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Objective This study aimed to determine the prevalence of the use of medicines, particularly over-the-counter medicines (OTC medicines), and to analyse its association with different personal and lifestyle aspects. Setting The study sample was an adolescent population in the Valencian Community (East Spain) aged 14–17 years. Method A total of 23,349 adolescents from 229 schools completed a questionnaire (response rate 89.54%). We analysed adolescents who were taking prescribed medicines at the time of the questionnaire, and who were users of OTC medicines that had not been prescribed by a doctor for a particular illness. We estimated this association with several personal and lifestyle factors using simple and multivariate analyses and logistic regression. Results A total of 15.18% of the participants reported that they were taking prescribed medicines when they answered the questionnaire, and 45.38% of the participants reported a frequent use of OTC medicines. Prescribed medicine use is more likely in older adolescents [Relative Prevalence Ratio adjusted by confounding factors (RPRa) 1.05, 95% CI: 1.01–1.10], in those who had tried to lose weight by dieting in the last year (RPRa 1.23, 95% CI: 1.11–1.37), in current smokers (RPRa 1.13, 95% CI: 1.02–1.27), in those who had a serious emotional problem (RPRa 1.85, 95% CI: 1.60–2.16) and in people who presented a chronic pathology (RPRa 8.24, 95% CI: 7.45–9.11). Respondents who reported a frequent use of OTC medicines were more likely to be older (RPRa 1.03, 95% CI: 1.00–1.06), have tried to lose weight by dieting in the last year (RPRa 1.15, 95% CI: 1.06–1.24), be a current smoker (RPRa 1.19, 95% CI: 1.10–1.28), have a serious emotional problem (RPRa 1.48, 95% CI: 1.31–1.67), and watch TV (RPRa 1.24, 95% CI: 1.16–1.32). Conclusions We noted an extensive use of medicines, especially OTC medicines, in adolescents, and an association with some personal and lifestyle factors. We conclude that prevention and early education of a responsible use of medicines should be a public health priority.