Sildenafil

Clinical data
Pronunciation	/ s ? l ? d ? n ? f ? l / sil- DEN -?-fil
Trade name s	Viagra, Revatio, others
AHFS / Drugs.com	Monograph
MedlinePlus	a699015
data	EU   EMA :  by INN US   FDA :  Sildenafil
Pregnancy category	AU : B1 [1]
Routes of administration	By mouth ( tablets ), intravenous
ATC code	G04BE03 ( WHO )
Legal status
Legal status	AU : S4 (Prescription only) CA : ?-only UK : over-the-counter (OTC) / P [4] [5] US : ?-only [6] EU : Rx-only [2] [3] In general: ? (Prescription only)
Pharmacokinetic data
Bioavailability	41% (mean) [7]
Protein binding	~96%
Metabolism	Liver : CYP3A4 (major route), CYP2C9 (minor route)
Metabolite s	N -desmethylsildenafil (~50% potency for PDE 5 )
Onset of action	20 minutes
Elimination half-life	3?4 hours
Excretion	Feces (~80%), urine (~13%) [6]
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   Y citrate:  171599-83-0   Y
PubChem CID	135398744 citrate: 135413523
DrugBank	DB00203   Y citrate:  DBSALT000347   Y
ChemSpider	5023   Y citrate: 56586   Y
UNII	3M7OB98Y7H citrate:  BW9B0ZE037   Y
KEGG	D08514   Y citrate:  D02229   Y
ChEBI	CHEBI:9139   Y citrate:  CHEBI:58987   Y
ChEMBL	CHEMBL192   Y citrate:  CHEMBL1737   Y
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	474.58 g·mol ?1
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)   N Key:BNRNXUUZRGQAQC-UHFFFAOYSA-N   N
N Y   (what is this?)    (verify)

Sildenafil ( ing-gu : Sildenafil, Viagra ; han-gu : 西地那非, 威而鋼) s? i?ng Viagra ting-ting e phin-pai lai siau-si?, s? tsı?t-tsiong i?ng-teh t?-liau khi-pu?t kong-leng chiong-g?i  [ en ] h?m Hi t?ng-me?h ko-ap  [ en ] e io?h-bu?t . ^{[6] [8]} Bo?k-tsian koh bo-tshing-tsho Sildenafil m?-tsai tui t?-liau lu-sing sing-kong-ling e tsiong-ai kam ?-h?u. ^[8] khau-hok hi?k-tsia ts?ng-me?h tsu-si?  [ en ] . ^[8] ?o?h-h?u khai-si tsok-i?ng thong-siong teh 20 hun-tsing tsi-l?i, ?-tang tshi-siok tong-kau 2 tiam-tsing ku. ^[8]

Tsu-kai [ siu-kai | kai goan-si-be ]

Tsham-ua?t [ siu-kai | kai goan-si-be ]

• Basmanny su-hoat  [ ru ] (Basmanny su-huat/Басманное правосудие)
• Lietuva P?o-tshing-ping Lian-bing  [ en ] (Lithuanian Riflemen's Union)
• James Mason (sin-Nazi)  [ en ] (James Mason (neo-Nazi))
• Ukraina kau-thong  [ en ]
• Aelia Eudocia  [ en ]

Gu?-p?o len-ket [ siu-kai | kai goan-si-be ]

• "Sildenafil" . Drug Information Portal . U.S. National Library of Medicine.   (Eng-gi)
• "Sildenafil citrate" . Drug Information Portal . U.S. National Library of Medicine.   (Eng-gi)
• Viagra at The Periodic Table of Videos (University of Nottingham) (Eng-gi)