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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Udenafil (DB06267)

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Weight

Average: 516.656
Monoisotopic: 516.25187436

Chemical Formula

C₂₅H₃₆N₆O₄S

Synonyms

• Udenafil

External IDs

• DA 8159
• DA-8159

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Pharmacology

Indication

Investigated for use/treatment in erectile dysfunction and hypertension.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Erectile dysfunction		••••••••••••			••••••• •••• ••••••
Treatment of	Erectile dysfunction		••••••••••••			••••••

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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.

Target	Actions	Organism
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

• Udenafil
  • N-desalkyludenafil

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abaloparatide	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

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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

G01AE10 — Combinations of sulfonamides

• G01AE — Sulfonamides
• G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
• G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
• 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 / Heteroaromatic compounds / Pyrazoles / Trialkylamines / Azacyclic compounds / Hydrocarbon derivatives / Organic oxides / Organopnictogen compounds

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Substituents

Alkyl aryl ether / Amine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenesulfonamide / Benzenesulfonyl group / Ether / Heteroaromatic compound / Hydrocarbon derivative / N-alkylpyrrolidine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic sulfonic acid or derivatives / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfonic acid amide / Organosulfonic acid or derivatives / Organosulfur compound / Phenol ether / Phenoxy compound / Pyrazole / Pyrazolopyrimidine / Pyrimidine / Pyrimidone / Pyrrolidine / Sulfonyl / Tertiary aliphatic amine / Tertiary amine / Vinylogous amide

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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

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. [Article]
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. [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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001i-9004400000-0342835bf35ef730c22f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0000090000-e98c1a40833863ea3842
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0000190000-f673cd5583f8a33abf3a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00kr-0000910000-1426cf6d19b639e0eb36
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014r-6206490000-e8ab32addc5a5c59b953
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052f-0017900000-27c6d62a6a5115e62615
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-06si-5411910000-351225a2fecfc5e688dd

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	240.5456213	predicted	DarkChem Lite v0.1.0
[M-H]-	216.33688	predicted	DeepCCS 1.0 (2019)
[M+H]+	241.3826213	predicted	DarkChem Lite v0.1.0
[M+H]+	218.73245	predicted	DeepCCS 1.0 (2019)
[M+Na]+	240.9858213	predicted	DarkChem Lite v0.1.0
[M+Na]+	224.64497	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. cGMP-specific 3',5'-cyclic phosphodiesterase

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 . [Article]
2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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. [Article]
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. [Article]
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. [Article]

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Drug created at March 19, 2008 16:20 / Updated at June 19, 2021 00:26