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Details

Stereochemistry ACHIRAL
Molecular Formula 2C25H28N6O.2ClH.3H2O
Molecular Weight 984.027
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IRBESARTAN HYDROCHLORIDE SESQUIHYDRATE

SMILES

O.O.O.Cl.Cl.CCCCC1=NC2(CCCC2)C(=O)N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NN=NN5.CCCCC6=NC7(CCCC7)C(=O)N6CC8=CC=C(C=C8)C9=CC=CC=C9C%10=NN=NN%10

InChI

InChIKey=WCTHVUNSKZGLLG-UHFFFAOYSA-N
InChI=1S/2C25H28N6O.2ClH.3H2O/c2*1-2-3-10-22-26-25(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;;;;;/h2*4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30);2*1H;3*1H2

HIDE SMILES / InChI
Irbesartan is an angiotensin receptor blocker (ARB) used mainly for the treatment of hypertension. It was developed by Sanofi Research (now part of Sanofi-Aventis). It is marketed under the trade names Aprovel, Karvea, and Avapro. AVAPRO is an angiotensin II receptor blocker (ARB) indicated for: • Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. • Treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes, an elevated serum creatinine, and proteinuria. Irbesartan is a specific competitive antagonist of AT1 receptors with a much greater affinity (more than 8500-fold) for the AT1 receptor than for the AT2 receptor and no agonist activity.

CNS Activity

Curator's Comment: Studies in animals indicate that radiolabeled irbesartan weakly crosses the blood-brain barrier and placenta.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AVAPRO

Approved Use

AVAPRO is an angiotensin II receptor blocker (ARB) indicated for: • Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. (1.1) • Treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes, an elevated serum creatinine, and proteinuria

Launch Date

1997
Primary
AVAPRO

Approved Use

AVAPRO is an angiotensin II receptor blocker (ARB) indicated for: • Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. (1.1) • Treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes, an elevated serum creatinine, and proteinuria

Launch Date

1997
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.9 μg/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.9 μg/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.9 μg/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
5.3 μg/mL
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.04 μg/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.3 μg/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.4 μg/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
5.6 μg/mL
900 mg 1 times / day multiple, oral
dose: 900 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9.7 μg × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
20 μg × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
32.6 μg × h/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
44.8 μg × h/mL
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
9.3 μg × h/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
19.8 μg × h/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
31.9 μg × h/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
34.2 μg × h/mL
900 mg 1 times / day multiple, oral
dose: 900 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16 h
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
14 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
14 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
17 h
900 mg single, oral
dose: 900 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
11 h
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
11 h
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
15 h
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
14 h
900 mg 1 times / day multiple, oral
dose: 900 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IRBESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
unknown, unknown
IRBESARTAN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
900 mg 1 times / day multiple, oral
Highest studied dose
Dose: 900 mg, 1 times / day
Route: oral
Route: multiple
Dose: 900 mg, 1 times / day
Sources:
healthy, 20-45
Health Status: healthy
Age Group: 20-45
Sex: M+F
Sources:
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Disorder fetal...
AEs leading to
discontinuation/dose reduction:
Disorder fetal
Sources:
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Hyperkalemia...
AEs leading to
discontinuation/dose reduction:
Hyperkalemia (2.1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Disorder fetal Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
Hyperkalemia 2.1%
Disc. AE
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
Overview

