Dutasteride5-alpha-reductase inhibitor CAS# 164656-23-9 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 164656-23-9 | SDF | Download SDF |
| PubChem ID | 152945 | Appearance | Powder |
| Formula | C27H30F6N2O2 | M.Wt | 528.53 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Avodart;GG 745;GG-745;GG745;GI198745 | ||
| Solubility | Soluble in DMSO > 10 mM | ||
| Chemical Name | (1S,3aS,3bS,5aR,9aR,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide | ||
| SMILES | CC12CCC3C(C1CCC2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CCC5C3(C=CC(=O)N5)C | ||
| Standard InChIKey | JWJOTENAMICLJG-VYZSUTEISA-N | ||
| Standard InChI | InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17?,19+,21+,24-,25+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Dutasteride (GG745) is a potent inhibitor of both 5 alpha-reductase isozymes. Dutasteride may possess off-target effects on the androgen receptor (AR) due to its structural similarity to DHT. IC50 Value: Target: 5 alpha-reductase in vitro: Dutasteride inhibited (3)H-T conversion to (3)H-DHT and, as anticipated, inhibited T-induced secretion of PSA and proliferation. However the drug also inhibited DHT-induced PSA secretion and cell proliferation (IC(50) approximately 1 microM). Dutasteride competed for binding the LNCaP cell AR with an IC(50) approximately 1.5 microM. High concentrations of dutasteride (10-50 microM), but not finasteride, in steroid-free medium, resulted in enhanced cell death, possibly by apoptosis. Dutasteride reduces cell viability and cell proliferation in both cell lines tested (androgen-responsive (LNCaP) and androgen-unresponsive (DU145) human prostate cancer (PCa)) . in vivo: GG745 has a terminal half-life of approximately 240 hr, and single doses of >10 mg decreased DHT levels significantly more than did single 5-mg doses of finasteride. In placebo treated men without prostate cancer there was an 8.3% median increase in PSA at month 24 compared with -59.5% in those who received dutasteride, using doubled values to correct for dutasteride treatment. Toxicity: Dutasteride may affect male fertility and steroid hormone dynamics. Therefore, a 21-day reproduction study was conducted to determine the effects of dutasteride (10, 32 and 100 μg/L) on fish reproduction. Exposure to dutasteride significantly reduced fecundity of fish and affected several aspects of reproductive endocrine functions in both males and females | |||||
Dutasteride Dilution Calculator
Dutasteride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.892 mL | 9.4602 mL | 18.9204 mL | 37.8408 mL | 47.301 mL |
| 5 mM | 0.3784 mL | 1.892 mL | 3.7841 mL | 7.5682 mL | 9.4602 mL |
| 10 mM | 0.1892 mL | 0.946 mL | 1.892 mL | 3.7841 mL | 4.7301 mL |
| 50 mM | 0.0378 mL | 0.1892 mL | 0.3784 mL | 0.7568 mL | 0.946 mL |
| 100 mM | 0.0189 mL | 0.0946 mL | 0.1892 mL | 0.3784 mL | 0.473 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Dutasteride (Avodart) is an inhibitor of dual 5-alpha-reductase for treating benign prostatic hyperplasia (BPH).
Dutasteride has been reported to inhibit conversion of 3H-testosterone to 3H-DHT by more than 99% in LNCaP cells. Dutasteride strongly reduces growth, proliferation, and viability of LNCaP cells as well. Dutasteride increased the enzymatic activities of caspase 7 and caspase 8 dose-dependently at 48 hours, providing functional significance and confirming that the apoptotic and survival pathways are being activated by dutasteride treatment in LNCaP cells [1].
In vivo, dutasteride, which inhibits both 5αR1/5αR2, is efficacious in blocking prostate cancer development or progression in C57BL/6 TRAMP x FVB mice [2].
References:
[1] Schmidt LJ1, Murillo H, Tindall DJ. Gene expression in prostate cancer cells treated with the dual 5 alpha-reductase inhibitor dutasteride. J Androl. 2004 Nov-Dec;25(6):944-53.
[2] Opoku-Acheampong AB1, Unis D, Henningson JN, Beck AP, Lindshield BL.Preventive and therapeutic efficacy of finasteride and dutasteride in TRAMP mice. PLoS One. 2013 Oct 18;8(10):e77738. doi: 10.1371/journal.pone.0077738. eCollection 2013.
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Persistent erectile dysfunction in men exposed to the 5alpha-reductase inhibitors, finasteride, or dutasteride.[Pubmed:28289563]
PeerJ. 2017 Mar 9;5:e3020.
