| Record Information |
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| Version | 2.0 |
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| Created at | 2024-09-10 18:54:55 UTC |
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| Updated at | 2024-09-10 18:54:55 UTC |
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| NP-MRD ID | NP0334562 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Sildenafil |
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| Description | Sildenafil, also known as aphrodil or caverta, 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. Sildenafil was first documented in 2000 (PMID: 10845762). Sildenafil is a very strong basic compound (based on its pKa) (PMID: 10725306) (PMID: 15797756) (PMID: 10693332) (PMID: 15213306). |
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| Structure | CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1 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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| 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 Mass | 474.5760 Da |
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| Monoisotopic Mass | 474.20492 Da |
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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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| CAS Registry Number | Not Available |
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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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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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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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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - 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. doi: 10.1038/sj.ijir.3900504. [PubMed:10845762 ]
- 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. [PubMed:10725306 ]
- 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. doi: 10.1016/j.healun.2004.01.017. [PubMed:15797756 ]
- Fekete F, Fabian E: [Effectiveness and adverse effects of sildenafil in erectile dysfunction]. Orv Hetil. 2000 Jan 16;141(3):115-8. [PubMed:10693332 ]
- 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. doi: 10.1124/mol.66.1.144. [PubMed:15213306 ]
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