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Managing anticoagulant therapy in patients with comorbidities such as kidney disease, liver disease, obesity, thrombophilia and increased bleeding risk with thrombocytopenia presents unique challenges. Renal impairment affects drug clearance. Liver disease alters coagulation and drug metabolism. Obesity affects drug distribution and dosing. Increased bleeding risk with thrombocytopenia often requires different dosing. This review finds that tailored therapeutic strategies are essential to balance the risks and benefits in these complex patient populations.