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To identify factors associated with nonadherence and unsuppressed viral load across adolescence among youth with perinatally-acquired HIV (PHIV).Longitudinal study at 15 US clinical sitesSelf-reported antiretroviral medication nonadherence (any missed dose, past week) and unsuppressed VL (HIV RNA>400 copies/mL) were assessed annually. Individual, caregiver, social and structural factors associated with nonadherence and unsuppressed VL were identified by age (years): 8–11 (“pre-adolescence”), 12–14 (“early adolescence”), 15–17 (“middle adolescence”), and 18–22 (“late adolescence/young adulthood”), utilizing multivariable generalized linear mixed effects models.During a median 3.3-year follow-up, 381 youth with PHIV contributed VL measurements and 379 completed 1190 adherence evaluations. From pre-adolescence to late adolescence/young adulthood, prevalence of nonadherence increased from 31% to 50% (p < 0.001); prevalence of unsuppressed VL increased from 16% to 40% (p < 0.001). In adjusted analyses, in pre-, middle-, and late adolescence/young adulthood, perceived antiretroviral side effects were associated with nonadherence. Additional factors associated with nonadherence included: in pre-adolescence, using a buddy system (as an adherence reminder); in early adolescence, identifying as black, using buddy system; in middle adolescence, CD4% < 15%, unmarried caregiver, indirect exposure to violence, stigma/fear of inadvertent disclosure, stressful life events. Associations with unsuppressed VL included: in early adolescence, youth unawareness of HIV status, lower income; in middle adolescence, perceived antiretroviral side effects, lower income; in late adolescence/young adulthood, distressing physical symptoms and perceived antiretroviral side effects.Prevalence of nonadherence and unsuppressed VL increased with age. Associated factors varied across adolescence. Recognition of age-specific factors is important when considering strategies to support adherence.