Avanafil

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Avanafil
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Avanafil is a PDE5 inhibitor
Clinical data
Trade namesStendra
AHFS/Drugs.comMonograph
MedlinePlusa614010
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Routes of
administration		By mouth
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Legal status
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Identifiers
  • (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
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Chemical and physical data
FormulaC23H26ClN7O3
Molar mass483.96 g·mol−1
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  • Clc1c(OC)ccc(c1)CNc3nc(ncc3C(=O)NCc2ncccn2)N4[C@@H](CCC4)CO
  • InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1 checkY
  • Key:WEAJZXNPAWBCOA-INIZCTEOSA-N checkY
Data page
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Avanafil is a PDE5 inhibitor approved for erectile dysfunction by the FDA on April 27, 2012[2] and by EMA on June 21, 2013.[3] Avanafil is sold under the brand names Stendra and Spedra. It was invented at Mitsubishi Tanabe Pharma, formerly known as Tanabe Seiyaku Co.,[4] and licensed to Vivus Inc., which partnered with Menarini Group to commercialise Spedra in over forty European countries, Australia, and New Zealand.[5] Metuchen Pharmaceuticals obtained exclusive rights within the United States.[6]

Avanafil acts by inhibiting a specific phosphodiesterase type 5 enzyme found in various body tissues, primarily in the corpus cavernosum penis.[7] Other similar drugs are sildenafil, tadalafil and vardenafil. The advantage of avanafil is that it has very fast onset of action compared with other PDE5 inhibitors. It is absorbed quickly, reaching a maximum serum concentration in about thirty to forty-five minutes.[8] About two-thirds of the participants were able to engage in sexual activity within fifteen minutes.[8]

Medical use

Avanafil is used to treat erectile dysfunction (ED).[9]

Adverse effects

Although avanafil is generally well tolerated, dose dependent adverse effects can occur.[8] The most common adverse effects include headache, flushing, nasopharyngitis, nasal congestion, and back pain.[8] While it is also uncommon, there is a potential for visual disturbances to occur in patients,[8] as well as hearing impairment.[10]

Mechanism of action

Avanafil inhibits phosphodiesterase-5, preventing the degradation of cGMP.[11][12] The increased levels of cGMP causes vasodilation, resulting in an increased blood flow in the penis.[12] Avanafil's mechanism of action takes place once nitric oxide is released, in association with sexual stimulation.[12]

Synthesis

Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:[4]

File:Avanafil synthesis.png

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Prescription medicines: registration of new chemical entities in Australia, 2016". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Stendra FDA Approval History". Drugs.com. Retrieved 6 March 2021.
  3. ^ Page Module:Citation/CS1/styles.css has no content."Spedra (avanafil)". European Medicines Agency. Archived from the original on 1 April 2014. Retrieved 17 April 2014.
  4. ^ a b Page Template:Citation/styles.css has no content.US 6797709, Yamada K, Matsuki K, Omori K Kikkawa K, "Aromatic nitrogen-containing 6-membered cyclic compounds", issued Script error: No such module "auto date formatter"., assigned to Tanabe Seiyaku Co 
  5. ^ Page Module:Citation/CS1/styles.css has no content."VIVUS Announces Avanafil Partnership With Menarini". Vivus Inc. Archived from the original on 2015-12-08.
  6. ^ Page Module:Citation/CS1/styles.css has no content."VIVUS and Metuchen Pharmaceuticals Announce License Agreement for Commercial Rights to Stendra". Vivus Inc. 3 October 2016. Archived from the original on 29 November 2022.
  7. ^ Page Module:Citation/CS1/styles.css has no content."avanafil, Spedra". Medicine Net. Retrieved 17 April 2014.
  8. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.Kyle JA, Brown DA, Hill JK (October 2013). "Avanafil for erectile dysfunction". The Annals of Pharmacotherapy. 47 (10). Sage Publishing: 1312–1320. doi:10.1177/1060028013501989. PMID 24259695. S2CID 6562049.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Burke RM, Evans JD (2012). "Avanafil for treatment of erectile dysfunction: review of its potential". Vascular Health and Risk Management. 8: 517–523. doi:10.2147/VHRM.S26712. PMC 3433322. PMID 22973106.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Zhang X, Xia L, Yang Q, Tang P (April 2024). "Phosphodiesterase type 5 inhibitors related hearing impairment: a real world study based on the FDA adverse event reporting system". Scientific Reports. 14. doi:10.1038/s41598-024-60493-w. ISSN 2045-2322. PMC 11056362. PMID 38679603. Retrieved 2025-12-08.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Kotera J, Mochida H, Inoue H, Noto T, Fujishige K, Sasaki T, et al. (August 2012). "Avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction". The Journal of Urology. 188 (2): 668–674. doi:10.1016/j.juro.2012.03.115. PMID 22704456.
  12. ^ a b c Page Module:Citation/CS1/styles.css has no content.Sanford M (October 2013). "Avanafil: A Review of Its Use in Patients with Erectile Dysfunction". Drugs & Aging. 30 (10): 853–62. doi:10.1007/s40266-013-0112-x. PMID 23955441. S2CID 23558269.

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