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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

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Description

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®Pfizer), a collection of 90 Pfizer-developed drugs and research tools. Click here to learn more.

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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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
36
WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

Articles

Anticoagulants

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, Biofiles, Cardiovascular, Pharmaceutical, Tools

Peer-Reviewed Papers

References

Set your institution to view full text papers.

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)

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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)

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

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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)

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

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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)

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

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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)

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

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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)

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

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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)

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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)

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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)

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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)

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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)

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

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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)

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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)

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

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[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)

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

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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)

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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)

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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)

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[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)

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[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)

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

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Merck 14,8489

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