Mirodenafil dihydrochloride
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MedKoo CAT#: 565451

CAS#: 862189-96-6 (HCl)

Description: Mirodenafil belongs to the drug class PDE5 inhibitors, which includes avanafil, sildenafil, tadalafil, udenafil, and vardenafil, and is the first-line treatment for erectile dysfunction.

Chemical Structure

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Mirodenafil dihydrochloride
CAS# 862189-96-6 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 565451
Name: Mirodenafil dihydrochloride
CAS#: 862189-96-6 (HCl)
Chemical Formula: C26H39Cl2N5O5S
Exact Mass: 603.20
Molecular Weight: 604.588
Elemental Analysis: C, 51.65; H, 6.50; Cl, 11.73; N, 11.58; O, 13.23; S, 5.30

Price and Availability

Size Price Availability Quantity
10mg USD 300 2 weeks
50mg USD 750 2 weeks
100mg USD 1150 2 weeks
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Related CAS #: 862189-95-5 (free base)   862189-96-6 (HCl)    

Synonym: Mirodenafil Dihydrochloride; M-vix; SK3530 dihydrochloride; SK3530; SK-3530; SK 3530;

IUPAC/Chemical Name: 5-Ethyl-2-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-7-propyl-1H-pyrrolo[3,2-d]pyrimidin-4-one dihydrochloride

InChi Key: CKPHITUXXABKDL-UHFFFAOYSA-N

InChi Code: InChI=1S/C26H37N5O5S.2ClH/c1-4-7-19-18-30(6-3)24-23(19)27-25(28-26(24)33)21-17-20(8-9-22(21)36-16-5-2)37(34,35)31-12-10-29(11-13-31)14-15-32;;/h8-9,17-18,32H,4-7,10-16H2,1-3H3,(H,27,28,33);2*1H

SMILES Code: O=C1C(N(CC)C=C2CCC)=C2NC(C3=CC(S(=O)(N4CCN(CCO)CC4)=O)=CC=C3OCCC)=N1.[H]Cl.[H]Cl

Appearance: A crystalline solid

Purity: >95% (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: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Mirodenafil (SK3530) dihydrochloride is an orally active, potent, reversible, and selective phosphodiesterase 5 (PDE5) inhibitor.
In vitro activity: In electrophysiological studies, whole-cell currents were recorded by the conventional patch-clamp technique in cultured smooth muscle cells of the human corpus cavernosum. The corpus cavernosum was relaxed in response to GBE in a dose-dependent manner (from 0.64%±8.35% at 0.01 mg ml⁻¹ to 52.28% ± 11.42% at 1 mg ml⁻¹). After pre-treatment with 0.03 mg ml⁻¹ of GBE, the relaxant effects of mirodenafil were increased at all concentrations. Reference: Asian J Androl. 2011 Sep;13(5):742-6. https://pubmed.ncbi.nlm.nih.gov/21478894/
In vivo activity: Here, mirodenafil is demonstrated to improve cognitive behavior in the APP-C105 mouse model. Mirodenafil not only reduced the Aβ and phosphorylated tau burdens in vivo, but also ameliorated AD pathology induced by Aβ through the modulation of the cGMP/PKG/CREB signaling pathway, glycogen synthase kinase 3β (GSK-3β) activity, GR transcriptional activity, and the Wnt/β-catenin signaling in neuronal cells. Reference: Alzheimers Res Ther. 2022 Jul 8;14(1):92. https://pubmed.ncbi.nlm.nih.gov/35804462/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 41.35
DMSO 75.0 124.05
DMSO:PBS (pH 7.2) (1:9) 0.1 0.17
Ethanol 11.5 19.02
Water 3.0 4.96

