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139755-83-2 (Sildenafil)

1

Identification

Sildenafil Sildenafil
Name Sildenafil
Formula C22H30N6O4S
MW 474.58
CAS No. 139755-83-2
EINECS 200-659-6
Smiles O=C1NC(C2=C(OCC)C=CC(S(N3CCN(C)CC3)(=O)=O)=C2)=NC(C(CCC)=N4)=C1N4C
Synonyms 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazol[4,3d]pyrimidin-7-one; 5-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
InChI InChI=1S/C22H30N6O4S/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/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
2

Introduction

Sildenafil, 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, 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.
Sildenfail is a vasoactive agent used to treat erectile dysfunction and reduce symptoms in patients with pulmonary arterial hypertension (PAH). Sildenafil elevates levels of the second messenger, cGMP, by inhibiting its breakdown via phosphodiesterase type 5 (PDE5). PDE5 is found in particularly high concentrations in the corpus cavernosum, erectile tissue of the penis. It is also found in the retina and vascular endothelium. Increased cGMP results in vasodilation which facilitates generation and maintenance of an erection. The vasodilatory effects of sildenafil also help reduce symptoms of PAH. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance: EBNumber:EB000022751

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
5

Mechanism and Indication

6

Clinical Information

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

Safety Data of Sildenafil

Hazard Symbols : Xi,T,F
Risk Statements : 36/37/38-39/23/24/25-23/24/25-11
Safety Statements : 22-24/25-36-26-45-36/37-16-7
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
Aladdin 250mg/RMB625();1g/RMB1989() China
CHEMSCENE, LLC USA
Cayman Chemical Company 10mg/USD37() USA
Hubie Xinyuanshun Pharm&Chem Co., Ltd. China
MedChemexpress Co., Ltd. 10mg/USD50(Get quote);50mg/USD95(Get quote);100mg/USD130(Get quote) USA
Santa Cruz Biotechnology, Inc. 1g/USD309() USA
Shandong Kingnod Pharmaceuticals Co., Ltd. China
Shanghai Haoyuan Chemexpress Co., Ltd. 10mg/USD40(Get quote);50mg/USD95(Get quote);100mg/USD162(Get quote) China
Shanghai Zhongkang Weiye Biological Science & Technology Co., Ltd. China
Target Molecule Corp. 5mg/USD20();25mg/USD78();100mg/USD165() USA
Toronto Research Chemicals Inc. 5mg/USD50() Canada
10

Related Products

Other Forms of 139755-83-2

Name CAS No Formula MW
Sildenafil (citrate) 171599-83-0 C28H38N6O11S 666.7

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
Sildenafil (citrate) 171599-83-0 C28H38N6O11S 666.7
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
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

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