Sildenafil

**Sildenafil**
Clinical data
Pronunciation	/sɪlˈdɛnəfɪl/ sil-DEN-ə-fil
Trade names	Viagra, Revatio, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699015
data	EU EMA: by INN; US FDA: Sildenafil;
Pregnancy; category	AU: B1 ; ;
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; US: ℞-only ; EU: Rx-only ; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	41% (mean)
Protein binding	~96%
Metabolism	Liver: CYP3A4 (major route), CYP2C9 (minor route)
Metabolites	N-desmethylsildenafil (~50% potency for PDE5)
Onset of action	20 minutes
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-7H-pyrazolo[4,3-d]pyrimidin-7-one;
CAS Number	139755-83-2 ; citrate: 171599-83-0 ;
PubChem CID	135398744; citrate: 135413523;
DrugBank	DB00203 ; citrate: DBSALT000347 ;
ChemSpider	5023 ; citrate: 56586 ;
UNII	3M7OB98Y7H; citrate: BW9B0ZE037 ;
KEGG	D08514 ; citrate: D02229 ;
ChEBI	CHEBI:9139 ; citrate: CHEBI:58987 ;
ChEMBL	CHEMBL192 ; citrate: CHEMBL1737 ;
PDB ligand	VIA (PDBe, RCSB PDB);
ECHA InfoCard	100.122.676
Chemical and physical data
Formula	C22H30N6O4S
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) ; Key:BNRNXUUZRGQAQC-UHFFFAOYSA-N ;
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Bo̽k-tsiân koh bô-tshing-tshó Sildenafil m̄-tsai tuì tī-liâu lú-sìng sìng-kong-lîng ê tsiong-ài kám ū-hāu. kháu-hok hi̍k-tsiá tsīng-me̽h tsù-siā [en]. İo̽h-hāu khai-sí tsok-iōng thong-siông teh 20 hun-tsing tsi-lāi, ē-tàng tshî-siok tòng-kàu 2 tiám-tsing kú.

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Tsham-ua̽t

Basmanny su-hoat [ru] (Basmanny su-huat/Басманное правосудие)
Lietuva Pōo-tshìng-ping Liân-bîng [en] (Lithuanian Riflemen's Union)
James Mason (sin-Nazi) [en] (James Mason (neo-Nazi))
Ukraina kau-thong [en]
Aelia Eudocia [en]

Guā-pōo lên-ket

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

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Sildenafil

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Clinical data


Pronunciation	/sɪlˈdɛnəfɪl/ sil-DEN-ə-fil
Trade names	Viagra, Revatio, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699015
data	EU EMA: by INN US FDA: Sildenafil
Pregnancy category	AU: B1
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 US: ℞-only EU: Rx-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	41% (mean)
Protein binding	~96%
Metabolism	Liver: CYP3A4 (major route), CYP2C9 (minor route)
Metabolites	N-desmethylsildenafil (~50% potency for PDE₅)
Onset of action	20 minutes
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-7H-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	C₂₂H₃₀N₆O₄S
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
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