Chemistry:Vardenafil

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Short description: Chemical compound
Vardenafil
Vardenafil structure.svg
Clinical data
Trade namesLevitra, Staxyn, Vivanza
AHFS/Drugs.comMonograph
MedlinePlusa603035
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only [1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability15%
Protein binding95%
MetabolismLiver (CYP3A4)
Elimination half-life4–5 hours
ExcretionBile duct
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC23H32N6O4S
Molar mass488.61 g·mol−1
3D model (JSmol)
  (verify)
Vardenafil 4 tablets Blister 20 mg

Vardenafil, sold under the brand name Levitra among others, is a medication that is used for treating erectile dysfunction.[1][2] It is a PDE5 inhibitor.[1] It is taken by mouth.[1]

Medical use

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. Vardenafil also does not have an effect on PDE6, which means that it does not have vision adverse effects.

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.[3]

Adverse reactions

The common, adverse drug reactions (side effects) are the same as with other PDE5 inhibitors. The frequent vardenafil-specific side-effect is nausea; the infrequent side effects are abdominal pain, back pain, photosensitivity, abnormal vision, eye pain, facial edema, hypotension, palpitation, tachycardia, arthralgia, myalgia, rash, itch, and priapism.

One possibly serious, but rare, side effect with vardenafil is heart attack. Also, in rare cases, vardenafil use may cause priapism, a very painful emergency condition that can cause impotence if left untreated.[4]

In October 2007, the U.S. Food and Drug Administration (FDA) announced that a warning about possible deafness (sudden hearing loss) would be added to the drug labels of vardenafil, and other PDE5 inhibitors.[5]

Interactions

Vardenafil should not be used by people taking nitrate medications, because combining them with vardenafil might provoke potentially life-threatening hypotension (low blood pressure).[6][7]

Further, vardenafil causes lengthening of the QT interval. Therefore, it should not be taken by people taking other medications that affect the QT interval (such as amiodarone).[8][9]

History

Vardenafil was co-marketed by Bayer Pharmaceuticals, GlaxoSmithKline, and Schering-Plough under the brand name Levitra. As of 2005, the co-promotion rights of GSK on Levitra have been returned to Bayer in many markets outside the US. 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[10] and Canada.[11]

Tainted supplements

The US Food and Drug Administration (FDA) has found vardenafil and other synthetic PDE5 inhibitors in numerous products marketed as "herbal" supplements or "all natural" products for male enhancement.[12][13]

References

  1. ↑ 1.0 1.1 1.2 1.3 "Levitra (vardenafil hydrochloride) tablets, for oral use Initial U.S. Approval: 2003". https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=595067. 
  2. ↑ "Levitra (Vardenafil) is A Drug Used to Treat Erectile Problems in Men" (in de). Deutschemedz. https://deutschemedz.de/levitra/. 
  3. ↑ "Effects of vardenafil administration on intravaginal ejaculatory latency time in men with lifelong premature ejaculation". International Journal of Impotence Research 21 (4): 221–7. July 2009. doi:10.1038/ijir.2009.21. PMID 19474796. 
  4. ↑ Schools of Pharmacy (Glen L. Stimmel, Pharm.D., and Mary A. Gutierrez, Pharm.D.) and Medicine (Glen L. Stimmel, Pharm.D.), University of Southern California, Los Angeles, California.. "Counseling Patients About Sexual Issues: Drug-Induced Priapism". Medscape. http://www.medscape.com/viewarticle/549253_6. 
  5. ↑ "FDA Announces Revisions to Labels for Cialis, Levitra and Viagra". Food and Drug Administration. 2007-10-18. https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2007/ucm109012.htm. 
  6. ↑ "Pharmacology and drug interaction effects of the phosphodiesterase 5 inhibitors: focus on alpha-blocker interactions". The American Journal of Cardiology 96 (12B): 42M–46M. December 2005. doi:10.1016/j.amjcard.2005.07.011. PMID 16387566. 
  7. ↑ "PDE5 inhibitors: are there differences?". The Canadian Journal of Urology 13 Suppl 1: 34–9. February 2006. PMID 16526979. 
  8. ↑ "The QT Interval and Selection of Alpha-Blockers for Benign Prostatic Hyperplasia". Reviews in Urology 10 (2): 85–91. 2008. PMID 18660858. 
  9. ↑ Learning, Jones & Bartlett (2010-06-29). 2011 Nurse's Drug Handbook. Jones & Bartlett Publishers. ISBN 9781449653729. https://books.google.com/books?id=PaiBU04wrrgC&q=vardenafil++QT+interval++amiodarone&pg=PA1079. 
  10. ↑ "New erectile dysfunction treatment Staxyn approved in the U.S. - Pharmaceutical Processing". 2010-06-21. https://www.pharmpro.com/News/Feeds/2010/06/pharmaceutical-companies-bayer-new-erectile-dysfunction-treatment-staxyn-approve. 
  11. ↑ "Staxyn - New Innovation in Erectile Dysfunction Helps Younger Men Rise to the Occasion". http://www.newswire.ca/en/story/832217/staxyn-new-innovation-in-erectile-dysfunction-helps-younger-men-rise-to-the-occasion. 
  12. ↑ "Tainted Products Marketed as Dietary Supplements". U.S. Food and Drug Administration (FDA). 3 August 2022. https://www.accessdata.fda.gov/scripts/sda/sdNavigation.cfm?sd=tainted_supplements_cder&displayAll=false&page=1. 
  13. ↑ "Unapproved Pharmaceutical Ingredients Included in Dietary Supplements Associated With US Food and Drug Administration Warnings". JAMA Network Open 1 (6): e183337. October 2018. doi:10.1001/jamanetworkopen.2018.3337. PMID 30646238. 

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