Vardenafil

Last updated

Vardenafil
Vardenafil structure.svg
Clinical data
Trade names Levitra, Staxyn, Vivanza
AHFS/Drugs.com Monograph
MedlinePlus a603035
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
Bioavailability 15%
Protein binding 95%
Metabolism Liver (CYP3A4)
Elimination half-life 4–5 hours
Excretion Bile duct
Identifiers
  • 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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.112.672 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H32N6O4S
Molar mass 488.61 g·mol−1
3D model (JSmol)
  • O=C2\N=C(/Nn1c(nc(c12)C)CCC)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC)CC4
  • 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) Yes check.svgY
  • Key:SECKRCOLJRRGGV-UHFFFAOYSA-N Yes check.svgY
   (verify)
Vardenafil 4 tablets Blister 20 mg Sexual enhancer (phosphodiesterase-5 inhibitors) - Vardenafil - Aristo Pharma - Vardenaristo - 4 tablets Blister 20 mg - Image 002.jpg
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]

Contents

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.[ citation needed ]

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]

Related Research Articles

Erectile dysfunction (ED), also referred to as impotence, is a form of sexual dysfunction in males characterized by the persistent or recurring inability to achieve or maintain a penile erection with sufficient rigidity and duration for satisfactory sexual activity. It is the most common sexual problem in males and can cause psychological distress due to its impact on self-image and sexual relationships.

<span class="mw-page-title-main">Sildenafil</span> Drug for erectile dysfunction and hypertension

Sildenafil, sold under the brand name Viagra, among others, is a medication used to treat erectile dysfunction and pulmonary arterial hypertension. It is also sometimes used off-label for the treatment of certain symptoms in secondary Raynaud's phenomenon. It is unclear if it is effective for treating sexual dysfunction in females. It can be taken orally, intravenously, or through the sublingual route. Onset when taken orally is typically within twenty minutes and lasts for about two hours.

Anorgasmia is a type of sexual dysfunction in which a person cannot achieve orgasm despite adequate sexual stimulation. Anorgasmia is far more common in females than in males and is especially rare in younger men. The problem is greater in women who are post-menopausal. In males, it is most closely associated with delayed ejaculation. Anorgasmia can often cause sexual frustration.

<span class="mw-page-title-main">Tadalafil</span> Medication used to treat erectile dysfunction

Tadalafil, sold under the brand name Cialis among others, is a medication used to treat erectile dysfunction, benign prostatic hyperplasia, and pulmonary arterial hypertension. It is taken by mouth. Onset is typically within half an hour and the duration is up to 36 hours.

Icos Corporation was an American biotechnology company and the largest biotechnology company in the U.S. state of Washington, before it was sold to Eli Lilly and Company in 2007. It was founded in 1989 by David Blech, Isaac Blech, Robert Nowinski, and George Rathmann, a pioneer in the industry and chief executive officer (CEO) and co-founder of Amgen. Icos focused on the development of drugs to treat inflammatory disorders. During its 17-year history, the company conducted clinical trials of twelve drugs, three of which reached the last phase of clinical trials. Icos also manufactured antibodies for other biotechnology companies.

<span class="mw-page-title-main">Isosorbide mononitrate</span> Chemical compound

Isosorbide mononitrate, sold under many brand names, is a medication used for heart-related chest pain (angina), heart failure and esophageal spasms. It can be used both to treat and to prevent heart-related chest pain; however, it is generally less preferred than beta blockers or calcium channel blockers. It is taken by mouth.

<span class="mw-page-title-main">PDE5 inhibitor</span> Vasodilating drug

A phosphodiesterase type 5 inhibitor is a vasodilating drug that works by blocking the degradative action of cGMP-specific phosphodiesterase type 5 (PDE5) on cyclic GMP in the smooth muscle cells lining the blood vessels supplying various tissues. These drugs dilate the corpora cavernosa of the penis, facilitating erection with sexual stimulation, and are used in the treatment of erectile dysfunction (ED). Sildenafil was the first effective oral treatment available for ED. Because PDE5 is also present in the smooth muscle of the walls of the arterioles within the lungs, two PDE5 inhibitors, sildenafil and tadalafil, are FDA-approved for the treatment of pulmonary hypertension. As of 2019, the wider cardiovascular benefits of PDE5 inhibitors are being appreciated.

cGMP-specific phosphodiesterase type 5 Mammalian protein found in Homo sapiens

Cyclic guanosine monophosphate-specific phosphodiesterase type 5 is an enzyme from the phosphodiesterase class. It is found in various tissues, most prominently the corpus cavernosum and the retina. It has also been recently discovered to play a vital role in the cardiovascular system.

