Vardenafil

Overview

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

Uses, dosage and effects

Medical uses

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. Despite the structural differences between vardenafil and sildenafil, they both show similar ocular side effects due to their similar selectivity overlap with PDE6, an enzyme found in the eye.[3] WP

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.[4] WP

Risks and side effects

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. WP

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.[5] WP

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.[6] WP

Interactions

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).[7][8] WP

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).[9][10] WP

History

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. WP

An orally disintegrating form, marketed as Staxyn and Levitra Soft, has been gaining approvals in countries such as the United States and Canada.[11][12] WP

Chemistry

Formula

C23H32N6O4S PC

Molar mass (g/mol)

488.6 PC

IUPAC name (computed by PubChem)

2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1H-imidazo[5,1-f][1,2,4]triazin-4-one PC

SMILES

CCCC1=NC(=C2N1NC(=NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CC)OCC)C PC

InChIKey

SECKRCOLJRRGGV-UHFFFAOYSA-N PC

PubChem CID

110634

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Levitra (vardenafil hydrochloride) tablets, for oral use Initial U.S. Approval: 2003
2. Other Levitra (Vardenafil) is A Drug Used to Treat Erectile Problems in Men
3. Journal / agency Bischoff E. Potency, selectivity, and consequences of nonselectivity of PDE inhibition. International Journal of Impotence Research. June 2004. doi:10.1038/sj.ijir.3901208 · PMID 15224129
4. Journal / agency Aversa A, Pili M, Francomano D, Bruzziches R, Spera E, La Pera G, Spera G. Effects of vardenafil administration on intravaginal ejaculatory latency time in men with lifelong premature ejaculation. International Journal of Impotence Research. July 2009. doi:10.1038/ijir.2009.21 · PMID 19474796
5. Other Stimmel GL, Gutierrez MA. Counseling Patients About Sexual Issues: Drug-Induced Priapism
6. Journal / agency FDA Announces Revisions to Labels for Cialis, Levitra and Viagra. October 18, 2007
7. Journal / agency Kloner RA. Pharmacology and drug interaction effects of the phosphodiesterase 5 inhibitors: focus on alpha-blocker interactions. The American Journal of Cardiology. December 2005. doi:10.1016/j.amjcard.2005.07.011 · PMID 16387566
8. Journal / agency Carson CC. PDE5 inhibitors: are there differences?. The Canadian Journal of Urology. February 2006. PMID 16526979
9. Journal / agency Lepor H, Lepor NE, Hill LA, Trohman RG. The QT Interval and Selection of Alpha-Blockers for Benign Prostatic Hyperplasia. Reviews in Urology. 2008. PMID 18660858 · PMC2483321
10. Other 2011 Nurse's Drug Handbook. June 29, 2010
11. Other New erectile dysfunction treatment Staxyn approved in the U.S. - Pharmaceutical Processing. June 21, 2010
12. Other Staxyn - New Innovation in Erectile Dysfunction Helps Younger Men Rise to the Occasion

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.