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A proportion of patients with initial presentation of ulcerative proctitis (UP) progress to more extensive colitis. We sought to characterize the natural history and identify clinical predictors of extension in UP.We performed a retrospective cohort study of participants with a new diagnosis of UP from January 2000 to December 2015. We used Cox proportional hazard modeling to identify predictors of disease extension.We identified 169 new cases of UP with a median age of diagnosis of 40 years (range: 16–91 yr) and a median follow–up of 4.3 years (range: 3.3–15.1 yr). Fifty-three (31%) patients developed extension over the follow-up time. Compared with nonextenders, the need for immunosuppressive or biologic therapy was significantly higher among extenders (34% versus 2.6%, P < 0.001). In multivariable analyses, compared with UP cases with body mass index <25, the adjusted hazard ratios of extension were 1.75 (95% confidence interval [CI], 0.95–3.23) and 2.77 (95% CI, 1.07–7.14) among overweight and obese patients, respectively (Ptrend = 0.03). Similarly, patients with a history of appendectomy or endoscopic finding of moderate to severe disease had a higher risk of extension (adjusted hazard ratio = 2.74, 95% CI, 1.07–7.01 and 1.96, 95% CI, 1.05–3.67, respectively).In a retrospective cohort study, we show that appendectomy, body mass index, and endoscopic activity at the time of diagnosis of proctitis are associated with an increased risk of extension. In addition, our data suggest that extenders are more likely to require immunosuppressive or biologic therapy.