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Details

Stereochemistry ACHIRAL
Molecular Formula C23H33N7O5S
Molecular Weight 519.617
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GISADENAFIL

SMILES

CCOC1=NC=C(C=C1C2=NC3=C(CC)N(CCOC)N=C3C(=O)N2)S(=O)(=O)N4CCN(CC)CC4

InChI

InChIKey=YPFZMBHKIVDSNR-UHFFFAOYSA-N
InChI=1S/C23H33N7O5S/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/h14-15H,5-13H2,1-4H3,(H,25,26,31)

HIDE SMILES / InChI
Molecular Formula C23H33N7O5S
Molecular Weight 519.617
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Pfizer
420
Curator's Comment: # Pfizer

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 1.23 nM [IC50]
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
The discovery of UK-369003, a novel PDE5 inhibitor with the potential for oral bioavailability and dose-proportional pharmacokinetics.
2012 Jan 1
Patents

Patents

06677335
2
07176311
2
JP2007516949A
8

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:02:09 UTC 2023
Edited
by admin
on Fri Dec 15 16:02:09 UTC 2023
Record UNII
S6G4R7DI1C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GISADENAFIL
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
Gisadenafil [WHO-DD]
Common Name English
UK-369,003
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)-
Systematic Name English
GISADENAFIL [USAN]
Common Name English
UK-369003
Code English
gisadenafil [INN]
Common Name 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
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C2127
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C83728
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
DRUG BANK
DB11902
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
PUBCHEM
135536943
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
SMS_ID
300000034221
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
USAN
UU-144
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
ChEMBL
CHEMBL1928262
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
CAS
334826-98-1
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
INN
9140
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID00955107
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
FDA UNII
S6G4R7DI1C
Created by admin on Fri Dec 15 16:02:09 UTC 2023 , Edited by admin on Fri Dec 15 16:02:09 UTC 2023
PRIMARY
Related Record Type Details
Structure of GISADENAFIL BESYLATE
SALT/SOLVATE -> PARENT
PHOSPHODIESTERASE 5A, HUMAN
TARGET -> INHIBITOR
Related Record Type Details
Structure of GISADENAFIL
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