GISADENAFIL BESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H33N7O5S.C6H6O3S
Molecular Weight	677.792
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC=CC=C1.CCOC2=NC=C(C=C2C3=NC4=C(CC)N(CCOC)N=C4C(=O)N3)S(=O)(=O)N5CCN(CC)CC5

InChI

InChIKey=STFRDYSZKVPPQF-UHFFFAOYSA-N

InChI=1S/C23H33N7O5S.C6H6O3S/c1-5-18-19-20(27-30(18)12-13-34-4)22(31)26-21(25-19)17-14-16(15-24-23(17)35-7-3)36(32,33)29-10-8-28(6-2)9-11-29;7-10(8,9)6-4-2-1-3-5-6/h14-15H,5-13H2,1-4H3,(H,25,26,31);1-5H,(H,7,8,9)

HIDE SMILES / InChI

Description
Sources: https://newdrugapprovals.org/2014/01/28/gisadenafil-for-erectile-dysfunction/
Curator's Comment: description was created based on several sources, including: http://en.pharmacodia.com/web/drug/1_2089.html | http://adisinsight.springer.com/drugs/800017097

Gisadenafil is a phosphodiesterase V inhibitor in clinical development at Pfizer. It had been in phase II clinical trials for the treatment of Benign prostatic hyperplasia; Chronic obstructive pulmonary disease; Erectile dysfunction; Overactive bladder. Treatment-emergent adverse events were: headache, myalgia, dyspepsia, back pain.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 5A 30 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22100260	Inhibitor 8297		1.23 nM [IC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21451120	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20184577 http://adisinsight.springer.com/drugs/800017097	Primary	Phase II 1132	Unknown Approved Use Unknown
Chronic obstructive pulmonary disease 174 Sources: http://adisinsight.springer.com/trials/700011081	Primary	Phase II 1132	Unknown Approved Use Unknown
Erectile dysfunction 35 Sources: https://newdrugapprovals.org/2014/01/28/gisadenafil-for-erectile-dysfunction/	Primary	Phase II 1132	Unknown Approved Use Unknown
Overactive bladder 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20151971 http://adisinsight.springer.com/drugs/800017097	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
204.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22100260	1.43 mg/kg single, oral dose: 1.43 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		GISADENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
95.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22100260	1.43 mg/kg single, oral dose: 1.43 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		GISADENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22100260	0.43 mg/kg single, intravenous dose: 0.43 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		GISADENAFIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
34% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21451120	unknown, unknown		GISADENAFIL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
800 mg single, intravenous Highest studied dose Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/21451120	healthy, ADULT n = 8 Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/21451120	Sources: https://pubmed.ncbi.nlm.nih.gov/21451120
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20151971 Page: p.671	unhealthy, ADULT n = 64 Health Status: unhealthy Condition: hypertonic bladder Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 64 Sources: https://pubmed.ncbi.nlm.nih.gov/20151971 Page: p.671	Sources: https://pubmed.ncbi.nlm.nih.gov/20151971 Page: p.671

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	14805	http://www.alfa-chemistry.com/search.aspx?q=14805
Alfa Chemistry	AFI334827984	http://www.alfa-chemistry.com/search.aspx?q=AFI334827984
ApexBio Technology	B7599	https://www.apexbt.com/catalogsearch/result/?q=B7599
Axon MedChem	2218	https://www.axonmedchem.com/product/2218
BOC Sciences	334827-98-4	http://www.bocsci.com/description.asp?cas=334827-98-4
MolPort	MolPort-039-101-269	https://www.molport.com/shop/molecule-link/MolPort-039-101-269
MolPort	MolPort-042-665-836	https://www.molport.com/shop/molecule-link/MolPort-042-665-836
Molnova	M14135	https://www.molnova.com/en/serch-list.html?keywords=M14135
MuseChem	I006963	https://www.musechem.com/product/I006963.html
MuseChem	I010674	https://www.musechem.com/product/I010674.html
Ryan Scientific	101-94177	https://ryansci.com/products?q=101-94177&list_q=&search_type=exact
Tocris	4165	https://www.tocris.com/search.php?Type=QuickSearch&Value=4165
Toronto Research Chemicals	G388700	https://www.trc-canada.com/product-detail/?CatNum=G388700
Toronto Research Chemicals	M567060	https://www.trc-canada.com/product-detail/?CatNum=M567060
eMolecules	32279293	https://orderbb.emolecules.com/search/#?query=32279293
eMolecules	49435318	https://orderbb.emolecules.com/search/#?query=49435318

PubMed

Title	Date	PubMed
A placebo-controlled study investigating the efficacy and safety of the phosphodiesterase type 5 inhibitor UK-369,003 for the treatment of men with lower urinary tract symptoms associated with clinical benign prostatic hyperplasia.	2010 Sep	20184577
A placebo-controlled exploratory study investigating the efficacy and safety of the phosphodiesterase type 5 inhibitor UK-369,003 for the treatment of men with storage lower urinary tract symptoms associated with a clinical diagnosis of overactive bladder.	2010 Sep	20151971
The discovery of UK-369003, a novel PDE5 inhibitor with the potential for oral bioavailability and dose-proportional pharmacokinetics.	2012 Jan 1	22100260

Patents

Sample Use Guides

In Vivo Use Guide

10, 25, 50 or 100 mg once a day for 12 weeks.

Route of Administration: Oral

In Vitro Use Guide

Apical to basolateral flux across Caco-2 cell monolayer at 25 uM for Gisadenafil is the apparent permeability coefficient = 16x10^6 cm/s).

Name

Type

Language

GISADENAFIL BESYLATE

Official Name

English

5-(2-ETHOXY-5-((4-ETHYLPIPERAZIN-1-YL)SULPHONYL)PYRIDIN-3-YL)-3-ETHYL-2-(2-METHOXYETHYL)-2,6-DIHYDRO-7H-PYRAZOLO(4,3-D)PYRIMIDIN-7-ONE BENZENESULPHONATE

Systematic Name

English

7H-PYRAZOLO(4,3-D)PYRIMIDIN-7-ONE, 5-(2-ETHOXY-5-((4-ETHYL-1-PIPERAZINYL)SULPHONYL)-3-PYRIDINYL)-3-ETHYL-2,6-DIHYDRO-2-(2-METHOXYETHYL)-, BENZENESULPHONATE (1:1)

Systematic Name

English

UK-369003-26

Code

English

5-{2-Ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]pyridin-3-yl}-3-ethyl-2-(2-methoxyethyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one benzenesulfonate

Systematic Name

English

GISADENAFIL BESYLATE [USAN]

Common Name

English

UK-369,003-26

Code

English

7H-PYRAZOLO(4,3-D)PYRIMIDIN-7-ONE, 5-(2-ETHOXY-5-((4-ETHYL-1-PIPERAZINYL)SULFONYL)-3-PYRIDINYL)-3-ETHYL-2,6-DIHYDRO-2-(2-METHOXYETHYL)-, BENZENESULFONATE (1:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2127