WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H329828
CAS#: 139755-85-4
Description: Lodenafil, also known as hydroxyhomosildenafil, 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.Lodenafil is formulated as a prodrug in the form of the carbonate ester dimer, lodenafil carbonate, which breaks down in the body to form two molecules of the active drug lodenafil. This formulation has higher oral bioavailability than the parent drug. It is manufactured by Cristália Produtos Químicos e Farmacêuticos in Brazil and sold there under the brand-name Helleva. It has undergone Phase III clinical trials, but is not yet approved for use in the United States by the U.S. Food and Drug Administration.
Hodoodo Cat#: H329828
Name: Lodenafil
CAS#: 139755-85-4
Chemical Formula: C23H32N6O5S
Exact Mass: 504.22
Molecular Weight: 504.606
Elemental Analysis: C, 54.75; H, 6.39; N, 16.65; O, 15.85; S, 6.35
This product is not in stock, which may be available by custom synthesis.
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Synonym: Lodenafil; hydroxyhomosildenafil; trade name Helleva.
IUPAC/Chemical Name: 5-(2-Ethoxy-5-((4-(2-hydroxyethyl)-1-piperazinyl)sulfonyl)phenyl)-1,6-dihydro-1-Methyl-3-propyl-7H-pyrazolo(4,3-d)pyriMidin-7-one
InChi Key: NEYKRKVLEWKOBI-UHFFFAOYSA-N
InChi Code: InChI=1S/C23H32N6O5S/c1-4-6-18-20-21(27(3)26-18)23(31)25-22(24-20)17-15-16(7-8-19(17)34-5-2)35(32,33)29-11-9-28(10-12-29)13-14-30/h7-8,15,30H,4-6,9-14H2,1-3H3,(H,24,25,31)
SMILES Code: O=C1C(N(C)N=C2CCC)=C2N=C(C3=CC(S(=O)(N4CCN(CCO)CC4)=O)=CC=C3OCC)N1
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
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:
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| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 504.61 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.
| 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: | |
| In vitro protocol: | |
| In vivo protocol: |
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2: Naccarato AM, Reis LO, Ferreira U, Denardi F. Psychotherapy and phosphodiesterase-5 inhibitor in early rehabilitation after radical prostatectomy: a prospective randomised controlled trial. Andrologia. 2016 Dec;48(10):1183-1187. doi: 10.1111/and.12557. Epub 2016 Apr 6. PubMed PMID: 27062069.
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5: Polonio IB, Acencio MM, Pazetti R, Almeida FM, Silva BS, Pereira KA, Souza R. Lodenafil treatment in the monocrotaline model of pulmonary hypertension in rats. J Bras Pneumol. 2014 Jul-Aug;40(4):421-4. English, Portuguese. PubMed PMID: 25210965; PubMed Central PMCID: PMC4201173.
6: Rubio-Aurioles E, El-Meliegy A, Abdulwahed S, Henneges C, Sorsaburu S, Gurbuz S. Decision tree analyses of key patient characteristics in Middle Eastern/North African and Latin American men treated with long-acting and short-acting PDE5 inhibitors for erectile dysfunction. Curr Med Res Opin. 2015 Feb;31(2):367-78. doi: 10.1185/03007995.2014.946125. Epub 2014 Jul 29. Erratum in: Curr Med Res Opin. 2015 Feb;31(2):378. PubMed PMID: 25068906.
7: Cairoli C, Reyes LA, Henneges C, Sorsaburu S. PDE5 inhibitor treatment persistence and adherence in Brazilian men: post-hoc analyses from a 6-month, prospective, observational study. Int Braz J Urol. 2014 May-Jun;40(3):390-9. doi: 10.1590/S1677-5538.IBJU.2014.03.14. PubMed PMID: 25010306.
8: Ückert S, Kuczyk MA, Oelke M. Phosphodiesterase inhibitors in clinical urology. Expert Rev Clin Pharmacol. 2013 May;6(3):323-32. doi: 10.1586/ecp.13.16. Review. PubMed PMID: 23656343.
