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Chemistry

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Also known as:
Molecular Formula
C28H38N6O11S
Molecular Weight
666.7  g/mol
InChI Key
DEIYFTQMQPDXOT-UHFFFAOYSA-N

Sildenafil Citrate
1 2D Structure

Sildenafil Citrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one;2-hydroxypropane-1,2,3-tricarboxylic acid
2.1.2 InChI
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)
2.1.3 InChI Key
DEIYFTQMQPDXOT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCC1=NN(C2=C1NC(=NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
2.1.5 Isomeric SMILES
CCCC1=NN(C2=C1NC(=NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
2.2 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 666.7 g/mol
Molecular Formula C28H38N6O11S
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count14
Rotatable Bond Count12
Exact Mass666.23192722 g/mol
Monoisotopic Mass666.23192722 g/mol
Topological Polar Surface Area250 A^2
Heavy Atom Count46
Formal Charge0
Complexity1070
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameRevatio
PubMed HealthSildenafil
Drug ClassesAntihypertensive, Peripheral Vasodilator, Erectile Dysfunction Agent, Vasodilator
Drug LabelREVATIO, phosphodiesterase-5 (PDE-5) inhibitor, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type-5 (PDE-5). Sildenafil is also marketed as VIAGRA for erectile dysfunct...
Active IngredientSildenafil citrate
Dosage FormTablet; Solution; For suspension
RouteOral; Intravenous
Strengtheq 20mg base; eq 10mg base/ml; eq 10mg base/12.5ml (eq 0.8mg base/ml)
Market StatusPrescription
CompanyPfizer

2 of 8  
Drug NameSildenafil citrate
Drug LabelVIAGRA, an oral therapy for erectile dysfunction, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5).Sildenafil citrate is designated chemically as 1-[[3-(6,7-d...
Active IngredientSildenafil citrate
Dosage FormTablet
Routeoral
Strength25mg; 100mg; 50mg
Market StatusTentative Approval
CompanyMacleods Pharma

3 of 8  
Drug NameSildenafil citrate
PubMed HealthSildenafil
Drug ClassesAntihypertensive, Peripheral Vasodilator, Erectile Dysfunction Agent, Vasodilator
Drug LabelVIAGRA, an oral therapy for erectile dysfunction, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5).Sildenafil citrate is designated chemically as 1-[[3-(6,7-d...
Active IngredientSildenafil citrate
Dosage FormTablet
Routeoral; Oral
Strengtheq 100mg base; 25mg; eq 50mg base; eq 20mg base; 100mg; 50mg; eq 25mg base
Market StatusTentative Approval; Prescription
CompanyAmneal Pharms; Mylan Pharms; Hetero Labs Ltd V; Mylan Pharma; Actavis Pharma; Apotex; Torrent Pharms; Watson Labs; Actavis Grp Ptc; Teva Pharms; Macleods Pharms; Dr Reddys Labs

4 of 8  
Drug NameViagra
Drug LabelVIAGRA, an oral therapy for erectile dysfunction, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5).Sildenafil citrate is designated chemically as 1-[[3-(6,7-d...
Active IngredientSildenafil citrate
Dosage FormTablet
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 25mg base
Market StatusPrescription
CompanyPfizer Ireland

5 of 8  
Drug NameRevatio
PubMed HealthSildenafil
Drug ClassesAntihypertensive, Peripheral Vasodilator, Erectile Dysfunction Agent, Vasodilator
Drug LabelREVATIO, phosphodiesterase-5 (PDE-5) inhibitor, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type-5 (PDE-5). Sildenafil is also marketed as VIAGRA for erectile dysfunct...
Active IngredientSildenafil citrate
Dosage FormTablet; Solution; For suspension
RouteOral; Intravenous
Strengtheq 20mg base; eq 10mg base/ml; eq 10mg base/12.5ml (eq 0.8mg base/ml)
Market StatusPrescription
CompanyPfizer

6 of 8  
Drug NameSildenafil citrate
Drug LabelVIAGRA, an oral therapy for erectile dysfunction, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5).Sildenafil citrate is designated chemically as 1-[[3-(6,7-d...
Active IngredientSildenafil citrate
Dosage FormTablet
Routeoral
Strength25mg; 100mg; 50mg
Market StatusTentative Approval
CompanyMacleods Pharma

7 of 8  
Drug NameSildenafil citrate
PubMed HealthSildenafil
Drug ClassesAntihypertensive, Peripheral Vasodilator, Erectile Dysfunction Agent, Vasodilator
Drug LabelVIAGRA, an oral therapy for erectile dysfunction, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5).Sildenafil citrate is designated chemically as 1-[[3-(6,7-d...
Active IngredientSildenafil citrate
Dosage FormTablet
Routeoral; Oral
Strengtheq 100mg base; 25mg; eq 50mg base; eq 20mg base; 100mg; 50mg; eq 25mg base
Market StatusTentative Approval; Prescription
CompanyAmneal Pharms; Mylan Pharms; Hetero Labs Ltd V; Mylan Pharma; Actavis Pharma; Apotex; Torrent Pharms; Watson Labs; Actavis Grp Ptc; Teva Pharms; Macleods Pharms; Dr Reddys Labs

8 of 8  
Drug NameViagra
Drug LabelVIAGRA, an oral therapy for erectile dysfunction, is the citrate salt of sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5).Sildenafil citrate is designated chemically as 1-[[3-(6,7-d...
Active IngredientSildenafil citrate
Dosage FormTablet
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 25mg base
Market StatusPrescription
CompanyPfizer Ireland