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Endometrial stromal sarcoma (ESS) is a very rare uterine tumor, composed of cells resembling endometrial stromal cells. As these tumors have indistinct clinical and radiological features, they are very rarely diagnosed preoperatively. We are reporting a series of five cases clinically mistaken as benign masses. The age range of these patients was 38–65 years, with a mean age of 49 years. The patients presented with vaginal bleeding, lower abdominal pain, and abdominal mass. All the cases were clinically diagnosed on ultrasound as leiomyoma and underwent total abdominal hysterectomy. Microscopically, all the cases showed a densely cellular tumor composed of small oval cells bearing a close resemblance to normal endometrial stromal cells and were diagnosed as low-grade ESS. This is an aggressive tumor but has a better prognosis in early stage.