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SML0141

Sigma-Aldrich

Trilostane

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C20H27NO3
Número de CAS:
13647-35-3
Peso molecular:
329.43
EC Number:
237-133-0
MDL number:
MFCD00199295
UNSPSC Code:
51111800
PubChem Substance ID:
329825189
NACRES:
NA.77

Quality Level

100

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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)
Emily Cross et al.
Topics in companion animal medicine, 27(1), 8-20 (2012-09-11)
A 12-year-old female spayed domestic short-haired cat presented for lethargy, poor hair coat, alopecia, difficulty walking, and mild polyuria/polydipsia. The cat's skin tore easily in the neck area during routine restraint for blood draw. Physical examination, blood analysis, and ultrasound
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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