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Sildenafil
Cayman Chemical Item Number 10008671
Description
Cyclic guanosine monophosphate (cGMP) is the ubiquitous second messenger for G-protein coupled receptors activated by endogenous substances such as nitric oxide and atrial natriuretic peptide. It can be generated by soluble guanylyl cyclase in response to binding of nitric oxide and degraded via members of the phosphodiesterase (PDE) protein family. Sildenafil, formulated for human use and marketed under the trade name Viagra™, is a potent cGMP-specific phosphodiesterase that is highly selective for PDE5. It inhibits PDE5 activity in isolated rabbit platelets with an IC50 value of 3.6 nM (3 nM in human corpus cavernosum) compared to inhibition of PDE1 and PDE3 activities (IC50s = 0.26 and 65 μM, respectively).1↗ Inhibition of type 5 PDE enhances the relaxation of smooth muscle in a range of vascular tissues by prolonging the nitric oxide/cGMP-mediated activation of cGMP-dependent protein kinase. While most notable for its use in the treatment of erectile dysfunction, sildenafil’s vasorelaxant properties have also been used to control vascular tone in pulmonary arterial hypertension and high-altitude pulmonary edema associated with altitude sickness.2↗,3↗
Synonyms Viagra™
Formal Name 5-[2-ethoxy-5-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one
CAS Number 139755-83-2
Molecular Formula C22H30N6O4S
Formula Weight 474.6
Formulation A crystalline solid
Purity ≥98%
λmax 212, 294 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES O=S(N1CCN(C)CC1)(C2=CC(C(NC3=C4N(C)N=C3CCC)=NC4=O)=C(OCC)C=C2)=O
InCHI Code 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)
InCHI Key BNRNXUUZRGQAQC-UHFFFAOYSA-N |