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MedKoo Cat#: 314211 | Name: Avanafil
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Avanafil is a PDE5 inhibitor approved for erectile dysfunction by FDA on April 27, 2012 and by EMA on June 21, 2013. Avanafil is known by the trademark names Stendra and Spedra and was developed by Vivus Inc. Avanafil acts by inhibiting a specific phosphodiesterase type 5 enzyme which is found in various body tissues, but primarily in the corpus cavernosum penis, as well as the retina.

Chemical Structure

Avanafil
Avanafil
CAS#330784-47-9 (free base)

Theoretical Analysis

MedKoo Cat#: 314211

Name: Avanafil

CAS#: 330784-47-9 (free base)

Chemical Formula: C23H26ClN7O3

Exact Mass: 483.1786

Molecular Weight: 483.95

Elemental Analysis: C, 57.08; H, 5.42; Cl, 7.33; N, 20.26; O, 9.92

Price and Availability

Size Price Availability Quantity
200mg USD 250.00 2 Weeks
2g USD 750.00 2 Weeks
5g USD 1,250.00 2 Weeks
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Related CAS #
330784-47-9 (free base) 330784-48-0 (dibesylate) Avanafil metabolite M4 2748151-94-0 (metabolite M16)
Synonym
TA-1790; TA 1790; TA1790; Avanafil; trade name: Stendra; Spedra
IUPAC/Chemical Name
(S)-4-[(3-Chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2pyrimidinylmethyl)-5-pyrimidinecarboxamide
InChi Key
WEAJZXNPAWBCOA-INIZCTEOSA-N
InChi Code
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
SMILES Code
O=C(C1=CN=C(N2[C@H](CO)CCC2)N=C1NCC3=CC=C(OC)C(Cl)=C3)NCC4=NC=CC=N4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO (10mg/mL)
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Avanafil(TA-1790) is a potent and highly selective phosphodiesterase-5(PDE-5) inhibitor(IC50=5.2 nM).
In vitro activity:
The results of the effect of DMSO and the three concentrations (10, 30, and 60 μM) of avanafil used in the study on KCl-induced contractility of isolated detrusor strips are shown in Table 1. As shown, DMSO did not significantly inhibit KCl-induced detrusor contractility (P > 0.05). The lowest concentration of avanafil (10 μM) also did not significantly inhibit the detrusor (P > 0.05), whereas the 30 and 60 μM concentrations of avanafil caused a significant inhibitory effect of KCl-induced detrusor contractility (P < 0.05). A representative tracing of the concentration-dependent inhibitory effects of avanafil on KCl-induced detrusor contractility is given in Figure 1. Reference: Int J Appl Basic Med Res. 2019 Oct-Dec; 9(4): 231–235. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6822320/
In vivo activity:
The IC injection of avanafil (30, 100 and 300 μg kg−1) produced concentration-dependent increases in ICP (Fig. 3a) and ICP/MAP (Fig. 3b). The increases in ICP (Fig. 3c) and ICP/MAP (Fig. 3d) in response to IC injection of SNP (1 μg kg−1) were significantly enhanced on pressure of avanafil (300 μg kg−1) compared to control rats. Reference: Andrologia. 2015 Oct;47(8):897-903. https://pubmed.ncbi.nlm.nih.gov/25233953/
Solvent mg/mL mM
Solubility
DMF 20.0 41.33
DMSO:PBS (pH 7.2) (1:20) 0.1 0.10
