Udenafil
Identification
- Summary
Udenafil is a PDE5 inhibitor used to treat erectile dysfunction.
- Generic Name
- Udenafil
- DrugBank Accession Number
- DB06267
- Background
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
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Erectile dysfunction •••••••••••• ••••••• •••• •••••• Treatment of Erectile dysfunction •••••••••••• •••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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.
Target Actions Organism AcGMP-specific 3',5'-cyclic phosphodiesterase inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic. Metabolized by CYP3A4 and CYP3A5.
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- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide The risk or severity of hypotension can be increased when Udenafil is combined with Abaloparatide. Abametapir The serum concentration of Udenafil can be increased when it is combined with Abametapir. Abatacept The metabolism of Udenafil can be increased when combined with Abatacept. Acalabrutinib The metabolism of Udenafil can be decreased when combined with Acalabrutinib. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Udenafil. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Zydena
Categories
- ATC Codes
- G04BE11 — Udenafil
- G04BE — Drugs used in erectile dysfunction
- G04B — UROLOGICALS
- G04 — UROLOGICALS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Amides
- Benzene Derivatives
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Substrates
- Drugs Used in Erectile Dysfunction
- Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Phosphodiesterase 5 Inhibitors
- Phosphodiesterase Inhibitors
- Sulfonamides
- Sulfones
- Sulfur Compounds
- Urologicals
- Vasodilating Agents
- 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
- Affected organisms
- Humans and other mammals
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
- 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. [Article]
- 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. [Article]
- External Links
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Supportive Care Rectal Cancer 1 4 Unknown Status Treatment Microvascular Angina 1 4 Unknown Status Treatment Prostate Cancer With Radical Prostatectomy 1 3 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) / Dyspnea / Pulmonary Hypertension (PH) 1 3 Completed Treatment Erectile Dysfunction 6
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral 100 mg Tablet, film coated Oral 100 mg Tablet, film coated Oral Tablet, coated Oral 200 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0798 mg/mL ALOGPS logP 3.2 ALOGPS logP 2.74 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 10.25 Chemaxon pKa (Strongest Basic) 8.44 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 117.92 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 153.11 m3·mol-1 Chemaxon Polarizability 56.34 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.5 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.8093 P-glycoprotein inhibitor I Inhibitor 0.6138 P-glycoprotein inhibitor II Inhibitor 0.658 Renal organic cation transporter Non-inhibitor 0.784 CYP450 2C9 substrate Non-substrate 0.6694 CYP450 2D6 substrate Substrate 0.6391 CYP450 3A4 substrate Substrate 0.721 CYP450 1A2 substrate Non-inhibitor 0.8355 CYP450 2C9 inhibitor Inhibitor 0.5391 CYP450 2D6 inhibitor Non-inhibitor 0.8885 CYP450 2C19 inhibitor Non-inhibitor 0.8588 CYP450 3A4 inhibitor Inhibitor 0.8863 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5793 Ames test Non AMES toxic 0.5747 Carcinogenicity Non-carcinogens 0.5502 Biodegradation Not ready biodegradable 0.8961 Rat acute toxicity 2.6102 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8455 hERG inhibition (predictor II) Inhibitor 0.805
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 240.5456213 predictedDarkChem Lite v0.1.0 [M-H]- 216.33688 predictedDeepCCS 1.0 (2019) [M+H]+ 241.3826213 predictedDarkChem Lite v0.1.0 [M+H]+ 218.73245 predictedDeepCCS 1.0 (2019) [M+Na]+ 240.9858213 predictedDarkChem Lite v0.1.0 [M+Na]+ 224.64497 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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
- 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 . [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
Drug created at March 19, 2008 16:20 / Updated at June 19, 2021 00:26