Inclusion Criteria:

        Subjects must meet the following inclusion criteria:

          1. Age 18 or older and willing and able to give informed consent.

          2. Histologically or cytologically confirmed adenocarcinoma of the prostate without
             significant and relevant neuroendocrine differentiation or small cell features, per
             investigator's judgment.

          3. Ongoing ADT with a GnRH analogue, antagonist or bilateral orchiectomy (i.e., surgical
             or medical castration).

          4. For patients who have not had a bilateral orchiectomy, there must be a plan to
             maintain effective GnRH analogue or antagonist therapy for the duration of the trial.

          5. Serum testosterone level < 1.7 nmol/L (50 ng/dL) at the Screening visit.

          6. Patients receiving bisphosphonate or denosumab therapy must have been on stable doses
             for at least four weeks (from Day 1 visit).

          7. Progressive disease at study entry defined as one or more of the following three
             criteria that occurred while the patient was on ADT as defined in eligibility
             criterion #3:

               1. PSA progression defined by a minimum of two rising PSA levels with an interval of
                  ≥ 1 week between each determination. Patients who received an anti-androgen agent
                  must have progression after withdrawal (≥ 4 weeks since last flutamide or ≥ 6
                  weeks since last bicalutamide or nilutamide). The PSA value at the Screening
                  visit should be ≥ 2 µg/L (2 ng/mL)

               2. Soft tissue disease progression defined by RECIST 1.1

               3. Bone disease progression defined by PCWG3 with two or more new lesions on bone
                  scan

          8. Metastatic disease documented by measurable soft tissue disease by CT/MRI per RECIST
             1.1 criteria. Patients are allowed to have any metastatic disease (i.e. bone
             metastasis) as long as they also have measurable soft tissue lesions per RECIST 1.1..

          9. No prior cytotoxic chemotherapy for prostate cancer.

         10. Asymptomatic or mildly symptomatic from prostate cancer.

         11. ECOG performance status of 0-1 per the Investigators' clinical assessment

         12. Estimated life expectancy of ≥ 6 months

         13. Able to swallow the study drug and comply with study requirements

         14. All sexually active patients are required to use a condom as well as meet 1 of the
             following:

               1. Patient is non-fertile (orchiectomy) or has a female partner of non-childbearing
                  potential (i.e., post-menopausal, surgically sterilized, hysterectomy)

               2. Patient and his female partner must agree to use an adequate contraceptive method
                  from the first day of dosing until 3 months after the last dose to prevent
                  pregnancies. Adequate contraceptive method is defined as:

             i. Established use of oral, injected, or implanted hormonal methods of contraception.

             ii. Placement of an intra-uterine device or intra-uterine system. iii. Occlusive cap
             (diaphragm or cervical/vault caps) with spermicidal foam/gel/film/cream/suppository.

             iv. Tubal ligation for at least 6 months prior to screening.

         15. Male patient engaged in sexual activity with a pregnant female is required to use a
             condom from the first day of dosing until 3 months after the last dose of treatment
             with study drugs.

        Exclusion Criteria:

        Subjects must NOT meet any of the following exclusion criteria:

          1. Severe concurrent disease, infection, or co-morbidity that, in the judgment of the
             investigator, would make the patient inappropriate for enrollment.

          2. Known or suspected brain metastasis or active leptomeningeal disease.

          3. Regular daily use of opiate analgesics for pain from prostate cancer within four weeks
             of enrollment (Day 1 visit).

          4. WBC count < 3,000/µL, or absolute neutrophil count < 1,500/µL, or platelet count <
             100,000/µL, or hemoglobin < 5.6 mmol/L (9 g/dL) at the Screening visit (NOTE: patients
             may not have received any growth factors or blood transfusions or any therapeutic
             invention within 14 days of the hematologic laboratory values obtained at the
             Screening visit).

          5. Total bilirubin, alanine aminotransferase (ALT) or aspartate aminotransferase (AST) >
             2.5 times the upper limit of normal at the Screening visit; no therapeutic invention
             within 14 days before screening.

          6. Creatinine clearance < 30 mL/min as calculated using the Cockcroft-Gault equation at
             the Screening visit. Creatinine Clearance (mL/min) = [[140-Age (years)] * Weight (kg)]
             / [72 * Serum Creatinine (mg/dL)]

          7. Albumin < 30 g/L (3.0 g/dL) at the Screening visit, no therapeutic invention within 14
             days before screening.

          8. History of another malignancy within the previous two years other than curatively
             treated non-melanomatous skin cancer.

          9. Treatment with flutamide within four weeks of enrollment (Day 1 visit).

         10. Treatment with bicalutamide or nilutamide within six weeks of enrollment (Day 1
             visit).

         11. Treatment with 5-α reductase inhibitors (finasteride, dutasteride), estrogens within
             four weeks of enrollment (Day 1 visit).

         12. Treatment with systemic biologic therapy for prostate cancer (other than approved bone
             targeted agents) within four weeks of enrollment (Day 1 visit).

         13. Use of herbal products that may have hormonal anti-prostate cancer activity and/or are
             known to decrease PSA levels (e.g., saw palmetto) or systemic corticosteroids greater
             than the equivalent of 10 mg of prednisone/prednisolone per day within four weeks of
             enrollment (Day 1 visit).

         14. Prior use, or participation in a clinical trial, of an agent that blocks androgen
             synthesis (e.g., abiraterone) or blocks the AR (e.g., apalutamide, darolutamide,
             enzalutamide, proxalutamide).

         15. Participation in a previous clinical trial of HC-1119.

         16. Use of an investigational agent within four weeks of enrollment (Day 1 visit).

         17. Radiation therapy for treatment of the primary tumor within three weeks of enrollment
             (Day 1 visit).

         18. Radionuclide therapy (Radium 223) for treatment of metastasis within four weeks of
             enrollment (Day 1 visit).

         19. Clinically significant cardiovascular disease or condition

         20. Treatment with strong CYP2C8 inhibitors and inducers, CYP3A4 inducers, medications
             which are known to prolong the QT interval (see Appendix C).

         21. History of seizure or any condition that may predispose to seizure.

         22. Conditions that predispose subjects to increased risk for falls or fractures according
             to the discretion of the Investigator.

         23. Gastrointestinal disorder affecting absorption (e.g., gastrectomy, active peptic ulcer
             disease within last three months).

         24. Major surgery within four weeks prior to enrollment (Day 1 visit).

         25. Have active infection with HBV measured by hepatitis B surface antigen (HBsAg) test,
             HCV measured by RNA test and HIV measured by antibody test.

         26. Have known active tuberculosis.

         27. Known hypersensitivity to HC-1119, enzalutamide, or any of the excipients.

         28. Rare hereditary problems of fructose intolerance due to sorbitol