Avanafil

Avanafil
Avanafil is a PDE5 inhibitor
Names
Trade namesStendra
IUPAC name
  • (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
Clinical data
Drug classPDE5 inhibitor[1]
Main usesErectile dysfunction[1]
Side effectsHeadache, flushing, stuffy nose, back pain[1]
InteractionsNitrovasodilator[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: N (Not classified yet)
    Routes of
    use    		By mouth
    Onset of actionWithin 15 min[2]
    Duration of action2 hr[2]
    Typical dose50 to 200 mg[2]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa614010
    Legal
    License data
    Legal status
    Chemical and physical data
    FormulaC23H26ClN7O3
    Molar mass483.96 g·mol−1
    3D model (JSmol)
    SMILES
    • Clc1c(OC)ccc(c1)CNc3nc(ncc3C(=O)NCc2ncccn2)N4[C@@H](CCC4)CO
    InChI
    • 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

    Avanafil, sold under the brand names Stendra and Spedra, is medication used to treat erectile dysfunction.[1] It is taken by mouth.[3] Effects generally begin within 15 minutes and last for up to 2 hours.[2]

    Common side effects include headache, flushing, stuffy nose, and back pain.[1] Other side effects may include priapism, vision loss, and hearing loss.[3] It should not be used with nitrovasodilator.[1] It should also be avoided in people with significant liver or kidney problems.[3] It is a PDE5 inhibitor and works by blocking the phosphodiesterase enzyme, thus increasing levels of cyclic guanosine monophosphate (cGMP).[1]

    Avanafil was approved for medical use in the United States in 2012 and Europe in 2013.[3][1] In the United Kingdom 4 pills of 100 mg costs the NHS about £14 as of 2021.[4] This amount in the United States is about 210 USD.[5]

    Medical use

    Dosage

    It is taken at a dose of 100 mg about 15 minutes before sex.[3]

    Mechanism of action

    Avanafil acts by inhibiting a specific phosphodiesterase type 5 enzyme found in various body tissues, primarily in the corpus cavernosum penis.[6] 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.[7]

    Synthesis

    Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:[8]

    History

    It was invented at Mitsubishi Tanabe Pharma, formerly known as Tanabe Seiyaku Co.,[8] and licensed to Vivus Inc., which partnered with Menarini Group to commercialise Spedra in over forty European countries, Australia, and New Zealand.[9] Metuchen Pharmaceuticals obtained exclusive rights within the United States.[10]

    References

    1. 1 2 3 4 5 6 7 8 9 "Spedra". Archived from the original on 11 April 2021. Retrieved 16 January 2022.
    2. 1 2 3 4 "Avanafil". American Society of Health-System Pharmacists. Archived from the original on 30 November 2020. Retrieved 16 January 2022.
    3. 1 2 3 4 5 "DailyMed - STENDRA- avanafil tablet". dailymed.nlm.nih.gov. Archived from the original on 17 April 2021. Retrieved 16 January 2022.
    4. ↑ BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 859. ISBN 978-0857114105.
    5. ↑ "Stendra Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 15 October 2021. Retrieved 16 January 2022.
    6. ↑ "avanafil, Spedra". Medicine Net. Archived from the original on 20 April 2014. Retrieved 17 April 2014.
    7. ↑ Kyle JA, Brown DA, Hill JK (October 2013). "Avanafil for erectile dysfunction". The Annals of Pharmacotherapy. Sage Publishing. 47 (10): 1312–20. doi:10.1177/1060028013501989. PMID 24259695. S2CID 6562049.
    8. 1 2 US 6797709, Yamada K, Matsuki K, Omori K Kikkawa K, "Aromatic nitrogen-containig 6-membered cyclic compounds", issued 11 December 2003, assigned to Tanabe Seiyaku Co 
    9. ↑ "VIVUS Announces Avanafil Partnership With Menarini". Vivus Inc. Archived from the original on 2015-12-08.
    10. ↑ "VIVUS and Metuchen Pharmaceuticals Announce License Agreement for Commercial Rights to Stendra". Vivus Inc. 3 October 2016. Archived from the original on 10 September 2019. Retrieved 17 April 2021.
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