Dutasteride
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MedKoo CAT#: 206219

CAS#: 164656-23-9

Description: Dutasteride (marketed as Avodart, Avidart, Avolve, Duagen, Dutas, Dutagen, Duprost) is a 5-alpha-reductase inhibitor that inhibits the conversion of testosterone into dihydrotestosterone (DHT). It is approved for the treatment of benign prostatic hyperplasia (BPH) and is prescibed off-label for the treatment of male pattern baldness (MPB). Avodart is manufactured and marketed by GlaxoSmithKline.


Chemical Structure

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Dutasteride
CAS# 164656-23-9

Theoretical Analysis

MedKoo Cat#: 206219
Name: Dutasteride
CAS#: 164656-23-9
Chemical Formula: C27H30F6N2O2
Exact Mass: 528.22115
Molecular Weight: 528.53
Elemental Analysis: C, 61.36; H, 5.72; F, 21.57; N, 5.30; O, 6.05

Price and Availability

Size Price Availability Quantity
200.0mg USD 90.0 Same day
500.0mg USD 150.0 Same day
1.0g USD 250.0 Same day
2.0g USD 450.0 Same day
5.0g USD 850.0 Same day
10.0g USD 1450.0 Same day
20.0g USD 1950.0 Same day
50.0g USD 2750.0 Same day
500.0g USD 8450.0 2 weeks
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Synonym: LS-173584; LS 173584; LS173584; Dutasteride; Brand name: Avodart; Avidart; Avolve; Duagen; Dutas; Dutagen; Duprost.

IUPAC/Chemical Name: (4aR,6aS,7S,9aS,9bS,11aR)-N-(2,5-bis(trifluoromethyl)phenyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide

InChi Key: JWJOTENAMICLJG-VYZSUTEISA-N

InChi Code: 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

SMILES Code: C[C@]12CCC3[C@@H](CC[C@@H]4[C@]3(C)C=CC(N4)=O)[C@@H]1CC[C@@H]2C(NC(C=C(C=C5)C(F)(F)F)=C5C(F)(F)F)=O

Appearance: white to pale yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Biological target: Dutasteride (GI198745, GG-745) is a dual 5-α reductase inhibitor that inhibits conversion of testosterone to dihydrotestosterone (DHT).
In vitro activity: The aim of this study is to investigate the cellular and molecular effects of dutasteride, a potent inhibitor of 5alpha-reductase type I and type II, in androgen-responsive (LNCaP) and androgen-unresponsive (DU145) human prostate cancer(PCa) cell lines. The expression pattern of 190 genes, selected on the basis of their proved or potential role in prostate cancerogenesis related to androgen signalling, were analysed using a low density home-made oligoarray (AndroChip 2). These results show that dutasteride reduces cell viability and cell proliferation in both cell lines tested. AndroChip 2 gene signature identified in LNCaP a total of 11 genes differentially expressed (FC >or= +/-1.5). Eight of these genes, were overexpressed and three were underexpressed. Overexpressed genes included genes encoding for proteins involved in biosynthesis and metabolism of androgen (HSD17B1;HSD17B3;CYP11B2), androgen receptor and androgen receptor co-regulators (AR;CCND1), and signal transduction(ERBB2; V-CAM; SOS1) whereas, underexpressed genes (KLK3; KLK2; DHCR24) were androgen-regulated genes (ARGs). No differentially expressed genes were scored in DU145. Microarray data were confirmed by quantitative real-time PCR assay (QRT-PCR). These data offer a selective genomic signature for dutasteride treatment in prostate epithelial cells and provide important insights in prostate cancer pathophysiology. Reference: Invest New Drugs. 2007 Oct;25(5):491-7. https://doi.org/10.1007/s10637-007-9070-7
In vivo activity: This research addressed the question of whether or not dutasteride, a pharmaceutical used to treat benign prostatic hyperplasia, may cause adverse effects in a teleost fish, the fathead minnow (Pimephales promelas), by inhibiting the activity of both isoforms of 5α-reductase (5αR), the enzyme that converts testosterone into dihydrotestosterone (DHT). Mammalian pharmacological and toxicological information were used to guide the experimental design and the selection of relevant endpoints, according to the so-called "read-across approach", suggesting that 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. However, none of the observed adverse effects occurred at concentrations of exposure lower than 32 μg/L; this, together with the low volume of drug prescribed every year (10.34 kg in the UK in 2011), and the extremely low predicted environmental concentration (0.03 ng/L), suggest that, at present, the potential presence of dutasteride in the environment does not represent a threat to wild fish populations. Reference: Aquat Toxicol. 2013 Mar 15;128-129:113-23. https://linkinghub.elsevier.com/retrieve/pii/S0166-445X(12)00322-0

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 33.33 63.06
Ethanol 25.0 47.3

Preparing Stock Solutions

The following data is based on the product molecular weight 528.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
In vitro protocol: 1. Biancolella M, Valentini A, Minella D, Vecchione L, D'Amico F, Chillemi G, Gravina P, Bueno S, Prosperini G, Desideri A, Federici G, Bernardini S, Novelli G. Effects of dutasteride on the expression of genes related to androgen metabolism and related pathway in human prostate cancer cell lines. Invest New Drugs. 2007 Oct;25(5):491-7. doi: 10.1007/s10637-007-9070-7. Epub 2007 Jul 18. PMID: 17636412.
In vivo protocol: 1. Margiotta-Casaluci L, Hannah RE, Sumpter JP. Mode of action of human pharmaceuticals in fish: the effects of the 5-alpha-reductase inhibitor, dutasteride, on reproduction as a case study. Aquat Toxicol. 2013 Mar 15;128-129:113-23. doi: 10.1016/j.aquatox.2012.12.003. Epub 2012 Dec 10. PMID: 23280489. 2. Gul A, Gul M, Ozsoy S, Sarac T, Celik DS, Semercioz A, Serefoglu EC. Impact of dutasteride on spermatogenesis and oxidative status in rats. Arch Esp Urol. 2020 Apr;73(3):230-235. English, Spanish. PMID: 32240114.

