Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H32N6O4S |
Molecular Weight | 488.603 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC1=NC(C)=C2N1NC(=NC2=O)C3=CC(=CC=C3OCC)S(=O)(=O)N4CCN(CC)CC4
InChI
InChIKey=SECKRCOLJRRGGV-UHFFFAOYSA-N
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)
Molecular Formula | C23H32N6O4S |
Molecular Weight | 488.603 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00862Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021400s017lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00862
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021400s017lbl.pdf
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22426465
Curator's Comment: Vardenafil crossed the BBB
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1827 Sources: http://www.drugbank.ca/drugs/DB00862 |
1.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Levitra Approved UseLEVITRA is a phosphodiesterase 5 (PDE5) inhibitor indicated for the treatment of erectile dysfunction. Launch Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27318021 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
VARDENAFIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.83 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27318021 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
VARDENAFIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27318021 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
VARDENAFIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
2.4 mg 12 times / day multiple, respiratory (starting) Highest studied dose Dose: 2.4 mg, 12 times / day Route: respiratory Route: multiple Dose: 2.4 mg, 12 times / day Sources: |
healthy, 27.5 years (range: 24-31 years) n = 8 Health Status: healthy Age Group: 27.5 years (range: 24-31 years) Sex: M+F Population Size: 8 Sources: |
|
120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: |
healthy, adult n = 8 Health Status: healthy Age Group: adult Sex: M Population Size: 8 Sources: |
Other AEs: Back pain, Myalgia... Other AEs: Back pain Sources: Myalgia Abnormal vision |
2.4 mg single, respiratory Highest studied dose Dose: 2.4 mg Route: respiratory Route: single Dose: 2.4 mg Sources: |
healthy, adult n = 6 Health Status: healthy Age Group: adult Sex: M+F Population Size: 6 Sources: |
|
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Disc. AE: Headache, Flushing... AEs leading to discontinuation/dose reduction: Headache (19 patients) Sources: Page: p. 34Flushing (10 patients) Rhinitis (5 patients) Tachycardia (4 patients) Nausea (5 patients) Liver function test abnormal (4 patients) Dizziness (3 patients) Hypesthesia (3 patients) Abdominal pain (3 patients) Palpitations (3 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abnormal vision | 120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: |
healthy, adult n = 8 Health Status: healthy Age Group: adult Sex: M Population Size: 8 Sources: |
|
Back pain | 120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: |
healthy, adult n = 8 Health Status: healthy Age Group: adult Sex: M Population Size: 8 Sources: |
|
Myalgia | 120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: |
healthy, adult n = 8 Health Status: healthy Age Group: adult Sex: M Population Size: 8 Sources: |
|
Flushing | 10 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Headache | 19 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Abdominal pain | 3 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Dizziness | 3 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Hypesthesia | 3 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Palpitations | 3 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Liver function test abnormal | 4 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Tachycardia | 4 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Nausea | 5 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Rhinitis | 5 patients Disc. AE |
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: Page: p. 34 |
unhealthy, adult n = 2203 Health Status: unhealthy Age Group: adult Population Size: 2203 Sources: Page: p. 34 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200179Orig1s000PharmR.pdf#page=19 Page: 19.0 |
major | yes (co-administration study) Comment: label: coadministration with ketoconazole (inhibitor) increased mean AUC and Cmax of vardenafil by 10-fold and 4-fold, respectively; coadministration with erythromycin (CYP3A4 substrate) increased mean AUC and Cmax of vardenafil, respectively; coadministration with indinavir (CYP3A4 inhibitor) increased mean AUC and Cmax of vardenafil by 16 fold and 7 fold, respectively; Ritonavir co-administered with vardenafil resulted in a 49-fold increase in vardenafil AUC and a 13 fold increase in vardenafil Cmax; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200179Orig1s000PharmR.pdf#page=19 Page: 19.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200179Orig1s000PharmR.pdf#page=19 Page: 19.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200179Orig1s000PharmR.pdf#page=19 Page: 19.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200179Orig1s000PharmR.pdf#page=19 Page: 19.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200179Orig1s000PharmR.pdf#page=19 Page: 19.0 |
minor | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/22775210/ Page: 7.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/22775210/ Page: 7.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/22775210/ Page: 7.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/200179Orig1s000PharmR.pdf#page=17 Page: 17.0 |
PubMed
Title | Date | PubMed |
---|---|---|
PDE-5 inhibition and sexual response: pharmacological mechanisms and clinical outcomes. | 2002 |
|
Vardenafil: a review of its use in erectile dysfunction. | 2003 |
|
Erectile dysfunction in the cardiac patient: how common and should we treat? | 2003 Aug |
|
US advertising campaign begins for alternative to sildenafil. | 2003 Aug 30 |
|
Oral drug treatment of erectile dysfunction. | 2003 Dec |
|
Pro-erectile effect of vardenafil: in vitro experiments in rabbits and in vivo comparison with sildenafil in rats. | 2003 Dec |
|
Vardenafil: a new approach to the treatment of erectile dysfunction. | 2003 Dec |
|
Molecular mechanisms and pharmacokinetics of phosphodiesterase-5 antagonists. | 2003 Dec |
|
New phosphodiesterase type 5 inhibitors in the management of erectile dysfunction. | 2003 Jun |
|
[New treatment options for erectile dysfunction. Pharmacologic and nonpharmacologic options]. | 2003 Jun |
|
[Conservative treatment of erectile dysfunction]. | 2003 Jun 1 |
|
[New PDE-5 inhibitor for treatment of impotence. 9 out of 10 have erections again]. | 2003 Jun 26 |
|
