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Identification
NameVardenafil
Accession NumberDB00862  (APRD00699)
TypeSmall Molecule
GroupsApproved
Description

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.

Structure
Thumb
Synonyms
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
External Identifiers
  • BAY 389456
  • DE 19750085 1997
  • WO 99/24433 1999
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Levitratablet, film coated20 mg/1oralPd Rx Pharmaceuticals, Inc.2011-04-22Not applicableUs
Levitratablet, film coated20 mg/1oralKAISER FOUNDATION HOSPITALS2011-10-28Not applicableUs
Levitratablet, film coated2.5 mg/1oralGlaxo Smith Kline Llc2003-08-25Not applicableUs
Levitratablet20 mgoralBayer Inc2004-03-17Not applicableCanada
Levitratablet, film coated10 mg/1oralPhysicians Total Care, Inc.2004-03-05Not applicableUs
Levitratablet10 mgoralBayer Inc2004-03-17Not applicableCanada
Levitratablet, film coated20 mg/1oralPhysicians Total Care, Inc.2004-01-27Not applicableUs
Levitratablet5 mgoralBayer Inc2004-03-17Not applicableCanada
Levitratablet, film coated20 mg/1oralAphena Pharma Solutions Tennessee, Inc.2011-04-22Not applicableUs
Levitratablet, film coated20 mg/1oralbryant ranch prepack2008-05-15Not applicableUs
Levitratablet, film coated10 mg/1oralAphena Pharma Solutions Tennessee, Inc.2008-05-15Not applicableUs
Levitratablet, film coated5 mg/1oralAphena Pharma Solutions Tennessee, Inc.2011-04-22Not applicableUs
Levitratablet, film coated20 mg/1oralGlaxo Smith Kline Llc2003-08-25Not applicableUs
Levitratablet, film coated20 mg/1oralAphena Pharma Solutions Tennessee, Inc.2008-05-15Not applicableUs
Levitratablet, film coated10 mg/1oralAphena Pharma Solutions Tennessee, Inc.2011-04-22Not applicableUs
Levitratablet, film coated10 mg/1oralGlaxo Smith Kline Llc2003-08-25Not applicableUs
Levitratablet, film coated10 mg/1oralPd Rx Pharmaceuticals, Inc.2008-05-15Not applicableUs
Levitratablet, film coated5 mg/1oralAphena Pharma Solutions Tennessee, Inc.2008-05-15Not applicableUs
Levitratablet, film coated5 mg/1oralGlaxo Smith Kline Llc2003-04-23Not applicableUs
Staxyntablet, orally disintegrating11.85 mg/1oralGlaxo Smith Kline Llc2011-04-21Not applicableUs
Staxyntablet (orally disintegrating)10 mgoralBayer Inc2011-08-25Not applicableCanada
Staxyntablet, orally disintegrating10 mg/1oralPhysicians Total Care, Inc.2012-03-08Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
VivanzaGlaxoSmithKline
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Vardenafil hydrochloride
ThumbNot applicableDBSALT000933
Vardenafil hydrochloride trihydrate
ThumbNot applicableDBSALT001741
Categories
UNIIUCE6F4125H
CAS number224785-90-4
WeightAverage: 488.603
Monoisotopic: 488.220574232
Chemical FormulaC23H32N6O4S
InChI KeyInChIKey=SECKRCOLJRRGGV-UHFFFAOYSA-N
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)
IUPAC Name
2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
SMILES
CCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Phenol ether
  • N-alkylpiperazine
  • Alkyl aryl ether
  • 1,2,4-triazine
  • Triazine
  • Piperazine
  • N-substituted imidazole
  • 1,4-diazinane
  • Heteroaromatic compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Imidazole
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed for the treatment of erectile dysfunction
PharmacodynamicsVardenafil 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.
Mechanism of actionVardenafil 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.
Related Articles
AbsorptionVardenafil is rapidly absorbed with absolute bioavailability of approximately 15%.
