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SML0141

Sigma-Aldrich

Trilostane

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C20H27NO3
Numéro CAS:
13647-35-3
Poids moléculaire :
329.43
Numéro CE :
237-133-0
Numéro MDL:
MFCD00199295
Code UNSPSC :
51111800
ID de substance PubChem :
329825189
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to tan

Solubilité

DMSO: ≥17 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

KVJXBPDAXMEYOA-CXANFOAXSA-N

Informations sur le gène

human ... HSD3B2(3284)

Description générale

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H361

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
J de Gier et al.
Theriogenology, 75(7), 1271-1279 (2011-02-08)
Interference with the pregnancy-maintaining influence of progesterone is the basis of most methods for termination of unwanted pregnancy in dogs. The currently available methods are based on induction of luteolysis or blocking of the progesterone receptor. Inhibition of progesterone synthesis
J R Helm et al.
Journal of veterinary internal medicine, 25(2), 251-260 (2011-03-01)
Trilostane is a recognized treatment for canine pituitary-dependent hyperadrenocorticism (PDH); however, its efficacy in dogs with adrenal-dependent hyperadrenocorticism (ADH) is unknown. To examine factors that might influence survival in the medical management of ADH, with particular emphasis on treatment selection.
W A Burkhardt et al.
Domestic animal endocrinology, 40(3), 155-164 (2011-01-05)
Adrenal necrosis has been reported as a complication of trilostane application in dogs with hyperadrenocorticism. One suspicion was that necrosis results from the increase of adrenocorticotropic hormone (ACTH) during trilostane therapy. The aim of the current study was to assess
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