A PDE5 inhibitor
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Sildenafil Citrate

Item No. 14008

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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, 2-hydroxy-1,2,3-propanetricarboxylate
CAS Number
171599-83-0
Synonyms
  • Apodefil
  • Tonafil
  • UK 92480
Molecular Formula
C22H30N6O4S • C6H8O7
Formula Weight
666.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 14 mg/ml
λmax
214, 294 nm
SMILES
O=S(N1CCN(C)CC1)(C2=CC(C(NC3=C4N(C)N=C3CCC)=NC4=O)=C(OCC)C=C2)=O.OC(CC(O)=O)(C(O)=O)CC(O)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $53

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    25 mg

    $93

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    50 mg

    $129

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    Product Description

    Sildenafil is a potent inhibitor of phosphodiesterase 5 (PDE5) with IC50 values of 3.6 and 3 nM for PDE5 activity in isolated rabbit platelets and human corpus cavernosum, respectively.1 It is selective for PDE5 over PDE1 and PDE3 (IC50s = 0.26 and 65 μM, respectively). Sildenafil reverses glucose-induced decreases in angiopoietin 1 (ANG1) expression and reduction of capillary-like tube formation by mouse dermal endothelial cells in vitro and increases the number of functional blood vessels and regional blood flow in the sciatic nerve in a db/db mouse model of diabetic peripheral neuropathy.2 It increases the ratio of maximum intracavernosal pressure to mean arterial blood pressure (ICP/MAP), a measure of erectile function, in castrated rats when administered at a dose of 20 mg/kg per day.3 Sildenafil (0.5 mg/kg) also reduces cardiac arrest and resuscitation-induced increases in angiotensin II (Item No. 17150), angiotensin converting enzyme (ACE), ACE2, and various angiotensin receptors and increases survival in a porcine model of ischemia/reperfusion injury.4 Formulations containing sildenafil have been used in the treatment of erectile dysfunction, pulmonary arterial hypertension, and high-altitude pulmonary edema associated with altitude sickness.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Terrett, N.K., Bell, A.S., Brown, D., et al. Sildenafil (ViagraT), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg. Med. Chem. Lett. 6(15), 1819-1824 (1996).

    2. Wang, L., Chopp, M., Szalad, A., et al. Sildenafil ameliorates long term peripheral neuropathy in type II diabetic mice. PLoS One 10(2), e0118134 (2015).

    3. Mulhall, J.P., Verma, N., Deveci, S., et al. Sildenafil citrate improves erectile function after castration in a rat model. BJU Int. 113(4), 656-661 (2014).

    4. Wang, G., Zhang, Q., Yuan, W., et al. Sildenafil protects against myocardial ischemia-reperfusion injury following cardiac arrest in a porcine model: Possible role of the renin-angiotensin system. Int. J. Mol. Sci. 16(11), 27015-27031 (2015).

    Product Citations

    Santillo, M.F., and Mapa, M.S.T. Phosphodiesterase (PDE5) inhibition assay for rapid detection of erectile dysfunction drugs and analogs in sexual enhancement products. Drug Test Anal. 10(8), 1315-1322 (2018).