Volume of distribution
  • 208 L
Protein binding95%
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 eliminationAfter 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 life4-5 hours
Clearance
  • 56 L/h
ToxicitySymptoms of overdose include vision changes and back and muscle pain.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.6682
Caco-2 permeable+0.5502
P-glycoprotein substrateSubstrate0.7415
P-glycoprotein inhibitor IInhibitor0.6976
P-glycoprotein inhibitor IIInhibitor0.8552
Renal organic cation transporterNon-inhibitor0.6975
CYP450 2C9 substrateNon-substrate0.6386
CYP450 2D6 substrateSubstrate0.7909
CYP450 3A4 substrateSubstrate0.697
CYP450 1A2 substrateNon-inhibitor0.8215
CYP450 2C9 inhibitorInhibitor0.7426
CYP450 2D6 inhibitorNon-inhibitor0.8464
CYP450 2C19 inhibitorNon-inhibitor0.7472
CYP450 3A4 inhibitorInhibitor0.8857
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7205
Ames testNon AMES toxic0.5748
CarcinogenicityNon-carcinogens0.6141
BiodegradationNot ready biodegradable0.8875
Rat acute toxicity2.6208 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8367
hERG inhibition (predictor II)Inhibitor0.7696
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral10 mg
Tabletoral20 mg
Tabletoral5 mg
Tablet, film coatedoral10 mg/1
Tablet, film coatedoral2.5 mg/1
Tablet, film coatedoral20 mg/1
Tablet, film coatedoral5 mg/1
Tablet (orally disintegrating)oral10 mg
Tablet, orally disintegratingoral10 mg/1
Tablet, orally disintegratingoral11.85 mg/1
Prices
Unit descriptionCostUnit
Levitra 10 mg tablet19.04USD tablet
Levitra 20 mg tablet19.04USD tablet
Levitra 5 mg tablet19.04USD tablet
Levitra 2.5 mg tablet18.66USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2309332 No2002-12-032018-10-31Canada
US6362178 No1998-10-312018-10-31Us
US7696206 No1998-10-312018-10-31Us
US8273876 No2007-07-232027-07-23Us
US8613950 No2008-12-232028-12-23Us
US8841446 No2003-07-032023-07-03Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point192 °CNot Available
water solubility0.11 mg/mL (HCl salt)Not Available
logP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.325 mg/mLALOGPS
logP2.18ALOGPS
logP1.33ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)6.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.13 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.71 m3·mol-1ChemAxon
Polarizability53.22 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Yogesh S. Deshpande, Sandra Brueck, Julia Schulze Nahrup, Birgit Schnitter, Ganesh Gat, Javed Hussain, “PROCESS FOR THE PREPARATION OF A MEDICAMENT COMPRISING VARDENAFIL HYDROCHLORIDE TRIHYDRATE.” U.S. Patent US20100159003, issued June 24, 2010.

US20100159003
General ReferencesNot Available
External Links
ATC CodesG04BE09
AHFS Codes
  • 24:12.12
PDB EntriesNot Available
FDA labelDownload (535 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololVardenafil may increase the antihypertensive activities of Acebutolol.
AlfuzosinVardenafil may increase the hypotensive activities of Alfuzosin.
AliskirenVardenafil may increase the antihypertensive activities of Aliskiren.
AlprostadilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Alprostadil.
AmilorideVardenafil may increase the antihypertensive activities of Amiloride.
AmlodipineVardenafil may increase the antihypertensive activities of Amlodipine.
Amyl NitriteVardenafil may increase the vasodilatory activities of Amyl Nitrite.
AprepitantThe serum concentration of Vardenafil can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Vardenafil can be increased when it is combined with Atazanavir.
AtenololVardenafil may increase the antihypertensive activities of Atenolol.
AvanafilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Avanafil.
Azilsartan medoxomilVardenafil may increase the antihypertensive activities of Azilsartan medoxomil.
BenazeprilVardenafil may increase the antihypertensive activities of Benazepril.
BendroflumethiazideVardenafil may increase the antihypertensive activities of Bendroflumethiazide.
BetaxololVardenafil may increase the antihypertensive activities of Betaxolol.
BisoprololVardenafil may increase the antihypertensive activities of Bisoprolol.
BoceprevirThe serum concentration of Vardenafil can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Vardenafil can be decreased when it is combined with Bosentan.
BumetanideVardenafil may increase the antihypertensive activities of Bumetanide.
CandesartanVardenafil may increase the antihypertensive activities of Candesartan.
CaptoprilVardenafil may increase the antihypertensive activities of Captopril.
