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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=C(C=CC=C4)C5=NN=NN5.CCCCC6=NC7(CCCC7)C(=O)N6CC8=CC=C(C=C8)C9=C(C=CC=C9)C%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

Description

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

CNS Penetrant
2554
Curator's Comment: Studies in animals indicate that radiolabeled irbesartan weakly crosses the blood-brain barrier and placenta.

Originator

Approval Year

1997
172
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 1.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Approved
8429
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
3.3 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
2.9 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
4.4 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
4.9 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
5.6 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
5.3 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
1.9 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19.8 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
20 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
31.9 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
32.6 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
34.2 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
44.8 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
9.7 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
14 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
15 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
14 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
17 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
16 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9549663
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020758s079lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/9549663
Page: p.247, p.250
healthy, 20-45
n = 9
Health Status: healthy
Age Group: 20-45
Sex: M+F
Population Size: 9
Sources:
https://pubmed.ncbi.nlm.nih.gov/9549663
Page: p.247, p.250
Sources:
https://pubmed.ncbi.nlm.nih.gov/9549663
Page: p.247, p.250
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension|diabetic nephropathy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.1
Disc. AE: Disorder fetal...
AEs leading to
discontinuation/dose reduction:
Disorder fetal
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.1
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.6
unhealthy
Health Status: unhealthy
Condition: Diabetic nephropathy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.6
Disc. AE: Hyperkalemia...
AEs leading to
discontinuation/dose reduction:
Hyperkalemia (2.1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.6
AEs

AEs

AESignificanceDosePopulation
Disorder fetal Disc. AE
300 mg 1 times / day multiple, oral (max)
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension|diabetic nephropathy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.1
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.6
unhealthy
Health Status: unhealthy
Condition: Diabetic nephropathy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020757s059s067lbl.pdf
Page: p.6
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587
substrate
1037

inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A1
110

CYP1A2
1524

CYP2A6
707

CYP2B6
810

CYP2E1
882

Kv4.3
16

P-gp
1461

BCRP
699

MRP2
383
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1925
 no [IC50 224 uM]
CYP1A2
1692
 no [IC50 483 uM]
CYP2A6
739
 no [IC50 >1000 uM]
CYP2D6
1891
 no [IC50 >1000 uM]
CYP2E1
970
 no [IC50 >1000 uM]
BCRP
773
 no
CYP1A1
218
 no
CYP2B6
1001
 no
MRP2
475
 no
P-gp
1650
 weak
CYP2C9
1819
 yes [IC50 172 uM]
Kv4.3
16
 yes [IC50 7.2 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1737
 yes
CYP2C9
1037
 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
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:5959
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5959
ChemicalBook
CB4454663
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4454663
MolPort
MolPort-003-666-550
https://www.molport.com/shop/molecule-link/MolPort-003-666-550
MolPort
MolPort-006-167-687
https://www.molport.com/shop/molecule-link/MolPort-006-167-687
Selleck Chemicals
Irbesartan(Avapro)
http://www.selleckchem.com/products/Irbesartan(Avapro).html
ZINC
ZINC000003872931
http://zinc15.docking.org/substances/ZINC000003872931
eMolecules
32278040
https://www.emolecules.com/cgi-bin/more?vid=32278040
eMolecules
901986
https://www.emolecules.com/cgi-bin/more?vid=901986
PubMed

