Lodenafil carbonate | CAS#398507-55-6 | PDE-5 inhibitor

MedKoo Cat#: 599151 | Name: Lodenafil carbonate

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Description:

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

Lodenafil carbonate is a new PDE-5 inhibitor used for oral therapy in erectile dysfunction.

Chemical Structure

Lodenafil carbonate

CAS#398507-55-6

Theoretical Analysis

MedKoo Cat#: 599151

Name: Lodenafil carbonate

CAS#: 398507-55-6

Chemical Formula: C47H62N12O11S2

Exact Mass: 1034.4102

Molecular Weight: 1035.21

Elemental Analysis: C, 54.53; H, 6.04; N, 16.24; O, 17.00; S, 6.19

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 850.00	2 weeks

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Related CAS #

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Synonym

Lodenafil carbonate;

IUPAC/Chemical Name

bis(2-(4-((4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)sulfonyl)piperazin-1-yl)ethyl) carbonate

InChi Key

MVYUCRDXZXLFSB-UHFFFAOYSA-N

InChi Code

1S/C47H62N12O11S2/c1-7-11-35-39-41(54(5)52-35)45(60)50-43(48-39)33-29-31(13-15-37(33)67-9-3)71(63,64)58-21-17-56(18-22-58)25-27-69-47(62)70-28-26-57-19-23-59(24-20-57)72(65,66)32-14-16-38(68-10-4)34(30-32)44-49-40-36(12-8-2)53-55(6)42(40)46(61)51-44/h13-16,29-30H,7-12,17-28H2,1-6H3,(H,48,50,60)(H,49,51,61)

SMILES Code

O=c1[nH]c(c2cc(S(=O)(N3CCN(CCOC(OCCN4CCN(CC4)S(=O)(c5ccc(OCC)c(c(nc6c(CCC)nn(C)c67)[nH]c7=O)c5)=O)=O)CC3)=O)ccc2OCC)nc8c(CCC)nn(C)c81

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lodenafil carbonate, a dimer that acts as a prodrug delivering Lodenafil in vivo, is an orally active phosphodiesterase type 5 (PDE5) inhibitor for the treatment of erectile dysfunction (ED).

In vitro activity:

This study therefore aimed to compare the effects of sildenafil, lodenafil and lodenafil carbonate on in vitro human and rabbit cavernosal relaxations, activity of crude PDE extracts from human platelets, as well as stability and metabolic studies in rat, dog and human plasma. Lodenafil carbonate was more potent to inhibit the cGMP hydrolysis in PDE extracts compared with lodenafil and sildenafil. Reference: Eur J Pharmacol. 2008 Sep 4;591(1-3):189-95. https://pubmed.ncbi.nlm.nih.gov/18593576/

In vivo activity:

The present work investigated the antinociceptive activity of a new PDE5 inhibitor, lodenafil carbonate, in inflammatory and neuropathic pain mouse models. Lodenafil carbonate (10 μmol/kg p.o.) significantly reduced nociceptive response as demonstrated by increased paw withdrawal latency to thermal stimulus (from 6.8 ± 0.7 to 10.6 ± 1.3 s, p= 0.0006) and paw withdrawal threshold to compressive force (from 188.0 ± 14.0 to 252.5 ± 5.3 g, p<0.0001) in carrageenan-induced paw inflammation model. Reference: J Pain Res. 2021 Mar 30;14:857-866. https://pubmed.ncbi.nlm.nih.gov/33833563/

Preparing Stock Solutions

The following data is based on the product molecular weight 1,035.21 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:

1. 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. PMID: 18593576. 2. Vieira MC, Monte FBM, Eduardo Dematte B, Montagnoli TL, Montes GC, da Silva JS, Mendez-Otero R, Trachez MM, Sudo RT, Zapata-Sudo G. Antinociceptive Effect of Lodenafil Carbonate in Rodent Models of Inflammatory Pain and Spinal Nerve Ligation-Induced Neuropathic Pain. J Pain Res. 2021 Mar 30;14:857-866. doi: 10.2147/JPR.S295265. PMID: 33833563; PMCID: PMC8020462. 3. Silva MMCD, Alencar AKN, Silva JSD, Montagnoli TL, Silva GFD, Rocha BS, Montes GC, Mendez-Otero R, Pimentel-Coelho PM, Vasques JF, Trahez MM, Sudo RT, Zapata-Sudo G. Therapeutic Benefit of the Association of Lodenafil with Mesenchymal Stem Cells on Hypoxia-induced Pulmonary Hypertension in Rats. Cells. 2020 Sep 18;9(9):2120. doi: 10.3390/cells9092120. PMID: 32961896; PMCID: PMC7565793.

In vitro protocol:

In vivo protocol:

1. Vieira MC, Monte FBM, Eduardo Dematte B, Montagnoli TL, Montes GC, da Silva JS, Mendez-Otero R, Trachez MM, Sudo RT, Zapata-Sudo G. Antinociceptive Effect of Lodenafil Carbonate in Rodent Models of Inflammatory Pain and Spinal Nerve Ligation-Induced Neuropathic Pain. J Pain Res. 2021 Mar 30;14:857-866. doi: 10.2147/JPR.S295265. PMID: 33833563; PMCID: PMC8020462. 2. Silva MMCD, Alencar AKN, Silva JSD, Montagnoli TL, Silva GFD, Rocha BS, Montes GC, Mendez-Otero R, Pimentel-Coelho PM, Vasques JF, Trahez MM, Sudo RT, Zapata-Sudo G. Therapeutic Benefit of the Association of Lodenafil with Mesenchymal Stem Cells on Hypoxia-induced Pulmonary Hypertension in Rats. Cells. 2020 Sep 18;9(9):2120. doi: 10.3390/cells9092120. PMID: 32961896; PMCID: PMC7565793.

1: 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. 2: 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. 3: 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. 4: 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. 5: 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. 6: 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. 7: 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. 8: 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. 9: 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. 10: Peak TC, Yafi FA, Sangkum P, Hellstrom WJ. Emerging drugs for the treatment of erectile dysfunction. Expert Opin Emerg Drugs. 2015 Jun;20(2):263-75. doi: 10.1517/14728214.2015.1021682. Epub 2015 Mar 5. Review. PubMed PMID: 25740087. 11: 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. 12: 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. 13: 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. 14: Bacconi L, Gressier F. [Efficacy and tolerance of PDE-5 in the treatment of erectile dysfunction in schizophrenic patients: A literature review]. Encephale. 2017 Feb;43(1):55-61. doi: 10.1016/j.encep.2016.07.003. Epub 2016 Sep 19. Review. French. PubMed PMID: 27658991.