IMPORTANCE: Case reports describe persistent erectile dysfunction (PED) associated with exposure to 5alpha-reductase inhibitors (5alpha-RIs). Clinical trial reports and the manufacturers' full prescribing information (FPI) for finasteride and Dutasteride state that risk of sexual adverse effects is not increased by longer duration of 5alpha-RI exposure and that sexual adverse effects of 5alpha-RIs resolve in men who discontinue exposure. OBJECTIVE: Our chief objective was to assess whether longer duration of 5alpha-RI exposure increases risk of PED, independent of age and other known risk factors. Men with shorter 5alpha-RI exposure served as a comparison control group for those with longer exposure. DESIGN: We used a single-group study design and classification tree analysis (CTA) to model PED (lasting >/=90 days after stopping 5alpha-RI). Covariates included subject attributes, diseases, and drug exposures associated with sexual dysfunction. SETTING: Our data source was the electronic medical record data repository for Northwestern Medicine. SUBJECTS: The analysis cohorts comprised all men exposed to finasteride or Dutasteride or combination products containing one of these drugs, and the subgroup of men 16-42 years old and exposed to finasteride 208.5 days of 5alpha-RI exposure had 4.8-fold higher risk of PED than men with shorter exposure (NNH 59.8, all p < 0.002). Among men 16-42 years old and exposed to finasteride 205 days of finasteride exposure had 4.9-fold higher risk of PED (NNH 108.2, p < 0.004) than men with shorter exposure. CONCLUSION AND RELEVANCE: Risk of PED was higher in men with longer exposure to 5alpha-RIs. Among young men, longer exposure to finasteride posed a greater risk of PED than all other assessed risk factors.
Dutasteride in Androgenetic Alopecia: An Update.[Pubmed:28294070]
Curr Clin Pharmacol. 2017;12(1):31-35.
BACKGROUND: Androgenetic alopecia is a common condition characterized by thinning of scalp hair. Conversion of testosterone to dihydrotestosterone, a more potent androgen, by the enzyme 5-alpha-reductase is responsible for underlying pathogenesis. Dutasteride, a synthetic 4-azasteroid, is a selective and competitive inhibitor of both type-1 and type-2 isoenzymes of 5-alpha-reductase. Finasteride and minoxidil are the only approved drugs for androgenetic alopecia. Dutasteride has been demonstrated to be effective in several randomized, double-blind, placebo controlled trials in androgenetic alopecia. In this review, after the pharmacology of Dutasteride, the authors have discussed the status of Dutasteride in androgenetic alopecia and have compared its efficacy with that of finasteride. OBJECTIVE: This article aims to review the current status of Dutasteride in androgenetic alopecia. The structure, mechanism of action, pharmacokinetics and side effects are discussed along with its comparison with finasteride in androgenetic alopecia. METHOD: The main sources of our information were Medline Pubmed, Google scholar and Scopus including original articles and review articles. The keywords 'Dutasteride', 'Dutasteride in androgenetic alopecia' were used for search. CONCLUSION: Like finasteride, Dutasteride is now becoming popular treatment option in AGA, due to its good response shown by various randomized control studies and meta-analysis. Also, in most of these studies, Dutasteride was found to be better than finasteride with comparable adverse effects. Therefore, Dutasteride could become a treatment of choice for AGA in near future.
Dutasteride add-on therapy reduces detrusor mass in patients with benign prostatic enlargement not satisfied with alpha-adrenergic antagonist monotherapy: A single center prospective study.[Pubmed:28257560]
Neurourol Urodyn. 2017 Nov;36(8):2096-2100.
AIMS: The ultrasound assessment of bladder wall thickness (BWT) and intravesical prostatic protrusion (IPP) have emerged as a non-invasive, inexpensive, time-saving alternatives to pressure-flow studies to assess benign prostatic obstruction (BPO). Aim of our study was to evaluate the effect on detrusor mass of Dutasteride add-on therapy in men with lower urinary tract symptoms (LUTS) and benign prostatic enlargement (BPE). METHODS: A consecutive series of BPE patients with a prostate volume (PV) >/=30 mL and an international prostate symptoms score (IPSS) >/=8 not satisfied with Tamsulosin monotherapy were enrolled. Free maximum flow (Qmax), PV, BWT, and IPP were recorded at baseline and at 24 weeks follow-up. RESULTS: Overall, 27 men were enrolled. Dutasteride significantly improved LUTS (-46.7%; P = 0.001) and Qmax (+18.7%; P = 0.001) and reduced PV (-13%; P = 0.002), BWT (-40.3%; P = 0.001), and IPP (-14.9%; P = 0.015). At baseline, based on BWT >/=5 mm and an IPP >10 mm, 13/27 (48%) and 15/27 (55%) patients were defined at risk for BPO, respectively; while after 24 weeks of treatment they were 3/27 (11.1%) and 11/27 (40%), respectively. CONCLUSIONS: Dutasteride add-on therapy significantly reduced IPP and detrusor mass and was effective in improving LUTS in patients with BPE not satisfied with alphaBs monotherapy. The possible role of BWT and IPP as proxies of medical treatment outcomes should be confirmed by further studies.