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 483.95 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Dhruva A, Hamsavardhini VK, Kamatham S, Kataria A, Kumar A, Shanthi M, Peedicayil J. Avanafil Inhibits the Contractility of the Isolated Caprine Detrusor Muscle. Int J Appl Basic Med Res. 2019 Oct-Dec;9(4):231-235. doi: 10.4103/ijabmr.IJABMR_339_18. Epub 2019 Oct 11. PMID: 31681549; PMCID: PMC6822320. 2. Kurakula M, Ahmed OA, Fahmy UA, Ahmed TA. Solid lipid nanoparticles for transdermal delivery of avanafil: optimization, formulation, in-vitro and ex-vivo studies. J Liposome Res. 2016 Dec;26(4):288-96. doi: 10.3109/08982104.2015.1117490. Epub 2016 Jan 19. PMID: 26784833. 3. Gur S, Sikka SC, Pankey EA, Lasker GF, Chandra S, Kadowitz PJ, Hellstrom WJ. Effect of avanafil on rat and human corpus cavernosum. Andrologia. 2015 Oct;47(8):897-903. doi: 10.1111/and.12344. Epub 2014 Sep 19. PMID: 25233953. 4. Kotera J, Mochida H, Inoue H, Noto T, Fujishige K, Sasaki T, Kobayashi T, Kojima K, Yee S, Yamada Y, Kikkawa K, Omori K. Avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction. J Urol. 2012 Aug;188(2):668-74. doi: 10.1016/j.juro.2012.03.115. Epub 2012 Jun 15. PMID: 22704456.
In vitro protocol:
1. Dhruva A, Hamsavardhini VK, Kamatham S, Kataria A, Kumar A, Shanthi M, Peedicayil J. Avanafil Inhibits the Contractility of the Isolated Caprine Detrusor Muscle. Int J Appl Basic Med Res. 2019 Oct-Dec;9(4):231-235. doi: 10.4103/ijabmr.IJABMR_339_18. Epub 2019 Oct 11. PMID: 31681549; PMCID: PMC6822320. 2. Kurakula M, Ahmed OA, Fahmy UA, Ahmed TA. Solid lipid nanoparticles for transdermal delivery of avanafil: optimization, formulation, in-vitro and ex-vivo studies. J Liposome Res. 2016 Dec;26(4):288-96. doi: 10.3109/08982104.2015.1117490. Epub 2016 Jan 19. PMID: 26784833.
In vivo protocol:
1. Gur S, Sikka SC, Pankey EA, Lasker GF, Chandra S, Kadowitz PJ, Hellstrom WJ. Effect of avanafil on rat and human corpus cavernosum. Andrologia. 2015 Oct;47(8):897-903. doi: 10.1111/and.12344. Epub 2014 Sep 19. PMID: 25233953. 2. Kotera J, Mochida H, Inoue H, Noto T, Fujishige K, Sasaki T, Kobayashi T, Kojima K, Yee S, Yamada Y, Kikkawa K, Omori K. Avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction. J Urol. 2012 Aug;188(2):668-74. doi: 10.1016/j.juro.2012.03.115. Epub 2012 Jun 15. PMID: 22704456.
1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Avanafil. 2017 Aug 2. PMID: 31643479. 2: Avanafil for erectile dysfunction. Aust Prescr. 2019 Jun;42(3):113-114. doi: 10.18773/austprescr.2019.043. Epub 2019 May 13. PMID: 31363316; PMCID: PMC6594841. 3: Kyle JA, Brown DA, Hill JK. Avanafil for erectile dysfunction. Ann Pharmacother. 2013 Oct;47(10):1312-20. doi: 10.1177/1060028013501989. Epub 2013 Sep 27. PMID: 24259695. 4: Boeri L, Capogrosso P, Ventimiglia E, Serino A, La Croce G, Russo A, Damiano R, Montorsi F, Salonia A. Avanafil - a further step to tailoring patient needs and expectations. Expert Rev Clin Pharmacol. 2016 Sep;9(9):1171-81. doi: 10.1080/17512433.2016.1195261. Epub 2016 Jun 13. PMID: 27232892. 5: Sanford M. Avanafil: a review of its use in patients with erectile dysfunction. Drugs Aging. 2013 Oct;30(10):853-62. doi: 10.1007/s40266-013-0112-x. PMID: 23955441. 6: Zurawin JL, Stewart CA, Anaissie JE, Yafi FA, Hellstrom WJ. Avanafil for the treatment of erectile dysfunction. Expert Rev Clin Pharmacol. 2016 Sep;9(9):1163-70. doi: 10.1080/17512433.2016.1212655. Epub 2016 Aug 2. PMID: 27416913. 7: Burke RM, Evans JD. Avanafil for treatment of erectile dysfunction: review of its potential. Vasc Health Risk Manag. 2012;8:517-23. doi: 10.2147/VHRM.S26712. Epub 2012 Aug 29. PMID: 22973106; PMCID: PMC3433322. 8: Egui-Rojo MA, Moncada-Iribarren I, Carballido-Rodríguez J, Martínez-Salamanca JI. Avanafil for the treatment of erectile dysfunction. An updated review. Arch Esp Urol. 2014 Dec;67(10):839-47. English, Spanish. PMID: 25582903. 9: Cui YS, Li N, Zong HT, Yan HL, Zhang Y. Avanafil for male erectile dysfunction: a systematic review and meta-analysis. Asian J Androl. 