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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01029
rdf:type
n3:Drug
n3:description
Irbesartan is an angiotensin receptor blocker (ARB) used mainly for the treatment of hypertension. It competes with angiotensin II for binding at the AT1 receptor subtype. Unlike ACE inhibitors, ARBs do not have the adverse effect of dry cough. The use of ARBs is pending revision due to findings from several clinical trials suggesting that this class of drugs may be associated with a small increased risk of cancer.
n3:dosage
n5:271B561F-363D-11E5-9242-09173F13E4C5 n5:271B5620-363D-11E5-9242-09173F13E4C5 n5:271B5621-363D-11E5-9242-09173F13E4C5 n5:271B5622-363D-11E5-9242-09173F13E4C5 n5:271B5623-363D-11E5-9242-09173F13E4C5 n5:271B5624-363D-11E5-9242-09173F13E4C5 n5:271B5625-363D-11E5-9242-09173F13E4C5 n5:271B5626-363D-11E5-9242-09173F13E4C5 n5:271B5627-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# 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":http://www.ncbi.nlm.nih.gov/pubmed/11565517 # Adams MA, Trudeau L: Irbesartan: review of pharmacology and comparative properties. Can J Clin Pharmacol. 2000 Spring;7(1):22-31. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10822210 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15101793
n3:group
investigational approved
n3:halfLife
11-15 hours
n3:indication
For the treatment of hypertension, as well as diabetic nephropathy with an elevated serum creatinine and proteinuria (>300 mg/day) in patients with type 2 diabetes and hypertension. Irbesartan is also used as a second line agent in the treatment of congestive heart failure.
owl:sameAs
n9:DB01029 n17:DB01029
dcterms:title
Irbesartan
adms:identifier
n11:DB01029 n12:5959 n13:3618 n18:Irbesartan n20:3749 n21:46506575 n22:0087-2771-31 n23:PA450084 n24:C07469 n25:D00523 n26:589 n27:589
n3:mechanismOfAction
Irbesartan is a nonpeptide tetrazole derivative and an angiotensin II antagonist that selectively blocks the binding of angiotensin II to the AT<sub>1</sub> receptor. In the renin-angiotensin system, angiotensin I is converted by angiotensin-converting enzyme (ACE) to form angiotensin II. Angiotensin II stimulates the adrenal cortex to synthesize and secrete aldosterone, which decreases the excretion of sodium and increases the excretion of potassium. Angiotensin II also acts as a vasoconstrictor in vascular smooth muscle. Irbesartan, by blocking the binding of angiotensin II to the AT<sub>1</sub> receptor, promotes vasodilation and decreases the effects of aldosterone. The negative feedback regulation of angiotensin II on renin secretion is also inhibited, but the resulting rise in plasma renin concentrations and consequent rise in angiotensin II plasma concentrations do not counteract the blood pressure&ndash;lowering effect that occurs. The action of ARBs is different from ACE inhibitors, which block the conversion of angiotensin I to angiotensin II, meaning that the production of angiotensin II is not completely inhibited, as the hormone can be formed via other enzymes. Also, unlike ACE inhibitors, irbesartan and other ARBs do not interfere with response to bradykinins and substance P, which allows for the absence of adverse effects that are present in ACE inhibitors (eg. dry cough).
n3:packager
n19:271B560B-363D-11E5-9242-09173F13E4C5 n19:271B560C-363D-11E5-9242-09173F13E4C5 n19:271B5609-363D-11E5-9242-09173F13E4C5 n19:271B560A-363D-11E5-9242-09173F13E4C5 n19:271B560F-363D-11E5-9242-09173F13E4C5 n19:271B5610-363D-11E5-9242-09173F13E4C5 n19:271B560D-363D-11E5-9242-09173F13E4C5 n19:271B560E-363D-11E5-9242-09173F13E4C5 n19:271B5613-363D-11E5-9242-09173F13E4C5 n19:271B5614-363D-11E5-9242-09173F13E4C5 n19:271B5611-363D-11E5-9242-09173F13E4C5 n19:271B5612-363D-11E5-9242-09173F13E4C5 n19:271B5617-363D-11E5-9242-09173F13E4C5 n19:271B5618-363D-11E5-9242-09173F13E4C5 n19:271B5615-363D-11E5-9242-09173F13E4C5 n19:271B5616-363D-11E5-9242-09173F13E4C5
n3:patent
n28:5994348 n28:2177772 n28:5270317 n28:2057913
n3:routeOfElimination
Irbesartan is metabolized via glucuronide conjugation and oxidation. Irbesartan and its metabolites are excreted by both biliary and renal routes. Irbesartan is excreted in the milk of lactating rats.
n3:synonym
BMS 186295 Irbesartan 2-Butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[4.4]non-1-en-4-one Avapro
n3:toxicity
Hypotension and tachycardia; bradycardia might also occur from overdose, LD<sub>50</sub>=mg/kg(orally in rat)
n3:volumeOfDistribution
* 53 to 93 L
n29:hasAHFSCode
n30:24-32-08
n3:foodInteraction
Take without regard to meals.
n3:mixture
n15:271B5607-363D-11E5-9242-09173F13E4C5 n15:271B5608-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
90% bound to serum proteins (primarily albumin and a1-acid glycoprotein) with negligible binding to cellular components of blood.
n3:synthesisReference
Gennady Nisnevich, "Novel synthesis of irbesartan." U.S. Patent US20040192713, issued September 30, 2004.
foaf:page
n7:irbesartan.html n14:irbesart.htm
n3:IUPAC-Name
n4:271B562C-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5632-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5631-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B562E-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B562F-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5630-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B562A-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5628-363D-11E5-9242-09173F13E4C5 n4:271B562B-363D-11E5-9242-09173F13E4C5 n4:271B5643-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5629-363D-11E5-9242-09173F13E4C5
n29:hasATCCode
n32:C09CA04
n3:H-Bond-Acceptor-Count
n4:271B5638-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5639-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5633-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5634-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5636-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5635-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5637-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapid and complete with an average absolute bioavailability of 60-80%. Food has no affect on bioavailability.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
138402-11-6
n3:category
n3:clearance
* 157-176 mL/min
n3:containedIn
n31:271B5619-363D-11E5-9242-09173F13E4C5 n31:271B561C-363D-11E5-9242-09173F13E4C5 n31:271B561D-363D-11E5-9242-09173F13E4C5 n31:271B561A-363D-11E5-9242-09173F13E4C5 n31:271B561B-363D-11E5-9242-09173F13E4C5 n31:271B561E-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B563E-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5640-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5641-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5642-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B563D-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B563C-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B563F-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B562D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B563A-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B563B-363D-11E5-9242-09173F13E4C5