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 7701	Erectile dysfunction Pulmonary arterial hypertension	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	Phosphodiesterase 5A	Approved 7997	VIAGRA Approved Use VIAGRA is a phosphodiesterase-5 (PDE5) inhibitor indicated for the treatment of erectile dysfunction. Launch Date 890956800000
Pulmonary arterial hypertension 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021845s016,022473s010,203109s009lbl.pdf	Primary	Phosphodiesterase 5A	Approved 7997	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 1117756800000

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	healthy, 33 Health Status: healthy Age Group: 33 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	Disc. AE: Flushing, Headache... AEs leading to discontinuation/dose reduction: Flushing Headache Tachycardia (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/26139313
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	healthy, 33 Health Status: healthy Age Group: 33 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	Disc. AE: Visual field defect... AEs leading to discontinuation/dose reduction: Visual field defect Sources: https://pubmed.ncbi.nlm.nih.gov/26139313
250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24661860	unhealthy, 45 Health Status: unhealthy Age Group: 45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/24661860	Disc. AE: Rhabdomyolysis, Visual disturbance NOS... AEs leading to discontinuation/dose reduction: Rhabdomyolysis Visual disturbance NOS Sources: https://pubmed.ncbi.nlm.nih.gov/24661860
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	unhealthy, 47.5 Health Status: unhealthy Age Group: 47.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/21546436	Sources: https://pubmed.ncbi.nlm.nih.gov/21546436
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	healthy, 56 Health Status: healthy Age Group: 56 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26139313	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
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 Health Status: healthy Age Group: 56 Sex: M 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 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	unhealthy, 58 Health Status: unhealthy Age Group: 58 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	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
100 mg 1 times / day multiple, oral 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	unhealthy, 60 Health Status: unhealthy Age Group: 60 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	Disc. AE: Headache, Flushing... AEs leading to discontinuation/dose reduction: Headache (0.61%) Flushing (0.61%) Sources: https://pubmed.ncbi.nlm.nih.gov/9580646
100 mg 1 times / day multiple, oral 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	unhealthy, 60 Health Status: unhealthy Age Group: 60 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9580646	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
400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30473955	unhealthy, 67 Health Status: unhealthy Age Group: 67 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/30473955	Disc. AE: Acute kidney injury... AEs leading to discontinuation/dose reduction: Acute kidney injury Sources: https://pubmed.ncbi.nlm.nih.gov/30473955

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9139	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9139
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

PubMed

Title	Date	PubMed
[Effectiveness and adverse effects of sildenafil in erectile dysfunction].	2000 Jan 16	10693332
Use of sildenafil in penile implant patients.	2001	11316977
Intracavernosal injection of sildenafil citrate: misapplication of the drug.	2001 Apr	11257683
Studies of Viagra offer some reassurance to men with concerns about cardiac effects.	2001 Apr 18	11308415
Central effects of sildenafil (Viagra) on auditory selective attention and verbal recognition memory in humans: a study with event-related brain potentials.	2001 Feb	11289570
Sildenafil citrate (VIAGRA) improves erectile function in elderly patients with erectile dysfunction: a subgroup analysis.	2001 Feb	11213274
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
Sildenafil-mediated reduction in retinal function in heterozygous mice lacking the gamma-subunit of phosphodiesterase.	2001 Feb	11157892
Sildenafil-simvastatin interaction: possible cause of rhabdomyolysis?	2001 Feb 15	11237079
[Research on impotence and marketing].	2001 Feb 20	11301624
The role of nitric oxide in penile erection.	2001 Jan	11336572
Effect of sildenafil in patients with erectile dysfunction taking antihypertensive therapy. Sildenafil Study Group.	2001 Jan	11206684
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
Alternatives to Viagra.	2001 Mar	11286776
Comparison of FDA reports of patient deaths associated with sildenafil and with injectable alprostadil.	2001 Mar	11261524
Phosphodiesterase inhibitor-mediated potentiation of adenovirus delivery to myocardium.	2001 Mar	11181024
Direct effects of selective type 5 phosphodiesterase inhibitors alone or with other vasodilators on the erectile response in cats.	2001 Mar	11176530
[Side effects of sildenafil: findings from two years practical experience].	2001 Mar 17	11284286
FIA of sildenafil citrate using UV-detection.	2001 May	11275442

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