Dutasteride
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
|---|---|
| (5α, 17β)-N-{2,5 bis(trifluoromethyl) phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide | |
| Identifiers | |
| CAS number | 164656-23-9 |
| ATC code | G04CB02 |
| PubChem | 6918296 |
| DrugBank | APRD00385 |
| ChemSpider | 5293502 |
| Chemical data | |
| Formula | C27H30F6N2O2 |
| Mol. mass | 528.53 g/mol |
| SMILES | eMolecules & PubChem |
| Pharmacokinetic data | |
| Bioavailability | 60% |
| Protein binding | 99% |
| Metabolism | Hepatic (CYP3A4-mediated) |
| Half life | 5 weeks |
| Excretion | Fecal |
| Therapeutic considerations | |
| Pregnancy cat. |
X(US) Not to be handled by pregnant women |
| Legal status | |
| Routes | Oral |
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Dutasteride (marketed as Avodart, Avidart, Avolve, Duagen, Dutas, Dutagen, Duprost) is a 5-alpha-reductase inhibitor, a drug which inhibits the conversion of testosterone into dihydrotestosterone (DHT). It is used to treat conditions caused by DHT, such as benign prostatic hyperplasia (BPH). Avodart is manufactured and marketed by GlaxoSmithKline.
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[edit] Classification and method of action
Dutasteride belongs to a class of drugs called 5-alpha-reductase inhibitors, which block the action of the 5-alpha-reductase enzymes that convert testosterone into dihydrotestosterone (DHT). Finasteride also belongs to this group. Dutasteride inhibits both isoforms of 5-alpha reductase, while finasteride inhibits only one. But a clinical study done by GlaxoSmithKline, the EPICS trial, did not find dutasteride to be more effective than finasteride in treating BPH.
[edit] Uses
While dutasteride is only officially approved to treat enlargement of the prostate gland (at a dose of 0.5 mg/day),[1] phase I and II clinical trials for dutasteride as a hair loss drug were also undertaken, but called off in late 2002. The reason the trials were called off is not publicly known. Industry sources speculate that Avodart would have been seen as too similar to Propecia to have proved profitable as a hair loss treatment. However, phase II results indicated that dutasteride 2.5 mg/day generated a superior hair count to finasteride 5 mg at 12 and 24 weeks.[2]
In December 2006, GlaxoSmithKline started a new Phase III, six month study in Korea to test the safety, tolerability and effectiveness of a once-daily dose of dutasteride (0.5 mg) for the treatment of male pattern baldness in the vertex region of the scalp (types IIIv, IV and V on the Hamilton-Norwood scale). The study has been completed as of January 2009. [3] The future impact that this study will have on the approval or disapproval by the U.S. Food and Drug Administration (FDA) of Avodart for the treatment of male pattern baldness in the United States is yet to be determined.
Dutasteride is also in development for Prostate cancer risk reduction.[4]
The results of the REDUCE trial were presented at the American Urologic Association meeting in 2009 which demonstrated that higher risk patients for prostate cancer with a PSA value of 2.5 to 10 and a prior negative prostate biopsy demonstrated a 23% reduction in the incidence of prostate cancer over a four year period in this population with daily 0.5 mg dutasteride dosage.
Dutasteride is sometimes prescribed off-label to male-to-female transsexual or transgender persons to inhibit the growth of body hair, though more commonly the older drug finasteride is used for this purpose.[citation needed]
[edit] Side effects
Because clinical trials are conducted under widely varying conditions, adverse reaction rates observed in the clinical trials of a drug cannot be directly compared to rates in the clinical trial of another drug and may not reflect the rates observed in practice.
The most common adverse reactions reported in subjects receiving AVODART were impotence, decreased libido, breast disorders (including gynecomastia), and ejaculation disorders. Study withdrawal due to adverse reactions occurred in 4% of subjects receiving AVODART and 3% of subjects receiving placebo. The most common adverse reaction leading to study withdrawal was impotence (1%).[citation needed]
[edit] Teratogenic effect
The teratogenic effect from Dutasteride is a very large risk for male children. The effect would be similar to 5-alpha-reductase deficiency, where a developing male child naturally is deficient in 5-alpha reductase type 2, and thus unable to synthesize DHT Type 2. As Dutasteride blocks the same process (although type 1 and 2 DHT) a developing male would have this deficiency as a result of medication, rather than simply naturally.
Women who are pregnant or in their childbearing years, and children, should be prevented from handling the capsules as inadvertent consumption may cause major birth defects.
[edit] See also
[edit] External links
- Effectiveness of Dutasteride as a treatment for Male Pattern Baldness, as reported by Science Daily.
- Official site
- http://www.hairlosshelp.com/html/Dutasteride_hair_loss_trials.cfm
[edit] References
- ^ Avodart 0.5mg soft capsules, SPC from the eMC
- ^ Olsen EA, Hordinsky M, Whiting D, et al. (Dec 2006). "The importance of dual 5alpha-reductase inhibition in the treatment of male pattern hair loss: results of a randomized placebo-controlled study of dutasteride versus finasteride". J Am Acad Dermatol. 55 (6): 1014–23. doi:. PMID 17110217.
- ^ ClinicalTrials.gov NCT00441116
- ^ Sound bites for NCE Entries into Phase III
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