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Pseudogynecomastia is the increased aggregation of fatty tissue in the area of the male breast with resultant female appearance. Two forms can appear: pseudogynecomastia after massive weight loss (pseudogynecomastia obese [PO]) and pseudogynecomastia, which is caused only by adipose tissue (pseudogynecomastia fat). For PO, only the Gusenoff classification with corresponding operative treatment options exists. However, this classification is limited by the fact that it underestimates the extensive variability of residual fat tissue and skin excess, both crucial factors for operative planning. For this reason, we propose a modification of the treatment algorithm for the Gusenoff classification based on our results to achieve more masculine results.A total of 43 male patients with PO were included in this retrospective study (grade 1a, n = 1; grade 1b, n = 1; grade 2, n = 17; grade 3, n = 24). Forty-two mastectomies with a free nipple-areola complex (NAC) transposition (grades 2 and 3) and 1 with a subcutaneous mastectomy (grade 1a) with periareolar lifting were performed. A retrospective chart review was performed to obtain data regarding age, body mass index, body mass index loss, weight loss, reason for weight loss, comorbidities, nicotine, and additional procedures, postoperative sensitive on the NAC transplants and complications.None of the free-nipple grafts were lost. Forty (95%) of 42 patients with mastectomy had a resensitivity on the NAC.For pseudogynecomastia, the treatment algorithm of the Gusenoff classification should be modified and adapted according to our recommendations to achieve more optimal masculine results.