Tìm theo
Vardenafil
Các tên gọi khác (7 ) :
  • 2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-F][1,2,4]triazin-4(1H)-one
  • Levitra
  • Vardenafil
  • Vardénafil
  • Vardenafil
  • Vardenafilum
  • verdenafil
Thuốc tim mạch
Thuốc Gốc
Small Molecule
CAS: 224785-90-4
ATC: G04BE09
ĐG : A-S Medication Solutions LLC , http://orders.a-smeds.com
CTHH: C23H32N6O4S
PTK: 488.603
Vardenafil (Levitra) is an oral therapy for the treatment of erectile dysfunction. It is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Penile erection is a hemodynamic process initiated by the relaxation of smooth muscle in the corpus cavernosum and its associated arterioles. During sexual stimulation, nitric oxide is released from nerve endings and endothelial cells in the corpus cavernosum. Nitric oxide activates the enzyme guanylate cyclase resulting in increased synthesis of cyclic guanosine monophosphate (cGMP) in the smooth muscle cells of the corpus cavernosum. The cGMP in turn triggers smooth muscle relaxation, allowing increased blood flow into the penis, resulting in erection. The tissue concentration of cGMP is regulated by both the rates of synthesis and degradation via phosphodiesterases (PDEs). The most abundant PDE in the human corpus cavernosum is the cGMPspecific phosphodiesterase type 5 (PDE5); therefore, the inhibition of PDE5 enhances erectile function by increasing the amount of cGMP.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C23H32N6O4S
Phân tử khối
488.603
Monoisotopic mass
488.220574232
InChI
InChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)
InChI Key
InChIKey=SECKRCOLJRRGGV-UHFFFAOYSA-N
IUPAC Name
2-[2-ethoxy-5-(4-ethylpiperazine-1-sulfonyl)phenyl]-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
Traditional IUPAC Name
vardenafil
SMILES
CCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1
Độ tan chảy
192 °C
Độ hòa tan
0.11 mg/mL (HCl salt)
logP
1.4
logS
-3.2
pKa (strongest acidic)
8.01
pKa (Strongest Basic)
6.21
PSA
109.13 Å2
Refractivity
142.71 m3·mol-1
Polarizability
53.22 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
8
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
MDDR-Like Rule
true
Dược Lực Học : Vardenafil is used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH). Part of the physiological process of erection involves the release of nitric oxide (NO) in the corpus cavernosum. This then activates the enzyme guanylate cyclase which results in increased levels of cyclic guanosine monophosphate (cGMP), leading to smooth muscle relaxation in the corpus cavernosum, resulting in increased inflow of blood and an erection. Vardenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. This means that, with vardenafil on board, normal sexual stimulation leads to increased levels of cGMP in the corpus cavernosum which leads to better erections. Without sexual stimulation and no activation of the NO/cGMP system, vardenafil should not cause an erection.
Cơ Chế Tác Dụng : Vardenafil (Levitra) is an oral therapy for the treatment of erectile dysfunction. It is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Penile erection is a hemodynamic process initiated by the relaxation of smooth muscle in the corpus cavernosum and its associated arterioles. During sexual stimulation, nitric oxide is released from nerve endings and endothelial cells in the corpus cavernosum. Nitric oxide activates the enzyme guanylate cyclase resulting in increased synthesis of cyclic guanosine monophosphate (cGMP) in the smooth muscle cells of the corpus cavernosum. The cGMP in turn triggers smooth muscle relaxation, allowing increased blood flow into the penis, resulting in erection. The tissue concentration of cGMP is regulated by both the rates of synthesis and degradation via phosphodiesterases (PDEs). The most abundant PDE in the human corpus cavernosum is the cGMPspecific phosphodiesterase type 5 (PDE5); therefore, the inhibition of PDE5 enhances erectile function by increasing the amount of cGMP. Vardenafil inhibits the cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum located around the penis. Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosal smooth muscle. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cGMP in smooth muscle cells. Cyclic GMP causes smooth muscle relaxation and increased blood flow into the corpus cavernosum. The inhibition of phosphodiesterase type 5 (PDE5) by vardenafil enhances erectile function by increasing the amount of cGMP.
Dược Động Học :
▧ Absorption :
Vardenafil is rapidly absorbed with absolute bioavailability of approximately 15%.
▧ Volume of Distribution :
* 208 L
▧ Protein binding :
95%
▧ Metabolism :
Vardenafil is metabolized predominantly by the hepatic enzyme CYP3A4, with contribution from the CYP3A5 and CYP2C isoforms. The major circulating metabolite, M1, results from desethylation at the piperazine moiety of vardenafil. M1 shows a phosphodiesterase selectivity profile similar to that of vardenafil and an in vitro inhibitory potency for PDE5 28% of that of vardenafil.
