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The objective of this study was to determine factors associated with syphilis among men who report sex with other men in New York City.We conducted a case–control study among 88 men who reported sex with men in the previous year, 18 to 55 years old and diagnosed with primary or secondary syphilis during 2001; and 176 control subjects frequently matched by age and type of health provider.HIV prevalence among syphilis cases was 48% compared with 15% among control subjects (P <0.001). Variables associated with syphilis in a multivariate model were HIV infection (odds ratio [OR], 7.3; 95% confidence interval [CI], 3.5–15.4), income >$30,000 per year (OR, 2.7; CI, 1.4–5.2), and barebacking (OR, 2.6; CI, 1.4–4.8). The median time since HIV diagnosis for HIV-positive was 6 years for cases and 7 years for control subjects (P = 0.70). Among HIV-infected participants, syphilis cases were more likely than control subjects to report being on antiretroviral therapy (69% vs. 44%, P = 0.05) and to report having undetectable viral load (58% vs. 24%, P = 0.02).HIV infection was strongly associated with syphilis in this study. High-risk behavior reported by both cases and control subjects indicates the potential for increased HIV transmission.