Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 06:42:54 UTC |
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Update Date | 2016-11-09 01:21:23 UTC |
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Accession Number | CHEM035843 |
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Identification |
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Common Name | Sildenafil |
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Class | Small Molecule |
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Description | In eliciting its mechanism of action, sildenafil ultimately prevents or minimizes the breakdown of cyclic guanosine monophosphate (cGMP) by inhibiting cGMP specific phosphodiesterase type 5 (PDE5) . The result of doing so allows cGMP present in both the penis and pulmonary vasculature to elicit smooth muscle relaxation and vasodilation that subsequently facilitates relief in pulmonary arterial hypertension and the increased flow of blood into the spongy erectile tissue of the penis that consequently allows it to grow in size and become erect and rigid .
Interestingly enough, it is precisely via this mechanism why sildenafil was at first researched as a potential treatment for angina - or chest pain associated with inadequate blood flow to the heart - before being serendipitously indicated for treating erectile dysfunction in the late 1980s . Nevertheless, it is because of this mechanism that sildenafil is also indicated for treating pulmonary arterial hypertension but is also additionally notorious for interacting with various anti-anginal or anti-hypertensive agents to develop potentially rapid, excessive, and/or fatal hypotensive crises .
Regardless, sildenafil, among a variety of other similar or related PDE5 inhibitors, has become a common and effective treatment for erectile dysfunction and since its formal approval for medical use in the public in 1998 , continues to see millions of prescriptions written for it internationally. Although the medication has historically been most popularly recognized as Pfizer's brand name Viagra, sildenafil is currently available generically and even as a non-prescription over the counter medication in some countries . |
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Contaminant Sources | - FooDB Chemicals
- STOFF IDENT Compounds
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine | ChEBI | Aphrodil | Kegg | 1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazine | Generator | Caverta | HMDB | Revatio | HMDB | Sildenafil citrate | HMDB | Viagra | HMDB | Desmethyl sildenafil | HMDB | Hydroxyhomosildenafil | HMDB | 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 | HMDB | Lactate, sildenafil | HMDB | NCX-911 | HMDB | Nitrate, sildenafil | HMDB | Acetildenafil | HMDB | Sildenafil nitrate | HMDB | NCX 911 | HMDB | Homosildenafil | HMDB | Citrate, sildenafil | HMDB | Sildenafil, desmethyl | HMDB | Desmethylsildenafil | HMDB | Sildenafil lactate | HMDB |
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Chemical Formula | C22H30N6O4S |
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Average Molecular Mass | 474.576 g/mol |
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Monoisotopic Mass | 474.205 g/mol |
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CAS Registry Number | 139755-83-2 |
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IUPAC Name | 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one |
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Traditional Name | revatio |
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SMILES | CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1 |
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InChI Identifier | 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) |
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InChI Key | BNRNXUUZRGQAQC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzenesulfonamides |
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Direct Parent | Benzenesulfonamides |
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Alternative Parents | |
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Substituents | - Benzenesulfonamide
- Pyrazolopyrimidine
- Benzenesulfonyl group
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Pyrimidone
- N-methylpiperazine
- N-alkylpiperazine
- Piperazine
- Pyrimidine
- Organosulfonic acid amide
- 1,4-diazinane
- Pyrazole
- Sulfonyl
- Organosulfonic acid or derivatives
- Organic sulfonic acid or derivatives
- Azole
- Heteroaromatic compound
- Tertiary aliphatic amine
- Tertiary amine
- Lactam
- Ether
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organosulfur compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-006t-9004300000-55c87eff7b6ad40ea3d5 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0059-2494500000-e3f8387aee5a0463363c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-05s0-3892000000-aa19715309275e16a6c0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0059-2494500000-e3f8387aee5a0463363c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-05s0-3892000000-aa19715309275e16a6c0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0002900000-b281f59f40caaba85ac9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-4436900000-0c5804e76b9d495c76d6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0459-6292000000-5a32bfcdda2067978be9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0001900000-51b4957d0b3d25c41773 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01vk-0302900000-86c63c2fd17f7c5b7d6f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03dj-8916100000-e941afc576d544ed32a7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0000900000-c92b21b6524ea5040313 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0000900000-06d94f4626e8bee6e389 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006t-9101300000-ef50cfadb7bd34e88187 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0000900000-1617a2dfdf2b96a0cd2c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0010900000-744efa093f1de0f36d62 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-003r-0272900000-aa5d9fef9c0fb52ad923 | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00203 |
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HMDB ID | HMDB0005039 |
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FooDB ID | FDB023606 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Sildenafil |
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Chemspider ID | 5023 |
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ChEBI ID | 9139 |
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PubChem Compound ID | 5212 |
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Kegg Compound ID | C07259 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Dunn, Peter James; Wood, Albert Shaw. Process for preparation of Sildenafil by cyclization. Eur. Pat. Appl. (1997), 18 pp. | 2. Kim NN, Goldstein I, Moreland RB, Traish AM: Alpha-adrenergic receptor blockade by phentolamine increases the efficacy of vasodilators in penile corpus cavernosum. Int J Impot Res. 2000 Mar;12 Suppl 1:S26-36. | 3. Warrington JS, Shader RI, von Moltke LL, Greenblatt DJ: In vitro biotransformation of sildenafil (Viagra): identification of human cytochromes and potential drug interactions. Drug Metab Dispos. 2000 Apr;28(4):392-7. | 4. Chua R, Keogh A, Miyashita M: Novel use of sildenafil in the treatment of portopulmonary hypertension. J Heart Lung Transplant. 2005 Apr;24(4):498-500. | 5. Fekete F, Fabian E: [Effectiveness and adverse effects of sildenafil in erectile dysfunction]. Orv Hetil. 2000 Jan 16;141(3):115-8. | 6. Blount MA, Beasley A, Zoraghi R, Sekhar KR, Bessay EP, Francis SH, Corbin JD: Binding of tritiated sildenafil, tadalafil, or vardenafil to the phosphodiesterase-5 catalytic site displays potency, specificity, heterogeneity, and cGMP stimulation. Mol Pharmacol. 2004 Jul;66(1):144-52. | 7. Kekilli M, Beyazit Y, Purnak T, Dogan S, Atalar E: Acute myocardial infarction after sildenafil citrate ingestion. Ann Pharmacother. 2005 Jul-Aug;39(7-8):1362-4. Epub 2005 May 24. |
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