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

Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N6O4S
Molecular Weight 474.576
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SILDENAFIL

SMILES

CCCC1=NN(C)C2=C1N=C(NC2=O)C3=CC(=CC=C3OCC)S(=O)(=O)N4CCN(C)CC4

InChI

InChIKey=BNRNXUUZRGQAQC-UHFFFAOYSA-N
InChI=1S/C22H30N6O4S/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/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)

HIDE SMILES / InChI

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

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
A risk-benefit assessment of sildenafil in the treatment of erectile dysfunction.
2001
Use of sildenafil in penile implant patients.
2001
'Viagra effect' - influence of mass media on patient behavior.
2001
Safe use of sildenafil in patients with coronary artery disease.
2001 Apr
Cost-sharing for prescriptions of sildenafil and finasteride: a case study in veteran patients.
2001 Apr
Sildenafil citrate effectively reverses sexual dysfunction induced by three-dimensional conformal radiation therapy.
2001 Apr
Sildenafil citrate for penile hemodynamic determination: an alternative to intracavernosal agents in Doppler ultrasound evaluation of erectile dysfunction.
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
Intracavernosal injection of sildenafil citrate: misapplication of the drug.
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
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.
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
Sildenafil citrate, a selective phosphodiesterase type 5 inhibitor: urologic and cardiovascular implications.
2001 Feb
Changes in ED therapy in the Viagra era.
2001 Feb
I've heard of an herbal alternative to Viagra for impotence. Does it work and is it safe?
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
Sildenafil citrate (VIAGRA) improves erectile function in elderly patients with erectile dysfunction: a subgroup analysis.
2001 Feb
Sildenafil modulates hemodynamics and pulmonary gas exchange.
2001 Feb
Should male patients with chest pain be questioned about Viagra use during triage screening?
2001 Feb
[Research on impotence and marketing].
2001 Feb 20
Cost-effectiveness of sildenafil.
2001 Feb 6
Cost-effectiveness of sildenafil.
2001 Feb 6
The role of nitric oxide in penile erection.
2001 Jan
Emergency sperm extraction for transient erectile dysfunction prior to assisted conception.
2001 Jan
Sildenafil citrate: a therapeutic update.
2001 Jan
Sexual aspects of headache. How sexual function relates to headaches and their causes and treatment.
2001 Jan
pH-mediated field-amplified sample stacking of pharmaceutical cations in high-ionic strength samples.
2001 Jan
Sildenafil citrate (Viagra) does not exacerbate myocardial ischemia in canine models of coronary artery stenosis.
2001 Jan
[Prescribing of sildenafil by national insurance program physicians. What basic sexual medicine qualification is required?].
2001 Jan 11
[Erectile dysfunction in coronary heart disease. No fear about the blue pill].
2001 Jan 18
Effect of sildenafil on non-adrenergic non-cholinergic neurotransmission in bovine penile small arteries.
2001 Jan 26
Regulation of human PDE5A2 intronic promoter by cAMP and cGMP: identification of a critical Sp1-binding site.
2001 Jan 26
Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum.
2001 Jan 5
Relapse prevention strategies and techniques with erectile dysfunction.
2001 Jan-Feb
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
Is the sildenafil product information adequate to facilitate informed therapeutic decisions?
2001 Mar
Comparison of FDA reports of patient deaths associated with sildenafil and with injectable alprostadil.
2001 Mar
Phosphodiesterase inhibitor-mediated potentiation of adenovirus delivery to myocardium.
2001 Mar
[Side effects of sildenafil: findings from two years practical experience].
2001 Mar 17
Subjective visual halos after sildenafil (Viagra) administration: Electroretinographic evaluation.
2001 May
Antimitogenic actions of organic nitrates are potentiated by sildenafil and mediated via activation of protein kinase A.
2001 May
FIA of sildenafil citrate using UV-detection.
2001 May
Patents

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: Oral; Intravenous
In Vitro Use Guide
Human bladder samples were treated with sildenafil (10 nM–30 µM) to test the ability of the drug to inhibit contraction.
Name Type Language
SILDENAFIL
EMA EPAR   HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
SILDENAFIL [VANDF]
Common Name English
SILDENAFIL RATIOPHARM
Brand Name English
APHRODIL
Brand Name English
HIP-0908
Code English
VIZARSIN
Brand Name English
PIPERAZINE, 1-((3-(6,7-DIHYDRO-1-METHYL-7-OXO-3-PROPYL-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-4-ETHOXYPHENYL)SULFONYL)-4-METHYL-
Systematic Name English
SILDENAFIL [MI]
Common Name English
HIP0908
Code English
SILDENAFIL [EMA EPAR]
Common Name English
SILDENAFIL [WHO-DD]
Common Name English
SILDENAFIL ACTAVIS
Brand Name English
1-((3-(6,7-DIHYDRO-1-METHYL-7-OXO-3-PROPYL-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-4-ETHOXYPHENYL)SULFONYL)-4-METHYLPIPERAZINE
Systematic Name English
SILDENAFIL [HSDB]
Common Name English
SILDENAFIL TEVA
Brand Name English
PATREX
Brand Name English
SILDENAFIL [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2127
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EMA ASSESSMENT REPORTS VIZARSIN (AUTHORIZED: ERECTILE DYSFUNCTION)
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EMA ASSESSMENT REPORTS REVATIO (AUTHORIZED: HYPERTENSION, PULMONARY)
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
WHO-VATC QG04BE03
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EMA ASSESSMENT REPORTS VIAGRA (AUTHORIZED: ERECTILE DYSFUNCTIONS)
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
NDF-RT N0000175599
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
NDF-RT N0000020026
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EMA ASSESSMENT REPORTS SILDENAFIL RATIOPHARM (AUTHORIZED: ERECTILE DYSFUNCTIONS)
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EMA ASSESSMENT REPORTS PATREX (WITHDRAWN: ERECTILE DYSFUNCTIONS)
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EMA ASSESSMENT REPORTS SILDENAFIL ACTAVIS (AUTHORIZED: ERECTILE DYSFUNCTIONS)
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
FDA ORPHAN DRUG 344211
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EMA ASSESSMENT REPORTS SILDENAFIL TEVA (AUTHORIZED: ERECTILE DYSFUNCTIONS)
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
WHO-ATC G04BE03
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
EU-Orphan Drug EU/3/17/1885
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
LIVERTOX 885
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
Code System Code Type Description
WIKIPEDIA
SILDENAFIL
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
EVMPD
SUB10517MIG
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
NCI_THESAURUS
C61940
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
CAS
139755-83-2
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
PUBCHEM
5212
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
RXCUI
136411
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL192
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
INN
7374
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
LactMed
139755-83-2
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
HSDB
139755-83-2
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
IUPHAR
4743
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
MESH
C101426
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
EPA CompTox
139755-83-2
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY
MERCK INDEX
M9898
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY Merck Index
DRUG BANK
DB00203
Created by admin on Mon Oct 21 20:53:53 UTC 2019 , Edited by admin on Mon Oct 21 20:53:53 UTC 2019
PRIMARY