Tìm theo
Irbesartan
Các tên gọi khác (4 ) :
  • 2-Butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[4.4]non-1-en-4-one
  • Avapro
  • BMS 186295
  • Irbesartan
Thuốc tim mạch
Thuốc Gốc
Small Molecule
CAS: 138402-11-6
ATC: C09CA04
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C25H28N6O
PTK: 428.5294
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.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C25H28N6O
Phân tử khối
428.5294
Monoisotopic mass
428.232459548
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)
InChI Key
InChIKey=YOSHYTLCDANDAN-UHFFFAOYSA-N
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
Traditional IUPAC Name
irbesartan
SMILES
CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1
Độ tan chảy
180-181 °C
Độ hòa tan
8.84e-03 g/l
logP
6
logS
-4.7
pKa (strongest acidic)
7.4
pKa (Strongest Basic)
4.12
PSA
87.13 Å2
Refractivity
136.72 m3·mol-1
Polarizability
47.59 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
5
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
5
Bioavailability
1
MDDR-Like Rule
true
Dược Lực Học : Angiotensin II, the principal pressor agent of the renin-angiotensin system, is responsible for effects such as vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. 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. Irbesartan's inhibition of angiotensin II binding to the AT1 receptor leads to multiple effects including vasodilation, a reduction in the secretion of vasopressin, and reduction in the production and secretion of aldosterone. The resulting effect is a decrease in blood pressure.
Cơ Chế Tác Dụng : 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. Irbesartan is a nonpeptide tetrazole derivative and an angiotensin II antagonist that selectively blocks the binding of angiotensin II to the AT1 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 AT1 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–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).
Dược Động Học :
▧ Absorption :
Rapid and complete with an average absolute bioavailability of 60-80%. Food has no affect on bioavailability.
▧ Volume of Distribution :
* 53 to 93 L
▧ Protein binding :
90% bound to serum proteins (primarily albumin and a1-acid glycoprotein) with negligible binding to cellular components of blood.
▧ Metabolism :
Hepatic. Irbesartan is metabolized via glucuronide conjugation and oxidation. In vitro studies of irbesartan oxidation by cytochrome P450 isoenzymes indicated irbesartan was oxidized primarily by 2C9; metabolism by 3A4 was negligible.
▧ Route of Elimination :
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.
▧ Half Life :
11-15 hours
▧ Clearance :
* 157-176 mL/min
Độc Tính : Hypotension and tachycardia; bradycardia might also occur from overdose, LD50=mg/kg(orally in rat)
Chỉ Định : 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.
Tương Tác Thuốc :
  • Amiloride Increased risk of hyperkalemia
  • Drospirenone Increased risk of hyperkalemia
  • Lithium The ARB increases serum levels of lithium
  • Potassium Increased risk of hyperkalemia
  • Spironolactone Increased risk of hyperkalemia
  • Tobramycin Increased risk of nephrotoxicity
  • Trandolapril The angiotensin II receptor blocker, Irbesartan, may increase the adverse effects of Trandolapril.
  • Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
  • Tretinoin The moderate CYP2C8 inhibitor, Irbesartan, may decrease the metabolism and clearance of oral Tretinoin. Monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Irbesartan is initiated, discontinued to dose changed.
  • Triamterene Increased risk of hyperkalemia
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Avapro
  • Công ty :
    Sản phẩm biệt dược : Irbesarran
  • Công ty :
    Sản phẩm biệt dược : Lrbesartan
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01029
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3749
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506575
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07469
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00523
ChemSpider
http://www.chemspider.com/Chemical-Structure.3618.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0087-2771-31
PharmGKB
http://www.pharmgkb.org/drug/PA450084
Wikipedia
http://en.wikipedia.org/wiki/Irbesartan
RxList
http://www.rxlist.com/cgi/generic/irbesart.htm
Drugs.com
http://www.drugs.com/cdi/irbesartan.html
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