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171599-83-0 (Sildenafil (citrate))

1

Identification

Sildenafil (citrate) Sildenafil (citrate)
Name Sildenafil (citrate)
Formula C28H38N6O11S
MW 666.7
CAS No. 171599-83-0
EINECS
Smiles O=C1N=C(NC(C(CCC)=N2)=C1N2C)C3=CC(S(N4CCN(C)CC4)(=O)=O)=CC=C3OCC.OC(CC(O)=O)(C(O)=O)CC(O)=O
Synonyms 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; 5-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(4H)-one 2-hydroxypropane-1,2,3-tricarboxylate
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

Introduction

Sildenafil citrate, one of the selective phosphodiesterase-5 (PDE5) inhibitors(IC50= 5.22 nM), is considered the best treatment for erectile dysfunction. IC50 Value: 5.22 nM [1] Target: PDE 5 in vitro: Pretreatment with 1 umol/L sildenafil potentiated the phosphorylation of ERK1/ERK2, an increase in the percentage of cells in S phase and cell proliferation, compared with serotonin stimulation alone (P < 0.05) [2].

Background Information

Sildenafil citrate, one of the selective phosphodiesterase-5 (PDE5) inhibitors(IC50= 5.22 nM), is considered the best treatment for erectile dysfunction. IC50 Value: 5.22 nM [1] Target: PDE 5 in vitro: Pretreatment with 1 umol/L sildenafil potentiated the phosphorylation of ERK1/ERK2, an increase in the percentage of cells in S phase and cell proliferation, compared with serotonin stimulation alone (P < 0.05) [2]. pretreatment of cells with sildenafilsuppressed serotonin-triggered activation of calcineurin/NFATc2 signaling pathway and resultant cyclin A expression, CDK2 activation and cell proliferation, while the presence of DT-3 [a specific protein kinase G (PKG) peptide inhibitor] reversed the effects of sildenafil on PASMCs [4]. in vivo: Sildenafil at a dose ranging from 10 to 40mg/kg statistically increased psychomotor seizure threshold in mice. Moreover, sildenafil enhanced the anticonvulsant action of all the studied AEDs in this test [3]. Administration of oral sildenafil (45 mg·kg(-1)·day(-1)) had no effect on blood pressure in control rats but decreased pressure in RUPP rats (115 ± 1 mmHg; P < 0.05) [5]. Toxicity: With a mean duration on tadalafil therapy of 243 ± 127 days at the time of analysis, 6MWD was unchanged. Patient-reported adverse events included headache (4%) and heartburn (2%). There was minimal change in BNP levels in the subset of patients receiving an ERA concomitantly [6]. Clinical trial: Sildenafil Impact on Ventricular Function in Patients With Heart Failure. Phase2/3 ......by MedChemexpress Co., Ltd.
Sildenafil Citrate, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5), is a well-tolerated and highly effective treatment for erectile dysfunction. ......by Selleck Chemicals LLC
Sildenafil, a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5), is a well-tolerated and highly effective treatment for erectile dysfunction. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000014010

Storage condition

Solubility

DMSO 23 mg/mL; Water <1 mg/mL; Ethanol <1 mg/mL by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 20 mg/mL warming (29.99 mM); Water<1 mg/mL (<1 mM); Ethanol<1 mg/mL (<1 mM); In vivo 30% PEG400+0.5% Tween80+5% Propylene glycol30 mg/mL by Selleck Chemicals LLC
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Mechanism and Indication

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Sildenafil (citrate) The University Health Network Pulmonary artery hypertension 2012/10/31 2016/11/1 Phase 4 Clinical
Sildenafil (citrate) All India Institute of Medical Sciences Pulmonary hypertension 2011/8/31 2013/7/31 Phase 4 Clinical
Sildenafil (citrate) Rabin Medical Center Chronic obstructive pulmonary disease 2011/9/30 2013/9/30 Phase 4 Clinical
Sildenafil (citrate) Pfizer Inc Pulmonary artery hypertension 2011/7/31 2011/10/31 Phase 4 Clinical
Sildenafil (citrate) Rambam Health Care Campus Erectile dysfunction 2011/6/30 2012/7/31 Phase 4 Clinical
Sildenafil (citrate) - Launched
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Safety Data of Sildenafil (citrate)

