WARNING: This product is for research use only, not for human or veterinary use.
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.
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
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
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
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.
