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)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
No adverse event 38.32 0 7 16 9521 2348541
Erectile dysfunction 31.17 0 3 20 24 2358038

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Erectile dysfunction 1524.87 62.41 300 1430 4197 1740854
Drug ineffective 527.34 62.41 238 1492 63563 1681488
Adverse event 408.68 62.41 104 1626 4564 1740487
Headache 391.89 62.41 162 1568 34214 1710837
Product used for unknown indication 326.39 62.41 49 1681 91 1744960
Erection increased 321.60 62.41 54 1676 259 1744792
Flushing 318.46 62.41 91 1639 6188 1738863
Nasal congestion 202.72 62.41 55 1675 3056 1741995
Optic ischaemic neuropathy 127.26 62.41 27 1703 512 1744539
Visual impairment 122.36 62.41 44 1686 6174 1738877
Vision blurred 109.36 62.41 44 1686 8379 1736672
No adverse event 99.38 62.41 36 1694 5146 1739905
Blindness unilateral 96.35 62.41 24 1706 942 1744109
Dizziness 89.74 62.41 61 1669 34300 1710751
Penis disorder 78.38 62.41 17 1713 358 1744693
Cyanopsia 77.63 62.41 14 1716 107 1744944
Blindness transient 65.06 62.41 16 1714 594 1744457
Priapism 64.03 62.41 19 1711 1445 1743606

Pharmacologic Action:

SourceCodeDescription
ATC G04BE09 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Drugs used in erectile dysfunction
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
CHEBI has role CHEBI:35620 vasodilator agent
MeSH PA D064804 Urological Agents
MeSH PA D014665 Vasodilator Agents

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
10MG LEVITRA BAYER HLTHCARE N021400 Aug. 19, 2003 RX TABLET ORAL 8273876 July 23, 2027 TREATEMENT OF ERECTIILE DYSFUNCTION BY ADMINISTERING A FILM-COATED TABLET
2.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** LEVITRA BAYER HLTHCARE N021400 Aug. 19, 2003 DISCN TABLET ORAL 8273876 July 23, 2027 TREATEMENT OF ERECTIILE DYSFUNCTION BY ADMINISTERING A FILM-COATED TABLET
20MG LEVITRA BAYER HLTHCARE N021400 Aug. 19, 2003 RX TABLET ORAL 8273876 July 23, 2027 TREATEMENT OF ERECTIILE DYSFUNCTION BY ADMINISTERING A FILM-COATED TABLET
5MG LEVITRA BAYER HLTHCARE N021400 Aug. 19, 2003 RX TABLET ORAL 8273876 July 23, 2027 TREATEMENT OF ERECTIILE DYSFUNCTION BY ADMINISTERING A FILM-COATED TABLET

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
D000069058 MESH_DESCRIPTOR_UI
4021404 VUID
N0000148820 NUI
C0971579 UMLSCUI
D03260 KEGG_DRUG
5M8S2CU0TS UNII
330808-88-3 SECONDARY_CAS_RN
407979001 SNOMEDCT_US
306674 RXNORM
d04893 MMSL
404858007 SNOMEDCT_US
4021404 VANDF
009915 NDDF
CHEMBL1339 ChEMBL_ID
CHEMBL1520 ChEMBL_ID
DB00862 DRUGBANK_ID
7950 INN_ID
VDN PDB_CHEM_ID
CHEBI:46295 CHEBI
CHEMBL2106480 ChEMBL_ID
135400189 PUBCHEM_CID
7320 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7652 TABLET, FILM COATED 2.50 mg ORAL ANDA 18 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7653 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7654 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-7655 TABLET, FILM COATED 20 mg ORAL ANDA 18 sections
Staxyn HUMAN PRESCRIPTION DRUG LABEL 1 0173-0822 TABLET, ORALLY DISINTEGRATING 11.85 mg ORAL NDA 18 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 0173-0829 TABLET, FILM COATED 5 mg ORAL NDA 17 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 0173-0830 TABLET, FILM COATED 10 mg ORAL NDA 17 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 0173-0831 TABLET, FILM COATED 20 mg ORAL NDA 17 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2800 TABLET 2.50 mg ORAL ANDA 19 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2801 TABLET 5 mg ORAL ANDA 19 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2802 TABLET 10 mg ORAL ANDA 19 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-2803 TABLET 20 mg ORAL ANDA 19 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33342-151 TABLET 2.50 mg ORAL ANDA 18 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33342-152 TABLET 5 mg ORAL ANDA 18 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33342-153 TABLET 10 mg ORAL ANDA 18 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33342-154 TABLET 20 mg ORAL ANDA 18 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-847 TABLET 10 mg ORAL ANDA 19 sections
Vardenafil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-848 TABLET 20 mg ORAL ANDA 19 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-323 TABLET, FILM COATED 5 mg ORAL NDA 14 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-741 TABLET, FILM COATED 10 mg ORAL NDA 14 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-744 TABLET, FILM COATED 5 mg ORAL NDA 14 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 43353-748 TABLET, FILM COATED 20 mg ORAL NDA 14 sections
Vardenafil HUMAN PRESCRIPTION DRUG LABEL 1 46708-235 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 18 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 54868-4967 TABLET, FILM COATED 20 mg ORAL NDA 14 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 54868-4984 TABLET, FILM COATED 10 mg ORAL NDA 14 sections
Staxyn HUMAN PRESCRIPTION DRUG LABEL 1 54868-6333 TABLET, ORALLY DISINTEGRATING 10 mg ORAL NDA 17 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 55289-193 TABLET, FILM COATED 20 mg ORAL NDA 17 sections
Vardenafil HUMAN PRESCRIPTION DRUG LABEL 1 62332-235 TABLET, ORALLY DISINTEGRATING 10 mg ORAL ANDA 18 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 63629-3372 TABLET, FILM COATED 20 mg ORAL NDA 13 sections
Levitra HUMAN PRESCRIPTION DRUG LABEL 1 67544-507 TABLET, FILM COATED 20 mg ORAL NDA 14 sections