<span class="mw-page-title-main">Udenafil</span> Chemical compound

The drug udenafil is marketed under the trade name Zydena. It is within the PDE5 inhibitor class (which also includes avanafil, sildenafil, tadalafil, and vardenafil). Like other PDE5 inhibitors, it is used to treat erectile dysfunction. Udenafil was developed by Dong-A Pharmaceutical. It has fairly rapid onset of action (peak plasma concentration after 1 to 1.5 hours), and has long duration of action (plasma half-life of 11 to 13 hours). Udenafil's pharmacokinetics allows once-daily dosage (in addition to on-demand use). Typical doses are 100 and 200 mg. Udenafil is available in Korea, Russia, and the Philippines. It has not yet been approved for use in the United States by the U.S. Food and Drug Administration.

<span class="mw-page-title-main">Avanafil</span> Chemical compound

Avanafil is a PDE5 inhibitor approved for erectile dysfunction by the FDA on April 27, 2012 and by EMA on June 21, 2013. Avanafil is sold under the brand names Stendra and Spedra. It was invented at Mitsubishi Tanabe Pharma, formerly known as Tanabe Seiyaku Co., and licensed to Vivus Inc., which partnered with Menarini Group to commercialise Spedra in over forty European countries, Australia, and New Zealand. Metuchen Pharmaceuticals obtained exclusive rights within the United States.

<span class="mw-page-title-main">Herbal viagra</span> A class of herbal products said to treat erectile dysfunction

Herbal viagra is a herbal product advertised as treating erectile dysfunction. Many different products are advertised as herbal viagra, but with varying ingredients. No clinical trials or scientific studies support the effectiveness of any of these ingredients for the treatment of erectile dysfunction and some products have been found to contain drugs and other adulterants, and have been the subject of FDA and FTC warnings and actions to remove them from the market.

<span class="mw-page-title-main">Acetildenafil</span> Chemical compound

Acetildenafil (hongdenafil) is a synthetic drug which acts as a phosphodiesterase inhibitor. It is an analog of sildenafil (Viagra) which has been detected in numerous different brands of "herbal aphrodisiac" products sold in convenience stores that claim to boost libido and alleviate erectile dysfunction.

<span class="mw-page-title-main">Lodenafil</span> Chemical compound

Lodenafil is a drug belonging to a class of drugs called PDE5 inhibitor, which many other erectile dysfunction drugs such as sildenafil, tadalafil, and vardenafil also belong to. Like udenafil and avanafil it belongs to a new generation of PDE5 inhibitors.

<span class="mw-page-title-main">Mirodenafil</span> Chemical compound

Mirodenafil belongs to the drug class PDE5 inhibitors, which includes avanafil, sildenafil, tadalafil, udenafil, and vardenafil, and is the first-line treatment for erectile dysfunction. Developed by SK Chemicals Life Science, mirodenafil is marketed in Korea under the trade name Mvix, offered both as tablets and as orally dissolving films.

<span class="mw-page-title-main">Sulfoaildenafil</span> Chemical compound

Sulfoaildenafil (thioaildenafil) is a synthetic drug that is a structural analog of sildenafil (Viagra). It was first reported in 2005, and it is not approved by any health regulation agency. Like sildenafil, sulfoaildenafil is a phosphodiesterase type 5 inhibitor.

<span class="mw-page-title-main">Aildenafil</span> Chemical compound

Aildenafil (methisosildenafil) is a synthetic drug that is a structural analog of sildenafil (Viagra). It was first reported in 2003. Like sildenafil, aildenafil is a phosphodiesterase type 5 inhibitor.

<span class="mw-page-title-main">Dapoxetine</span> Medication used to treat premature ejaculation

Dapoxetine, marketed as Priligy, among others, is a selective serotonin reuptake inhibitor (SSRI) used for the treatment of premature ejaculation (PE) in men 18–64 years old. Dapoxetine works by inhibiting the serotonin transporter, increasing serotonin's action at the postsynaptic cleft, and as a consequence promoting ejaculatory delay. As a member of the selective serotonin reuptake inhibitor (SSRI) family, dapoxetine was initially created as an antidepressant. However, unlike other SSRIs, dapoxetine is absorbed and eliminated rapidly in the body. Its fast-acting property makes it suitable for the treatment of PE, but not as an antidepressant.