OverviewOther

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes (co-administration study)
Comment: in clinical studies the consequences of concomitant irbesartan on the pharmacodynamics of warfarin were negligible
Page: 12.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Irbesartan slows the development of diabetic nephropathy by up to 70% in hypertensive diabetic patients.
2002-01-05
Irbesartan prevents the progression of kidney disease or death in patients with type 2 diabetes and high blood pressure.
2002-01-05
Vasoconstriction is determined by interstitial rather than circulating angiotensin II.
2002-01
Angiotensin peptides modulate bradykinin levels in the interstitium of the dog heart in vivo.
2002-01
The protective effect of blocking angiotensin in both type I and type II diabetics with nephropathy.
2001-12
AT(2) receptor-mediated vasodilation in the heart: effect of myocardial infarction.
2001-12
Irbesartan, an angiotensin type 1 receptor inhibitor, regulates the vascular oxidative state in patients with coronary artery disease.
2001-11-15
Drug companies should not have the final say in the design of clinical trials.
2001-11
Influence of irbesartan and enalapril on changes of renal function associated with the established phase of l-NAME hypertension.
2001-11
Renal protection by angiotensin II receptor antagonists in patients with type 2 diabetes.
2001-10-15
Vasoconstrictor effect of the angiotensin-converting enzyme-resistant, chymase-specific substrate [Pro(11)(D)-Ala(12)] angiotensin I in human dorsal hand veins: in vivo demonstration of non-ace production of angiotensin II in humans.
2001-10-09
Comparative efficacy of olmesartan, losartan, valsartan, and irbesartan in the control of essential hypertension.
2001-10-06
[Irbesartan in hypertension. A plus for therapy compliance].
2001-10-04
[Effect of irbesartan on the development of diabetic nephropathy in patients with type 2 diabetes].
2001-10-01
[Clinical study of the month. Nephroprotective role of angiotensin II receptor antagonists in type 2 diabetes: results of the IDNT and RENAAL trials].
2001-10
Selective angiotensin II receptor antagonism reduces insulin resistance in obese Zucker rats.
2001-10
Relation between clinical and therapeutic variables and quality of life in hypertension.
2001-10
Comparative effects of losartan and irbesartan on serum uric acid in hypertensive patients with hyperuricaemia and gout.
2001-10
Treatment with irbesartan or atenolol improves endothelial function in essential hypertension.
2001-10
Angiotensin converting enzyme gene polymorphism predicts blood pressure response to angiotensin II receptor type 1 antagonist treatment in hypertensive patients.
2001-10
A clinical trial in type 2 diabetic nephropathy.
2001-10
Angiotensin II receptor blockers and nephropathy trials.
2001-10
pK(a) determination of angiotensin II receptor antagonists (ARA II) by spectrofluorimetry.
2001-10
The effect of irbesartan on the development of diabetic nephropathy in patients with type 2 diabetes.
2001-09-20
Renoprotective effect of the angiotensin-receptor antagonist irbesartan in patients with nephropathy due to type 2 diabetes.
2001-09-20
Impact of the renin-angiotensin system on cerebral perfusion following subarachnoid haemorrhage in the rat.
2001-09-01
Adenovirus-mediated overexpression and stimulation of the human angiotensin II type 2 receptor in porcine cardiac fibroblasts does not modulate proliferation, collagen I mRNA expression and ERK1/ERK2 activity, but inhibits protein tyrosine phosphatases.
2001-09
Effect of angiotensin II type 1 receptor blockade on experimental hepatic fibrogenesis.
2001-09
Differentiation in the angiotensin II receptor 1 blocker class on autonomic function.
2001-09
Angiotensin II-induced apoptosis in rat cardiomyocyte culture: a possible role of AT1 and AT2 receptors.
2001-09
The pharmacokinetics and pharmacodynamics of irbesartan in heart failure.
2001-09
Irbesartan effects on renal function in patients with renal impairment and hypertension: a drug-withdrawal study.
2001-09
Angiotensin AT1 receptor antagonist irbesartan decreases lesion size, chemokine expression, and macrophage accumulation in apolipoprotein E-deficient mice.
2001-09
[Effects of inhibitors of angiotensin-converting enzyme combined with antagonists of angiotensin II receptors on endothelial function in patients with chronic cardiac insufficiency].
2001-08-25
New stuff about the diabetic kidney.
2001-08-11
[Treatment of hypertension in patients with type 2 diabetes. Sartan also protects the kidneys].
2001-08-09
Acute oliguric renal failure associated with angiotensin II receptor antagonists.
2001-08
Hemodynamic effects of the angiotensin II receptor antagonist irbesartan in patients with cirrhosis and portal hypertension.
2001-08
Irbesartan achieves consistent and effective use over 1 year.
2001-07-28
[Angiotensin II receptor antagonists: different or equivalent?].
2001-07-27
Irbesartan normalises the deficiency in glomerular nephrin expression in a model of diabetes and hypertension.
2001-07
Different types of antagonism by losartan and irbesartan on the effects of angiotensin II and its degradation products in rabbit arteries.
2001-04
Pharmacology of AT1-receptor blockers.
2001
The relationship between dose and antihypertensive effect for different AT1-receptor blockers.
2001
Clinical comparative trials of angiotensin II type 1 (AT1)-receptor blockers.
2001
[Current treatment of diabetic nephropathy in patients with type II diabetes mellitus. Most recent progress].
2001
Drug interactions with irbesartan.
2001
[Choosing the dose of aprovel (irbesartan) in patients with chronic heart insufficiency].
2001
Hypertension and diabetes: the scope of the problem.
2001
Clinical differences among angiotensin II receptor antagonists.
2001
Patents

Sample Use Guides

Usual Adult Dose for Hypertension Initial dose: 150 mg orally once a day Maximum dose: 300 mg orally once a day Usual Adult Dose for Diabetic Nephropathy Target maintenance dose: 300 mg orally once a day Use: Treatment of diabetic nephropathy with an elevated serum creatinine and proteinuria (greater than 300 mg/day) in patients with type 2 diabetes and hypertension.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Contraction responses to increasing concentrations of Ang I (1 nM-1 uM) were evaluated in organ baths in the presence of captopril (10 uM-1 mM) with or without a chymase inhibitor (1 uM soybean trypsin inhibitor), or irbesartan (0.1 nM-uM), in internal mammary arteries from 25 patients undergoing coronary bypass surgery.
0.1 uM irbesartan completely blocked the maximum response to Ang I (from 45.8 +/- 6.7% to 1.9 +/- 1.9%, p < 0.001)
Name Type Language
1,3-DIAZASPIRO(4.4)NON-1-EN-4-ONE, 2-BUTYL-3-((2'-(1H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-, MONOHYDROCHLORIDE, HYDRATE (2:3)
Preferred Name English
IRBESARTAN HYDROCHLORIDE SESQUIHYDRATE
Common Name English
1,3-DIAZASPIRO(4.4)NON-1-EN-4-ONE, 2-BUTYL-3-((2'-(2H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-, HYDROCHLORIDE, HYDRATE (2:2:3)
Systematic Name English
Code System Code Type Description
CAS
874657-02-0
Created by admin on Wed Apr 02 11:18:58 GMT 2025 , Edited by admin on Wed Apr 02 11:18:58 GMT 2025
PRIMARY
FDA UNII
B4WCH9U6Q3
Created by admin on Wed Apr 02 11:18:58 GMT 2025 , Edited by admin on Wed Apr 02 11:18:58 GMT 2025
PRIMARY
PUBCHEM
162625107
Created by admin on Wed Apr 02 11:18:58 GMT 2025 , Edited by admin on Wed Apr 02 11:18:58 GMT 2025
PRIMARY
SMS_ID
300000000781
Created by admin on Wed Apr 02 11:18:58 GMT 2025 , Edited by admin on Wed Apr 02 11:18:58 GMT 2025
PRIMARY