Inclusion Criteria:

1. Histologic confirmation of adenocarcinoma of the prostate

2. Biochemically relapsed disease with a rising PSA on at least two consecutive
measurements at least two weeks apart after prior definitive local therapy (radical
prostatectomy, external beam radiation, or brachytherapy) or combination of radical
prostatectomy and radiotherapy (RT) with curative intent

3. Prior primary or salvage radiation or not a candidate for salvage radiation due to
patient preference or clinical assessment based upon disease characteristics and/or
patient co-morbidities.

4. Minimum PSA: If no prior androgen deprivation therapy (ADT) for biochemical relapse:

- 1.0 ng/mL if prior radical prostatectomy with or without adjuvant/salvage
radiation therapy, confirmed by repeat measurement at least 2 weeks later, or

- Nadir + 2 ng/mL if prior RT alone without prior radical prostatectomy, confirmed
by repeat measurement at least 2 weeks later If prior ADT for biochemical
relapse:

- 4.0 ng/mL or > 2 ng/mL above nadir on prior cycle of ADT, whichever is higher,
confirmed by repeat measurement at least 2 weeks later

5. No evidence of metastatic disease on imaging by whole body bone scan (technetium-99
or Na-F PET bone scan) and cross-sectional imaging of the abdomen/pelvis (CT or MRI)
within 6 weeks of Day 1 of protocol therapy

6. Prior androgen deprivation therapy (ADT) with LHRH agonist and/or antagonist allowed
for either (neo)adjuvant treatment with local therapy or for biochemical relapse

7. Last effective dose of LHRH agonist/antagonist "expired" > 3 months prior to study
entry.

8. For example, a patient receiving LHRH agonist injection every 3 months would be
eligible provided their last injection was > 6 months prior to Day 1 of protocol
therapy. A patient receiving LHRH agonist injections every 4 months will be eligible
provided last injection was > 7 months prior to Day 1 of protocol therapy.

9. Serum testosterone level: If no prior androgen deprivation therapy:

- A single measurement greater than 150 ng/dL within 3 months of day 1 of protocol
therapy If prior androgen deprivation therapy (either in adjuvant or biochemical
relapse setting):

The two most recent measurements of serum testosterone prior to Day 1 of protocol
therapy must fulfill the following criteria:

- Both measurements are greater than 150 ng/dL.

- The two measurements are spaced at least 14 days apart.

- Both must be measured within 3 months of Day 1 of protocol therapy.

- There must not be an increase of > 50 ng/dL between these two successive
measurements.

10. PSA doubling time (PSADT) ≤ 15 months, calculated based upon all serum PSA
measurements obtained within 3 months prior to Day 1 of protocol therapy, with a
minimum of three PSA measurements spaced at least 14 days apart (see section 6). PSA
values obtained when serum testosterone was known to be less than 150 ng/dL, prior to
local therapy, or within three months of last dose of LHRH agonist/antagonist or
antiandrogen will be excluded from the calculation of the PSADT. PSADT calculation to
be carried out using the following website:
http://nomograms.mskcc.org/Prostate/PsaDoublingTime.aspx

11. Total bilirubin less than 1.5 times upper limit of normal (ULN), or less than 3 times
ULN at study entry in a patient with documented Gilbert‟s disease.

12. ALT and AST levels less than 1.5 times ULN at study entry

13. Serum potassium greater than 3.5 mmol/L without oral supplementation

14. No history of uncontrolled hypertension (blood pressure > 160/100 mm Hg despite
anti-hypertensive medication)

15. ECOG performance status of 0 or 1

16. Estimated life expectancy greater than 5 years

17. Age greater than or equal to 18 years at time of study entry

18. Ability to sign written informed consent

19. Ability to swallow study drug whole as a capsule

20. Primary prostate cancer tissue available for analysis is not required for inclusion
onto this study but is strongly encouraged.

Exclusion Criteria:

1. Castrate-resistant disease, as evidenced by either:

- Rising PSA on 2 consecutive measurements at least 2 weeks apart with concurrent
documented serum testosterone < 50 ng/dL at the time of PSA measurement, or

- Rising PSA on 2 consecutive measurements at least 2 weeks apart measured within
3 months after last LHRH agonist/antagonist injection

2. Prior bilateral orchiectomy

3. Congestive heart failure of NYHA class III or higher severity at study entry

4. History of chronic active hepatitis

5. Grade 2 or higher peripheral neuropathy at the time of study entry

6. Use of 5-alpha reductase antagonist (i.e. finasteride, dutasteride) or antiandrogen
(i.e. flutamide, bicalutamide) within 6 weeks of Day 1 of protocol therapy

7. Use of systemic steroids at an equivalent dose of prednisone 5 mg/day or higher
within 6 weeks of Day 1 of protocol therapy

8. Use of medications or herbal supplements which are known to potentially lower serum
PSA within 6 weeks of Day 1 of protocol therapy

9. Use of other medications that may potentially interact with itraconazole within 1
week of study entry

10. Use of other investigational agents within 6 weeks of Day 1 of protocol therapy

11. Prior pathology consistent with small cell carcinoma or prostate cancer with
predominantly neuroendocrine differentiation