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1: Gupta AK, Charrette A. The efficacy and safety of 5α-reductase inhibitors in androgenetic alopecia: a network meta-analysis and benefit-risk assessment of finasteride and dutasteride. J Dermatolog Treat. 2014 Apr;25(2):156-61. doi: 10.3109/09546634.2013.813011. Epub 2013 Jul 5. Review. PubMed PMID: 23768246.

2: Wu C, Kapoor A. Dutasteride for the treatment of benign prostatic hyperplasia. Expert Opin Pharmacother. 2013 Jul;14(10):1399-408. doi: 10.1517/14656566.2013.797965. Review. PubMed PMID: 23750593.

3: Keating GM. Dutasteride/tamsulosin: in benign prostatic hyperplasia. Drugs Aging. 2012 May 1;29(5):405-19. doi: 10.2165/11208920-000000000-00000. Review. PubMed PMID: 22550968.

4: Slater S, Dumas C, Bubley G. Dutasteride for the treatment of prostate-related conditions. Expert Opin Drug Saf. 2012 Mar;11(2):325-30. doi: 10.1517/14740338.2012.658040. Epub 2012 Feb 8. Review. PubMed PMID: 22316171.

5: Rove KO, Crawford ED. Dutasteride: novel milestones in prostate cancer chemoprevention. Drugs Today (Barc). 2011 Feb;47(2):135-44. doi: 10.1358/dot.2011.47.2.1561069. Review. PubMed PMID: 21431101.

6: Chen HJ, Chen YR. [Dutasteride in the treatment of benign prostatic hyperplasia: an update]. Zhonghua Nan Ke Xue. 2011 Jan;17(1):63-7. Review. Chinese. PubMed PMID: 21351536.

7: van Leeuwen PJ, Kölble K, Huland H, Hambrock T, Barentsz J, Schröder FH. Prostate cancer detection and dutasteride: utility and limitations of prostate-specific antigen in men with previous negative biopsies. Eur Urol. 2011 Feb;59(2):183-90. doi: 10.1016/j.eururo.2010.09.035. Epub 2010 Dec 4. Review. PubMed PMID: 21130560.

8: Djavan B, Handl MJ, Dianat S. Combined medical treatment using dutasteride and tamsulosin for lower urinary tract symptoms suggestive of benign prostatic hyperplasia. Expert Opin Pharmacother. 2010 Oct;11(15):2535-47. doi: 10.1517/14656566.2010.516901. Review. PubMed PMID: 20854184.

9: Miller J, Tarter TH. Combination therapy with dutasteride and tamsulosin for the treatment of symptomatic enlarged prostate. Clin Interv Aging. 2009;4:251-8. Epub 2009 Jun 9. Review. PubMed PMID: 19554096; PubMed Central PMCID: PMC2697590.

10: Dutasteride (Avodart) with tamsulosin (Flomax) for benign prostatic hyperplasia. Med Lett Drugs Ther. 2008 Oct 6;50(1296):79-80. Review. PubMed PMID: 18833033.



Additional Information

 
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, which is also approved for BPH, but also the treatment of hair loss, belongs to this group of drugs. Dutasteride inhibits both isoforms of 5-alpha reductase, Type I and Type II, while finasteride only inhibits Type II. A clinical study done by GlaxoSmithKline, the EPICS trial, did not find dutasteride to be more effective than finasteride in treating BPH.   AVODART is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5α-reductase, an intracellular enzyme that converts testosterone to DHT. Dutasteride is chemically designated as (5α,17β)-N-{2,5 bis(trifluoromethyl)phenyl}-3oxo-4-azaandrost-1-ene-17-carboxamide. The empirical formula of dutasteride is C27H30F6N2O2, representing a molecular weight of 528.5. Dutasteride is a white to pale yellow powder with a melting point of 242° to 250°C. It is soluble in ethanol (44 mg/mL), methanol (64 mg/mL), and polyethylene glycol 400 (3 mg/mL), but it is insoluble in water. Each AVODART Soft Gelatin Capsule, administered orally, contains 0.5 mg of dutasteride dissolved in a mixture of mono-di-glycerides of caprylic/capric acid and butylated hydroxytoluene. The inactive excipients in the capsule shell are gelatin (from certified BSE-free bovine sources), glycerin, and ferric oxide (yellow). The soft gelatin capsules are printed with edible red ink. Mechanism of Action: Dutasteride inhibits the conversion of testosterone to dihydrotestosterone (DHT). DHT is the androgen primarily responsible for the initial development and subsequent enlargement of the prostate gland. Testosterone is converted to DHT by the enzyme 5α-reductase, which exists as 2 isoforms, type 1 and type 2. The type 2 isoenzyme is primarily active in the reproductive tissues, while the type 1 isoenzyme is also responsible for testosterone conversion in the skin and liver. Dutasteride is a competitive and specific inhibitor of both type 1 and type 2 5α-reductase isoenzymes, with which it forms a stable enzyme complex. Dissociation from this complex has been evaluated under in vitro and in vivo conditions and is extremely slow. Dutasteride does not bind to the human androgen receptor