U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N6O4S.HNO3
Molecular Weight 537.589
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SILDENAFIL NITRATE

SMILES

O[N+]([O-])=O.CCCC1=NN(C)C2=C1N=C(NC2=O)C3=CC(=CC=C3OCC)S(=O)(=O)N4CCN(C)CC4

InChI

InChIKey=RBQNFEVGNSBKSU-UHFFFAOYSA-N
InChI=1S/C22H30N6O4S.HNO3/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28;2-1(3)4/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);(H,2,3,4)

HIDE SMILES / InChI
Molecular Formula C22H30N6O4S
Molecular Weight 474.576
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula HNO3
Molecular Weight 63.0128
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Sildenafil (Viagra, Revatio) is a PDE5 inhibitor which was approved by FDA for the treatment of erectile disfunction and adults with pulmonary arterial hypertension. Upon administration sildenafil inhibits PDE5 and results in elevated level of cyclic guanosine monophosphate and smooth muscle relaxation.

CNS Activity

CNS Active
3913
Curator's Comment: CNS activity was observed on rats.

Originator

Approval Year

1998
116
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 3.5 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
VIAGRA

Approved Use

VIAGRA is a phosphodiesterase-5 (PDE5) inhibitor indicated for the treatment of erectile dysfunction.

Launch Date

1998
Primary
Approved
8429
REVATIO

Approved Use

REVATIO is a phosphodiesterase-5 (PDE-5) inhibitor indicated for the treatment of pulmonary arterial hypertension (PAH) (WHO Group I) in adults to improve exercise ability and delay clinical worsening.

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
159 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/11879254
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SILDENAFIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
530 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/11879254
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SILDENAFIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.07 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/11879254
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SILDENAFIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/20895s039s042lbl.pdf
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SILDENAFIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
4%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/20895s039s042lbl.pdf
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SILDENAFIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
Disc. AE: Flushing, Headache...
AEs leading to
discontinuation/dose reduction:
Flushing
Headache
Tachycardia (mild)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
2400 mg single, oral
Overdose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
Disc. AE: Visual field defect...
AEs leading to
discontinuation/dose reduction:
Visual field defect
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/24661860
Page: p.258
unhealthy, 45
n = 1
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 45
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24661860
Page: p.258
Disc. AE: Rhabdomyolysis, Visual disturbance NOS...
AEs leading to
discontinuation/dose reduction:
Rhabdomyolysis
Visual disturbance NOS
Sources:
https://pubmed.ncbi.nlm.nih.gov/24661860
Page: p.258
80 mg 3 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 3 times / day
Route: oral
Route: multiple
Dose: 80 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21546436
Page: p.1278
unhealthy, 47.5
n = 135
Health Status: unhealthy
Condition: Pulmonary arterial hypertension
Age Group: 47.5
Sex: M+F
Population Size: 135
Sources:
https://pubmed.ncbi.nlm.nih.gov/21546436
Page: p.1278
Sources:
https://pubmed.ncbi.nlm.nih.gov/21546436
Page: p.1278
6.5 g single, oral
Overdose
Dose: 6.5 g
Route: oral
Route: single
Dose: 6.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
healthy, 56
n = 1
Health Status: healthy
Age Group: 56
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
Disc. AE: Vomiting, Blurred vision...
AEs leading to
discontinuation/dose reduction:
Vomiting (severe)
Blurred vision
Sinus tachycardia
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
https://pubmed.ncbi.nlm.nih.gov/12507258
healthy, 56
n = 1
Health Status: healthy
Age Group: 56
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
https://pubmed.ncbi.nlm.nih.gov/12507258
Disc. AE: Cardiomegaly, Fibrosis myocardial...
AEs leading to
discontinuation/dose reduction:
Cardiomegaly (grade 5)
Fibrosis myocardial (grade 5)
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
https://pubmed.ncbi.nlm.nih.gov/12507258
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Disc. AE: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea (0.32%)
Vomiting (0.32%)
Leg pain (0.32%)
Backache (0.32%)
Intermittent headache (0.32%)
Dyspepsia (0.32%)
Headache (0.32%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1403
unhealthy, 60
n = 163
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 163
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1403
Disc. AE: Headache, Flushing...
AEs leading to
discontinuation/dose reduction:
Headache (0.61%)
Flushing (0.61%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1403
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
unhealthy, 60
n = 225
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 225
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
Disc. AE: Headache, Flushing...
AEs leading to
discontinuation/dose reduction:
Headache (0.9%)
Flushing (0.44%)
Blurred vision (0.44%)
Groin pain (1.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
400 mg single, oral
Overdose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/30473955
Page: p.1,2
unhealthy, 67
n = 1
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 67
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/30473955
Page: p.1,2
Disc. AE: Acute kidney injury...
AEs leading to
discontinuation/dose reduction:
Acute kidney injury
Sources:
https://pubmed.ncbi.nlm.nih.gov/30473955
Page: p.1,2
AEs

