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Introduction: Obstructed hemivagina, ipsilateral renal agenesis (OHVIRA) syndrome or Herlyn?Werner?Wunderlich syndrome (HWWS) is a rare complex congenital developmental anomaly of the genitourinary tract with limited reported cases in the medical literature.It is the result of an abnormal embryological development of paramesonephric (Mullerian) and mesonephric (Wolffian) ducts. Aims and Objectives: This Case report aims to contribute to the understanding of OHVIRA syndromes clinical presentation, diagnostic challenges and management strategies. Case : A 14-year-old girl presented to the gynecology outpatient department at AIIMS Raipur with a history of intermittent, colicky lower abdominal pain for the past two months. She had menarche at the age of 12 and had been experiencing regular menstrual cycles. On examination, there was mild tenderness in the lower abdomen and a vague mass palpated in the same area. Ultrasound abdomen showed large right endometriotic cyst of 10*10 cm. An MRI scan was done to confirme the diagnosis which revealed uterine didelphys with a right-sided obstructed hemivagina, hematocolpos, hematometra, and moderate hematosalpinx, along with a right ovarian complex cyst of 4*3 cm and an absent right kidney. Hysteroscopy was performed under laparoscopic guidance, and the MRI findings were confirmed. During the procedure, hematocolpos was observed on the right side, and the left cervix was visualized. Using a Collins knife, an incision was made at the most prominent point of the hematocolpos, and approximately 400 cc of blood was drained. Vaginal septal resection was then performed. A 14 Fr Malecot catheter was inserted through the right uterine horn for continuous drainage and to prevent vaginal stenosis, and was left in place for 3 days. Conclusion: OHVIRA syndrome, a rare congenital anomaly poses a diagnostic challenge to gynaecologists due to its infrequent presentation. Accurate diagnosis requires comprehensive symptomatic and clinical evaluation ,supplemented by radiological assessment, with MRI serving as imaging modality of choice for mullerian anomalies. Fortunately advances in minimally invasive surgery have simplified management, with hysteroscopic guided resection of vaginal septum under laparoscopic guidance emerging as a preferred treatment approach.