Identification

Name
Udenafil
Accession Number
DB06267
Description

Udenafil is a new phosphodiesterase type 5 (PDE5) inhibitor used to treat erectile dysfunction (ED). It has been approved in South Korea and will be marketed under the brand name Zydena. It is not yet approved for use in the U.S., E.U., or Canada.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 516.656
Monoisotopic: 516.25187436
Chemical Formula
C25H36N6O4S
Synonyms
  • Udenafil
External IDs
  • DA 8159
  • DA-8159

Pharmacology

Indication

Investigated for use/treatment in erectile dysfunction and hypertension.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Udenafil is a potent selective phosphodiesterase type 5 (PDE5) inhibitor.

Mechanism of action

Udenafil inhibits the cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum located around the penis. Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosal smooth muscle. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cGMP in smooth muscle cells. Cyclic GMP causes smooth muscle relaxation and increased blood flow into the corpus cavernosum. The inhibition of phosphodiesterase type 5 (PDE5) by udenafil enhances erectile function by increasing the amount of cGMP.

TargetActionsOrganism
AcGMP-specific 3',5'-cyclic phosphodiesterase
inhibitor
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic. Metabolized by CYP3A4 and CYP3A5.

Hover over products below to view reaction partners

Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Udenafil can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Udenafil can be increased when combined with Abatacept.
AcalabrutinibThe metabolism of Udenafil can be decreased when combined with Acalabrutinib.
AcebutololUdenafil may increase the antihypertensive activities of Acebutolol.
AdalimumabThe metabolism of Udenafil can be increased when combined with Adalimumab.
AlfentanilThe metabolism of Udenafil can be decreased when combined with Alfentanil.
AlfuzosinThe risk or severity of hypotension, dyspepsia, and headache can be increased when Udenafil is combined with Alfuzosin.
AliskirenUdenafil may increase the antihypertensive activities of Aliskiren.
AlprazolamThe metabolism of Udenafil can be decreased when combined with Alprazolam.
AlprostadilThe risk or severity of hypotension and priapism can be increased when Udenafil is combined with Alprostadil.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

International/Other Brands
Zydena

Categories

ATC Codes
G04BE11 — Udenafil
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Pyrazolopyrimidines / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Pyrimidones / N-alkylpyrrolidines / Organosulfonamides / Vinylogous amides / Aminosulfonyl compounds
show 7 more
Substituents
Alkyl aryl ether / Amine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenesulfonamide / Benzenesulfonyl group / Ether / Heteroaromatic compound
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
L5IB4XLY36
CAS number
268203-93-6
InChI Key
IYFNEFQTYQPVOC-UHFFFAOYSA-N
InChI
InChI=1S/C25H36N6O4S/c1-5-8-20-22-23(31(4)29-20)25(32)28-24(27-22)19-16-18(10-11-21(19)35-15-6-2)36(33,34)26-13-12-17-9-7-14-30(17)3/h10-11,16-17,26H,5-9,12-15H2,1-4H3,(H,27,28,32)
IUPAC Name
3-{1-methyl-7-oxo-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-propoxybenzene-1-sulfonamide
SMILES
CCCOC1=C(C=C(C=C1)S(=O)(=O)NCCC1CCCN1C)C1=NC(=O)C2=C(N1)C(CCC)=NN2C

References

Synthesis Reference

Chan-Ho Lee, Chang-Yong Shin, Seul-Min Choi, Kyung-Koo Kang, Dong-Seong Kim, Byoung-Ok Ahn, Moo-Hi Yoo, "ACID ADDITION SALT OF UDENAFIL, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME." U.S. Patent US20110306762, issued December 15, 2011.

