerulonephritis / Kidney Diseases / Proteinuria1
2, 3CompletedTreatmentHigh Blood Pressure (Hypertension)1
3Active Not RecruitingTreatmentIgA Nephropathy1
3CompletedPreventionAtrial Fibrillation (AF) / Cardiovascular Heart Disease1
3CompletedPreventionChronic Renal Failure (CRF)1
3CompletedTreatmentAtrial Fibrillation (AF)1
3CompletedTreatmentChronic Allograft Nephropathy (CAN) / End-Stage Renal Disease (ESRD)1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentCongestive Heart Failure1
3CompletedTreatmentHigh Blood Pressure (Hypertension)8
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias1
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Microalbuminuria / Type 2 Diabetes Mellitus1
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Myocardial Ischemia1
3CompletedTreatmentHigh Cholesterol1
3CompletedTreatmentTransplantation, Kidney1
3RecruitingTreatmentEhlers-Danlos Syndrome, Vascular Type1
3RecruitingTreatmentGlomerulosclerosis, Focal Segmental1
3RecruitingTreatmentImmunoglobulin A Nephropathy1
3Unknown StatusPreventionAtrial Fibrillation (AF) / High Blood Pressure (Hypertension)1
3Unknown StatusTreatmentSevere Sepsis1
4Active Not RecruitingTreatmentDiabetes Mellitus (DM) / Hypertensive Disease1
4CompletedNot AvailableType 2 Diabetes Mellitus1
4CompletedPreventionMyocardial Infarction1
4CompletedTreatmentAlbuminuria1
4CompletedTreatmentCardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke1
4CompletedTreatmentChronic Heart Failure (CHF)1
4CompletedTreatmentDyslipidemias / High Blood Pressure (Hypertension)1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHigh Blood Pressure (Hypertension)16
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Metabolic Syndromes1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentMicroalbuminuria / Type 2 Diabetes Mellitus1
4CompletedTreatmentType 2 Diabetes Mellitus1
4CompletedTreatmentType 2 Diabetic Nephropathy1
4RecruitingTreatmentHeart Diseases / Type 2 Diabetes Mellitus1
4Unknown StatusPreventionDiabetic Nephropathies1
4Unknown StatusTreatmentAntihypertensive Drugs / Diastolic Function / Hypertensive Heart Disease / Left Atrial Volume / Renin Angiotensin System1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Obesity, Abdominal1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Sexual Dysfunctions1
4Unknown StatusTreatmentPersistent Atrial Fibrillation1
4WithdrawnDiagnosticBMI >30 kg/m2 / High Blood Pressure (Hypertension)1
Not AvailableActive Not RecruitingNot AvailableChronic Kidney Disease (CKD)1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedEducational/Counseling/TrainingHealthy Volunteers1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension)4
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableSuspendedScreeningPreeclampsia / Pregnancy associated hypertension1
Not AvailableTerminatedTreatmentMetabolic Syndromes1
Not AvailableTerminatedTreatmentObesity and Glomerulopathy1
Not AvailableUnknown StatusBasic ScienceHigh Blood Pressure (Hypertension) / Insulin Resistance / Microcirculation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Diversified Healthcare Services Inc.
  • Heartland Repack Services LLC
  • Murfreesboro Pharmaceutical Nursing Supply
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Promex Medical Inc.
  • Resource Optimization and Innovation LLC
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral150 mg/1
TabletOral300 mg/1
TabletOral75 mg/1
TabletOral150 mg/150mg
TabletOral300 mg/300mg
TabletOral75 mg/75mg
Tablet, coatedOral150 mg/1
Tablet, coatedOral300 mg/1
Tablet, coatedOral75 mg/1
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral75 mg/1
TabletOral150 mg
TabletOral300 mg
TabletOral75 mg
Tablet, film coatedOral150 mg
Tablet, film coatedOral300 mg
Tablet, film coatedOral75 mg
TabletOral
Tablet, film coatedOral
TabletOral
Prices
Unit descriptionCostUnit
Avalide 300-25 mg tablet3.92USD tablet
Avalide 300-12.5 mg tablet3.63USD tablet
Avalide 150-12.5 mg tablet3.33USD tablet
Avapro 300 mg tablet2.64USD tablet
Avapro 150 mg tablet2.33USD tablet
Avapro 75 mg tablet2.21USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5270317No1993-12-142011-09-30Us
CA2177772No2007-04-102016-05-30Canada
CA2057913No1997-07-082011-03-20Canada
US6342247Yes2002-01-292015-12-07Us
US5994348Yes1999-11-302015-12-07Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)180-181 °Chttp://www.chemspider.com/Chemical-Structure.3618.html
boiling point (°C)648.6http://www.chemspider.com/Chemical-Structure.3618.html
water solubility<1mg/mLhttp://www.chemspider.com/Chemical-Structure.3618.html
logP4.5http://www.chemspider.com/Chemical-Structure.3618.html
Predicted Properties
PropertyValueSource
Water Solubility0.00884 mg/mLALOGPS
logP4.51ALOGPS
logP5.5ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.4ChemAxon
pKa (Strongest Basic)4.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.13 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity136.72 m3·mol-1ChemAxon
