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Basic Information

Molecular Structure:
CAS No.:	171599-83-0
Name:	Sildenafil citrate

Formula:	C₂₈H₃₈N₆O₁₁S
Molecular Weight:	666.70
Synonyms:	Piperazine,1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-(9CI);5-[2-Ethoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one;Revatio;
EINECS:	200-659-6
Density:	1.447g/cm3
Melting Point:	187-189 °C
Boiling Point:	672.4 °C at 760 mmHg
Flash Point:	360.5 °C
Solubility:	insoluble in water, ethanol
Appearance:	White solid
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	36
Transport Information:	N/A
PSA:	253.93000
LogP:	1.31900

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Chemistry

Molecular Structure:

Molecular Formula: C₂₈H₃₈N₆O₁₁S
Molecular Weight: 666.70
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
Synonyms of Sildenafil Citrate (CAS NO.171599-83-0): 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 (1:1) ; Caverta ; Revatio ; Sildenafil citrate ; Viagra ; Piperazine, 1-((3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
CAS NO: 171599-83-0
H bond acceptors: 10
H bond donors: 1
Freely Rotating Bonds: 7
Polar Surface Area: 108.72 Å²
Flash Point: 360.5 °C
Enthalpy of Vaporization: 98.77 kJ/mol
Boiling Point: 672.4 °C at 760 mmHg
Vapour Pressure: 6.1E-18 mmHg at 25°C
Melting Point: 187-189°C
Appearance: White Solid
SMILES: O=S(=O)(N1CCN(C)CC1)c4cc(C\2=N\C(=O)c3c(N/2)c(nn3C)CCC)c(OCC)cc4.O=C(O)C(O)(CC(=O)O)CC(=O)O
InChI: InChI=1/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)
InChIKey: DEIYFTQMQPDXOT-UHFFFAOYAI
Std. 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)
Std. InChIKey: DEIYFTQMQPDXOT-UHFFFAOYSA-N
Product Categories of Sildenafil Citrate (CAS NO.171599-83-0): Intermediates & Fine Chemicals;Pharmaceuticals;Sildenafil

History

Sildenafil Citrate (CAS NO.171599-83-0) was synthesized by a group of pharmaceutical chemists working at Pfizer's Sandwich, Kent, research facility in England. It was initially studied for use in hypertension and angina pectoris. The first clinical trials were conducted in Morriston Hospital in Swansea. 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.Pfizer therefore decided to market it for erectile dysfunction, rather than for angina. The drug was patented in 1996, approved for use in erectile dysfunction by the US Food and Drug Administration on March 27, 1998, becoming the first oral treatment approved to treat erectile dysfunction in the United States, and offered for sale in the United States later that year. It soon became a great success: annual sales of Viagra in the period 1999–2001 exceeded $1 billion.
Pfizer's worldwide patents on sildenafil citrate will expire in 2011–2013. The UK patent held by Pfizer on the use of PDE5 inhibitors as treatment of impotence was invalidated in 2000 because of obviousness; this decision was upheld on appeal in 2002.

Uses

Sildenafil Citrate (CAS NO.171599-83-0) is used as an orally active selective type 5 cGMP phosphodiesterase inhibitor.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	oral	1429ug/kg/3W- (1.429mg/kg)	PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE	American Journal of Ophthalmology. Vol. 126, Pg. 476, 1998.
rat	LDLo	oral	300mg/kg (300mg/kg)		Gekkan Yakuji. Pharmaceuticals

Safety Profile

Risk Statements of Sildenafil Citrate (CAS NO.171599-83-0): 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.

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