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Clinical data
Pronunciation	/ s ? l ? d ? n ? f ? l / sil- DEN -?-fil
Trade names	Viagra, Revatio, others
AHFS / Drugs.com	monograph
MedlinePlus	a699015
data	EU EMA : yes ; US FDA : Sildenafil ;
Pregnancy ; category	AU : B1 ; US : B (No risk in non-human studies) ; ;
Routes of ; administration	By mouth ( tablets ), IV
ATC code	G04BE03 ( WHO ) ;
Legal status
Legal status	AU : S4 (Prescription only) ; CA : ?-only ; UK : Pharmacy medicines ; US : ?-only ; ? (Prescription only) ;
Pharmacokinetic data
Bioavailability	41% (mean)
Protein binding	~96%
Metabolism	Liver : CYP3A4 (major route), CYP2C9 (minor route)
Metabolites	N -desmethylsildenafil (~50% potency for PDE 5 )
Elimination half-life	3?4 hours
Excretion	Feces (~80%), urine (~13%)
Identifiers
	IUPAC name 5-{2-Ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,6-dihydro-7 H -pyrazolo[4,3- d ]pyrimidin-7-one ;
CAS Number	139755-83-2 ; Citrate: 171599-83-0 ;
PubChem CID	5212 ;
DrugBank	DB00203 ;
ChemSpider	5023 ;
UNII	3M7OB98Y7H ;
KEGG	D08514 ;
ChEBI	CHEBI:9139 ;
ChEMBL	CHEMBL192 ;
PDB ligand	VIA ( PDBe , RCSB PDB ) ;
ECHA InfoCard	100.122.676
Chemical and physical data
Formula	C 22 H 30 N 6 O 4 S
Molar mass	474.5764 g/mol
3D model ( JSmol )	Interactive image ;
	SMILES CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C ;
	InChI 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) ; Key:BNRNXUUZRGQAQC-UHFFFAOYSA-N ;
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https://or.wikipedia.org/wiki/Sildenafil

?????????? ( ?????? ?????? Sildenafil , ?????? ??? ???????? / Viagra ) ?? ???? ( medication ) ??? ???? ????? ?????? ( erectile dysfunction ) ?????? ? ???????? ?????????? ( pulmonary arterial hypertension ) ???????? ??????? ?????? ? ^[?] ???????????? ??? ?????? ??????? ????????? ?? ?????, ?? ???? ?????? ???????? ? ^[?] ??? ?????? ( by mouth ) ?? ??????????? ???????? ( injection into a vein ) ?????? ?????? ? ^[?] ????? ?? ????? ?????? ??? ??????????? ??? ? ? ????? ????????? ?????? ??? ? ^[?]

?????? ??????? ????????????? ????? ?????? , ?????????? ( heartburn ) ? ???? ??? ??????? ? ^[?] ?????????? ??????? ??? ???? ( cardiovascular disease ) ???????? ????? ??? ?????? ? ^[?] ?????? ?????????? ????? ?????? ( prolonged erection ) ??????? ???? ??????? ???? ?????????? ? ^[?] ???????????????? ( nitroglycerin / glycerin trinitrate) ??? ???????? ( nitrate ) ????? ?????????? ???? ??????? ( blood pressure ) ???????? ????? ???????????? ??? ??????????? ? ^[?]

?????????-????????? ?????????????? ???? ? ( phosphodiesterase 5 / PDE ₅), ?? ??????? ( enzyme ) ???? ???????? ???????? ????????? ( cGMP ) ?????? ?????? ( penis ) ????????????? ????????? ??? ?????? ?????????? ????? ??? ??????????? ??? ? ^[?] ??? ?????????? ???? ??????? ??? ???????? ( sexual arousal ) ????? ?????? ? ^[?] ??????? ?????????? ???? ????? ?????? ? ^[?]

?? ?????? ????? ( Pfizer ) ?????? ?????????? ????????? ???????? ?? ???????? ( heart related chest pain ) ???? ??????? ?????????? ??????? ??????? ? ^[?] ?? ?????? ??????? ???????? ??????? ???????????? ??????? ? ??????? ??? ??????? ??????? ? ^[?]^[?] ?? ?????? ???????????? ????????? ????? ? ????? ?????????? ???????????? ??????????? ? ^[?] ?? ?????? ??? ??????? ??? ( generic medication ) ????? ?????? ? ^[?] ??????? ????????? ??? ???? ?????????????? ( over the counter ) ???? ? ^[?] ?? ?????? ???????????? ????????? ???? ?????? ????? ? ?????? ??? ???? ? ^[?]

