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MedKoo product information:

Trilostane

MedKoo Code#: 203020

Name: Trilostane

CAS#: 13647-35-3

 

Synonym:   WIN 24,540. Trilostane;Modrenal;Desopan;Modrenal;DB01108;D01180. (4α,5α,17β)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile. US brand name: Modrastane. Foreign brand names: Desopan; Modrenal. Code names: WIN 24,540; WIN 24540.  Chemical structure names: * (4Alpha,5alpha,17beta)-4,5-epoxy-3,17-dihydroxyandrost-2-ene-2-carbonitrile; * 2Alpha-cyano-4alpha,5alpha-epoxyandrostan-17beta-ol-3-one; * 4,5-Epoxy-17-hydroxy-3-oxoandrostane-2-carbonitrile

 

IUPAC/Chemical name: 

(1aR,4aR,4bS,6aS,7S,9aS,9bS,11aS)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile.

 

Chemical structure: Theoretical analysis

 

 

 

Chemical Formula: C20H27NO3

Exact Mass: 329.19909

Molecular Weight: 329.43

 

m/z: 329.19909 (100.0%), 330.20245 (21.6%), 331.20580 (2.2%)

 

Elemental Analysis: C, 72.92; H, 8.26; N, 4.25; O, 14.57

Availability and price:

This agent is not in stock, which may be available through custom synthesis. To inquire quotation and lead time or to ask questions, please send email to sales@medkoo.com to describe your needs. A representative will respond your email shortly. We offer big discount for orders of bulk quantities.

 

Quality control data:

Product will be shipped with supporting analytical data.

 

 

Information about this agent

According to wikipedia.com, Trilostane is an inhibitor of 3 β-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome. It is perhaps best known under the trade name Vetoryl. It was withdrawn from the United States market in April 1994. However, it was recently approved in 2008 for the treatment of Cushing's disease (hyperandrenocorticism) in dogs. It is also the first drug approved to treat both pituitary- and adrenal-dependent Cushing's in dogs. This prescription drug works by stopping the production of cortisol in the adrenal glands. In studies of the drug, the most common side effects were vomiting, lack of energy, diarrhea, and weight loss.  The safety and effectiveness of trilostane were shown in several studies. Success was measured by improvements in both blood test results and physical symptoms (increased appetite and activity level, and decreased panting, thirst and urination). Only one other drug, Anipryl (selegiline), is FDA-approved to treat Cushing's disease in dogs, but only to treat uncomplicated, pituitary-dependent Cushing's.

 

Current developer:   Stegram Pharmaceuticals Inc

 

References

 

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2: Igaz P, Tömböl Z, Szabó PM, Likó I, Rácz K. Steroid biosynthesis inhibitors in the therapy of hypercortisolism: theory and practice. Curr Med Chem. 2008;15(26):2734-47. Review. PubMed PMID: 18991633.

3: Thomas JL, Bucholtz KM, Sun J, Mack VL, Kacsoh B. Structural basis for the selective inhibition of human 3beta-hydroxysteroid dehydrogenase 1 in human breast tumor MCF-7 cells. Mol Cell Endocrinol. 2009 Mar 25;301(1-2):174-82. Epub 2008 Oct 8. PubMed PMID: 18955108; PubMed Central PMCID: PMC2667100.

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5: Thomas JL, Mack VL, Glow JA, Moshkelani D, Terrell JR, Bucholtz KM. Structure/function of the inhibition of human 3beta-hydroxysteroid dehydrogenase type 1 and type 2 by trilostane. J Steroid Biochem Mol Biol. 2008 Jul;111(1-2):66-73. Epub 2008 May 3. PubMed PMID: 18524572; PubMed Central PMCID: PMC2580795.

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15: Eastwood JM, Elwood CM, Hurley KJ. Trilostane treatment of a dog with functional adrenocortical neoplasia. J Small Anim Pract. 2003 Mar;44(3):126-31. PubMed PMID: 12653328.

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21: Ishido H, Yamashita N, Kitaoka M, Tanaka Y, Ogata E. A case of ectopic ACTH syndrome associated with Zollinger-Ellison syndrome: long-term survival with chemical adrenalectomy. Endocr J. 1994 Apr;41(2):171-6. PubMed PMID: 7951565.

22: Saito J, Nishikawa T. [Clinical usefulness of pharmacological treatment of Cushing's syndrome]. Nippon Rinsho. 1994 Mar;52(3):793-6. Review. Japanese. PubMed PMID: 8164384.

23: Murray R, Pitt P. Treatment of advanced breast cancer with formestane. Ann Oncol. 1994;5 Suppl 7:S11-3. PubMed PMID: 7873455.

24: Williams CJ, Barley VL, Blackledge GR, Rowland CG, Tyrrell CJ. Multicentre cross over study of aminoglutethimide and trilostane in advanced postmenopausal breast cancer. Br J Cancer. 1993 Dec;68(6):1210-5. PubMed PMID: 8260375; PubMed Central PMCID: PMC1968660.