Polarizability47.59 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9271
Caco-2 permeable-0.5679
P-glycoprotein substrateSubstrate0.7046
P-glycoprotein inhibitor IInhibitor0.639
P-glycoprotein inhibitor IINon-inhibitor0.6458
Renal organic cation transporterNon-inhibitor0.5091
CYP450 2C9 substrateNon-substrate0.6401
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.5749
CYP450 1A2 substrateNon-inhibitor0.6782
CYP450 2C9 inhibitorInhibitor0.5928
CYP450 2D6 inhibitorNon-inhibitor0.7584
CYP450 2C19 inhibitorInhibitor0.6619
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6192
Ames testNon AMES toxic0.5238
CarcinogenicityNon-carcinogens0.7492
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7762 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9171
hERG inhibition (predictor II)Non-inhibitor0.7728
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-0000900000-b6619e18dca63147588d
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004l-0801900000-b884691a3577ffab749f
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-130056acf88b6caed131
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-97919ed4377a869dc8cc
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-55cf0ae2c686af5c38e3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0007-0908000000-0c994ee86857e7d63e48
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0000900000-b610a12a9852ff1a11c1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900100000-c9024d0b00a0ec781fa2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-cb54b7c0917d67313110
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-4e0d1ebbc0609ecaa59d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-ec0fc575bb22a99c258d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0900000000-f1f0658a24e5097674e0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0000900000-12da76073bae1768b7e2
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-cce4e6a8c5bbaa66c902
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-c7202e4de31fc762cf2d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-ad31324f1b1a0e9be0b8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-2301c02c521c3dab9c79
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0900000000-8b6e9e772c5af1365e87
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0007-0908000000-97706153fba817a654e4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-002f-0900400000-f9f11306595c7a9de207
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a6r-0180900000-009718baea4be3419b76
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0190000000-97e745948e54828d3cb9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0190000000-da94b482f79a90e5784c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0590000000-122d562d8d5352dd2a88
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290100000-e3c8e0950f0290ccefdc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0000900000-61da6c552b6d170d8283
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290100000-0e7bf8c50467ae6a7604
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290000000-21c875faccf2cb3a15b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0490000000-e7c75f4866b7b9f0d0e8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-1960000000-a6601ea10b0fe87e6c0a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a5c-0920000000-d7f5d3920f8586eac33f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0000900000-57215a52cacf3c9ede5c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290100000-29a34a51d9b42976905f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290000000-e6e7f5d1e696ec43651d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1690000000-217de4040066a20fd367
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-1950000000-ac722925e6b2aa2930fb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a5c-0930000000-0b8d8a97e3db30de0e21
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290100000-ee3d21bc8110bf939cdd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a59-2791700000-a5bc1c8b020f7731fb1e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056r-0361900000-10d459e7561fdaacc9d4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a6r-0490500000-2693358cc0b819b773a5

Taxonomy

Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Phenyltetrazoles and derivatives / Alpha amino acids and derivatives / Imidazolinones / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Biphenyl / Phenyltetrazole / Alpha-amino acid or derivatives / Imidazolinone / Azole / 2-imidazoline / Heteroaromatic compound / Tetrazole / Amidine / Carboxylic acid amidine
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
azaspiro compound, biphenylyltetrazole (CHEBI:5959)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Gene Name
AGTR1
Uniprot ID
P30556
Uniprot Name
Type-1 angiotensin II receptor
Molecular Weight
