Tìm theo
Tadalafil
Các tên gọi khác (7 ) :
  • (6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione
  • (6R,12AR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione
  • 6-BENZO[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
  • Adcirca
  • Cialis
  • ICOS 351
  • Tadanafil
Hormon, Nội tiết tố
Thuốc Gốc
Small Molecule
CAS: 171596-29-5
ATC: G04BE08
ĐG : A-S Medication Solutions LLC , http://orders.a-smeds.com
CTHH: C22H19N3O4
PTK: 389.404
Tadalafil is an orally adminstered drug used to treat male erectile dysfunction (impotence). It is marketed worldwide under the brand name Cialis. It is a phosphodiesterase 5 (PDE5) inhibitor. Tadalafil's distinguishing pharmacologic feature is its longer half-life (17.5 hours) compared with Viagra and Levitra (4-5 hours). This longer half-life results in a longer duration of action and is, in part, responsible for the Cialis nickname of the "weekend pill." This longer half-life also is the basis of current investigation for tadalafil's use in pulmonary arterial hypertension as a once-daily therapy. [Wikipedia]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H19N3O4
Phân tử khối
389.404
Monoisotopic mass
389.137556111
InChI
InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
InChI Key
InChIKey=WOXKDUGGOYFFRN-IIBYNOLFSA-N
IUPAC Name
(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene-4,7-dione
Traditional IUPAC Name
tadalafil
SMILES
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1
Độ tan chảy
301-302 °C
Độ hòa tan
Practically insoluble in water
logP
1.7
logS
-3.2
pKa (strongest acidic)
15.17
pKa (Strongest Basic)
-4.2
PSA
74.87 Å2
Refractivity
104.08 m3·mol-1
Polarizability
40.92 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
4
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
6
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Tadalafil 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. Tadalafil 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 tadalafil 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, tadalafil should not cause an erection.
Cơ Chế Tác Dụng : Tadalafil is an orally adminstered drug used to treat male erectile dysfunction (impotence). It is marketed worldwide under the brand name Cialis. It is a phosphodiesterase 5 (PDE5) inhibitor. Tadalafil's distinguishing pharmacologic feature is its longer half-life (17.5 hours) compared with Viagra and Levitra (4-5 hours). This longer half-life results in a longer duration of action and is, in part, responsible for the Cialis nickname of the "weekend pill." This longer half-life also is the basis of current investigation for tadalafil's use in pulmonary arterial hypertension as a once-daily therapy. [Wikipedia] Tadalafil 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 tadalafil enhances erectile function by increasing the amount of cGMP.
Dược Động Học :
▧ Absorption :
After single oral-dose administration, the maximum observed plasma concentration (Cmax) of tadalafil is achieved between 30 minutes and 6 hours (median time of 2 hours). Absolute bioavailability of tadalafil following oral dosing has not been determined.
▧ Volume of Distribution :
* 63 L
▧ Protein binding :
94%
▧ Metabolism :
Tadalafil is predominantly metabolized by CYP3A4 to a catechol metabolite. The catechol metabolite undergoes extensive methylation and glucuronidation to form the methylcatechol and methylcatechol glucuronide conjugate, respectively. In vitro data suggests the metabolites are not expected to be pharmacologically active at observed metabolite concentrations.
▧ Route of Elimination :
Tadalafil is excreted predominantly as metabolites, mainly in the feces (approximately 61% of the dose) and to a lesser extent in the urine (approximately 36% of the dose).
▧ Half Life :
17.5 hours
▧ Clearance :
* oral cl=2.5 L/hr
Độc Tính : Oral, Rat LD50 = 2000 mg/kg, no deaths or toxicity.
Chỉ Định : Used for the treatment of erectile dysfunction.
Tương Tác Thuốc :
  • Alfuzosin Tadalafil may enhance the hypotensive effect of Alfusozin. Monitor for hypotension during concomitant therapy.
  • Amprenavir Amprenavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Atazanavir Atazanavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Azilsartan medoxomil Pharmacodynamic synergist- increases effects.
