Study of Itraconazole in Castrate-resistant Prostate Cancer (CRPC) Post-chemotherapy

INCLUSION CRITERIA * Male aged ≥ 18 years * Life expectancy ≥ 6 months * Histologically- or cytologically-confirmed adenocarcinoma of the prostate * Metastatic disease or prior history of metastases, as documented by positive bone scan or metastatic lesions on CT or MRI * Prostate cancer progression, as documented by PSA according to PCWG2 or radiographic progression according to RECIST criteria version 1.1 * Progression must have been during or after docetaxel based chemotherapy. * Surgically or medically castrated, with testosterone levels of \< 50 ng/dL (\< 2.0 nM). If the patient is currently being treated with LHRH agonists (patient who have not undergone an orchiectomy), this therapy must have been initiated at least 4 weeks prior to Cycle 1 Day 1 and treatment must be continued throughout the study. * Eastern Cooperative Oncology Group (ECOG) Performance Status of ≤ 2 * Hemoglobin ≥ 10.0 g/dL * Platelet count ≥100,000 microliters * Serum creatinine ≤ 2, OR a calculated creatinine clearance ≥ 40 mL/min * Serum bilirubin \< 1.5 x ULN (except for patients Gilbert's disease) * AST or ALT \< 2.5 x ULN * Able to swallow the study drug whole as a tablet * Willing and able to provide written informed consent EXCLUSION CRITERIA * Known brain metastasis * Radiation therapy within 4 weeks of Cycle 1, Day 1 * Prior systemic treatment with an azole drug (eg, fluconazole, ketoconazole) within 4 weeks of Cycle 1, Day 1 * Prior flutamide (Eulexin) treatment within 4 weeks of Cycle 1, Day 1 (patients whose PSA did not decline for ≥ 3 months months in response to antiandrogen given as a 2nd line or later intervention will require only a 2-week washout prior to Cycle 1,Day 1) * Prior Bicalutamide (Casodex), nilutamide (Nilandron) treatment within 6 weeks of Cycle 1 Day 1 (patients whose PSA did not decline for ≥ 3 months in response to antiandrogen given as a 2nd line or later intervention will require only a 2-week washout prior to Cycle 1 Day 1) * Known active or symptomatic viral hepatitis or chronic liver disease * Clinically significant heart disease as evidenced by myocardial infarction or arterial thrombotic events in the past 6 months; severe or unstable angina * Other malignancy, except non-melanoma skin cancer, with a ≥ 30% probability of recurrence within 24 months * Administration of an investigational therapeutic within 30 days of Cycle 1, Day 1 * Any condition which, in the opinion of the investigator, would preclude the patient's participation in this trial. * No more than 3 prior chemotherapy regimens.