Phosphodiesterases (PDEs) are a superfamily of enzymes. This superfamily is further classified into 11 families, PDE1 - PDE11, on the basis of regulatory properties, amino acid sequences, substrate specificities, pharmacological properties and tissue distribution. Their function is to degrade intracellular second messengers such as cyclic adenine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP) which leads to several biological processes like effect on intracellular calcium level by the Ca2+ pathway.

<span class="mw-page-title-main">Homosildenafil</span> Chemical compound

Homosildenafil is a synthetic drug which acts as a phosphodiesterase inhibitor. It is an analog of sildenafil and vardenafil. Homosildenafil was first identified as an adulterant in sex enhancement products in 2003 and was more recently detected in dietary supplements.

Drugs and Sexual Performance refers to the influence of substances on sexual function and experience. Sexual performance is known as the execution of the act of sex and the quality of sexual activity. This includes elements such as libido, sexual function, sensation . Drugs are termed as any chemical substance that produces a physiological and or psychological change in an organism. Drugs categorized as psychoactive drugs, antihypertensive drugs, antihistamines, cancer treatment, and hormone medication have a significant impact on sexual performance. Various drugs result in different effects, both positive and negative. Negative effects may include low libido, erection issues, vaginal dryness and anorgasmia. Positive effects usually address these issues, overall enhancing sexual performance and contributing to a more enjoyable sexual experience. It is crucial to know that the impact of drugs on sexual performance varies among individuals, especially among different genders. 

References

  1. 1 2 3 4 "Levitra (vardenafil hydrochloride) tablets, for oral use Initial U.S. Approval: 2003". DailyMed. Retrieved April 3, 2023.
  2. "Levitra (Vardenafil) is A Drug Used to Treat Erectile Problems in Men" (in German). Deutschemedz. Retrieved May 12, 2010.
  3. Aversa A, Pili M, Francomano D, Bruzziches R, Spera E, La Pera G, et al. (July 2009). "Effects of vardenafil administration on intravaginal ejaculatory latency time in men with lifelong premature ejaculation". International Journal of Impotence Research. 21 (4): 221–7. doi:10.1038/ijir.2009.21. PMID   19474796. S2CID   26078130.
  4. Stimmel GL, Gutierrez MA. "Counseling Patients About Sexual Issues: Drug-Induced Priapism". Medscape. Retrieved December 6, 2010.
  5. "FDA Announces Revisions to Labels for Cialis, Levitra and Viagra". Food and Drug Administration. October 18, 2007. Retrieved August 6, 2009.
  6. Kloner RA (December 2005). "Pharmacology and drug interaction effects of the phosphodiesterase 5 inhibitors: focus on alpha-blocker interactions". The American Journal of Cardiology. 96 (12B): 42M–46M. doi:10.1016/j.amjcard.2005.07.011. PMID   16387566.
  7. Carson CC (February 2006). "PDE5 inhibitors: are there differences?". The Canadian Journal of Urology. 13 (Suppl 1): 34–9. PMID   16526979.
  8. Lepor H, Lepor NE, Hill LA, Trohman RG (2008). "The QT Interval and Selection of Alpha-Blockers for Benign Prostatic Hyperplasia". Reviews in Urology. 10 (2): 85–91. PMC   2483321 . PMID   18660858.
  9. Ciranowicz-Steenburg M, ed. (June 29, 2010). 2011 Nurse's Drug Handbook. Jones & Bartlett Publishers. ISBN   978-1-4496-5372-9.
  10. "New erectile dysfunction treatment Staxyn approved in the U.S. - Pharmaceutical Processing". pharmpro.com. June 21, 2010. Archived from the original on April 6, 2012.
  11. "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). August 3, 2022.
  13. Tucker J, Fischer T, Upjohn L, Mazzera D, Kumar M (October 2018). "Unapproved Pharmaceutical Ingredients Included in Dietary Supplements Associated With US Food and Drug Administration Warnings". JAMA Network Open. 1 (6): e183337. doi:10.1001/jamanetworkopen.2018.3337. PMC   6324457 . PMID   30646238.