  • Boceprevir Boceprevir increases levels by affecting CYP3A4 metabolism. Concomitant therapy is contraindicated.
  • Clarithromycin Clarithromycin may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Conivaptan Conivaptan may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Darunavir Darunavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Delavirdine Delavirdine may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Doxazosin Tadalafil may enhance the hypotensive effect of Doxazosin. Monitor for hypotension during concomitant therapy.
  • Fosamprenavir Fosamprenavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Imatinib Imatinib may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Indinavir Indinavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Isoniazid Isoniazid may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Isosorbide Dinitrate The vasodilatory effects of Isosorbide dinitrate may be increased by Tadalafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
  • Isosorbide Mononitrate The vasodilatory effects of Isosobide mononitrate may be increased by Tadalafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
  • Itraconazole Itraconazole may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Ketoconazole Ketoconazole may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Lopinavir Lopinavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Miconazole Miconazole may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Nefazodone Nefazodone may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Nelfinavir Nelfinavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Nicardipine Nicardipine may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Nitroglycerin The vasodilatory effects of Nitroglycerin may be increased by Tadalafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
  • Pentaerythritol Tetranitrate Possible significant hypotension with this combination
  • Phenoxybenzamine Tadalafil may enhance the hypotensive effect of Phenoxybenzamine. Monitor for hypotension during concomitant therapy.
  • Phentolamine Tadalafil may enhance the hypotensive effect of Phentolamine. Monitor for hypotension during concomitant therapy.
  • Posaconazole Posaconzole may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Prazosin Tadalafil may enhance the hypotensive effect of Prazosin. Monitor for hypotension during concomitant therapy.
  • Quinidine Quinidine may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Rifampicin Rifampin may reduce Tadalafil plasma concentrations and efficacy.
  • Ritonavir Ritonavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Saquinavir Saquinavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Tamsulosin Tadalafil may enhance the hypotensive effect of Tamsulosin. Monitor for hypotension during concomitant therapy.
  • Telaprevir Telaprevir increases levels by affecting CYP3A4 metabolism. Concomitant therapy is contraindicated.
  • Telithromycin Telithromycin may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Terazosin Tadalafil may enhance the hypotensive effect of Terazosin. Monitor for hypotension during concomitant therapy.
  • Tipranavir Tipranavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of tadalafil by decreasing its metabolism. Concomitant therapy should be avoided if possible due to high risk of tadalafil toxicity.
Liều Lượng & Cách Dùng : Tablet, film coated - Oral - 10 mg
Tablet, film coated - Oral - 2.5 mg
Tablet, film coated - Oral - 20 mg
Tablet, film coated - Oral - 5 mg
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Cialis 2.5 mg tablet
    Giá bán buôn : USD >4.76
    Đơn vị tính : tablet
  • Biệt dược thương mại : Cialis 5 mg tablet
    Giá bán buôn : USD >4.76
    Đơn vị tính : tablet
  • Biệt dược thương mại : Cialis 10 mg tablet
    Giá bán buôn : USD >20.92
    Đơn vị tính : tablet
  • Biệt dược thương mại : Cialis 20 mg tablet
    Giá bán buôn : USD >20.92
    Đơn vị tính : tablet
  • Biệt dược thương mại : Cialis 30 5 mg tablet Box
    Giá bán buôn : USD >140.77
    Đơn vị tính : box
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : ADCIRCA
  • Công ty : Eli Lilly
    Sản phẩm biệt dược : Cialis
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00820
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=110635
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507646
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02008
ChemSpider
http://www.chemspider.com/Chemical-Structure.99301.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=14777
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0002-4465-34
PharmGKB
http://www.pharmgkb.org/drug/PA10333
Wikipedia
http://en.wikipedia.org/wiki/Tadalafil
RxList
http://www.rxlist.com/cgi/generic3/cialis.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cia1687.shtml
Drugs.com
http://www.drugs.com/tadalafil.html
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