Preparing Stock Solutions

The following data is based on the product molecular weight 604.59 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. Kim JJ, Han DH, Lim SH, Kim TH, Chae MR, Chung KJ, Kam SC, Jeon JH, Park JK, Lee SW. Effects of Ginkgo biloba extracts with mirodenafil on the relaxation of corpus cavernosal smooth muscle and the potassium channel activity of corporal smooth muscle cells. Asian J Androl. 2011 Sep;13(5):742-6. doi: 10.1038/aja.2010.184. Epub 2011 Apr 11. PMID: 21478894; PMCID: PMC3739598. 2. Kang BW, Kim F, Cho JY, Kim S, Rhee J, Choung JJ. Phosphodiesterase 5 inhibitor mirodenafil ameliorates Alzheimer-like pathology and symptoms by multimodal actions. Alzheimers Res Ther. 2022 Jul 8;14(1):92. doi: 10.1186/s13195-022-01034-3. PMID: 35804462; PMCID: PMC9264543. 3. Roh JS, Jeong H, Lee B, Song BW, Han SJ, Sohn DH, Lee SG. Mirodenafil ameliorates skin fibrosis in bleomycin-induced mouse model of systemic sclerosis. Anim Cells Syst (Seoul). 2021 Nov 3;25(6):387-395. doi: 10.1080/19768354.2021.1995486. PMID: 35059138; PMCID: PMC8765282.
In vitro protocol: 1. Kim JJ, Han DH, Lim SH, Kim TH, Chae MR, Chung KJ, Kam SC, Jeon JH, Park JK, Lee SW. Effects of Ginkgo biloba extracts with mirodenafil on the relaxation of corpus cavernosal smooth muscle and the potassium channel activity of corporal smooth muscle cells. Asian J Androl. 2011 Sep;13(5):742-6. doi: 10.1038/aja.2010.184. Epub 2011 Apr 11. PMID: 21478894; PMCID: PMC3739598.
In vivo protocol: 1. Kang BW, Kim F, Cho JY, Kim S, Rhee J, Choung JJ. Phosphodiesterase 5 inhibitor mirodenafil ameliorates Alzheimer-like pathology and symptoms by multimodal actions. Alzheimers Res Ther. 2022 Jul 8;14(1):92. doi: 10.1186/s13195-022-01034-3. PMID: 35804462; PMCID: PMC9264543. 2. Roh JS, Jeong H, Lee B, Song BW, Han SJ, Sohn DH, Lee SG. Mirodenafil ameliorates skin fibrosis in bleomycin-induced mouse model of systemic sclerosis. Anim Cells Syst (Seoul). 2021 Nov 3;25(6):387-395. doi: 10.1080/19768354.2021.1995486. PMID: 35059138; PMCID: PMC8765282.

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1: Liao X, Qiu S, Bao Y, Wang W, Yang L, Wei Q. Comparative efficacy and safety of phosphodiesterase type 5 inhibitors for erectile dysfunction in diabetic men: a Bayesian network meta-analysis of randomized controlled trials. World J Urol. 2019 Jun;37(6):1061-1074. doi: 10.1007/s00345-018-2583-1. Epub 2018 Dec 6. Review. PubMed PMID: 30523399.

2: Sridharan K, Sivaramakrishnan G, Sequeira RP, Al-Khaja KA. Pharmacological interventions for premature ejaculation: a mixed-treatment comparison network meta-analysis of randomized clinical trials. Int J Impot Res. 2018 Oct;30(5):215-223. doi: 10.1038/s41443-018-0030-x. Epub 2018 Jun 20. PubMed PMID: 29921893.

3: Cho MC, Paick JS. A review of the efficacy and safety of mirodenafil in the management of erectile dysfunction. Ther Adv Urol. 2016 Apr;8(2):100-17. doi: 10.1177/1756287215625408. Epub 2016 Jan 19. Review. PubMed PMID: 27034723; PubMed Central PMCID: PMC4772359.

4: Shim JS, Bae JH. Drug Concentration in Rat Plasma, Bladder, and Prostate After Mirodenafil Administration in a Chronic Pelvic Ischemia Model. Urology. 2016 May;91:244.e1-5. doi: 10.1016/j.urology.2016.02.017. Epub 2016 Feb 23. PubMed PMID: 26919966.

5: Ventimiglia E, Capogrosso P, Montorsi F, Salonia A. The safety of phosphodiesterase type 5 inhibitors for erectile dysfunction. Expert Opin Drug Saf. 2016;15(2):141-52. doi: 10.1517/14740338.2016.1131818. Epub 2016 Jan 9. Review. PubMed PMID: 26752541.

6: Choi H, Bae JH, Shim JS, Park JY, Moon du G, Lee JG. Mirodenafil prevents bladder dysfunction induced by chronic bladder ischemia in rats. Int Neurourol J. 2015 Mar;19(1):19-26. doi: 10.5213/inj.2015.19.1.19. Epub 2015 Mar 26. PubMed PMID: 25833477; PubMed Central PMCID: PMC4386487.

7: 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.

8: Kong do H, Yun CJ, Park HJ, Park NC. The efficacy of mirodenafil for chronic prostatitis/chronic pelvic pain syndrome in middle-aged males. World J Mens Health. 2014 Dec;32(3):145-50. doi: 10.5534/wjmh.2014.32.3.145. Epub 2014 Dec 29. PubMed PMID: 25606563; PubMed Central PMCID: PMC4298817.

