Post-mortem detection and identification of sildenafil (Viagra) and its metabolites by LC/MS and LC/MS/MS

Weinmann, Wolfgang; Bohnert, Michael; Wiedemann, Alexander; Renz, M.; Lehmann, Natalie; Pollak, Stefan

doi:10.1007/s004140000178

Cited by 48 publications

(27 citation statements)

References 15 publications

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“…Peak sildenafil concentrations from oral "therapeutic" doses of 50mg, 100 mg, and 0.68 mg/kg were 260, 450, and 212 ng/ml, respectively (11). Pharmacogenetic differences may exist between ethnic populations.…”

Section: Discussionmentioning

confidence: 98%

Sildenafil citrate ingestion and prolonged priapism and tachycardia in a pediatric patient

Wills

Albinson

Wahl

et al. 2007

Clinical Toxicology

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Introduction.Little is known about the toxicity of sildenafil overdose in the pediatric population. We present a case of prolonged priapism and tachycardia due to unintentional sildenafil overdose in a child. Case report. A 19-month-old male ingested up to six 50 mg Viagra tablets 45 minutes prior to presentation at the emergency department. Initial vital signs included temperature 98.2 o F, blood pressure 90/58 mmHg, heart rate 140, respirations 20, and oxygen saturation of 100% on room air. The child weighed 10.4 kg. Physical exam revealed a happy, smiling, laughing toddler who was cooperative with all aspects of his exam. He had mild facial flushing and an erect penis which was normal in color and had a capillary refill of two seconds. Precordial palpation did not show evidence of increase dynamic force, his heart sounds were regular, and no ectopy was noted. His peripheral pulses were strong and regular in all four extremities. No gastrointestinal decontamination was performed. The patient was started on maintenance IV fluids and admitted to the pediatric floor for observation. The patient had a non-painful tumescent penis and mild tachycardia for about 24 hours post-ingestion. The child never had pain from the constant erection. Sildenafil concentration drawn approximately seven hours after ingestion was 3900 ng/ml (reporting limit 24 ng/ml) and N-desmethylsildenafil level was 1700 ng/ml (reporting limit 24 ng/ml). Conclusion. This case of pediatric sildenafil ingestion (up to 30mg/kg) initially resulted in facial flushing and priapism. The child had asymptomatic tachycardia and prolonged priapism that persisted until hospital discharge approximately 24 hours after ingestion. The erection was non-painful and required no urologic intervention, most likely representing a high flow state. In this ingestion, only supportive care was required.

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Section: Discussionmentioning

confidence: 98%

Sildenafil citrate ingestion and prolonged priapism and tachycardia in a pediatric patient

Wills

Albinson

Wahl

et al. 2007

Clinical Toxicology

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“…The CID of protonated desmethylsildenafil was observed to give rise to a product ion at m/z 85, corresponding to a product ion at m/z 99 of sildenafil. 7 This result strongly suggests that the ions at m/z 99 and 85 originated from the piperazine moiety.…”

Section: Rcm Letter To the Editormentioning

confidence: 93%

“…Representative fragment ions of sildenafil were observed at m/z 377, 313, 311, 299, 283, 163, 100 and 99, and this fragmentation has been well described previously. 6,7 Among these product ions, we were especially interested in the ions at m/z 377, 313 and 311. Compound 1 is a structural analogue of sildenafil in which the oxygen atom is substituted with a sulfur atom in the pyrazolopyrimidine moiety.…”

mentioning

confidence: 99%

Low‐energy collision‐induced dissociation of sildenafil thiono analogues: gas‐phase intramolecular nucleophilic substitution through ion‐neutral complexes between a cationic substrate and a thione‐containing neutral nucleophile

Lee¹,

Yoo²,

Kang³

et al. 2005

Rapid Comm Mass Spectrometry

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“…Furthermore, with internal (deuterated) standards, a quantitation of selected compounds by MS/MS is possible in one LC-run -similar to a method published for selected drugs in serum by flow-injection MS/MS-analysis [5]. The identification of metabolites by the similarity of the CID-spectra of metabolites and parent drugs is another possible application of a MS/MS-spectra library, and has recently been demonstrated by the identification of oxidised sildenafil and two more sildenafil metabolites in urine [19].…”

Section: Dossier Structure Elucidation By Lc-ms Conclusionmentioning

confidence: 99%

MS/MS-libraries with triple quadrupole-tandem mass spectrometers for drug identification and drug screening

Weinmann¹,

Gergov²,

Goerner³

2000

Analusis

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Two MS/MS libraries of drugs created by electrospray ionisation (ESI) and collision-induced dissociation (CID) of the quasimolecular ionshave been developed with triple-quadrupole ionspray mass spectrometers. For both libraries three and four different collision energies were used, respectively, to obtain a variety of CID spectra, which were all included separately into the MS/MS libraries. The MS/MS product ion spectra of more than 400 drugs were acquired in positive or negative mode in two laboratories independently. Recently, one of these MS/MS libraries was applied successfully for the identification of drug metabolites and the other has been used for qualitative analysis of drugs in urine samples with data dependent experiments (DDE). In this work, the reproducibility of CID spectra has been tested with three instruments (including two different instruments) in three laboratories. For comparison of CID-spectra, library searching with a combination of the two libraries was performed and fit values were compared. With regard to library fit values CID-spectra were found to be highly reproducible between the instruments, when similar CID gas pressure and collision energy were applied. In addition, the long-time reproducibility of CID over 30 months with the API 365 was demonstrated. Furthermore, comparisons of in-source CID and CID by MS/MS was given. It can be concluded, that both MS/MS libraries created with APIs 365 can be used with both types of triple-quadrupole instruments from Sciex (API 365 and 2000) for drug identification. Two applications of these MS/MS spectra libraries in combination with data dependent experiments are summarised.

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Post-mortem detection and identification of sildenafil (Viagra) and its metabolites by LC/MS and LC/MS/MS

Cited by 48 publications

References 15 publications

Sildenafil citrate ingestion and prolonged priapism and tachycardia in a pediatric patient

Sildenafil citrate ingestion and prolonged priapism and tachycardia in a pediatric patient

Low‐energy collision‐induced dissociation of sildenafil thiono analogues: gas‐phase intramolecular nucleophilic substitution through ion‐neutral complexes between a cationic substrate and a thione‐containing neutral nucleophile

MS/MS-libraries with triple quadrupole-tandem mass spectrometers for drug identification and drug screening

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