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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Sildenafil (ing-gú: Sildenafil, Viagra; hàn-gú: 西地那非, 威而鋼) sī iōng Viagra tíng-tíng ê phín-pâi lâi siau-siū, sī tsı̽t-tsióng iōng-teh tī-liâu khí-pu̍t kong-lêng chiòng-gāi [en] hām Hì tōng-me̍h ko-ap [en] ê io̽h-bu̽t.^[6]^[8] Bo̽k-tsiân koh bô-tshing-tshó Sildenafil m̄-tsai tuì tī-liâu lú-sìng sìng-kong-lîng ê tsiong-ài kám ū-hāu.^[8] kháu-hok hi̍k-tsiá tsīng-me̽h tsù-siā [en].^[8] İo̽h-hāu khai-sí tsok-iōng thong-siông teh 20 hun-tsing tsi-lāi, ē-tàng tshî-siok tòng-kàu 2 tiám-tsing kú.^[8]

Tsù-kái[siu-kái | kái goân-sí-bé]

↑ "Sildenafil Use During Pregnancy". Drugs.com. 7 October 2019. 6 October 2020 khòaⁿ--ê.
↑ "Viagra EPAR". European Medicines Agency. 6 October 2020 khòaⁿ--ê.
↑ "Revatio EPAR". European Medicines Agency. 6 October 2020 khòaⁿ--ê.
↑ "Viagra 25mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 7 August 2020. 6 October 2020 khòaⁿ--ê.
↑ "Viagra Connect 50 mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 5 December 2017. 6 October 2020 khòaⁿ--ê.
↑ ^6.0 ^6.1 ^6.2 "Viagra- sildenafil citrate tablet, film coated". DailyMed. 6 October 2020 khòaⁿ--ê.
↑ 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 (Suppl 1): 5S–12S. doi:10.1046/j.0306-5251.2001.00027.x. PMC 1874258 . PMID 11879254.
↑ ^8.0 ^8.1 ^8.2 ^8.3 "Sildenafil Citrate". The American Society of Health-System Pharmacists. 1 December 2014 khòaⁿ--ê.

Tsham-ua̽t[siu-kái | kái goân-sí-bé]

Tāi-sè-chì pho·-sat liām-hu̍t oân-thong-chiong (hàn-gí: 大勢至菩薩念佛圓通章)
Kṣitigarbha bodhisattva pūrvapraṇidhāna sūtra (Kṣitigarbha sūtra; hoân-gí: क्षितिगर्भ बोधिसत्त्व पूर्वप्रणिधान सूत्र; hàn-gí: 地藏菩薩本願經)
095-hêng he̍k chiâm-théng [en] (095-hîng hı̽k tsiâm-thíng/Type 095 submarine)
Thài-iông o͘-tiám [en] (Thài-iông oo-tiám/Sunspot/Thài-iông oo-tsí)
Jī-ióng hòa-thài [en](Jī-ióng huà-thài/Titanium dioxide/E171)
Neuralink [en]
Hibiscus syriacus [en] (hàn-gú: Bo̍k-kīn; ha̍k-miâ: Hibiscus syriacus)
Balaeniceps rex [en] (Kîng-thâu kuàn/Shoebill/Ê-tshuì tsiáu)
Die Welt [en]
F-35 siám-tiān II chiàn-tàu-ki [en] (F-35 siám-tēn II sèn-tàu ki/Lockheed Martin F-35 Lightning II)
Sò͘-jī tiān-tâi [en] (Sòo-jī tēn-tâi/Numbers station)
Nosaka Akiyuki [en] (野坂昭如)
Umberto Eco [en]
Muî-kuì chi miâ [en] (Muî-kuì tsi miâ/The Name of the Rose/Il nome della rosa)
Muî-kuì chi miâ (tiān-iáⁿ) [en] (Muî-kuì tsi miâ (tēn-iáñ)/The Name of the Rose (film))
Iván Guzmán de Rojas [en]
Al-Shabaab (Somalia) [en] (Al-Shabaab (militant group))
Thê-ô͘ [en] (thê-ôo/Pelican/hái-gô)
Jin-kip chhàng-chuí-kàm [en] (Jin-kip tshàng-tsuí-kàm/Jin-class submarine)
Planet Labs [en]
Hông-ka kok-chè sū-bū gián-kiù-só͘ [en] (hông-ka kok-tsè sū-bū gián-kiù-sóo/Chatham House)
UP Special [ru]
Moscow basmanny koān hoat-īⁿ [en] (Moscow basmanny kuān huat-īñ/Басманный районный суд города Москвы)
Basmanny su-hoat [ru] (Basmanny su-huat/Басманное правосудие)

Guā-pōo lên-ket[siu-kái | kái goân-sí-bé]

"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)

[Drugs.com_pregnancy-1] "Sildenafil Use During Pregnancy". Drugs.com. 7 October 2019. 6 October 2020 khòaⁿ--ê.

[Viagra_EPAR-2] "Viagra EPAR". European Medicines Agency. 6 October 2020 khòaⁿ--ê.

[Revatio_EPAR-3] "Revatio EPAR". European Medicines Agency. 6 October 2020 khòaⁿ--ê.

[4] "Viagra 25mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 7 August 2020. 6 October 2020 khòaⁿ--ê.

[5] "Viagra Connect 50 mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 5 December 2017. 6 October 2020 khòaⁿ--ê.

[Viagra_FDA_label-6] 6.0 ^6.1 ^6.2 "Viagra- sildenafil citrate tablet, film coated". DailyMed. 6 October 2020 khòaⁿ--ê.

[7] 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 (Suppl 1): 5S–12S. doi:10.1046/j.0306-5251.2001.00027.x. PMC 1874258 . PMID 11879254.

[AHFS2014-8] 8.0 ^8.1 ^8.2 ^8.3 "Sildenafil Citrate". The American Society of Health-System Pharmacists. 1 December 2014 khòaⁿ--ê.

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[5]

[6]

[2]

[3]

[7]

[8]

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 ^[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)
Metabolites	N-desmethylsildenafil (~50% potency for PDE₅)
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-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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Sildenafil

Tsù-kái[siu-kái | kái goân-sí-bé]

Tsham-ua̽t[siu-kái | kái goân-sí-bé]

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