Hazard Symbols : Xi
Risk Statements : 36/37/38
Safety Statements : 36
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
Abcam 50mg/USD491() USA
Avanztec Inc. USA
BioVision, Inc., 50mg/USD335() USA
CHEMSCENE, LLC USA
Hangzhou Shenying Medicine Chemical Co., Ltd. China
MedChemexpress Co., Ltd. 10mg/USD50(In stock);50mg/USD95(In stock);100mg/USD130(In stock) USA
SOCOSUR Distribution Company France
Santa Cruz Biotechnology, Inc. 50mg/USD146() USA
Selleck Chemicals LLC 25mg/USD70(In stock);10mM/1mLIn DMSO/USD90(In stock);50mg/USD110(In stock);500mg/USD670(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 10mg/USD40(In stock);50mg/USD95(In stock);100mg/USD162(In stock) China
Sigma-Aldrich, Inc. 5mg/USD82() USA
Target Molecule Corp. 2mg/USD20();10mg/USD70();25mg/USD118();50mg/USD198();100mg/USD348() USA
Tocris Bioscience Inc. 10mg/USD149() USA
Xiangfan Goto Chemical Co., Ltd CHINA
10

Related Products

Other Forms of 171599-83-0

Name CAS No Formula MW
Sildenafil 139755-83-2 C22H30N6O4S 474.58

Recommended Compounds in Phosphodiesterase (PDE) Autophagy

Name CAS No Formula MW
(R)-(-)-Rolipram 85416-75-7 C16H21NO3 275.34
Mirodenafil (dihydrochloride) 862189-96-6 C26H39Cl2N5O5S 604.59
Vardenafil (hydrochloride) 224785-91-5 C23H33ClN6O4S 525.06
Ibudilast 50847-11-5 C14H18N2O 230.31
Pentoxifylline 6493-05-6 C13H18N4O3 278.31
Anagrelide (hydrochloride) 58579-51-4 C10H8Cl3N3O 292.55
Vardenafil 224785-90-4 C23H32N6O4S 488.6
(S)-(+)-Rolipram 85416-73-5 C16H21NO3 275.34
Irsogladine (maleate) 84504-69-8 C13H11Cl2N5O4 372.16
Irsogladine 57381-26-7 C9H7Cl2N5 256.09
Dipyridamole (hydrochloride)(1:x) 35763-39-4 C24H41ClN8O4 541.09
Dipyridamole 58-32-2 C24H40N8O4 504.63
Pimobendan (hydrochloride) 77469-98-8 C19H19ClN4O2 370.83
Pimobendan 74150-27-9 C19H18N4O2 334.37
Aminophylline 317-34-0 C16H24N10O4 420.43
Diphylline 479-18-5 C10H14N4O4 254.24
Cilostazol 73963-72-1 C20H27N5O2 369.46
Deltarasin (hydrochloride) 1440898-82-7 C40H38ClN5O 640.22
Rolipram 61413-54-5 C16H21NO3 275.34
Deltarasin 1440898-61-2 C40H37N5O 603.75

Recommended Compounds in Same Indication

Name CAS No Formula MW
sitaxsentan 184036-34-8 C18H15ClN2O6S2 454.9
Carvedilol 72956-09-3 C24H26N2O4 406.47
PRX-08066 866206-54-4 C19H17ClFN5S 401.89
SCH 527123 473727-83-2 C21H23N3O5 397.42
Vilanterol 503068-34-6 C24H33Cl2NO5 486.43
PH-797804 586379-66-0 C22H19BrF2N2O3 477.3
Glycopyrrolate 596-51-0 C19H28BrNO3 398.33
Tolazoline 59-98-3 C10H12N2 160.22
Umeclidinium (bromide) 869113-09-7 C29H34BrNO2 508.49
Indacaterol 312753-06-3 C24H28N2O3 392.49
Aclidinium (Bromide) 320345-99-1 C26H30BrNO4S2 564.55
Vilanterol (trifenatate) 503070-58-4 C44H49Cl2NO7 774.77
(R,R)-Formoterol 67346-49-0 C19H24N2O4 344.4
Tadalafil 171596-29-5 C22H19N3O4 389.4
Milrinone 78415-72-2 C12H9N3O 211.22
Formoterol (Fumarate) 43229-80-7 0.0
Macitentan 441798-33-0 C19H20Br2N6O4S 588.27
Riociguat 625115-55-1 C20H19FN8O2 422.42
Sildenafil 139755-83-2 C22H30N6O4S 474.58
Yohimbine 146-48-5 C21H26N2O3 354.44
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Route of Synthesis

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References

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More Information

Sildenafil (citrate)

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