9: Codevilla CF, Castilhos Tdos S, Cirne CA, Froehlich PE, Bergold AM. Development and validation of a dissolution test for lodenafil carbonate based on in vivo data. Drug Dev Ind Pharm. 2014 Apr;40(4):488-93. doi: 10.3109/03639045.2013.768633. Epub 2013 Apr 24. PubMed PMID: 23614829.
10: Rubio-Aurioles E, Reyes LA, Borregales L, Cairoli C, Sorsaburu S. A 6 month, prospective, observational study of PDE5 inhibitor treatment persistence and adherence in Latin American men with erectile dysfunction. Curr Med Res Opin. 2013 Jun;29(6):695-706. doi: 10.1185/03007995.2013.791262. Epub 2013 Apr 16. PubMed PMID: 23540375.
11: Kedia GT, Uckert S, Assadi-Pour F, Kuczyk MA, Albrecht K. Avanafil for the treatment of erectile dysfunction: initial data and clinical key properties. Ther Adv Urol. 2013 Feb;5(1):35-41. doi: 10.1177/1756287212466282. PubMed PMID: 23372609; PubMed Central PMCID: PMC3547533.
12: Nunes LV, Lacaz FS, Bressan RA, Nunes SO, Mari Jde J. Adjunctive treatment with lodenafil carbonate for erectile dysfunction in outpatients with schizophrenia and spectrum: a randomized, double-blind, crossover, placebo-controlled trial. J Sex Med. 2013 Apr;10(4):1136-45. doi: 10.1111/jsm.12040. Epub 2013 Jan 25. PubMed PMID: 23350632.
13: Mendes GD, dos Santos Filho HO, dos Santos Pereira A, Mendes FD, Ilha JO, Alkharfy KM, De Nucci G. A Phase I clinical trial of lodenafil carbonate, a new phosphodiesterase Type 5 (PDE5) inhibitor, in healthy male volunteers. Int J Clin Pharmacol Ther. 2012 Dec;50(12):896-906. doi: 10.5414/CP201624. PubMed PMID: 23073140.
14: Codevilla CF, Lemos AM, Delgado LS, Rolim CM, Adams AI, Bergold AM. Development and validation of a stability-indicating LC method for the assay of lodenafil carbonate in tablets. J Chromatogr Sci. 2011 Aug;49(7):502-7. PubMed PMID: 21801480.
15: Leonardi R, Alemanni M. The management of erectile dysfunction: innovations and future perspectives. Arch Ital Urol Androl. 2011 Mar;83(1):60-2. PubMed PMID: 21585174.
16: Silva AC, Toffoletto O, Lucio LA, Santos PF, Afiune JB, Massud Filho J, Tufik S. [Cardiovascular repercussion of lodenafil carbonate, a new PDE5 inhibitor, with and without alcohol consumption]. Arq Bras Cardiol. 2010 Feb;94(2):150-6, 160-7, 152-8. English, Portuguese, Spanish. PubMed PMID: 20428608.
17: Glina S, Fonseca GN, Bertero EB, Damião R, Rocha LC, Jardim CR, Cairoli CE, Teloken C, Torres LO, Faria GE, da Silva MB, Pagani E. Efficacy and tolerability of lodenafil carbonate for oral therapy of erectile dysfunction: a phase III clinical trial. J Sex Med. 2010 May;7(5):1928-36. doi: 10.1111/j.1743-6109.2010.01711.x. Epub 2010 Feb 25. PubMed PMID: 20214718.
18: Glina S, Toscano I, Gomatzky C, de Góes PM, Júnior AN, Claro JF, Pagani E. Efficacy and tolerability of lodenafil carbonate for oral therapy in erectile dysfunction: a phase II clinical trial. J Sex Med. 2009 Feb;6(2):553-7. doi: 10.1111/j.1743-6109.2008.01079.x. Epub 2008 Nov 17. PubMed PMID: 19040623.
19: Toque HA, Teixeira CE, Lorenzetti R, Okuyama CE, Antunes E, De Nucci G. Pharmacological characterization of a novel phosphodiesterase type 5 (PDE5) inhibitor lodenafil carbonate on human and rabbit corpus cavernosum. Eur J Pharmacol. 2008 Sep 4;591(1-3):189-95. doi: 10.1016/j.ejphar.2008.06.055. Epub 2008 Jun 19. PubMed PMID: 18593576.