2014 May- Jun;16(3):472-7. doi: 10.4103/1008-682X.123670. PMID: 24589460; PMCID: PMC4023381. 10: Kumar M, Pathade AD, Gupta SV, Goyal S, Rath D, Thakre M, Sanmukhani J, Mittal R. Efficacy and safety of avanafil as compared with sildenafil in the treatment of erectile dysfunction: A randomized, double blind, multicenter clinical trial. Int J Urol. 2022 Apr;29(4):351-359. doi: 10.1111/iju.14785. Epub 2022 Jan 26. PMID: 35080051; PMCID: PMC9303470. 11: Segal R, Burnett AL. Avanafil for the treatment of erectile dysfunction. Drugs Today (Barc). 2012 Jan;48(1):7-15. doi: 10.1358/dot.2012.48.1.1722068. PMID: 22384456. 12: Derosa G, D'Angelo A, Preti PS, Maffioli P. Evaluation of the Effect on Sexual Performance of a Nutraceutical Combination Containing Alpha Lipoic Acid, Vitis vinifera L. and Ginkgo biloba, Compared to Placebo, Avanafil or a Combination of Nutraceutical Plus Avanafil in Males With Type 2 Diabetes Mellitus With Erectile Dysfunction. Front Endocrinol (Lausanne). 2022 Apr 7;13:847240. doi: 10.3389/fendo.2022.847240. PMID: 35464055; PMCID: PMC9022207. 13: Limin M, Johnsen N, Hellstrom WJ. Avanafil, a new rapid-onset phosphodiesterase 5 inhibitor for the treatment of erectile dysfunction. Expert Opin Investig Drugs. 2010 Nov;19(11):1427-37. doi: 10.1517/13543784.2010.518955. Epub 2010 Oct 13. PMID: 20939743. 14: Corona G, Rastrelli G, Burri A, Jannini EA, Maggi M. The safety and efficacy of Avanafil, a new 2(nd) generation PDE5i: comprehensive review and meta- analysis. Expert Opin Drug Saf. 2016;15(2):237-47. doi: 10.1517/14740338.2016.1130126. Epub 2016 Jan 20. Erratum in: Expert Opin Drug Saf. 2016;15(2):v. PMID: 26646748. 15: Dhruva A, Hamsavardhini VK, Kamatham S, Kataria A, Kumar A, Shanthi M, Peedicayil J. Avanafil Inhibits the Contractility of the Isolated Caprine Detrusor Muscle. Int J Appl Basic Med Res. 2019 Oct-Dec;9(4):231-235. doi: 10.4103/ijabmr.IJABMR_339_18. Epub 2019 Oct 11. PMID: 31681549; PMCID: PMC6822320. 16: Wang H, Yuan J, Hu X, Tao K, Liu J, Hu D. The effectiveness and safety of avanafil for erectile dysfunction: a systematic review and meta-analysis. Curr Med Res Opin. 2014 Aug;30(8):1565-71. doi: 10.1185/03007995.2014.909391. Epub 2014 Apr 14. PMID: 24701971. 17: Katz EG, Tan RB, Rittenberg D, Hellstrom WJ. Avanafil for erectile dysfunction in elderly and younger adults: differential pharmacology and clinical utility. Ther Clin Risk Manag. 2014 Aug 27;10:701-11. doi: 10.2147/TCRM.S57610. PMID: 25210457; PMCID: PMC4155803. 18: Kotera J, Mochida H, Inoue H, Noto T, Fujishige K, Sasaki T, Kobayashi T, Kojima K, Yee S, Yamada Y, Kikkawa K, Omori K. Avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction. J Urol. 2012 Aug;188(2):668-74. doi: 10.1016/j.juro.2012.03.115. Epub 2012 Jun 15. PMID: 22704456. 19: Chowdari Gurram P, Satarker S, Kumar G, Begum F, Mehta C, Nayak U, Mudgal J, Arora D, Nampoothiri M. Avanafil mediated dual inhibition of IKKβ and TNFR1 in an experimental paradigm of Alzheimer's disease: in silico and in vivo approach. J Biomol Struct Dyn. 2022 Dec 19:1-19. doi: 10.1080/07391102.2022.2156924. Epub ahead of print. PMID: 36533331. 20: Aydin P, Magden ZBA, Uzuncakmak SK, Halici H, Akgun N, Mendil AS, Mokhtare B, Cadirci E. Avanafil as a Novel Therapeutic Agent Against LPS-Induced Acute Lung Injury via Increasing CGMP to Downregulate the TLR4-NF-κB-NLRP3 Inflammasome Signaling Pathway. Lung. 2022 Oct;200(5):561-572. doi: 10.1007/s00408-022-00564-9. Epub 2022 Aug 30. PMID: 36040529.

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