vardenafil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
inhibitors of phosphodiesterase PDE5 with vasodilator action 2809 224785-90-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • vardenafil hydrochloride hydrate
  • vardenafil dihydrochloride
  • vivanza
  • vardenafil
  • vardenafil hydrochloride
  • vardenafil hydrochloride trihydrate
  • levitra
  • vardenafil HCl
A piperazine derivative, PHOSPHODIESTERASE 5 INHIBITOR and VASODILATOR AGENT that is used as a UROLOGICAL AGENT in the treatment of ERECTILE DYSFUNCTION.
  • Molecular weight: 488.61
  • Formula: C23H32N6O4S
  • CLOGP: 2.23
  • LIPINSKI: 0
  • HAC: 10
  • HDO: 1
  • TPSA: 109.13
  • ALOGS: -3.18
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.11 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 4 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.58 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 15 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 3 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 13 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.05 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 19, 2003 FDA BAYER HLTHCARE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC G04BE09 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Drugs used in erectile dysfunction
FDA MoA N0000020026 Phosphodiesterase 5 Inhibitors
FDA EPC N0000175599 Phosphodiesterase 5 Inhibitor
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D058986 Phosphodiesterase 5 Inhibitors
MeSH PA D010726 Phosphodiesterase Inhibitors
MeSH PA D064804 Urological Agents
MeSH PA D014665 Vasodilator Agents
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:50218 phosphodiesterase inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Impotence indication 397803000
Induratio penis plastica contraindication 1335005 DOID:8616
Priapism contraindication 6273006 DOID:9286
Hearing loss contraindication 15188001
Myocardial infarction contraindication 22298006 DOID:5844
Fibrosis of corpus cavernosum contraindication 32608004
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Aortic valve stenosis contraindication 60573004 DOID:1712
Blood coagulation disorder contraindication 64779008 DOID:1247
Leukemia, disease contraindication 93143009 DOID:1240
Multiple myeloma contraindication 109989006 DOID:9538
Hb SS disease contraindication 127040003 DOID:10923
Acute peptic ulcer contraindication 196682000
Cerebrovascular accident contraindication 230690007
Penis bent contraindication 249247007
Idiopathic hypertrophic subaortic stenosis contraindication 360465008
Acute coronary syndrome contraindication 394659003
Anterior ischemic optic neuropathy contraindication 404659001
Congenital long QT syndrome contraindication 442917000
Hypertensive urgency contraindication 443482000
Pigmentary Retinopathy contraindication
Life-Threatening Cardiac Arrhythmias contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.87 Basic
pKa2 6.57 Basic
pKa3 5.17 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
cGMP-specific 3',5'-cyclic phosphodiesterase Enzyme INHIBITOR IC50 9.15 WOMBAT-PK CHEMBL
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A Enzyme IC50 7.04 WOMBAT-PK
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha Enzyme IC50 7.46 WOMBAT-PK
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A Enzyme IC50 6.34 CHEMBL
Phosphodiesterase 4 Enzyme IC50 5.35 CHEMBL
cGMP-dependent 3',5'-cyclic phosphodiesterase Enzyme IC50 5.51 CHEMBL
Phosphodiesterase 3 Enzyme IC50 5.68 CHEMBL
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A Enzyme IC50 6.89 CHEMBL
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Enzyme IC50 6.10 CHEMBL
Phosphodiesterase 1 Enzyme IC50 6.74 CHEMBL

External reference:

IDSource
4021404 VUID
N0000148820 NUI
D03260 KEGG_DRUG
224789-15-5 SECONDARY_CAS_RN
4021404 VANDF
C2700155 UMLSCUI
CHEBI:46295 CHEBI
VDN PDB_CHEM_ID
CHEMBL1339 ChEMBL_ID
CHEMBL1520 ChEMBL_ID
CHEMBL2106480 ChEMBL_ID
D000069058 MESH_DESCRIPTOR_UI
7950 INN_ID
DB00862 DRUGBANK_ID
UCE6F4125H UNII
135400189 PUBCHEM_CID
7320 IUPHAR_LIGAND_ID
1309396 RXNORM
17549 MMSL
47302 MMSL
83725 MMSL
d04893 MMSL
009915 NDDF
009916 NDDF
404858007 SNOMEDCT_US
407979001 SNOMEDCT_US
412528004 SNOMEDCT_US
426182008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7652 TABLET, FILM COATED 2.50 mg ORAL ANDA 27 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7653 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7654 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7655 TABLET, FILM COATED 20 mg ORAL ANDA 27 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 0173-0829 TABLET, FILM COATED 5 mg ORAL NDA 26 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 0173-0830 TABLET, FILM COATED 10 mg ORAL NDA 26 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 0173-0831 TABLET, FILM COATED 20 mg ORAL NDA 26 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2800 TABLET 2.50 mg ORAL ANDA 28 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2801 TABLET 5 mg ORAL ANDA 28 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2802 TABLET 10 mg ORAL ANDA 28 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2803 TABLET 20 mg ORAL ANDA 28 sections
Vardenafil Hydrochloride Human Prescription Drug Label 1 33342-151 TABLET 2.50 mg ORAL ANDA 27 sections
Vardenafil Hydrochloride Human Prescription Drug Label 1 33342-152 TABLET 5 mg ORAL ANDA 27 sections
Vardenafil Hydrochloride Human Prescription Drug Label 1 33342-153 TABLET 10 mg ORAL ANDA 27 sections
Vardenafil Hydrochloride Human Prescription Drug Label 1 33342-154 TABLET 20 mg ORAL ANDA 27 sections
Vardenafil Human Prescription Drug Label 1 33342-203 TABLET 11.85 mg ORAL ANDA 27 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-847 TABLET 10 mg ORAL ANDA 28 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-848 TABLET 20 mg ORAL ANDA 28 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-323 TABLET, FILM COATED 5 mg ORAL NDA 23 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-741 TABLET, FILM COATED 10 mg ORAL NDA 23 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-744 TABLET, FILM COATED 5 mg ORAL NDA 23 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-748 TABLET, FILM COATED 20 mg ORAL NDA 23 sections
Vardenafil Human Prescription Drug Label 1 46708-235 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 27 sections
VARDENULLFIL HYDROCHLORIDE Human Prescription Drug Label 1 46708-236 TABLET, FILM COATED 2.50 mg ORAL ANDA 27 sections
VARDENULLFIL HYDROCHLORIDE Human Prescription Drug Label 1 46708-237 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
VARDENULLFIL HYDROCHLORIDE Human Prescription Drug Label 1 46708-238 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
VARDENULLFIL HYDROCHLORIDE Human Prescription Drug Label 1 46708-239 TABLET, FILM COATED 20 mg ORAL ANDA 27 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 54868-4967 TABLET, FILM COATED 20 mg ORAL NDA 23 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 54868-4984 TABLET, FILM COATED 10 mg ORAL NDA 23 sections
Staxyn HUMAN PRESCRIPTION DRUG LABEL 1 54868-6333 TABLET, ORALLY DISINTEGRATING 10 mg ORAL NDA 26 sections