Showing Compound Sildenafil (FDB023606)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:19 UTC

Update date

2015-07-21 06:57:47 UTC

Primary ID

FDB023606

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sildenafil

Description

Sildenafil is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. It was initially studied for use in hypertension (high blood pressure) and angina pectoris (a form of ischaemic cardiovascular disease). Phase I clinical trials under the direction of Ian Osterloh suggested that the drug had little effect on angina, but that it could induce marked penile erections; Sildenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. The molecular structure of sildenafil is similar to that of cGMP and acts as a competitive binding agent of PDE5 in the corpus cavernosum, resulting in more cGMP and better erections. Without sexual stimulation, and therefore lack of activation of the NO/cGMP system, sildenafil should not cause an erection. Other drugs that operate by the same mechanism include tadalafil (Cialis) and vardenafil (Levitra); Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. Viagra pills are blue and diamond-shaped with the words 'Pfizer' on one side, and 'VGR xx' (where xx stands for '25', '50' or '100', the dose of that pill in milligrams) on the other. Its primary competitors on the market are tadalafil (Cialis), and vardenafil (Levitra). [HMDB]

CAS Number

139755-83-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine	ChEBI
1-((3-(4,7-dihydro-1-Methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine	ChEBI
1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazine	Generator
1-((3-(4,7-dihydro-1-Methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazine	Generator
1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrate	HMDB
Acetildenafil	HMDB
Aphrodil	Kegg
Caverta	HMDB
Citrate, sildenafil	HMDB
Desmethyl sildenafil	HMDB

Showing 1 to 10 of 23 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	2.35	ALOGPS
logP	1.65	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	5.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.44 m³·mol⁻¹	ChemAxon
Polarizability	51.18 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C22H30N6O4S

IUPAC name

5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one

InChI Identifier

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)

InChI Key

BNRNXUUZRGQAQC-UHFFFAOYSA-N

Isomeric SMILES

CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1

Average Molecular Weight

474.576

Monoisotopic Molecular Weight

474.204924168

Classification

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Pyrazolopyrimidine
Benzenesulfonyl group
Phenoxy compound
Phenol ether
Alkyl aryl ether
Pyrimidone
N-methylpiperazine
N-alkylpiperazine
Piperazine
Pyrimidine
Organosulfonic acid amide
1,4-diazinane
Pyrazole
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Azole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Lactam
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:9139 )
piperazines (CHEBI:9139 )
pyrazolopyrimidine (CHEBI:9139 )

Ontology

Disposition

Biological location:

Organ and components:

Liver

Tissue and substructures:

Smooth muscle

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Sildenafil, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006t-9004300000-55c87eff7b6ad40ea3d5	Spectrum
Predicted GC-MS	Sildenafil, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0059-2494500000-e3f8387aee5a0463363c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05s0-3892000000-aa19715309275e16a6c0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0059-2494500000-e3f8387aee5a0463363c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-05s0-3892000000-aa19715309275e16a6c0	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0002900000-b281f59f40caaba85ac9	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-4436900000-0c5804e76b9d495c76d6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0459-6292000000-5a32bfcdda2067978be9	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0001900000-51b4957d0b3d25c41773	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01vk-0302900000-86c63c2fd17f7c5b7d6f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dj-8916100000-e941afc576d544ed32a7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-c92b21b6524ea5040313	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000900000-06d94f4626e8bee6e389	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9101300000-ef50cfadb7bd34e88187	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-1617a2dfdf2b96a0cd2c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0010900000-744efa093f1de0f36d62	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-0272900000-aa5d9fef9c0fb52ad923	2021-09-24	View Spectrum