SILDENAFIL CITRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H30N6O4S.C6H8O7
Molecular Weight	666.7
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCCC1=NN(C)C2=C1N=C(NC2=O)C3=C(OCC)C=CC(=C3)S(=O)(=O)N4CCN(C)CC4

InChI

InChIKey=DEIYFTQMQPDXOT-UHFFFAOYSA-N

InChI=1S/C22H30N6O4S.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

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

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

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 8297		3.5 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Erectile dysfunction 35 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020895s045lbl.pdf	Curative		Approved 8429	VIAGRA Approved Use VIAGRA is a phosphodiesterase-5 (PDE5) inhibitor indicated for the treatment of erectile dysfunction. Launch Date 1998
Pulmonary arterial hypertension 35 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021845s016,022473s010,203109s009lbl.pdf	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

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
Phenelzine-induced sexual dysfunction treated with sildenafil.	1999 Apr-Jun	10327382
Sildenafil ameliorates effects of inhaled nitric oxide withdrawal.	1999 Jul	10422958
Inhibition of cyclic GMP-binding cyclic GMP-specific phosphodiesterase (Type 5) by sildenafil and related compounds.	1999 Jul	10385692
Atrial fibrillation and continuous hypotension induced by sildenafil in an intermittent WPW syndrome patient.	1999 Nov	10737566
Sildenafil and erectile dysfunction.	2000 Dec	11097980
[Effectiveness and adverse effects of sildenafil in erectile dysfunction].	2000 Jan 16	10693332
Acute, symptomatic atrial fibrillation after sildenafil citrate therapy in a patient with hypertrophic obstructive cardiomyopathy.	2000 Jul	10910376
Alpha-adrenergic receptor blockade by phentolamine increases the efficacy of vasodilators in penile corpus cavernosum.	2000 Mar	10845762
'Viagra effect' - influence of mass media on patient behavior.	2001	11316976
Characterization of TbPDE2A, a novel cyclic nucleotide-specific phosphodiesterase from the protozoan parasite Trypanosoma brucei.	2001 Apr 13	11134002
Studies of Viagra offer some reassurance to men with concerns about cardiac effects.	2001 Apr 18	11308415
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.	2001 Feb	11289574
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
Changes in ED therapy in the Viagra era.	2001 Feb	11289566
Phosphodiesterase isoenzymes as pharmacological targets in the treatment of male erectile dysfunction.	2001 Feb	11289565
Interposition sural nerve grafting during radical retropubic prostatectomy.	2001 Feb	11182323
Sildenafil modulates hemodynamics and pulmonary gas exchange.	2001 Feb	11179103
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
Sildenafil inhibits gastroduodenal motility.	2001 Feb	11148432
Cost-effectiveness of sildenafil.	2001 Feb 6	11177340
The role of nitric oxide in penile erection.	2001 Jan	11336572
Sildenafil citrate (Viagra) does not exacerbate myocardial ischemia in canine models of coronary artery stenosis.	2001 Jan	11153753
Preliminary observations of sildenafil treatment for erectile dysfunction in dialysis patients.	2001 Jan	11136178
[Paths to sexual satisfaction. What will stimulate the tired man?].	2001 Jan 18	11215339
Identification and regulation of human PDE5A gene promoter.	2001 Jan 26	11162575
Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum.	2001 Jan 5	11137871
Alternatives to Viagra.	2001 Mar	11286776
Is the sildenafil product information adequate to facilitate informed therapeutic decisions?	2001 Mar	11261532
Comparison of FDA reports of patient deaths associated with sildenafil and with injectable alprostadil.	2001 Mar	11261524
Combination of phentolamine and L-arginine or sildenafil synergistically improves neurogenic relaxation of rabbit corpus cavernosum smooth muscle.	2001 Mar	11248652
Phosphodiesterase inhibitor-mediated potentiation of adenovirus delivery to myocardium.	2001 Mar	11181024
Subjective visual halos after sildenafil (Viagra) administration: Electroretinographic evaluation.	2001 May	11320016

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 `Fri Dec 15 15:44:31 GMT 2023` Edited by `admin` on `Fri Dec 15 15:44:31 GMT 2023`
Record UNII	BW9B0ZE037
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SILDENAFIL CITRATE

Official Name

English

SILDENAFIL CITRATE [USP MONOGRAPH]

Common Name

English

UK-92,480-10

Code

English

SILDENAFIL CITRATE [EP MONOGRAPH]

Common Name

English

NSC-744009

Code

English

SILDENAFIL CITRATE [VANDF]

Common Name

English

NSC-758669

Code

English

UK-92480-10

Code

English

SILDENAFIL CITRATE [MART.]

Common Name

English

SILDENAFIL CITRATE [USP-RS]

Common Name

English

SILDENAFIL CITRATE [MI]

Common Name

English

LIQREV

Brand Name

English

SILDENAFIL CITRATE [USAN]

Common Name

English

REVATIO

Brand Name

English

SILDENAFIL CITRATE [JAN]

Common Name

English

VIAGRA

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 citrate (1:1)

Systematic Name

English

SILDENAFIL (AS CITRATE)

Common Name

English

SILDENAFIL CITRATE [ORANGE BOOK]

Common Name

English

Sildenafil citrate [WHO-DD]

Common 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-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

Systematic Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

VIAGRA (AUTHORIZED: ERECTILE DYSFUNCTIONS)