Isolation and identification of a new sildenafil analogue, hydroxycarbodenafil, found as an adulterant in a health supplement

Yufan Gu; Qing Hu; Jian Sun; Hong Yu; Huiqin Pan; Xiaotong Zhao; Shen Ji

doi:10.1016/j.jpba.2020.113222

Isolation and identification of a new sildenafil analogue, hydroxycarbodenafil, found as an adulterant in a health supplement

J Pharm Biomed Anal. 2020 Jun 5:185:113222. doi: 10.1016/j.jpba.2020.113222. Epub 2020 Feb 29.

Authors

Yufan Gu¹, Qing Hu², Jian Sun², Hong Yu², Huiqin Pan², Xiaotong Zhao², Shen Ji³

Affiliations

¹ China State Institute of Pharmaceutical Industry, 285 Gebaini Road, Shanghai 201203, China; NMPA Key Laboratory for Quality Control of Traditional Chinese Medicine, Shanghai Institute for Food and Drug Control, 1500 Zhangheng Road, Shanghai 201203, China.
² NMPA Key Laboratory for Quality Control of Traditional Chinese Medicine, Shanghai Institute for Food and Drug Control, 1500 Zhangheng Road, Shanghai 201203, China.
³ China State Institute of Pharmaceutical Industry, 285 Gebaini Road, Shanghai 201203, China; NMPA Key Laboratory for Quality Control of Traditional Chinese Medicine, Shanghai Institute for Food and Drug Control, 1500 Zhangheng Road, Shanghai 201203, China. Electronic address: [email protected].

PMID: 32145539
DOI: 10.1016/j.jpba.2020.113222

Abstract

During routine screening of illegal adulterants in health supplements, a novel sildenafil analogue was discovered, and subsequently isolated by recrystallization. Its structure was elucidated by extensive analyses of high resolution mass spectrometry (HRMS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) data. The analogue was finally determined as hydroxycarbodenafil, featuring a hydroxyethyl group instead of an ethyl group on piperazine ring in comparison with carbodenafil.

Keywords: Adulterated health supplement; HR-MS and NMR; Hydroxycarbodenafil; Sildenafil analogue.

MeSH terms

Dietary Supplements / analysis*
Dietary Supplements / standards
Drug Contamination / prevention & control*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Sildenafil Citrate / analogs & derivatives
Sildenafil Citrate / analysis*
Sildenafil Citrate / standards

Substances

Sildenafil Citrate