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↑ Nichols, DJ; Muirhead, GJ; Harness, JA (6 March 2002). "Pharmacokinetics of Sildenafil after Single Oral Doses in Healthy Male Subjects: Absolute Bioavailability, Food Effects and Dose Proportionality" . British Journal of Clinical Pharmacology . 53 : 5S?12S. doi : 10.1046/j.0306-5251.2001.00027.x . PMC 1874258 . PMID 11879254 .
↑ "Viagra (sildenafil citrate) Tablets, for Oral Use. Full Prescribing Information" . Pfizer Labs. Division of Pfizer, Inc., NY, NY 10017 . Retrieved 5 November 2016 .
↑ ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? "Sildenafil Citrate" . The American Society of Health-System Pharmacists . Retrieved 1 December 2014 .
↑ ^?.? ^?.? Goldstein, I; Burnett, AL; Rosen, RC; Park, PW; Stecher, VJ (6 October 2018). "The Serendipitous Story of Sildenafil: An Unexpected Oral Therapy for Erectile Dysfunction". Sexual Medicine Reviews . 7 (1): 115?128. doi : 10.1016/j.sxmr.2018.06.005 . PMID 30301707 .
↑ "The Top 300 of 2019" . clincalc.com (in ??????) . Retrieved 21 November 2018 .
↑ "Generic Viagra: Two versions of sildenafil hit the market today" (in ??????) . Retrieved 24 November 2018 .
↑ LaMattina, John. "With Viagra Now Available Over-The-Counter In The U.K., Will The U.S. Follow Suit?" . Forbes (in ??????) . Retrieved 24 November 2018 .
↑ "NADAC as of 2018-11-21" . Centers for Medicare and Medicaid Services (in ??????). Archived from the original on 2019-06-01 . Retrieved 24 November 2018 .

????? ????? [ ???????? ]

FDA Information
MedlinePLUS information, including side effects
U.S. National Library of Medicine: Drug Information Portal ? Sildenafil
Viagra at The Periodic Table of Videos (University of Nottingham)

[1] Nichols, DJ; Muirhead, GJ; Harness, JA (6 March 2002). "Pharmacokinetics of Sildenafil after Single Oral Doses in Healthy Male Subjects: Absolute Bioavailability, Food Effects and Dose Proportionality" . British Journal of Clinical Pharmacology . 53 : 5S?12S. doi : 10.1046/j.0306-5251.2001.00027.x . PMC 1874258 . PMID 11879254 .

[PI-2] "Viagra (sildenafil citrate) Tablets, for Oral Use. Full Prescribing Information" . Pfizer Labs. Division of Pfizer, Inc., NY, NY 10017 . Retrieved 5 November 2016 .

[AHFS2014-3] ?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? ^?.?? "Sildenafil Citrate" . The American Society of Health-System Pharmacists . Retrieved 1 December 2014 .

[Gold2018-4] ?.? ^?.? Goldstein, I; Burnett, AL; Rosen, RC; Park, PW; Stecher, VJ (6 October 2018). "The Serendipitous Story of Sildenafil: An Unexpected Oral Therapy for Erectile Dysfunction". Sexual Medicine Reviews . 7 (1): 115?128. doi : 10.1016/j.sxmr.2018.06.005 . PMID 30301707 .

[5] "The Top 300 of 2019" . clincalc.com (in ??????) . Retrieved 21 November 2018 .

[6] "Generic Viagra: Two versions of sildenafil hit the market today" (in ??????) . Retrieved 24 November 2018 .

[7] LaMattina, John. "With Viagra Now Available Over-The-Counter In The U.K., Will The U.S. Follow Suit?" . Forbes (in ??????) . Retrieved 24 November 2018 .

[8] "NADAC as of 2018-11-21" . Centers for Medicare and Medicaid Services (in ??????). Archived from the original on 2019-06-01 . Retrieved 24 November 2018 .

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