▧ Route of Elimination :
After oral administration, vardenafil is excreted as metabolites predominantly in the feces (approximately 91-95% of administered oral dose) and to a lesser extent in the urine (approximately 2-6% of administered oral dose).
▧ Half Life :
4-5 hours
▧ Clearance :
* 56 L/h
Độc Tính : Symptoms of overdose include vision changes and back and muscle pain.
Chỉ Định : Used for the treatment of erectile dysfunction
Tương Tác Thuốc :
  • Alfuzosin Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Alfuzosin, may occur. Monitor for hypotension during concomitant therapy.
  • Amiodarone Increased risk of cardiotoxicity and arrhythmias
  • Amprenavir Amprenavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Atazanavir Atazanavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Clarithromycin Clarithromycin, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Conivaptan Conivaptan, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Darunavir Darunavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Delavirdine Delavirdine, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Doxazosin Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Doxazosin, may occur. Monitor for hypotension during concomitant therapy.
  • Erythromycin Erythromycin, a moderate CYP3A4 inhibitor, may reduce the metabolism and clearance of vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of vardenafil if erythromycin is initiated, discontinued or dose changed.
  • Fosamprenavir Fosamprenavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Imatinib Imatinib, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Indinavir Indinavir, a potent CYP3A4 inhibitor, may decrease the metabolism and clearance of Vardenafil. Concomitant therapy is contraindicated.
  • Isoniazid Isoniazid, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Isosorbide Dinitrate The vasodilatory effects of Isosorbide dinitrate may be increased by Vardenafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
  • Isosorbide Mononitrate The vasodilatory effects of Isosorbide mononitrate may be increased by Vardenafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
  • Itraconazole Itraconazole, a potent CYP3A4 inhibitor, may decrease the metabolism and clearance of Vardenafil. Concomitant therapy is contraindicated.
  • Ketoconazole Ketoconazole, a potent CYP3A4 inhibitor, may decrease the metabolism and clearance of Vardenafil. Concomitant therapy is contraindicated.
  • Lopinavir Lopinavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Miconazole Miconazole, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Nefazodone Nefazodone, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Nelfinavir Nelfinavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Nicardipine Nicardipine, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Nitroglycerin The vasodilatory effects of Nitroglycerin may be increased by Vardenafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
  • Pentaerythritol Tetranitrate Possible significant hypotension with this combination
  • Phenoxybenzamine Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Phenoxybenzamine, may occur. Monitor for hypotension during concomitant therapy.
  • Phentolamine Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Phentolamine, may occur. Monitor for hypotension during concomitant therapy.
  • Posaconazole Posaconazole, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Prazosin Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Prazosin, may occur. Monitor for hypotension during concomitant therapy.
  • Procainamide Increased risk of cardiotoxicity and arrhythmias
  • Quinidine Quinidine, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Ritonavir Ritonavir, a potent CYP3A4 inhibitor, may decrease the metabolism and clearance of Vardenafil. Concomitant therapy is contraindicated.
  • Saquinavir Saquinavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Silodosin Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Silodosin, may occur. Monitor for hypotension during concomitant therapy.
  • Tamsulosin Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Tamsulosin, may occur. Monitor for hypotension during concomitant therapy.
  • Telithromycin Telithromycin, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Terazosin Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Terazosin, may occur. Monitor for hypotension during concomitant therapy.
  • Tipranavir Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Vardenafil. Concomitant therapy is contraindicated.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of vardenafil by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of vardenafil if voriconazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Levitra 2.5 mg tablet
    Giá bán buôn : USD >18.66
    Đơn vị tính : tablet
  • Biệt dược thương mại : Levitra 10 mg tablet
    Giá bán buôn : USD >19.04
    Đơn vị tính : tablet
  • Biệt dược thương mại : Levitra 20 mg tablet
    Giá bán buôn : USD >19.04
    Đơn vị tính : tablet
  • Biệt dược thương mại : Levitra 5 mg tablet
    Giá bán buôn : USD >19.04
    Đơn vị tính : tablet
Nhà Sản Xuất
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00862
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=110634
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506777
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D09989
ChemSpider
http://www.chemspider.com/Chemical-Structure.99300.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=14776
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0085-1923-01
PharmGKB
http://www.pharmgkb.org/drug/PA10229
Wikipedia
http://en.wikipedia.org/wiki/Vardenafil
RxList
http://www.rxlist.com/cgi/generic3/levitra.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/lev1688.shtml
Drugs.com
http://www.drugs.com/cdi/vardenafil.html
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