CarvedilolVardenafil may increase the antihypertensive activities of Carvedilol.
CeritinibThe serum concentration of Vardenafil can be increased when it is combined with Ceritinib.
ChlorothiazideVardenafil may increase the antihypertensive activities of Chlorothiazide.
ChlorthalidoneVardenafil may increase the antihypertensive activities of Chlorthalidone.
CilazaprilVardenafil may increase the antihypertensive activities of Cilazapril.
CitalopramVardenafil may increase the QTc-prolonging activities of Citalopram.
ClarithromycinThe serum concentration of Vardenafil can be increased when it is combined with Clarithromycin.
ClevidipineVardenafil may increase the antihypertensive activities of Clevidipine.
ClonidineVardenafil may increase the antihypertensive activities of Clonidine.
CobicistatThe serum concentration of Vardenafil can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Vardenafil can be increased when it is combined with Conivaptan.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Vardenafil.
DarunavirThe serum concentration of Vardenafil can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Vardenafil can be increased when it is combined with Dasatinib.
DiltiazemVardenafil may increase the antihypertensive activities of Diltiazem.
DofetilideVardenafil may increase the QTc-prolonging activities of Dofetilide.
DoxazosinVardenafil may increase the hypotensive activities of Doxazosin.
EnalaprilVardenafil may increase the antihypertensive activities of Enalapril.
EnalaprilatVardenafil may increase the antihypertensive activities of Enalaprilat.
EplerenoneVardenafil may increase the antihypertensive activities of Eplerenone.
EprosartanVardenafil may increase the antihypertensive activities of Eprosartan.
Erythrityl TetranitrateVardenafil may increase the vasodilatory activities of Erythrityl Tetranitrate.
ErythromycinThe serum concentration of Vardenafil can be increased when it is combined with Erythromycin.
EsmololVardenafil may increase the antihypertensive activities of Esmolol.
Etacrynic acidVardenafil may increase the antihypertensive activities of Ethacrynic acid.
EthanolEthanol may increase the hypotensive activities of Vardenafil.
EtravirineThe serum concentration of Vardenafil can be decreased when it is combined with Etravirine.
FelodipineVardenafil may increase the antihypertensive activities of Felodipine.
FluconazoleThe metabolism of Vardenafil can be decreased when combined with Fluconazole.
FosaprepitantThe serum concentration of Vardenafil can be increased when it is combined with Fosaprepitant.
FosinoprilVardenafil may increase the antihypertensive activities of Fosinopril.
FurosemideVardenafil may increase the antihypertensive activities of Furosemide.
Fusidic AcidThe serum concentration of Vardenafil can be increased when it is combined with Fusidic Acid.
GoserelinVardenafil may increase the QTc-prolonging activities of Goserelin.
GuanfacineVardenafil may increase the antihypertensive activities of Guanfacine.
HydralazineVardenafil may increase the antihypertensive activities of Hydralazine.
HydrochlorothiazideVardenafil may increase the antihypertensive activities of Hydrochlorothiazide.
IdelalisibThe serum concentration of Vardenafil can be increased when it is combined with Idelalisib.
IndapamideVardenafil may increase the antihypertensive activities of Indapamide.
IndinavirThe serum concentration of Vardenafil can be increased when it is combined with Indinavir.
IrbesartanVardenafil may increase the antihypertensive activities of Irbesartan.
IsosorbideVardenafil may increase the vasodilatory activities of Isosorbide.
Isosorbide DinitrateVardenafil may increase the vasodilatory activities of Isosorbide Dinitrate.
Isosorbide MononitrateVardenafil may increase the vasodilatory activities of Isosorbide Mononitrate.
IsradipineVardenafil may increase the antihypertensive activities of Isradipine.
ItraconazoleThe serum concentration of Vardenafil can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Vardenafil can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Vardenafil can be increased when it is combined with Ketoconazole.
LabetalolVardenafil may increase the antihypertensive activities of Labetalol.
LeuprolideVardenafil may increase the QTc-prolonging activities of Leuprolide.
LisinoprilVardenafil may increase the antihypertensive activities of Lisinopril.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Vardenafil.
LosartanVardenafil may increase the antihypertensive activities of Losartan.
LuliconazoleThe serum concentration of Vardenafil can be increased when it is combined with Luliconazole.
