Vardenafil

Vardenafil

Clinical data
Trade names	Levitra, Staxyn, Vivanza
AHFS/Drugs.com	Monograph
MedlinePlus	a603035
Pregnancy category	AU: B3 US: B (No risk in non-human studies)
Routes of administration	Oral
ATC code	G04BE09 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	15%
Protein binding	95%
Metabolism	Hepatic (CYP3A4)
Biological half-life	4–5 hours
Excretion	Biliary
Identifiers
IUPAC name 4-[2-Ethoxy-5-(4-ethylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,6,8-tetrazabicyclo[4.3.0]nona-3,7,9-trien-2-one
CAS Number	224785-90-4 Y
PubChem CID	110634
IUPHAR/BPS	7320
DrugBank	DB00862 Y
ChemSpider	99300 Y
UNII	UCE6F4125H
ChEMBL	CHEMBL1520 Y
ECHA InfoCard	100.112.672
Chemical and physical data
Formula	C23H32N6O4S
Molar mass	488.604 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2\N=C(/Nn1c(nc(c12)C)CCC)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC)CC4
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) Y Key:SECKRCOLJRRGGV-UHFFFAOYSA-N Y

Vardenafil (INN) is a PDE₅ inhibitor used for treating erectile dysfunction that is sold under the trade names Levitra (Bayer AG, GSK, and SP), Staxyn in India, and Vivanza in Italy.

Vardenafil was co-marketed by Bayer Pharmaceuticals, GlaxoSmithKline, and Schering-Plough under the trade name Levitra. As of 2005, the co-promotion rights of GSK on Levitra have been returned to Bayer in many markets outside the U.S. In Italy, Bayer sells vardenafil as Levitra and GSK sells it as Vivanza. Thus, because of European Union trade rules, parallel imports might result in Vivanza sold next to Levitra in the EU.

An orally disintegrating form, marketed as Staxyn and Levitra Soft, has been gaining approvals in countries such as the United States and Canada.

Vardenafil's indications and contraindications are the same as with other PDE₅ inhibitors; it is closely related in function to sildenafil citrate (Viagra) and tadalafil (Cialis). The difference between the vardenafil molecule and sildenafil citrate is a nitrogen atom's position and the change of sildenafil's piperazine ring methyl group to an ethyl group. Tadalafil is structurally different from both sildenafil and vardenafil. Vardenafil's relatively short effective time is comparable to but somewhat longer than sildenafil's.

Beyond its indications for erectile dysfunction, vardenafil may be effective in the treatment of premature ejaculation, where it may significantly increase the time from penetration to ejaculation.