AEs

AESignificanceDosePopulation
Flushing Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
Headache Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
Tachycardia mild
Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
Visual field defect Disc. AE
2400 mg single, oral
Overdose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.2
Rhabdomyolysis Disc. AE
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/24661860
Page: p.258
unhealthy, 45
n = 1
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 45
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24661860
Page: p.258
Visual disturbance NOS Disc. AE
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/24661860
Page: p.258
unhealthy, 45
n = 1
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 45
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24661860
Page: p.258
Blurred vision Disc. AE
6.5 g single, oral
Overdose
Dose: 6.5 g
Route: oral
Route: single
Dose: 6.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
healthy, 56
n = 1
Health Status: healthy
Age Group: 56
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
Sinus tachycardia Disc. AE
6.5 g single, oral
Overdose
Dose: 6.5 g
Route: oral
Route: single
Dose: 6.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
healthy, 56
n = 1
Health Status: healthy
Age Group: 56
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
Vomiting severe
Disc. AE
6.5 g single, oral
Overdose
Dose: 6.5 g
Route: oral
Route: single
Dose: 6.5 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
healthy, 56
n = 1
Health Status: healthy
Age Group: 56
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
Page: p.1
Cardiomegaly grade 5
Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
https://pubmed.ncbi.nlm.nih.gov/12507258
healthy, 56
n = 1
Health Status: healthy
Age Group: 56
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
https://pubmed.ncbi.nlm.nih.gov/12507258
Fibrosis myocardial grade 5
Disc. AE
600 mg single, oral
Overdose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
https://pubmed.ncbi.nlm.nih.gov/12507258
healthy, 56
n = 1
Health Status: healthy
Age Group: 56
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/26139313
https://pubmed.ncbi.nlm.nih.gov/12507258
Backache 0.32%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Dyspepsia 0.32%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Headache 0.32%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Intermittent headache 0.32%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Leg pain 0.32%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Nausea 0.32%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Vomiting 0.32%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
unhealthy, 58
n = 316
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 58
Sex: M
Population Size: 316
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1400
Flushing 0.61%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1403
unhealthy, 60
n = 163
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 163
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1403
Headache 0.61%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1403
unhealthy, 60
n = 163
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 163
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1403
Blurred vision 0.44%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
unhealthy, 60
n = 225
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 225
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
Flushing 0.44%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
unhealthy, 60
n = 225
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 225
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
Headache 0.9%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
unhealthy, 60
n = 225
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 225
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
Groin pain 1.3%
Disc. AE
100 mg 1 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
unhealthy, 60
n = 225
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 60
Sex: M
Population Size: 225
Sources:
https://pubmed.ncbi.nlm.nih.gov/9580646
Page: p.1401
Acute kidney injury Disc. AE
400 mg single, oral
Overdose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/30473955
Page: p.1,2
unhealthy, 67
n = 1
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 67
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/30473955
Page: p.1,2
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:9139
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9139
ChemicalBook
CB2747316
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2747316
ChemicalBook
CB82675677
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB82675677
MolPort
MolPort-001-995-394
https://www.molport.com/shop/molecule-link/MolPort-001-995-394
MolPort
MolPort-002-885-861
https://www.molport.com/shop/molecule-link/MolPort-002-885-861
MolPort
MolPort-046-854-547
https://www.molport.com/shop/molecule-link/MolPort-046-854-547
MolPort
MolPort-047-113-940
https://www.molport.com/shop/molecule-link/MolPort-047-113-940
ZINC
ZINC000019796168
http://zinc15.docking.org/substances/ZINC000019796168
eMolecules
902463
https://www.emolecules.com/cgi-bin/more?vid=902463
PubMed