US20110306762
General References
  1. Ji HY, Shim HJ, Yoo M, Park ES, Lee HS: Transport of a new erectogenic udenafil in Caco-2 cells. Arch Pharm Res. 2007 Sep;30(9):1168-73. [PubMed:17958337]
  2. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836]
Human Metabolome Database
HMDB0015628
KEGG Drug
D10027
PubChem Compound
6918523
PubChem Substance
99443240
ChemSpider
5293720
ChEBI
135926
ChEMBL
CHEMBL2103849
Therapeutic Targets Database
DAP000960
PharmGKB
PA164776753
Wikipedia
Udenafil

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedSupportive CareRectal Carcinoma1
4Not Yet RecruitingTreatmentProstate Cancer With Radical Prostatectomy1
4Unknown StatusTreatmentMicrovascular Angina1
3Active Not RecruitingTreatmentFunctional Single Ventricle Heart Disease1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Dyspnea / Pulmonary Hypertension (PH)1
3CompletedTreatmentErectile Dysfunction6
3CompletedTreatmentSingle Ventricle Heart Disease1
3TerminatedTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
3Unknown StatusTreatmentAlzheimer's Disease (AD)1
3Unknown StatusTreatmentDiastolic Heart Failure1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0798 mg/mLALOGPS
logP3.2ALOGPS
logP1.66ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.21ChemAxon
pKa (Strongest Basic)8.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.92 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity153.11 m3·mol-1ChemAxon
Polarizability56.34 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.5
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8093
P-glycoprotein inhibitor IInhibitor0.6138
P-glycoprotein inhibitor IIInhibitor0.658
Renal organic cation transporterNon-inhibitor0.784
CYP450 2C9 substrateNon-substrate0.6694
CYP450 2D6 substrateSubstrate0.6391
CYP450 3A4 substrateSubstrate0.721
CYP450 1A2 substrateNon-inhibitor0.8355
CYP450 2C9 inhibitorInhibitor0.5391
CYP450 2D6 inhibitorNon-inhibitor0.8885
CYP450 2C19 inhibitorNon-inhibitor0.8588
CYP450 3A4 inhibitorInhibitor0.8863
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5793
Ames testNon AMES toxic0.5747
CarcinogenicityNon-carcinogens0.5502
BiodegradationNot ready biodegradable0.8961
Rat acute toxicity2.6102 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8455
hERG inhibition (predictor II)Inhibitor0.805
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight
99984.14 Da
References
  1. Gur S, Sikka SC, Hellstrom WJ: Novel phosphodiesterase-5 (PDE5) inhibitors in the alleviation of erectile dysfunction due to diabetes and ageing-induced oxidative stress. Expert Opin Investig Drugs. 2008 Jun;17(6):855-64. doi: 10.1517/13543784.17.6.855 . [PubMed:18491987]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  3. Ahn GJ, Chung HK, Lee CH, Kang KK, Ahn BO: Increased expression of the nitric oxide synthase gene and protein in corpus cavernosum by repeated dosing of udenafil in a rat model of chemical diabetogenesis. Asian J Androl. 2009 Jul;11(4):435-42. doi: 10.1038/aja.2009.27. Epub 2009 May 25. [PubMed:19465935]
  4. Zhao C, Kim SH, Lee SW, Jeon JH, Kang KK, Choi SB, Park JK: Activity of phosphodiesterase type 5 inhibitors in patients with lower urinary tract symptoms due to benign prostatic hyperplasia. BJU Int. 2011 Jun;107(12):1943-7. doi: 10.1111/j.1464-410X.2010.09759.x. Epub 2010 Nov 5. [PubMed:21054754]
  5. Kouvelas D, Goulas A, Papazisis G, Sardeli C, Pourzitaki C: PDE5 inhibitors: in vitro and in vivo pharmacological profile. Curr Pharm Des. 2009;15(30):3464-75. [PubMed:19860692]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ji HY, Lee HW, Kim HH, Kim DS, Yoo M, Kim WB, Lee HS: Role of human cytochrome P450 3A4 in the metabolism of DA-8159, a new erectogenic. Xenobiotica. 2004 Nov-Dec;34(11-12):973-82. [PubMed:15801542]
  2. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836]

Drug created on March 19, 2008 10:20 / Updated on June 12, 2020 10:52

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