MannitolVardenafil may increase the antihypertensive activities of Mannitol.
MecamylamineVardenafil may increase the antihypertensive activities of Mecamylamine.
MethyclothiazideVardenafil may increase the antihypertensive activities of Methyclothiazide.
MethyldopaVardenafil may increase the antihypertensive activities of Methyldopa.
MetolazoneVardenafil may increase the antihypertensive activities of Metolazone.
MetoprololVardenafil may increase the antihypertensive activities of Metoprolol.
MifepristoneThe serum concentration of Vardenafil can be increased when it is combined with Mifepristone.
MinoxidilVardenafil may increase the antihypertensive activities of Minoxidil.
MoexiprilVardenafil may increase the antihypertensive activities of Moexipril.
MolsidomineMolsidomine may increase the hypotensive activities of Vardenafil.
MoxonidineVardenafil may increase the antihypertensive activities of Moxonidine.
NadololVardenafil may increase the antihypertensive activities of Nadolol.
NebivololVardenafil may increase the antihypertensive activities of Nebivolol.
NefazodoneThe serum concentration of Vardenafil can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Vardenafil can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Vardenafil can be increased when it is combined with Netupitant.
NicardipineVardenafil may increase the antihypertensive activities of Nicardipine.
NifedipineVardenafil may increase the antihypertensive activities of Nifedipine.
NimodipineVardenafil may increase the antihypertensive activities of Nimodipine.
NisoldipineVardenafil may increase the antihypertensive activities of Nisoldipine.
NitroglycerinVardenafil may increase the vasodilatory activities of Nitroglycerin.
NitroprussideVardenafil may increase the antihypertensive activities of Nitroprusside.
OlmesartanVardenafil may increase the antihypertensive activities of Olmesartan.
PalbociclibThe serum concentration of Vardenafil can be increased when it is combined with Palbociclib.
PenbutololVardenafil may increase the antihypertensive activities of Penbutolol.
PerindoprilVardenafil may increase the antihypertensive activities of Perindopril.
PhenoxybenzamineVardenafil may increase the hypotensive activities of Phenoxybenzamine.
PhentolamineVardenafil may increase the hypotensive activities of Phentolamine.
PindololVardenafil may increase the antihypertensive activities of Pindolol.
PosaconazoleThe serum concentration of Vardenafil can be increased when it is combined with Posaconazole.
PrazosinVardenafil may increase the hypotensive activities of Prazosin.
PropranololVardenafil may increase the antihypertensive activities of Propranolol.
QuinaprilVardenafil may increase the antihypertensive activities of Quinapril.
RamiprilVardenafil may increase the antihypertensive activities of Ramipril.
ReserpineVardenafil may increase the antihypertensive activities of Reserpine.
RiociguatVardenafil may increase the hypotensive activities of Riociguat.
RitonavirThe serum concentration of Vardenafil can be increased when it is combined with Ritonavir.
SapropterinTetrahydrobiopterin may increase the hypotensive activities of Vardenafil.
SaquinavirThe serum concentration of Vardenafil can be increased when it is combined with Saquinavir.
SildenafilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Sildenafil.
SilodosinVardenafil may increase the hypotensive activities of Silodosin.
SimeprevirThe serum concentration of Vardenafil can be increased when it is combined with Simeprevir.
SotalolVardenafil may increase the antihypertensive activities of Sotalol.
SpironolactoneVardenafil may increase the antihypertensive activities of Spironolactone.
StiripentolThe serum concentration of Vardenafil can be increased when it is combined with Stiripentol.
TadalafilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Tadalafil.
TamsulosinVardenafil may increase the hypotensive activities of Tamsulosin.
TelaprevirThe serum concentration of Vardenafil can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Vardenafil can be increased when it is combined with Telithromycin.
TelmisartanVardenafil may increase the antihypertensive activities of Telmisartan.
TerazosinVardenafil may increase the hypotensive activities of Terazosin.
TimololVardenafil may increase the antihypertensive activities of Timolol.
TorasemideVardenafil may increase the antihypertensive activities of Torasemide.
TrandolaprilVardenafil may increase the antihypertensive activities of Trandolapril.
TriamtereneVardenafil may increase the antihypertensive activities of Triamterene.
