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Y0001578

Sildenafil citrate

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Sildenafil citrate salt, 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

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About This Item

Empirical Formula (Hill Notation):
C22H30N6O4S ·C6H8O7
CAS Number:
171599-83-0
Molecular Weight:
666.70
MDL number:
MFCD09026931
UNSPSC Code:
41116107
PubChem Substance ID:
329831492
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

sildenafil

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCCc1nn(C)c2C(=O)NC(=Nc12)c3cc(ccc3OCC)S(=O)(=O)N4CCN(C)CC4

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

Gene Information

human ... PDE5A(8654)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Sildenafil citrate EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

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.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Sigma-Aldrich

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Sigma-Aldrich

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U Ozturk et al.
Irish journal of medical science, 183(3), 449-453 (2013-11-06)
It has been shown on experimental rat models that type 5-phosphodiesterase isoenzyme (PDE5) inhibitors have anti-fibrotic effects for Peyronie's disease (PD); however, this issue has not been addressed clinically. The aim of this study was to document the effects of
M Paranjpe et al.
International journal of pharmaceutics, 476(1-2), 41-49 (2014-09-28)
For the development of any colloidal system, thorough characterization is extremely essential. This article discusses the physicochemical characterization of sildenafil-loaded solid lipid nanoparticle dispersions (SLN) including stability analysis over 6 months time period for possible pulmonary administration for the treatment
Jing Peng et al.
Urology, 84(6), 1389-1394 (2014-10-13)
To evaluate the results of nocturnal penile erection test and response to daily sildenafil in patients with erectile dysfunction (ED) due to pelvic fracture urethral disruption. From January 2010 to January 2012, we included 38 patients with ED due to
Lisa Nivison-Smith et al.
Experimental eye research, 128, 43-56 (2014-09-23)
Sildenafil, the active ingredient in Viagra, has been reported to cause transient visual disturbance from inhibition of phosphodiesterase 6 (PDE6), a key enzyme in the visual phototransduction pathway. This study investigated the effects of sildenafil on the rd1(+/-) mouse, a
D Adam Lauver et al.
PloS one, 9(11), e113598-e113598 (2014-11-27)
Contrast-induced acute kidney injury (CIAKI) is one of the commonest complications associated with contrast media (CM). Although the exact etiology of CIAKI remains unclear, one hypothesis involves vasoconstriction of afferent arterioles resulting in renal ischemia. Increased renal blood flow, therefore
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