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Statements

Subject Item
n2:DB00820
rdf:type
n3:Drug
n3:description
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]
n3:dosage
n9:271B43F6-363D-11E5-9242-09173F13E4C5 n9:271B43F7-363D-11E5-9242-09173F13E4C5 n9:271B43F8-363D-11E5-9242-09173F13E4C5 n9:271B43F9-363D-11E5-9242-09173F13E4C5 n9:271B43F5-363D-11E5-9242-09173F13E4C5 n9:271B43F2-363D-11E5-9242-09173F13E4C5 n9:271B43F3-363D-11E5-9242-09173F13E4C5 n9:271B43F4-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Naeije R, Huez S: Expert opinion on available options treating pulmonary arterial hypertension. Expert Opin Pharmacother. 2007 Oct;8(14):2247-65. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17927481 # Burnett AL: Molecular Pharmacotherapeutic Targeting of PDE5 for Preservation of Penile Health. J Androl. 2007 Oct 17;. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17942972 # Guazzi M, Samaja M: The role of PDE5-inhibitors in cardiopulmonary disorders: from basic evidence to clinical development. Curr Med Chem. 2007;14(20):2181-91. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17691956
n3:group
approved investigational
n3:halfLife
17.5 hours
n3:indication
Used for the treatment of erectile dysfunction.
n3:manufacturer
n4:271B43EC-363D-11E5-9242-09173F13E4C5 n4:271B43EA-363D-11E5-9242-09173F13E4C5 n4:271B43EB-363D-11E5-9242-09173F13E4C5
owl:sameAs
n7:DB00820 n14:DB00820
dcterms:title
Tadalafil
adms:identifier
n20:Tadalafil n24:99301 n25:DB00820 n26:14777 n27:0002-4465-34 n28:CIA n29:D02008 n30:46507646 n31:PA10333 n32:110635
n3:mechanismOfAction
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.
n3:packager
n4:271B43E9-363D-11E5-9242-09173F13E4C5 n4:271B43E7-363D-11E5-9242-09173F13E4C5 n4:271B43E8-363D-11E5-9242-09173F13E4C5 n4:271B43E5-363D-11E5-9242-09173F13E4C5 n4:271B43E6-363D-11E5-9242-09173F13E4C5 n4:271B43E3-363D-11E5-9242-09173F13E4C5 n4:271B43E4-363D-11E5-9242-09173F13E4C5 n4:271B43E1-363D-11E5-9242-09173F13E4C5 n4:271B43E2-363D-11E5-9242-09173F13E4C5 n4:271B43DF-363D-11E5-9242-09173F13E4C5 n4:271B43E0-363D-11E5-9242-09173F13E4C5 n4:271B43DE-363D-11E5-9242-09173F13E4C5
n3:patent
n8:2181377 n8:6821975 n8:2379948 n8:6140329
n3:routeOfElimination
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).
n3:synonym
(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 Cialis Adcirca Tadanafil 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 (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 ICOS 351
n3:toxicity
Oral, Rat LD<sub>50</sub> = 2000 mg/kg, no deaths or toxicity.
n3:volumeOfDistribution
* 63 L
n10:hasAHFSCode
n18:24-12-12
n3:proteinBinding
94%
n3:synthesisReference
Ben-Zion Dolitzky, Dov Diller, "Preparation of tadalafil intermediates." U.S. Patent US20060276652, issued December 07, 2006.
n12:hasConcept
n13:M0431130
foaf:page
n17:tadalafil.html n22:cia1687.shtml n23:cialis.htm
n3:IUPAC-Name
n5:271B43FE-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B4404-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B4403-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B4400-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B4401-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B4402-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B4414-363D-11E5-9242-09173F13E4C5 n5:271B43FC-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B4416-363D-11E5-9242-09173F13E4C5 n5:271B43FD-363D-11E5-9242-09173F13E4C5 n5:271B43FA-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B43FB-363D-11E5-9242-09173F13E4C5
n10:hasATCCode
n11:G04BE08
n3:H-Bond-Acceptor-Count
n5:271B440A-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B440B-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B4405-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B4406-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B4408-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B4407-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B4409-363D-11E5-9242-09173F13E4C5
n3: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.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
171596-29-5
n3:category
n3:clearance
* oral cl=2.5 L/hr
n3:containedIn
n15:271B43EF-363D-11E5-9242-09173F13E4C5 n15:271B43F0-363D-11E5-9242-09173F13E4C5 n15:271B43ED-363D-11E5-9242-09173F13E4C5 n15:271B43EE-363D-11E5-9242-09173F13E4C5 n15:271B43F1-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n5:271B4410-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B4412-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B4413-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n5:271B4415-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B440F-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B440E-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B4411-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B43FF-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n5:271B440C-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n5:271B440D-363D-11E5-9242-09173F13E4C5