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SML0141

Sigma-Aldrich

Trilostane

≥98% (HPLC)

Synonym(s):

(4α,5α,17β)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile

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About This Item

Empirical Formula (Hill Notation):
C20H27NO3
CAS Number:
13647-35-3
Molecular Weight:
329.43
EC Number:
237-133-0
MDL number:
MFCD00199295
UNSPSC Code:
51111800
PubChem Substance ID:
329825189
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥17 mg/mL

storage temp.

2-8°C

SMILES string

C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O)=C(C[C@]35C)C#N)[C@@H]1CC[C@@H]2O

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

InChI key

KVJXBPDAXMEYOA-CXANFOAXSA-N

Gene Information

human ... HSD3B2(3284)

General description

Trilostane inhibits the production of adrenal steroids, such as cortisol and aldosterone. It is used to treat aldosteronism.

Application

Trilostane has been used to evaluate its capability to regulate the sex-dependent differences in the lipopolysaccharide (LPS)-induced inflammatory responses of astrocytes.
Trilostane was used to inhibit the activity of 3β-hydroxysteroid dehydrogenase in mouse ovary.

Biochem/physiol Actions

Trilostane is an inhibitor of 3 β-hydroxysteroid dehydrogenase (3-β-HSD or delta 5-delta 4-isomerase), an essential enzyme for the biosynthesis of all classes of hormonal steroids. It has been used in the treatment of Cushing′s syndrome for stopping the production of cortisol, and is currently approved for dogs in the US, but is still a human drug in the UK and other countries. It is being investigated as a possible treatment for both breast cancer and prostate cancer to prevent the synthesis of estrogens and androgens from endogenous precursors. It has also been used to inhibit endogenous production of progesterone in research studies.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H361

Hazard Classifications

Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nyssa J Reine
Clinical techniques in small animal practice, 22(1), 18-25 (2007-06-05)
Pituitary-dependent hyperadrenocorticism is a common endocrine disorder in dogs in the United States. Once a diagnosis is established, a decision must be made whether or not to pursue treatment, and if so, which medication to use. Historically, mitotane (Lysodren, o,p'-DDD
Minghui Li et al.
Cellular and molecular life sciences : CMLS, 77(23), 4921-4938 (2020-01-20)
A novel insulin-like growth factor (igf3), which is exclusively expressed in the gonads, has been widely identified in fish species. Recent studies have indicated that Igf3 regulates spermatogonia proliferation and differentiation in zebrafish; however, detailed information on the role of
P M Y Smets et al.
Journal of veterinary internal medicine, 26(3), 565-574 (2012-04-03)
Systemic hypertension and proteinuria are frequent complications in dogs with Cushing's syndrome and do not always resolve after treatment of hypercortisolism. Therefore, dogs with Cushing's syndrome may be at risk for renal dysfunction before and after treatment. To assess renal
Sex-Mediated Differences in LPS Induced Alterations of TNFalpha, IL-10 Expression, and Prostaglandin Synthesis in Primary Astrocytes
Chistyakov D ,et al.
International Journal of Molecular Sciences, 19(9), 2793-2793 (2018)
Chiemi Miura et al.
Reproduction (Cambridge, England), 142(6), 869-877 (2011-10-07)
Gh plays important roles in development, somatic growth and gametogenesis in vertebrates. To determine the physiological role of Gh in reproduction in male teleosts, the expression of genes encoding Gh and the two Gh receptors (Ghrs) during spermatogenesis, and the
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