PubMed

TitleDatePubMed
Drug interactions with irbesartan.
2001
Vasoconstrictive drugs increase carbonic anhydrase I in vascular smooth muscle while vasodilating drugs reduce the activity of this isozyme by a direct mechanism of action.
2001
Is the balance between nitric oxide and superoxide altered in spontaneously hypertensive rats with endothelial dysfunction?
2001
Drug interaction: omeprazole and phenprocoumon.
2001
Obese female SHHF/Mcc-fa(cp) rats resist antihypertensive effects of renin-angiotensin system inhibition.
2001 Apr
Inhibition of the acute effects of angiotensin II by the receptor antagonist irbesartan in normotensive men.
2001 Apr
The peripheral renin-angiotensin system is not involved in the hypertension of sheep exposed to prenatal dexamethasone.
2001 Apr
Renal safety of combined cyclooxygenase 2 (COX-2) inhibitor and angiotensin II receptor blocker administration in mild volume depletion.
2001 Apr 7
Irbesartan slows the development of diabetic nephropathy by up to 70% in hypertensive diabetic patients.
2001 Aug-Sep
The protective effect of blocking angiotensin in both type I and type II diabetics with nephropathy.
2001 Dec
AT(2) receptor-mediated vasodilation in the heart: effect of myocardial infarction.
2001 Dec
Left ventricular hypertrophy and angiotensin II antagonists.
2001 Feb
Irbesartan, an angiotensin type 1 receptor inhibitor, regulates markers of inflammation in patients with premature atherosclerosis.
2001 Feb
A two-state receptor model for the interaction between angiotensin II type 1 receptors and non-peptide antagonists.
2001 Feb 1
Angiotensin II type 1 receptor blockers.
2001 Feb 13
Angiotensin receptor blockers -- finally the evidence is coming in: IDNT and RENAAL.
2001 Jul
Efficacy of an angiotensin II receptor antagonist in managing hyperaldosteronism.
2001 Jun
Apoptosis and changes in contractile protein pattern in the skeletal muscle in heart failure.
2001 Mar
Inhibition of angiotensin II-induced facilitation of sympathetic neurotransmission in the pithed rat: a comparison between losartan, irbesartan, telmisartan, and captopril.
2001 Mar
Prevention of hypertension by irbesartan in Dahl S rats relates to central angiotensin II type 1 receptor blockade.
2001 Mar
Drug companies should not have the final say in the design of clinical trials.
2001 Nov
Irbesartan, an angiotensin type 1 receptor inhibitor, regulates the vascular oxidative state in patients with coronary artery disease.
2001 Nov 15
[Clinical study of the month. Nephroprotective role of angiotensin II receptor antagonists in type 2 diabetes: results of the IDNT and RENAAL trials].
2001 Oct
A clinical trial in type 2 diabetic nephropathy.
2001 Oct
Angiotensin II receptor blockers and nephropathy trials.
2001 Oct
Renal protection by angiotensin II receptor antagonists in patients with type 2 diabetes.
2001 Oct 15
[Irbesartan in hypertension. A plus for therapy compliance].
2001 Oct 4
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 Sep
Effect of angiotensin II type 1 receptor blockade on experimental hepatic fibrogenesis.
2001 Sep
Differentiation in the angiotensin II receptor 1 blocker class on autonomic function.
2001 Sep
Impact of the renin-angiotensin system on cerebral perfusion following subarachnoid haemorrhage in the rat.
2001 Sep 1
Comparative efficacy of olmesartan, losartan, valsartan, and irbesartan in the control of essential hypertension.
2001 Sep-Oct
Vasoconstriction is determined by interstitial rather than circulating angiotensin II.
2002 Jan
Patents

Patents

JP2001089393A
6
JP2005041875A
12
JP2006513266A
25
JP2006515566A
3
JP2010053048A
3
JP2011510003A
48

Sample Use Guides

In Vivo Use Guide
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
IRBESARTAN HYDROCHLORIDE SESQUIHYDRATE
Common Name English
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)
Systematic 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 Sat Dec 16 18:29:03 GMT 2023 , Edited by admin on Sat Dec 16 18:29:03 GMT 2023
PRIMARY
FDA UNII
B4WCH9U6Q3
Created by admin on Sat Dec 16 18:29:03 GMT 2023 , Edited by admin on Sat Dec 16 18:29:03 GMT 2023
PRIMARY
PUBCHEM
162625107
Created by admin on Sat Dec 16 18:29:03 GMT 2023 , Edited by admin on Sat Dec 16 18:29:03 GMT 2023
PRIMARY
SMS_ID
300000000781
Created by admin on Sat Dec 16 18:29:03 GMT 2023 , Edited by admin on Sat Dec 16 18:29:03 GMT 2023
PRIMARY
PARENT (SALT/SOLVATE)
Structure of IRBESARTAN
NIH
NCATS
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