9: Lee S, Choi B, Kim J, In S, Baeck S, Oh SM, Chung KH. An LC-MS/MS method for the determination of five erectile dysfunction drugs and their selected metabolites in hair. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 26;978-979:1-10. doi: 10.1016/j.jchromb.2014.11.024. Epub 2014 Dec 5. PubMed PMID: 25531864.

10: Li J, Shi Q, Wei Q, Han P. Re: Efficacy and safety of mirodenafil for patients with erectile dysfunction: a meta-analysis of three multicenter, randomized, double-blind, placebo-controlled clinical trials. Aging Male. 2015 Jun;18(2):71. doi: 10.3109/13685538.2014.954994. Epub 2014 Aug 27. PubMed PMID: 25162329.

11: Park HJ, Moon KH, Lee SW, Lee WK, Kam SC, Lee JH, Park NC. Mirodenafil for the treatment of erectile dysfunction: a systematic review of the literature. World J Mens Health. 2014 Apr;32(1):18-27. doi: 10.5534/wjmh.2014.32.1.18. Epub 2014 Apr 25. Review. PubMed PMID: 24872948; PubMed Central PMCID: PMC4026230.

12: Lee DS, Choe HS, Kim SW, Jung KU, Lee SJ. Impact of the change in urinary and sexual function on health-related quality of life after once daily low-dose mirodenafil treatment in patients with organic erectile dysfunction. Urol Int. 2014;93(1):84-91. doi: 10.1159/000355360. Epub 2014 Jan 23. PubMed PMID: 24457224.

13: Du W, Li J, Fan N, Shang P, Wang Z, Ding H. Efficacy and safety of mirodenafil for patients with erectile dysfunction: a meta-analysis of three multicenter, randomized, double-blind, placebo-controlled clinical trials. Aging Male. 2014 Jun;17(2):107-11. doi: 10.3109/13685538.2013.858114. Epub 2013 Nov 12. PubMed PMID: 24219508.

14: Lee WK, Lee SH, Cho ST, Lee YS, Oh CY, Yoo C, Cho JS, Lee SK, Yang DY. Comparison between on-demand dosing of dapoxetine alone and dapoxetine plus mirodenafil in patients with lifelong premature ejaculation: prospective, randomized, double-blind, placebo-controlled, multicenter study. J Sex Med. 2013 Nov;10(11):2832-41. doi: 10.1111/jsm.12287. Epub 2013 Aug 12. PubMed PMID: 23937271.

15: Kang JY, Kim EK, Kim KM. Effects of mirodenafil, a phosphodiesterase-5 inhibitor, on female rat bladder in a partial bladder outlet obstruction model: physiological and immunohistochemical aspects. Korean J Urol. 2013 May;54(5):339-44. doi: 10.4111/kju.2013.54.5.339. Epub 2013 May 14. PubMed PMID: 23700501; PubMed Central PMCID: PMC3659229.

16: Bruzziches R, Francomano D, Gareri P, Lenzi A, Aversa A. An update on pharmacological treatment of erectile dysfunction with phosphodiesterase type 5 inhibitors. Expert Opin Pharmacother. 2013 Jul;14(10):1333-44. doi: 10.1517/14656566.2013.799665. Epub 2013 May 16. Review. PubMed PMID: 23675780.

17: Cho DY, Bae SH, Shon JH, Bae SK. High-sensitive LC-MS/MS method for the simultaneous determination of mirodenafil and its major metabolite, SK-3541, in human plasma: application to microdose clinical trials of mirodenafil. J Sep Sci. 2013 Mar;36(5):840-8. doi: 10.1002/jssc.201200919. Epub 2013 Feb 6. PubMed PMID: 23390072.

18: 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.

19: Lee S, Kang SY, Ji D, Baeck S, Lee S, Oh SM, Chung KH. Quantitative LC-MS/MS method in urine for the detection of drugs used to reverse the effects of chemical castration. Anal Bioanal Chem. 2013 Apr;405(10):3185-94. doi: 10.1007/s00216-013-6769-5. Epub 2013 Feb 1. PubMed PMID: 23371534.

20: Bang WJ, Oh CY, Yoo C, Cho JS, Yang DY, Lee DH, Lee SH, Chung BH. Efficacy and safety of the simultaneous administration of mirodenafil and an α-blocker in men with BPH-LUTS: a multicenter open-label prospective study. Int J Impot Res. 2013 Jul-Aug;25(4):149-54. doi: 10.1038/ijir.2012.44. Epub 2013 Jan 10. PubMed PMID: 23303333.