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PZ0003 Sigma

Sildenafil citrate salt

≥98% (HPLC)

Synonym: 1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine citrate salt, 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-4H-pyrazolo[5,4-e]pyrimidin-7-one citrate salt, Revatio, UK-92,480

  • CAS Number 171599-83-0

  • Empirical Formula (Hill Notation) C22H30N6O4S ·C6H8O7

  • Molecular Weight 666.70

  •  MDL number MFCD09026931



Legal Information

Sold for research purposes under agreement from Pfizer Inc.

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Biochem/physiol Actions

Sildenafil is a potent, selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5). Sildenafil is used to treat erectile dysfunction and pulmonary arterial hypertension. NO activates guanylate cyclase, which results in increased levels of cGMP, producing smooth muscle relaxation. Sildenafil enhances the effect of NO by inhibiting PDE5, which is responsible for degradation of cGMP.

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This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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≥98% (HPLC)


solid, ≥98% (HPLC)



Safety & Documentation

Safety Information

GHS07  GHS07
Signal word 
Hazard statements 
Precautionary statements 
WGK Germany 


Certificate of Analysis

Protocols & Articles



Download BioFiles v7 n5 (3.18 Mb PDF) Back to Pharmaceutical Drugs and Drug Candidates homepage
Sami Barghshoon
BioFiles v7 n5, 2012, 25–26
Keywords: Anticoagulants, Cardiovascular, Pharmaceutical

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Peer-Reviewed Papers


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Phosphodiesterase 5 inhibition improves synaptic function, memory, and amyloid-beta load in an Alzheimer's disease mouse model. Puzzo D., et al J. Neurosci. 25, 8075-8076, (2009)


Nitric oxide as an endogenous peripheral modulator of visceral sensory neuronal function. Page AJ., et al J. Neurosci. 22, 7246-7255, (2009)


Regulator of G protein signaling 2 mediates cardiac compensation to pressure overload and antihypertrophic effects of PDE5 inhibition in mice. Takimoto E., et al J. Clin. Invest. 119, 408-420, (2009)


Effect of phosphodiesterase-5 inhibition on exercise capacity and clinical status in heart failure with preserved ejection fraction: a randomized clinical trial. Redfield MM, Chen HH, Borlaug BA, et al. JAMA 309(12), 1268-77, (2013)


Sildenafil and diastolic dysfunction after acute myocardial infarction in patients with preserved ejection fraction: the Sildenafil and Diastolic Dysfunction After Acute Myocardial Infarction (SIDAMI) trial. Andersen MJ, Ersbøll M, Axelsson A, et al. Circulation 127(11), 1200-8, (2013)


Protection through postconditioning or a mitochondria-targeted S-nitrosothiol is unaffected by cardiomyocyte-selective ablation of protein kinase G. Methner C, Lukowski R, Grube K, et al. Basic Res. Cardiol. 108(2), 337, (2013)


[The prescription]. Rabe J MMW Fortschr. Med. 155(1), 28, (2013)


Hemoptysis and respiratory failure following sildenafil use for pulmonary hypertension. Nour SM, Nour HA, Mehta JB, et al. Tenn. Med. 106(3), 34-5, (2013)


[Non-arteritic anterior ischemic optic neuropathy associated with erectile dysfunction medications]. Krashin-Bichler I and Dotan G Harefuah 152(2), 84-7, 123, (2013)


Modulation of paracetamol-induced hepatotoxicity by phosphodiesterase isozyme inhibition in rats: a preliminary study. Ekor M, Odewabi AO, Kale OE, et al. J. Basic Clin. Physiol. Pharmacol. 24(1), 73-9, (2013)


Sildenafil preserves exercise capacity in patients with idiopathic pulmonary fibrosis and right-sided ventricular dysfunction. Han MK, Bach DS, Hagan PG, et al. Chest 143(6), 1699-708, (2013)


Endothelial TLR4 activation impairs intestinal microcirculatory perfusion in necrotizing enterocolitis via eNOS-NO-nitrite signaling. Yazji I, Sodhi CP, Lee EK, et al. Proc. Natl. Acad. Sci. U. S. A. 110(23), 9451-6, (2013)


Sildenafil is not a useful modulator of ABCB1 and ABCG2 mediated drug resistance in vivo. Lin F, Hoogendijk L, Buil L, et al. Eur. J. Cancer 49(8), 2059-64, (2013)


Inhibition of calpain-regulated p35/cdk5 plays a central role in sildenafil-induced protection against chemical hypoxia produced by malonate. Barros-Miñones L, Martín-de-Saavedra D, Perez-Alvarez S, et al. Biochim. Biophys. Acta 1832(6), 705-17, (2013)


Role of phosphodiesterase type 5 inhibitors for lower urinary tract symptoms. Miller MS Ann. Pharmacother. 47(2), 278-83, (2013)


Sildenafil stimulates aqueous humor turnover in rabbits. Alvarez LJ, Zamudio AC, and Candia OA Exp. Eye Res. 111, 67-70, (2013)


Pharmacokinetic comparison of an orally disintegrating film formulation with a film-coated tablet formulation of sildenafil in healthy Korean subjects: a randomized, open-label, single-dose, 2-period crossover study. Roh H, Son H, Lee D, et al. Clin. Ther. 35(3), 205-14, (2013)


When to initiate intravenous therapy and/or refer. Champion HC Am. J. Cardiol. 111(8 Suppl), 21C-4C, (2013)


Saw palmetto extract enhances erectile responses by inhibition of phosphodiesterase 5 activity and increase in inducible nitric oxide synthase messenger ribonucleic acid expression in rat and rabbit corpus cavernosum. Yang S, Chen C, Li Y, et al. Urology 81(6), 1380.e7-13, (2013)


Sildenafil prevents the up-regulation of transient receptor potential canonical channels in the development of cardiomyocyte hypertrophy. Kiso H, Ohba T, Iino K, et al. Biochem. Biophys. Res. Commun. 436(3), 514-8, (2013)


[Pulmonary hypertension and Langerhans' cell granulomatosis: successful treatment with sildenafil and iloprost]. Held M, Jany B, Warth A, et al. Dtsch. Med. Wochenschr. 138(11), 524-7, (2013)


Serum homocysteine levels and sildenafil 50 mg response in young-adult male patients without vascular risk factors. Basar MM, Ozkan Y, Kisa U, et al. Indian J. Biochem. Biophys. 50(3), 215-20, (2013)


[Medicinal therapy of benign prostate syndrome with phosphodiesterase-5 inhibitors]. Herlemann A, Gratzke C, Andersson KE, et al. Urologe. A 52(2), 204-11, (2013)


[Efficacy and safety of sildenafil in patients with systemic scleroderma]. Alekperov RT, Ananyeva LP, Korzeneva EG, et al. Ter. Arkh. 85(5), 60-7, (2013)


Gene expression quantitation by real-time PCR. White JR BJU Int. 111(1), 157-8, (2013)


Clinical Inquiry: which treatments help women with reduced libido? Hobbs K and Handler L J. Fam. Pract. 62(2), 102-3, (2013)


Postcoital vomiting after taking sildenafil? Lamb M, Brahm N, and Fox MD J. Fam. Pract. 62(2), 61-2, (2013)


A 120-hour case of priapism from an over-the-counter herbal supplement. Coralic Z, Lenhoff T, Kanzaria HK, et al. Ann. Pharmacother. 47(2), 289-90, (2013)


Merck 14,8489

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