ValsartanVardenafil may increase the antihypertensive activities of Valsartan.
VerapamilVardenafil may increase the antihypertensive activities of Verapamil.
VoriconazoleThe serum concentration of Vardenafil can be increased when it is combined with Voriconazole.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, PubMed:15489334). Specifically regulates nitric-oxide-generated cGMP (PubMed:15489334).
Gene Name:
PDE5A
Uniprot ID:
O76074
Molecular Weight:
99984.14 Da
References
  1. Blount MA, Zoraghi R, Ke H, Bessay EP, Corbin JD, Francis SH: A 46-amino acid segment in phosphodiesterase-5 GAF-B domain provides for high vardenafil potency over sildenafil and tadalafil and is involved in phosphodiesterase-5 dimerization. Mol Pharmacol. 2006 Nov;70(5):1822-31. Epub 2006 Aug 22. [PubMed:16926278 ]
  2. Carrier S: Pharmacology of phosphodiesterase 5 inhibitors. Can J Urol. 2003 Feb;10 Suppl 1:12-6. [PubMed:12625845 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Kim NN, Huang YH, Goldstein I, Bischoff E, Traish AM: Inhibition of cyclic GMP hydrolysis in human corpus cavernosum smooth muscle cells by vardenafil, a novel, selective phosphodiesterase type 5 inhibitor. Life Sci. 2001 Sep 28;69(19):2249-56. [PubMed:11669467 ]
  5. Saenz de Tejada I, Angulo J, Cuevas P, Fernandez A, Moncada I, Allona A, Lledo E, Korschen HG, Niewohner U, Haning H, Pages E, Bischoff E: The phosphodiesterase inhibitory selectivity and the in vitro and in vivo potency of the new PDE5 inhibitor vardenafil. Int J Impot Res. 2001 Oct;13(5):282-90. [PubMed:11890515 ]
  6. Scheen AJ: [Medication of the month. Vardenafil (Levitra)]. Rev Med Liege. 2003 Sep;58(9):576-9. [PubMed:14626653 ]
  7. Sung BJ, Hwang KY, Jeon YH, Lee JI, Heo YS, Kim JH, Moon J, Yoon JM, Hyun YL, Kim E, Eum SJ, Park SY, Lee JO, Lee TG, Ro S, Cho JM: Structure of the catalytic domain of human phosphodiesterase 5 with bound drug molecules. Nature. 2003 Sep 4;425(6953):98-102. [PubMed:12955149 ]
  8. Wang H, Ye M, Robinson H, Francis SH, Ke H: Conformational variations of both phosphodiesterase-5 and inhibitors provide the structural basis for the physiological effects of vardenafil and sildenafil. Mol Pharmacol. 2008 Jan;73(1):104-10. Epub 2007 Oct 24. [PubMed:17959709 ]
  9. Zoraghi R, Francis SH, Corbin JD: Critical amino acids in phosphodiesterase-5 catalytic site that provide for high-affinity interaction with cyclic guanosine monophosphate and inhibitors. Biochemistry. 2007 Nov 27;46(47):13554-63. Epub 2007 Nov 3. [PubMed:17979301 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
allosteric modulator
General Function:
Enzyme inhibitor activity
Specific Function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6G
Uniprot ID:
P18545
Molecular Weight:
9643.09 Da
References
  1. Zhang XJ, Cahill KB, Elfenbein A, Arshavsky VY, Cote RH: Direct allosteric regulation between the GAF domain and catalytic domain of photoreceptor phosphodiesterase PDE6. J Biol Chem. 2008 Oct 31;283(44):29699-705. doi: 10.1074/jbc.M803948200. Epub 2008 Sep 8. [PubMed:18779324 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
allosteric modulator
General Function:
Enzyme inhibitor activity
Specific Function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6H
Uniprot ID:
Q13956
Molecular Weight:
9074.36 Da
References
  1. Zhang XJ, Cahill KB, Elfenbein A, Arshavsky VY, Cote RH: Direct allosteric regulation between the GAF domain and catalytic domain of photoreceptor phosphodiesterase PDE6. J Biol Chem. 2008 Oct 31;283(44):29699-705. doi: 10.1074/jbc.M803948200. Epub 2008 Sep 8. [PubMed:18779324 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on May 29, 2016 02:12