ContaminantDB: Sildenafil citrate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:28:34 UTC

Update Date

2026-04-03 00:10:54 UTC

Accession Number

CHEM018719

Identification

Common Name

Sildenafil citrate

Class

Small Molecule

Description

The citrate salt of sildenafil.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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	ChEBI
Caverta	ChEBI
Revatio	ChEBI
Viagra	ChEBI
1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citric acid	Generator
1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazine citrate	Generator
1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazine citric acid	Generator
Sildenafil citric acid	Generator
Citrate, sildenafil	MeSH
Lactate, sildenafil	MeSH
Nitrate, sildenafil	MeSH
Sildenafil nitrate	MeSH
Sildenafil, desmethyl	MeSH
Acetildenafil	MeSH
Desmethylsildenafil	MeSH
Hydroxyhomosildenafil	MeSH
NCX-911	MeSH
Sildenafil	MeSH
NCX 911	MeSH
Desmethyl sildenafil	MeSH
Homosildenafil	MeSH
Sildenafil lactate	MeSH

Chemical Formula

C₂₈H₃₈N₆O₁₁S

Average Molecular Mass

666.700 g/mol

Monoisotopic Mass

666.232 g/mol

CAS Registry Number

171599-83-0

IUPAC Name

Not Available

Traditional Name

citric acid; sildenafil

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCCC1=NN(C)C2=C1N=C(NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1

InChI Identifier

InChI=1S/C22H30N6O4S.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChI Key

DEIYFTQMQPDXOT-UHFFFAOYSA-N

Chemical Taxonomy

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

Molecular Framework

Not Available

External Descriptors

citrate salt (CHEBI:58987 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.35	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.92	ChemAxon
pKa (Strongest Basic)	5.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	139.87 m³·mol⁻¹	ChemAxon
Polarizability	49.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0011900000-feea41103bd5b1474781	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0193000000-8fcc303e535fe1d23179	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000009000-3525ba3c599a1376d342	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000009000-3525ba3c599a1376d342	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0000009000-3525ba3c599a1376d342	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000009000-f6f10d3eed062d8820e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000009000-f6f10d3eed062d8820e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0000009000-f6f10d3eed062d8820e0	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DBSALT000347

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Sildenafil_Citrate

Chemspider ID

Not Available

ChEBI ID

58987

PubChem Compound ID

62853

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Sildenafil citrate (CHEM018719)

Structure for CHEM018719: Sildenafil citrate