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

Molecular Formula C22H30N6O4S
Molecular Weight 474.576
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Intracavernous alprostadil alfadex (EDEX/VIRIDAL) is effective and safe in patients with erectile dysfunction after failing sildenafil (Viagra).
2000 Apr
Cyclic nucleotide phosphodiesterase type 5 activity limits blood flow to hypoperfused myocardium during exercise.
2000 Dec 12
[Effectiveness and adverse effects of sildenafil in erectile dysfunction].
2000 Jan 16
Hypotensive interaction of sildenafil and nicorandil in rats through the cGMP pathway but not by K(ATP) channel activation.
2000 Nov
'Viagra effect' - influence of mass media on patient behavior.
2001
Strategies for the treatment of antidepressant-related sexual dysfunction.
2001
Sildenafil citrate effectively reverses sexual dysfunction induced by three-dimensional conformal radiation therapy.
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
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.
2001 Feb
Changes in ED therapy in the Viagra era.
2001 Feb
Intracerebral haemorrhage associated with sildenafil citrate.
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
Interposition sural nerve grafting during radical retropubic prostatectomy.
2001 Feb
Should male patients with chest pain be questioned about Viagra use during triage screening?
2001 Feb
Are things looking up for the treatment of gastroparesis? Sildenafil in animal models of diabetic gastropathy.
2001 Feb
Sildenafil inhibits gastroduodenal motility.
2001 Feb
Sildenafil-simvastatin interaction: possible cause of rhabdomyolysis?
2001 Feb 15
[Research on impotence and marketing].
2001 Feb 20
Cost-effectiveness of sildenafil.
2001 Feb 6
Sildenafil citrate: a therapeutic update.
2001 Jan
Effect of sildenafil in patients with erectile dysfunction taking antihypertensive therapy. Sildenafil Study Group.
2001 Jan
Viagra: are anaesthetists rising to the challenge?
2001 Jan
Practice patterns in the diagnosis and treatment of erectile dysfunction among family practice physicians.
2001 Jan
Sildenafil citrate (Viagra) does not exacerbate myocardial ischemia in canine models of coronary artery stenosis.
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
[Erectile dysfunction in coronary heart disease. No fear about the blue pill].
2001 Jan 18
[Paths to sexual satisfaction. What will stimulate the tired man?].
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
Identification and regulation of human PDE5A gene promoter.
2001 Jan 26
[Drug treatment of erection disorders in patients with cardiovascular disease].
2001 Jan 27
Phosphodiesterase 5 inhibitors and nitrergic transmission-from zaprinast to sildenafil.
2001 Jan 5
Relapse prevention strategies and techniques with erectile dysfunction.
2001 Jan-Feb
Three-year update of sildenafil citrate (Viagra) efficacy and safety.
2001 Mar
Anterior ischemic optic neuropathy associated with viagra.
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
Phosphodiesterase inhibitor-mediated potentiation of adenovirus delivery to myocardium.
2001 Mar
In vivo and in vitro investigation of the effects of sildenafil on rat cavernous smooth muscle.
2001 Mar
Direct effects of selective type 5 phosphodiesterase inhibitors alone or with other vasodilators on the erectile response in cats.
2001 Mar
Clinical efficacy of sildenafil in patients on chronic dialysis.
2001 Mar
Cardiovascular events in users of sildenafil: results from first phase of prescription event monitoring in England.
2001 Mar 17
Narrowbore high-performance liquid chromatography for the simultaneous determination of sildenafil and its metabolite UK-103,320 in human plasma using column switching.
2001 Mar 5
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:53:53 UTC 2019
Edited
by admin
on Mon Oct 21 20:53:53 UTC 2019
Record UNII
3M7OB98Y7H
Record Status Validated (UNII)
Record Version
  • Download
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
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