41060.53 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Voigt JP, Bramlage P, Fink H: Hypophagic effect of the angiotensin AT1 receptor antagonist irbesartan in rats. Eur J Pharmacol. 2007 Jun 14;564(1-3):131-7. Epub 2007 Mar 3. [PubMed:17408613]
  3. Waeber B, Burnier M: AT1-receptor antagonism in hypertension: what has been learned with irbesartan? Expert Rev Cardiovasc Ther. 2003 May;1(1):23-33. [PubMed:15030294]
  4. Dol F, Martin G, Staels B, Mares AM, Cazaubon C, Nisato D, Bidouard JP, Janiak P, Schaeffer P, Herbert JM: Angiotensin AT1 receptor antagonist irbesartan decreases lesion size, chemokine expression, and macrophage accumulation in apolipoprotein E-deficient mice. J Cardiovasc Pharmacol. 2001 Sep;38(3):395-405. [PubMed:11486244]
  5. Martin G, Dol F, Mares AM, Berezowski V, Staels B, Hum DW, Schaeffer P, Herbert JM: Lesion progression in apoE-deficient mice: implication of chemokines and effect of the AT1 angiotensin II receptor antagonist irbesartan. J Cardiovasc Pharmacol. 2004 Feb;43(2):191-9. [PubMed:14716205]
  6. van den Meiracker AH, Admiraal PJ, Janssen JA, Kroodsma JM, de Ronde WA, Boomsma F, Sissmann J, Blankestijn PJ, Mulder PG, Man In 't Veld AJ, et al.: Hemodynamic and biochemical effects of the AT1 receptor antagonist irbesartan in hypertension. Hypertension. 1995 Jan;25(1):22-9. [PubMed:7843749]
  7. Carraway JW, Park S, McCune SA, Holycross BJ, Radin MJ: Comparison of irbesartan with captopril effects on cardiac hypertrophy and gene expression in heart failure-prone male SHHF/Mcc-fa(cp) rats. J Cardiovasc Pharmacol. 1999 Mar;33(3):451-60. [PubMed:10069682]
  8. Hope S, Brecher P, Chobanian AV: Comparison of the effects of AT1 receptor blockade and angiotensin converting enzyme inhibition on atherosclerosis. Am J Hypertens. 1999 Jan;12(1 Pt 1):28-34. [PubMed:10075381]
  9. Mazzolai L, Maillard M, Rossat J, Nussberger J, Brunner HR, Burnier M: Angiotensin II receptor blockade in normotensive subjects: A direct comparison of three AT1 receptor antagonists. Hypertension. 1999 Mar;33(3):850-5. [PubMed:10082498]
  10. Morsing P, Adler G, Brandt-Eliasson U, Karp L, Ohlson K, Renberg L, Sjoquist PO, Abrahamsson T: Mechanistic differences of various AT1-receptor blockers in isolated vessels of different origin. Hypertension. 1999 Jun;33(6):1406-13. [PubMed:10373224]
  11. Adams MA, Trudeau L: Irbesartan: review of pharmacology and comparative properties. Can J Clin Pharmacol. 2000 Spring;7(1):22-31. [PubMed:10822210]
  12. Croom KF, Plosker GL: Irbesartan: a review of its use in hypertension and diabetic nephropathy. Drugs. 2008;68(11):1543-69. [PubMed:18627212]
  13. Croom KF, Curran MP, Goa KL, Perry CM: Irbesartan: a review of its use in hypertension and in the management of diabetic nephropathy. Drugs. 2004;64(9):999-1028. [PubMed:15101793]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Transcriptional activator activity, rna polymerase ii transcription factor binding
Specific Function
Transcription factor that recognizes and binds to the enhancer heptamer motif 5'-TGA[CG]TCA-3'. Promotes activity of NR5A1 when phosphorylated by HIPK3 leading to increased steroidogenic gene expre...
Gene Name
JUN
Uniprot ID
P05412
Uniprot Name
Transcription factor AP-1
Molecular Weight
35675.32 Da
References
  1. Zhu ZS, Wang JM, Chen SL: Mesenteric artery remodeling and effects of imidapril and irbesartan on it in spontaneously hypertensive rats. World J Gastroenterol. 2004 May 15;10(10):1471-5. [PubMed:15133856]
  2. Cheng SM, Yang SP, Ho LJ, Tsao TP, Chang DM, Lai JH: Irbesartan inhibits human T-lymphocyte activation through downregulation of activator protein-1. Br J Pharmacol. 2004 Jul;142(6):933-42. Epub 2004 Jun 21. [PubMed:15210574]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
  2. Forni V, Wuerzner G, Pruijm M, Burnier M: Long-term use and tolerability of irbesartan for control of hypertension. Integr Blood Press Control. 2011;4:17-26. doi: 10.2147/IBPC.S12211. Epub 2011 Apr 18. [PubMed:21949635]
  3. Flockhart Table of Drug Interactions [Link]
  4. Irbesartan FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: 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. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Taavitsainen P, Kiukaanniemi K, Pelkonen O: In vitro inhibition screening of human hepatic P450 enzymes by five angiotensin-II receptor antagonists. Eur J Clin Pharmacol. 2000 May;56(2):135-40. [PubMed:10877007]
  2. Marino MR, Vachharajani NN: Drug interactions with irbesartan. Clin Pharmacokinet. 2001;40(8):605-14. doi: 10.2165/00003088-200140080-00004. [PubMed:11523726]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Irbesartan Oral Tablets [Link]
  2. FDA Approved Drug Products: Irbesartan and Hydrochlorothiazide Oral Tablets [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. FDA Approved Drug Products: Irbesartan Oral Tablets [Link]
  2. FDA Approved Drug Products: Irbesartan and Hydrochlorothiazide Oral Tablets [Link]

Drug created on June 13, 2005 07:24 / Updated on December 06, 2019 11:53