Switching patients with erectile dysfunction from sildenafil citrate to tadalafil: results of a European multicenter, open-label study of patient preference. | 2003 Nov |
|
Overview of phosphodiesterase 5 inhibition in erectile dysfunction. | 2003 Nov 6 |
|
New tools 2003. | 2003 Nov-Dec |
|
[Drug therapy of erectile dysfunction--the current status]. | 2003 Oct |
|
Phosphodiesterase type 5 inhibitors: a biochemical and clinical correlation survey. | 2003 Oct |
|
Safety and efficacy of vardenafil for the treatment of men with erectile dysfunction after radical retropubic prostatectomy. | 2003 Oct |
|
New drugs and dosage forms. | 2003 Oct 1 |
|
Novel PDE5 inhibitors for the treatment of male erectile dysfunction. | 2003 Oct-Nov |
|
[Medication of the month. Vardenafil (Levitra)]. | 2003 Sep |
|
Phosphodiesterase 5 inhibitors in male sexual dysfunction. | 2003 Sep |
|
Vardenafil (levitra) for erectile dysfunction. | 2003 Sep 29 |
|
Structure of the catalytic domain of human phosphodiesterase 5 with bound drug molecules. | 2003 Sep 4 |
|
FDA approves new drug for treatment of erectile dysfunction in men. | 2003 Sep-Oct |
|
Spotlight on vardenafil in erectile dysfunction. | 2004 |
|
[Comparison of efficacy and safety of phosphodiesterase type 5 inhibitors in the treatment of erectile dysfunction]. | 2004 Apr |
|
Tadalafil and vardenafil. | 2004 Apr |
|
Novel phosphodiesterase type 5 inhibitors: assessing hemodynamic effects and safety parameters. | 2004 Apr |
|
Phosphodiesterase type 5 inhibitor differentiation based on selectivity, pharmacokinetic, and efficacy profiles. | 2004 Apr |
|
Role of the cardiologist: clinical aspects of managing erectile dysfunction. | 2004 Apr |
|
Vardenafil: a novel type 5 phosphodiesterase inhibitor for the treatment of erectile dysfunction. | 2004 Apr |
|
Pills for erectile dysfunction: now there are three. | 2004 Apr |
|
Treatment of erectile dysfunction. | 2004 Apr |
|
Erectile dysfunction: management update. | 2004 Apr 27 |
|
Tadalafil (Cialis) and vardenafil (Levitra) recently approved drugs for erectile dysfunction. | 2004 Feb |
|
[Erectile dysfunction. Epidemiology, physiology, etiology, diagnosis and therapy]. | 2004 Feb |
|
Drug approval highlights for 2003. | 2004 Feb |
|
Cardioprotection with phosphodiesterase-5 inhibition--a novel preconditioning strategy. | 2004 Feb |
|
Cialis is here. The soft sell. | 2004 Feb 2 |
|
[Treatment of erectile dysfunction]. | 2004 Feb 29 |
|
Vardenafil treatment for erectile dysfunction. | 2004 Jan |
|
Are they better than Viagra? Two new drugs for erectile dysfunction work like Viagra and carry similar risks and benefits. Their subtle differences, however, may make a difference for some men. | 2004 Jan |
|
Sustained efficacy and tolerability with vardenafil over 2 years of treatment in men with erectile dysfunction. | 2004 Mar |
|
Vardenafil--PDE5 inhibitor number 3. | 2004 Mar |
|
Pharmacokinetics, pharmacodynamics, and efficacy of phosphodiesterase type 5 inhibitors. | 2004 Mar |
|
Therapeutic options for patients returning to sexual activity. | 2004 Mar |
|
Therapy of ED: PDE-5 Inhibitors. | 2004 Mar-Apr |
|
Emerging oral drugs for erectile dysfunction. | 2004 May |
|
The efficacy and safety of flexible-dose vardenafil (levitra) in a broad population of European men. | 2004 May |
Sample Use Guides
For most patients, the starting dose is 10 mg, up to once daily. Increase to 20 mg or decrease to 5 mg based on efficacy/tolerability.
A starting dose of 5 mg LEVITRA should be considered in patients ≥ 65
years of age.
LEVITRA is taken orally, approximately 60 minutes before sexual
activity.
The maximum recommended dosing frequency is one tablet per day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25736325
Treatment with vardenafil at concentrations of 50, 100, and 250 umol/L increased expression of PlGF in a dose-dependent manner in human umbilical vein endothelial cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:44:26 GMT 2023
by
admin
on
Fri Dec 15 15:44:26 GMT 2023
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Record UNII |
UCE6F4125H
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
LEVITRA (AUTHORIZED: ERECTILE DYSFUNCTIONS)
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NDF-RT |
N0000020026
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FDA ORPHAN DRUG |
679319
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WHO-ATC |
G04BE09
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WHO-VATC |
QG04BE09
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LIVERTOX |
NBK548920
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NCI_THESAURUS |
C2127
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NDF-RT |
N0000175599
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EMA ASSESSMENT REPORTS |
VIVANZA (AUTHORIZED: ERECTILE DYSFUNCTIONS)
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Code System | Code | Type | Description | ||
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UCE6F4125H
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7950
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C426063
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NN-53
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VARDENAFIL
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100000089525
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C66650
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7304
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7320
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Vardenafil
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306674
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135400189
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DTXSID3048318
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CHEMBL1520
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224785-90-4
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DB00862
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UCE6F4125H
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2809
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m11394
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PRIMARY | Merck Index | ||
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SUB20047
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PRIMARY |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TRANSPORTER -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
FECAL; PLASMA
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METABOLITE -> PARENT |
CYP2C9 also contributes to the metabolism of vardenafil.
MINOR
FECAL; PLASMA; URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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FASTED STATE |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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