R787 4-Aza-5alpha-androstan-1-ene-3-one-17beta-carboxylic acid - AK Scientific
 
 
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  Catalog ID # R787
4-Aza-5alpha-androstan-1-ene-3-one-17beta-carboxylic acid
, 98% (HPLC)
 



IDENTITY
CAS Registry #:[104239-97-6]
MDL Number:MFCD08063794
MF:C19H27NO3
MW:317.426
SPECIFICATIONS & PROPERTIES
Purity:98% (HPLC)
Available Spectra:LCMS, HPLC
Physical Form:Off-white to yellow-brown powder
Melting Point:>250?C
Shipping:Normal Temperature

REVIEW

 4-Aza-5alpha-androstan-1-ene-3-one-17beta-carboxylic acid or Dutasteride (trademark name Avodart, manufactured by GlaxoSmithKline) is a dual (type 1 and 2) 5-alpha reductase inhibitor that inhibits conversion of testosterone to dihydrotestosterone (DHT). It is used for benign prostatic hyperplasia and its chemopreventation, however increases the risk of erectile dysfunction and decrease sexual desire.

REFERENCES
[1]Zhao, Shuang; Bioorganic & Medicinal Chemistry Letters 2011, V21(11), P3439-3442
[2] Satyanarayana, Komati; Organic Process Research & Development 2007, V11(5), P842-845
[3] Zhang, Kui-Ping; Journal of Chinese Pharmaceutical Sciences 2007, V16(3), P233-235
[4] Rasmusson, Gary H.; Reynolds, Glenn F.; Steinberg, Nathan G.; Walton, Edward; Patel, Gool F.; Liang, Tehming; Cascieri, Margaret A.; Cheung, Anne H.; Brooks, Jerry R.; Berman, Charles; Azasteroids: structure-activity relationships for inhibition of 5alpha-reductase and of androgen receptor binding. Journal of Medicinal Chemistry (1986), 29(11), 2298-315.
[5] Carlin, Josephine R.; Rasmusson, Gary H.; Vandenheuvel, W. J. A. Preparation of antiandrogenic, oxidized analogs of 17beta-(N-monosubstituted carbamoyl)-4-aza-5lpha-androstan-3-ones Eur. Pat. Appl. (1988), EP 271220 A1 19880615.
[6] Panzeri, Achille; Di Salle, Enrico; Nesi, Marcella; Preparation of 17beta-carbamoyl-4-azaandrostan-3-ones as testosterone 5alpha-reductase inhibitors. PCT Int. Appl. (1991), WO 9112261 A1 19910822.
[7] Tolman, Richard L.; Sahoo, Soumya P.; Bakshi, Raman K.; Gratale, Dominick; Patel, Gool; Patel, Sushma; Toney, Jeffrey; Chang, Benedict; Harris, Georgianna S. 4-Methyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-N-aryl-carboxamides: an approach to combined androgen blockade [5alpha-reductase inhibition with androgen receptor binding in vitro] Journal of Steroid Biochemistry and Molecular Biology (1997), 60(5/6), 303-309.
[8] Satyanarayana, Komati; Srinivas, Katkam; Himabindu, Vurimidi; Reddy, Ghanta Mahesh, A Scalable Synthesis of Dutasteride: A Selective 5?-Reductase Inhibitor Organic Process Research & Development (2007), 11(5), 842-845.
[9] Evans HC, Goa KL.Dutasteride. Drugs Aging. 2003;20(12):905-16.
[10] Dolder CR. Dutasteride: a dual 5-alpha reductase inhibitor for the treatment of symptomatic benign prostatic hyperplasia. Ann Pharmacother. 2006 Apr;40(4):658-65.
[11] Brown CT, Nuttall MC. Dutasteride: a new 5-alpha reductase inhibitor for men with lower urinary tract symptoms secondary to benign prostatic hyperplasia. Int J Clin Pract. 2003 Oct;57(8):705-9.
[12] Djavan B, Milani S, Fong YK. Dutasteride: a novel dual inhibitor of 5alpha-reductase for benign prostatic hyperplasia. Expert Opin Pharmacother. 2005 Feb;6(2):311-7+Keam SJ, Scott LJ. Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85.
[13] Rove KO, Crawford ED, Dutasteride: novel milestones in prostate cancer chemoprevention. Drugs Today (Barc). 2011 Feb;47(2):135-44.
[14] Gur S, Kadowitz PJ, Hellstrom WJ. Effects of 5-alpha reductase inhibitors on erectile function, sexual desire and ejaculation. Expert Opin Drug Saf. 2013 Jan;12(1):81-90.
[15] Traish AM, Hassani J, Guay AT, Zitzmann M, Hansen ML. Adverse side effects of 5alpha-reductase inhibitors therapy: persistent diminished libido and erectile dysfunction and depression in a subset of patients. J Sex Med. 2011 Mar;8(3):872-84.

Risk Description(s)
R36/37/38:Irritating to eyes, respiratory system and skin

Safety Description(s)
S24/25:Avoid contact with skin and eyes.


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CATEGORIES

 APIs and Bioactives > Antiandrogens, Steroid Hormones

USEFUL LINKS

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