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sildenafil

File:Sildenafil_structure.svg · Wikimedia Commons · See Wikimedia Commons

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sildenafil

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Also known as 5-[2-ethoxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one, 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one, 1-{[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl}-4-methylpiperazine, C₂₂H₃₀N₆O₄S

Sildenafil, sold under the brand name Viagra among others, is a medication used to treat erectile dysfunction and pulmonary arterial hypertension. It is also sometimes used off-label for the treatment of certain symptoms in secondary Raynaud's phenomenon. It is unclear if it is effective for treating sexual dysfunction in females. It can be taken orally (swallowed by mouth), intravenously (injection into a vein), or through the sublingual route (dissolved under the tongue). Onset when taken orally is typically within twenty minutes and lasts for about two hours.

AI overview

Sildenafil, commonly known by the brand name Viagra, is a medication primarily used to treat erectile dysfunction and a heart condition called pulmonary arterial hypertension. It works relatively quickly when taken by mouth—usually within twenty minutes—and its effects last about two hours, though doctors sometimes use it for other conditions as well.

AI-generated from the Wikipedia summary — may contain errors.

Key facts

Drug.image
Sildenafil structure.svg
Drug.image_class
skin-invert-image
Drug.width
250
Drug.image2
Sildenafil-from-xtal-3D-balls.png
Drug.image_class2
bg-transparent
Drug.tradename
Viagra, others
Drug.MedlinePlus
a699015
Drug.DailyMedID
Sildenafil
Drug.pregnancy_AU
B1
Drug.routes_of_administration
By mouth, sublingual, intravenous
Drug.class
PDE5 inhibitor
Drug.ATC_prefix
G04
Drug.ATC_suffix
BE03
Drug.legal_AU
S4
Drug.legal_CA
Rx-only
Drug.legal_UK
POM
Drug.legal_UK_comment
/Pharmacy
Drug.legal_US
Rx-only

via Wikipedia infobox

Chemical data

Formula
C22H30N6O4S
Molecular weight
474.6 g/mol
IUPAC name
5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,5-d]pyrimidin-7-one
SMILES
CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C
InChIKey
BNRNXUUZRGQAQC-UHFFFAOYSA-N
XLogP
1.5
Polar surface area
118 Ų
H-bond donors
1
H-bond acceptors
8
Formal charge
0

via PubChem

~27 min read

Encyclopedic overview

36 sections
Contents
  • Medical uses
  • Erectile dysfunction
  • Antidepressant-associated erectile dysfunction
  • Pulmonary hypertension
  • Raynaud's phenomenon
  • Altitude sickness
  • High-altitude pulmonary edema
  • Adverse effects
  • Interactions
  • Contraindications
  • Non-medical use
  • Recreational use
  • Jet lag research
  • Sports
  • Analogs
  • Detection in biological fluids
  • Mechanism of action
  • Route of administration
  • Chemical synthesis
  • History
  • Society and culture
  • Marketing and sales
  • Counterfeits
  • Regional issues
  • United States
  • Brazil
  • Canada
  • China
  • Egypt
  • European Union
  • India
  • New Zealand
  • South Korea
  • United Kingdom
  • References
  • External links

{{Infobox drug | image = Sildenafil structure.svg | image_class = skin-invert-image | alt = | width = 250 | image2 = Sildenafil-from-xtal-3D-balls.png | image_class2 = bg-transparent | alt2 =

| pronounce = | tradename = Viagra, others | Drugs.com = | MedlinePlus = a699015 | DailyMedID = Sildenafil | pregnancy_AU = B1 | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth, sublingual, intravenous | class = PDE5 inhibitor | ATC_prefix = G04 | ATC_suffix = BE03 | ATC_supplemental =

Excerpted from Wikipedia’s “sildenafil” article, available under the CC BY-SA 4.0 licence.

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