Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H27NO3 |
Molecular Weight | 329.4333 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12O[C@]13CC[C@@]4([H])[C@]5([H])CC[C@H](O)[C@@]5(C)CC[C@]4([H])[C@@]3(C)CC(C#N)=C2O
InChI
InChIKey=KVJXBPDAXMEYOA-CXANFOAXSA-N
InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
Trilostane is a synthetic steroid, which interferes with the formation of both cortisol and aldosterone. It is an inhibitor of 3 beta-hydroxysteroid dehydrogenase. This drug under trade name MODRASTANE was withdrawn from human use in the United States market. But marketed under the trade names Modrenal and is already approved in the United Kingdom for the treatment of advanced post-menopausal breast cancer and Cushing 's disease. In addition, this drug has been successfully developed and marketed for veterinary use in the United Kingdom under the trade name Vetoryl.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6589100 |
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Target ID: CHEMBL1958 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6589100 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | modrenal Approved UseUnknown |
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Primary | VETORYL Approved UseUnknown |
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Primary | modrenal Approved UseUnknown |
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Primary | modrenal Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis. | 1978 Nov |
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Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro. | 1983 Jun |
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Evidence that the preovulatory rise in intrafollicular progesterone may not be required for ovulation in cattle. | 2007 Mar |
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Effects of a 3beta-hydroxysteroid dehydrogenase inhibitor, trilostane, on the fathead minnow reproductive axis. | 2008 Jul |
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Cushing's disease in dogs and humans. | 2009 Jan |
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The 3beta-hydroxysteroid dehydrogenase inhibitor trilostane shows antidepressant properties in mice. | 2009 Jun |
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Decreased cytochrome c oxidase IV expression reduces steroidogenesis. | 2011 Aug |
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The antidepressant-like effect of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane involves a regulation of β-type estrogen receptors. | 2011 Mar |
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Expression of LH receptor in nonpregnant mouse endometrium: LH induction of 3β-HSD and de novo synthesis of progesterone. | 2012 Oct |
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Effects of fibroblast growth factor 9 (FGF9) on steroidogenesis and gene expression and control of FGF9 mRNA in bovine granulosa cells. | 2012 Sep |
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Temporal changes in biological responses and uncertainty in assessing risks of endocrine-disrupting chemicals: insights from intensive time-course studies with fish. | 2015 Apr |
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17β-trenbolone, an anabolic-androgenic steroid as well as an environmental hormone, contributes to neurodegeneration. | 2015 Jan 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17109615
for human: in postmenopausal cancer at a dose of 720 – 960 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2824205
Curator's Comment: Trilostane may have on cellular cultures of human mammary carcinoma (MCF-7 Evsa-T). Trilostane does not react with any of the main hormonal sex steroid receptors, nor does it interfere with cultures of human mammary cancer cells either containing estrogen receptors and therefore allegedly hormone-dependent (MCF-7 line), or estrogen receptor-negative cells, presumably independent of hormonal manipulations (Evsa-T cell line).
Unknown
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 520.2598
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NCI_THESAURUS |
C2355
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C2184
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H02CA01
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QH02CA01
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C2017
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758904
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SUB11297MIG
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6850
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CHEMBL1200907
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L0FPV48Q5R
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38668
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13647-35-3
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C1263
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DB01108
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TRILOSTANE
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237-133-0
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C009954
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3928
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ACTIVE MOIETY