SILDENAFIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H30N6O4S
Molecular Weight	474.5783
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCc1c2c(c(=O)[nH]c(-c3cc(ccc3OCC)S(=O)(=O)N4CCN(C)CC4)n2)n(C)n1

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	474.5783
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020895s045lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021845s016,022473s010,203109s009lbl.pdf

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

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 5A 30 Target ID: CHEMBL1827 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020895s045lbl.pdf	Inhibitor 7728		3.5 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Erectile dysfunction 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020895s045lbl.pdf	Curative		Approved 8043	VIAGRA Approved Use VIAGRA is a phosphodiesterase-5 (PDE5) inhibitor indicated for the treatment of erectile dysfunction. Launch Date 8.9095681E11
Pulmonary arterial hypertension 34 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021845s016,022473s010,203109s009lbl.pdf	Primary		Approved 8043	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 1.11775685E12

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
A risk-benefit assessment of sildenafil in the treatment of erectile dysfunction.	2001	11330655
Use of sildenafil in penile implant patients.	2001	11316977
'Viagra effect' - influence of mass media on patient behavior.	2001	11316976
Sildenafil citrate effectively reverses sexual dysfunction induced by three-dimensional conformal radiation therapy.	2001 Apr	11306401
Modulation of human platelet aggregation by the phosphodiesterase type 5 inhibitor sildenafil.	2001 Apr	11300654
Intracavernosal injection of sildenafil citrate: misapplication of the drug.	2001 Apr	11257683
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.	2001 Feb	11289574
Sildenafil citrate, a selective phosphodiesterase type 5 inhibitor: urologic and cardiovascular implications.	2001 Feb	11289569
I've heard of an herbal alternative to Viagra for impotence. Does it work and is it safe?	2001 Feb	11216037
Sildenafil citrate (VIAGRA) improves erectile function in elderly patients with erectile dysfunction: a subgroup analysis.	2001 Feb	11213274
Determination of sildenafil citrate in plasma by high-performance liquid chromatography and a case for the potential interaction of grapefruit juice with sildenafil citrate.	2001 Feb	11206038
Interposition sural nerve grafting during radical retropubic prostatectomy.	2001 Feb	11182323
Sildenafil modulates hemodynamics and pulmonary gas exchange.	2001 Feb	11179103
Viagra for impotence of pulmonary vasodilator therapy?	2001 Feb	11179097
Should male patients with chest pain be questioned about Viagra use during triage screening?	2001 Feb	11174258
Sex and the heart: what is the role of the cardiologist?	2001 Feb	11161931
Are things looking up for the treatment of gastroparesis? Sildenafil in animal models of diabetic gastropathy.	2001 Feb	11159901
Sildenafil-mediated reduction in retinal function in heterozygous mice lacking the gamma-subunit of phosphodiesterase.	2001 Feb	11157892
[Endocrinology 1999-2000].	2001 Feb 15	11284421
Cost-effectiveness of sildenafil.	2001 Feb 6	11177342
Cost-effectiveness of sildenafil.	2001 Feb 6	11177341
Cost-effectiveness of sildenafil.	2001 Feb 6	11177340
The role of nitric oxide in penile erection.	2001 Jan	11336572
Sildenafil citrate: a therapeutic update.	2001 Jan	11219477
Intracavernosal injection therapy. Does it still have a role in erectile dysfunction?	2001 Jan	11211711
Effect of sildenafil in patients with erectile dysfunction taking antihypertensive therapy. Sildenafil Study Group.	2001 Jan	11206684
Sexual aspects of headache. How sexual function relates to headaches and their causes and treatment.	2001 Jan	11198260
pH-mediated field-amplified sample stacking of pharmaceutical cations in high-ionic strength samples.	2001 Jan	11197180
Viagra: are anaesthetists rising to the challenge?	2001 Jan	11167459
Practice patterns in the diagnosis and treatment of erectile dysfunction among family practice physicians.	2001 Jan	11164161
Sildenafil citrate (Viagra) does not exacerbate myocardial ischemia in canine models of coronary artery stenosis.	2001 Jan	11153753
[Prescribing of sildenafil by national insurance program physicians. What basic sexual medicine qualification is required?].	2001 Jan 11	11217683
[Erectile dysfunction in coronary heart disease. No fear about the blue pill].	2001 Jan 18	11215348
[Paths to sexual satisfaction. What will stimulate the tired man?].	2001 Jan 18	11215339
Effect of sildenafil on non-adrenergic non-cholinergic neurotransmission in bovine penile small arteries.	2001 Jan 26	11165227
Regulation of human PDE5A2 intronic promoter by cAMP and cGMP: identification of a critical Sp1-binding site.	2001 Jan 26	11162576
Identification and regulation of human PDE5A gene promoter.	2001 Jan 26	11162575
[Drug treatment of erection disorders in patients with cardiovascular disease].	2001 Jan 27	11213561
Viagra: a three-year sexual revolution and the need to recognise its role within the NHS.	2001 Mar	11321862
Initial uptake in use of sildenafil in general practice.	2001 Mar	11317480
Anterior ischemic optic neuropathy associated with viagra.	2001 Mar	11315976
Identification of the cytochrome P450 enzymes involved in the N-demethylation of sildenafil.	2001 Mar	11298070
Sildenafil citrate and sperm function.	2001 Mar	11262489
Phosphodiesterase inhibitor-mediated potentiation of adenovirus delivery to myocardium.	2001 Mar	11181024
In vivo and in vitro investigation of the effects of sildenafil on rat cavernous smooth muscle.	2001 Mar	11176531
Direct effects of selective type 5 phosphodiesterase inhibitors alone or with other vasodilators on the erectile response in cats.	2001 Mar	11176530
Clinical efficacy of sildenafil in patients on chronic dialysis.	2001 Mar	11176477
Cardiovascular events in users of sildenafil: results from first phase of prescription event monitoring in England.	2001 Mar 17	11250850
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	11254188
Antimitogenic actions of organic nitrates are potentiated by sildenafil and mediated via activation of protein kinase A.	2001 May	11306686

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: Other

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 `Sat Jun 26 15:33:35 UTC 2021` Edited by `admin` on `Sat Jun 26 15:33:35 UTC 2021`
Record UNII	3M7OB98Y7H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SILDENAFIL

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