PubMed

TitleDatePubMed
Sildenafil in the treatment of female sexual dysfunction induced by selective serotonin reuptake inhibitors.
1999 Jun
Sildenafil treatment of paroxetine-induced anorgasmia in a woman.
1999 May
Sildenafil and erectile dysfunction.
2000 Dec
Alpha-adrenergic receptor blockade by phentolamine increases the efficacy of vasodilators in penile corpus cavernosum.
2000 Mar
Acute myocardial infarction associated wiht Sildenafil (Viagra) ingestion.
2000 May
Hypotensive interaction of sildenafil and nicorandil in rats through the cGMP pathway but not by K(ATP) channel activation.
2000 Nov
[Myocardial ischemia after administration de sildenafil: description of a case and review of the literature].
2000 Sep
A risk-benefit assessment of sildenafil in the treatment of erectile dysfunction.
2001
Strategies for the treatment of antidepressant-related sexual dysfunction.
2001
Safe use of sildenafil in patients with coronary artery disease.
2001 Apr
Modulation of human platelet aggregation by the phosphodiesterase type 5 inhibitor sildenafil.
2001 Apr
Efficacy and safety of sildenafil citrate in the treatment of men with mild to moderate erectile dysfunction.
2001 Apr
Studies of Viagra offer some reassurance to men with concerns about cardiac effects.
2001 Apr 18
Assessment of as needed use of pharmacotherapy and the pause-squeeze technique in premature ejaculation.
2001 Feb
Central effects of sildenafil (Viagra) on auditory selective attention and verbal recognition memory in humans: a study with event-related brain potentials.
2001 Feb
Intracerebral haemorrhage associated with sildenafil citrate.
2001 Feb
Efficacy of oral sildenafil in the treatment of erectile dysfunction in diabetic men with positive response to intracavernosal injection of alprostadil.
2001 Feb
Are things looking up for the treatment of gastroparesis? Sildenafil in animal models of diabetic gastropathy.
2001 Feb
Sildenafil-mediated reduction in retinal function in heterozygous mice lacking the gamma-subunit of phosphodiesterase.
2001 Feb
Cost-effectiveness of sildenafil.
2001 Feb 6
The role of nitric oxide in penile erection.
2001 Jan
pH-mediated field-amplified sample stacking of pharmaceutical cations in high-ionic strength samples.
2001 Jan
Viagra: are anaesthetists rising to the challenge?
2001 Jan
A dose-escalation study to assess the efficacy and safety of sildenafil citrate in men with erectile dysfunction.
2001 Jan
[Prescribing of sildenafil by national insurance program physicians. What basic sexual medicine qualification is required?].
2001 Jan 11
[Paths to sexual satisfaction. What will stimulate the tired man?].
2001 Jan 18
[Drug treatment of erection disorders in patients with cardiovascular disease].
2001 Jan 27
Viagra: a three-year sexual revolution and the need to recognise its role within the NHS.
2001 Mar
Three-year update of sildenafil citrate (Viagra) efficacy and safety.
2001 Mar
Initial uptake in use of sildenafil in general practice.
2001 Mar
Anterior ischemic optic neuropathy associated with viagra.
2001 Mar
Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil.
2001 Mar
Is brachytherapy comparable with radical prostatectomy and external-beam radiation for clinically localized prostate cancer?
2001 Mar
Sildenafil citrate and sperm function.
2001 Mar
Comparison of FDA reports of patient deaths associated with sildenafil and with injectable alprostadil.
2001 Mar
Combination of phentolamine and L-arginine or sildenafil synergistically improves neurogenic relaxation of rabbit corpus cavernosum smooth muscle.
2001 Mar
Clinical efficacy of sildenafil in patients on chronic dialysis.
2001 Mar
[Side effects of sildenafil: findings from two years practical experience].
2001 Mar 17
Cardiovascular events in users of sildenafil: results from first phase of prescription event monitoring in England.
2001 Mar 17
Subjective visual halos after sildenafil (Viagra) administration: Electroretinographic evaluation.
2001 May
Patents

Patents

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Sample Use Guides

In Vivo Use Guide
Erectile disfunction: For most patients, the recommended dose is 50 mg taken, as needed, approximately 1 hour before sexual activity. Pulmonary arterial hypertension: 5 mg or 20 mg three times a day, 46 hours apart (oral); 2.5 mg or 10 mg three times a day administered as an intravenous bolus injection.
Route of Administration: Other
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/20590607
Human bladder samples were treated with sildenafil (10 nM–30 µM) to test the ability of the drug to inhibit contraction.
Substance Class Chemical
Created
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on Sat Dec 16 10:54:43 GMT 2023
Edited
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on Sat Dec 16 10:54:43 GMT 2023
Record UNII
8B699ZY1CH
Record Status Validated (UNII)
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Name Type Language
SILDENAFIL NITRATE
Common Name English
7H-PYRAZOLO(4,3-D)PYRIMIDIN-7-ONE, 5-(2-ETHOXY-5-((4-METHYL-1-PIPERAZINYL)SULFONYL)PHENYL)-1,6-DIHYDRO-1-METHYL-3-PROPYL-, NITRATE (1:1)
Systematic Name English
PIPERAZINE, 1-((3-(4,7-DIHYDRO-1-METHYL-7-OXO-3-PROPYL-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-4-ETHOXYPHENYL)SULFONYL)-4-METHYL-, MONONITRATE
Systematic Name English
NCX-911
Code English
Code System Code Type Description
CAS
252951-59-0
Created by admin on Sat Dec 16 10:54:43 GMT 2023 , Edited by admin on Sat Dec 16 10:54:43 GMT 2023
PRIMARY
PUBCHEM
135484084
Created by admin on Sat Dec 16 10:54:43 GMT 2023 , Edited by admin on Sat Dec 16 10:54:43 GMT 2023
PRIMARY
FDA UNII
8B699ZY1CH
Created by admin on Sat Dec 16 10:54:43 GMT 2023 , Edited by admin on Sat Dec 16 10:54:43 GMT 2023
PRIMARY
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