MIRODENAFIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H37N5O5S
Molecular Weight	531.667
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCOC1=CC=C(C=C1C2=NC3=C(N(CC)C=C3CCC)C(=O)N2)S(=O)(=O)N4CCN(CCO)CC4

InChI

InChIKey=MIJFNYMSCFYZNY-UHFFFAOYSA-N

InChI=1S/C26H37N5O5S/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)

HIDE SMILES / InChI

Molecular Formula	C26H37N5O5S
Molecular Weight	531.667
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27034723
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17640490

The inhibition of cyclic nucleotide Phosphodiesterase type 5 (PDE5) has been clinically validated as an effective treatment for erectile dysfunction. One of them is mirodenafil (formerly known as SK-3530) approved only in Korea. This drug was developed by SK Chemicals and marketed under the trade name Mvix.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 5A 30 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27034723	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Erectile dysfunction 35 Sources: https://www.skchemicals.com/page/ls/eng/product/info4_01.do	Primary	Approved 8429	Mvix Approved Use Treatment of erectile dysfunction(ED)
Urologic diseases 2 Sources: https://clinicaltrials.gov/ct2/show/NCT01232010	Primary	Phase I 428	Unknown Approved Use Unknown
Kidney disease 6 Sources: https://clinicaltrials.gov/ct2/show/NCT01232010	Primary	Phase I 428	Unknown Approved Use Unknown
Renal insufficiency 40 Sources: https://clinicaltrials.gov/ct2/show/NCT01232010	Primary	Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Metabolism and excretion of 5-ethyl-2-{5-[4-(2-hydroxyethyl)piperazine-1-sulfonyl]-2-propoxyphenyl}-7-propyl-3,5-dihydropyrrolo[3,2-d]-pyrimidin-4-one (SK3530) in rats.	2007	17318927
Pharmacokinetics and tissue distribution of a novel PDE5 inhibitor, SK-3530, in rats.	2007 Aug	17640490
Validation of a HPLC method for the quantification and purity determination of SK3530 in drug substance and tablet.	2007 Feb 19	17134866
Formation of supramolecular hydrogels with controlled microstructures and stability via molecular assembling in a two-component system.	2007 Mar 1	17141263
Development of LC/MS/MS assay for the determination of 5-ethyl-2-{5-[4-(2-hydroxyethyl)piperazine-1-sulfonyl]-2-propoxyphenyl}-7-propyl-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one (SK3530) in human plasma: application to a clinical pharmacokinetic study.	2007 Sep 21	17689219
Identification of cytochrome P450 enzymes responsible for N -dealkylation of a new oral erectogenic, mirodenafil.	2008 Jan	18098061
Editorial comment on: chronic treatment with a type 5 phosphodiesterase inhibitor suppresses apoptosis of corporal smooth muscle by potentiating Akt signalling in a rat model of diabetic erectile dysfunction.	2008 Jun	18243512
Chronic treatment with a type 5 phosphodiesterase inhibitor suppresses apoptosis of corporal smooth muscle by potentiating Akt signalling in a rat model of diabetic erectile dysfunction.	2008 Jun	18243503
The penile erection efficacy of a new phosphodiesterase type 5 inhibitor, mirodenafil (SK3530), in rabbits with acute spinal cord injury.	2008 Nov	19057138
Efficacy and safety of mirodenafil, a new oral phosphodiesterase type 5 inhibitor, for treatment of erectile dysfunction.	2008 Nov	18638004
Efficacy and safety of oral SK3530 for the treatment of erectile dysfunction in Korean men: a multicenter, randomized, double-blind, placebo-controlled, fixed dose, parallel group clinical trial.	2008 Sep	18645683
The effects of ketoconazole and rifampicin on the pharmacokinetics of mirodenafil in healthy Korean male volunteers: an open-label, one-sequence, three-period, three-treatment crossover study.	2009 Dec	20110038
Determination of mirodenafil and sildenafil in the plasma and corpus cavernous of SD male rats.	2009 Feb 20	19095395
Influence of alcohol on the hemodynamic effects and pharmacokinetic properties of mirodenafil: a single-dose, randomized-sequence, open-label, crossover study in healthy male volunteers in Korea.	2009 Jun	19695390
Hormonal testing and pharmacologic treatment of erectile dysfunction: a clinical practice guideline from the American College of Physicians.	2009 Nov 3	19884625
Faster clearance of mirodenafil in rats with acute renal failure induced by uranyl nitrate: contribution of increased protein expression of hepatic CYP3A1 and intestinal CYP1A1 and 3A1/2.	2009 Oct	19814864
Dose-dependent pharmacokinetics and first-pass effects of mirodenafil, a new erectogenic, in rats.	2009 Sep	19639551
Pharmacokinetics of mirodenafil, a new erectogenic, and its metabolite, SK3541, in rats: involvement of CYP1A1/2, 2B1/2, 2D subfamily, and 3A1/2 for the metabolism of both mirodenafil and SK3541.	2010	20456834
Efficacy and safety of oral mirodenafil in the treatment of erectile dysfunction in diabetic men in Korea: a multicenter, randomized, double-blind, placebo-controlled clinical trial.	2010 Aug	20626604
Crystal forms of SK-3530.	2010 Dec	21191770
Pharmacokinetics of mirodenafil and its two metabolites, SK3541 and SK3544, after intravenous and oral administration of mirodenafil to streptozotocin-induced diabetes mellitus rats.	2010 Feb	19929308
Efficacy and Safety of Tadalafil 5 mg Administered Once Daily in Korean Men with Erectile Dysfunction: A Prospective, Multicenter Study.	2010 Sep	20856651
Efficacy and safety of mirodenafil in men taking antihypertensive medications.	2010 Sep	20649936
The effect of mirodenafil on the penile erection and corpus cavernosum in the rat model of cavernosal nerve injury.	2010 Sep-Oct	20861845

Sample Use Guides

In Vivo Use Guide

One tablet (Mirodenafil 50mg or 100mg) recommended dosing frequency is once per day. Taken orally approximately 60 minutes before sexual activity. Sexual stimulation is required for a response to treatment.

Route of Administration: Oral

In Vitro Use Guide

The in vitro incubation of [14C]SK-3530 (MIRODENAFIL )with rat and human plasma samples resulted in high protein binding rates of more than 97%; binding was concentration-independent over the range tested (1–100 µmol/L), with no difference between the species show.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:30:03 UTC 2023` Edited by `admin` on `Fri Dec 15 18:30:03 UTC 2023`
Record UNII	504G362H0H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MIRODENAFIL

Official Name

English

Mirodenafil [WHO-DD]

Common Name

English

SK-3530 FREE BASE

Code

English

MIRODENAFIL [INCI]

Common Name

English

5-ETHYL-2-(5-((4-(2-HYDROXYETHYL)PIPERAZIN-1-YL)SULFONYL)-2-PROPOXYPHENYL)-7-PROPYL-3,5-DIHYDRO-4H-PYRROLO(3,2-D)PYRIMIDIN-4-ONE

Systematic Name

English

SK3530 FREE BASE

Code

English

mirodenafil [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2127