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1094598-75-0Sildenafil EP Impurity B
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| Catalogue No.: | VL136006 |
|---|---|
| CAS No.: | 1094598-75-0 |
| Mol. Formula: | C22H30N6O5S |
| Mol. Weight: | 490.58 g/mol |
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Additional information on CAS 1094598-75-0
Parent drug
SildenafilIUPAC Name
1-Methyl-4-[4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzene-1-sulfonyl]piperazine 1-oxidePharmacopeial Synonyms
Sildenafil N-OxideSynonyms
4-(4-ethoxy-3-{1-methyl-7-oxo-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}benzenesulfonyl)-1-methylpiperazin-1-ium-1-olate ;7H-Pyrazolo(4,3-d)pyrimidin-7-one, 5-(2-ethoxy-5-((4-methyl-4-oxido-1-piperazinyl)sulfonyl)phenyl)-1,6-dihydro-1-methyl-3-propyl; 1-{[3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl}-4-methylpiperazine N4-oxideSmiles
O=C1C(N(C)N=C2CCC)=C2N=C(C3=CC(S(=O)(N4CC[N+]([O-])(C)CC4)=O)=CC=C3OCC)N1InChI
InChI=1S/C22H30N6O5S/c1-5-7-17-19-20(26(3)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)33-6-2)34(31,32)27-10-12-28(4,30)13-11-27/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)Shipping Condition
Ambient TemperatureDescription
Sildenafil EP Impurity B, also designated sildenafil N-oxide (CAS 1094598-75-0), is an oxidative impurity of the phosphodiesterase-5 inhibitor sildenafil arising from N-oxidation of the piperazine nitrogen. Its structure, C22H30N6O5S, molecular weight 490.58 g/mol, corresponds to a zwitterionic N-oxide metabolite-like species rather than a nitrosamine. Formation may occur during oxidative stress, storage, or synthetic processing involving peroxides. Owing to low-level occurrence and polarity shifts relative to the parent drug, characterization typically requires LC-MS/MS, high-resolution MS, and, where needed, UPLC with diode-array detection for chromatographic separation and trace quantification under impurity control specifications.References
Ghofrani, Hossein A., et al. “Sildenafil: From Angina to Erectile Dysfunction to Pulmonary Hypertension and Beyond.” Nature Reviews Drug Discovery, vol. 5, no. 8, Aug. 2006, pp. 689–702, https://doi.org/10.1038/nrd2030.Request a Quote
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