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28: Takahashi M, Luu-The V, Labrie F. Inhibitory effect of synthetic progestins, 4-MA and cyanoketone on human placental 3 beta-hydroxysteroid dehydrogenase/5----4-ene-isomerase activity. J Steroid Biochem Mol Biol. 1990 Oct;37(2):231-6. PubMed PMID: 2268554.

29: Nakada T, Koike H, Katayama T. Uneventful delivery following series of successive treatments for virilized Cushing syndrome due to adrenocortical carcinoma. Urology. 1990 Oct;36(4):359-63. PubMed PMID: 2219621.

30: Ingle JN, Krook JE, Schaid DJ, Everson LK, Mailliard JA, Long HJ, McCormack GW. Evaluation of trilostane plus hydrocortisone in women with metastatic breast cancer and prior hormonal therapy exposure. Am J Clin Oncol. 1990 Apr;13(2):93-7. PubMed PMID: 2316487.

31: Nakada T, Furuta H, Katayama T, Sumiya H, Shimazaki J. The effect of adrenal surgery on plasma atrial natriuretic factor and sodium escape phenomenon in patients with primary aldosteronism. J Urol. 1989 Jul;142(1):13-8. PubMed PMID: 2525199.

32: Menashe Y, Shalev J, Serr DM. [RU-486: clinical application in gynecology]. Harefuah. 1989 May 10;116(10):532-5. Review. Hebrew. PubMed PMID: 2676767.

33: Chu PS, Buzdar AU, Hortobagyi GN. Trilostane with hydrocortisone in treatment of metastatic breast cancer. Breast Cancer Res Treat. 1989 Mar;13(2):117-21. PubMed PMID: 2659103.

34: Stimpel M, Ivens K, Volkmann HP, Wambach G, Kaufmann W. Therapeutic value of calcium antagonists in autonomous hyperaldosteronism. Klin Wochenschr. 1989 Feb 15;67(4):248-52. PubMed PMID: 2648061.

35: Iino Y, Izuo M, Takikawa H. Effects of trilostane on 7,12-dimethylbenz[a]anthracene-induced rat mammary cancers and body weight of rats in relation to estrogen receptors. Oncology. 1989;46(5):301-5. PubMed PMID: 2506498.

36: Williams CJ, Barley V, Blackledge G, Hutcheon A, Kaye S, Smith D, Keen C, Webster DJ, Rowland C, Tyrrell C. Multicenter study of trilostane: a new hormonal agent in advanced postmenopausal breast cancer. Cancer Treat Rep. 1987 Dec;71(12):1197-201. PubMed PMID: 3690530.

37: Tueni E, Devleeschouwer N, Leclercq G, Nijs M, Coune A, Vermeulen A, Paridaens R. Endocrine effects of Trilostane: in vitro and in vivo studies. Eur J Cancer Clin Oncol. 1987 Oct;23(10):1461-7. PubMed PMID: 2824205.

38: Nakada T, Koike H, Katayama T. Evidence for a defect in urinary concentrating ability in primary aldosteronism and its reversal by adrenal surgery. Urol Int. 1987;42(4):295-301. PubMed PMID: 3672660.

39: Wilkinson JR, Williams JC, Singh D, Goss PE, Easton D, Coombes RC. Response of nitrosomethylurea-induced rat mammary tumor to endocrine therapy and comparison with clinical response. Cancer Res. 1986 Sep;46(9):4862-5. PubMed PMID: 3731133.

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41: Adams EF, Ashby MJ, Burrin J, Yeo TH, Drucker R, Stringer K, Mashiter K. Effect of nivazol on ACTH secretion by human pituitary corticotrophic tumours in cell culture. Clin Endocrinol (Oxf). 1985 May;22(5):631-8. PubMed PMID: 2992847.

42: Coombes RC, Powles TJ, Muindi J, Hunt J, Ward M, Perez D, Neville AM. Trilostane therapy for advanced breast cancer. Cancer Treat Rep. 1985 Apr;69(4):351-4. PubMed PMID: 3995507.

43: Nakada T, Kazama T, Koike H, Yoshikawa M, Ishikawa S, Katayama T. Primary aldosteronism treated by trilostane (3 beta-hydroxysteroid dehydrogenase inhibitor). Urology. 1985 Feb;25(2):207-14. PubMed PMID: 2982227.

44: Winterberg B, Vetter W, Groth H, Greminger P, Vetter H. Primary aldosteronism: treatment with trilostane. Cardiology. 1985;72 Suppl 1:117-21. PubMed PMID: 3863713.

45: Nakada T, Kimura M. Primary aldosteronism associated with chronic renal failure. Report of a case. Int Urol Nephrol. 1984;16(2):165-73. PubMed PMID: 6469482.

46: Carlström K, Döberl A, Pousette A, Rannevik G, Wilking N. Inhibition of steroid sulfatase activity by danazol. Acta Obstet Gynecol Scand Suppl. 1984;123:107-11. PubMed PMID: 6238495.

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48: Dewis P, Anderson DC, Bu'lock DE, Earnshaw R, Kelly WF. Experience with trilostane in the treatment of Cushing's syndrome. Clin Endocrinol (Oxf). 1983 Jun;18(6):533-40. PubMed PMID: 6883729.

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