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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

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)

Related Categories

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

Inhibitor of 3 β-hydroxysteroid dehydrogenase
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

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Certificates of Analysis (COA)

Lot/Batch Number
0000082991
0000385837
0000378935
0000378934
0000378935

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Trilostane treatment of 78 dogs with pituitary-dependent hyperadrenocorticism
Neiger R , et al.
The Veterinary Record, 150(26), 799-803 (2002)
K-D Cho et al.
Journal of veterinary internal medicine, 27(1), 91-98 (2012-11-22)
Trilostane is commonly used to treat pituitary-dependent hyperadrenocorticism (PDH) in dogs. There are differing opinions regarding the dose and frequency of trilostane administration in dogs with PDH. To compare the efficacy of 2 trilostane protocols in the treatment of dogs
Edward C Feldman
Journal of the American Veterinary Medical Association, 238(11), 1441-1451 (2011-06-02)
To evaluate effectiveness and incidence of adverse reactions to twice-daily lower-dose oral administration of trilostane in the treatment of dogs with naturally occurring hyperadrenocorticism (NOH). Clinical trial. 47 dogs with NOH. 47 dogs were treated orally with trilostane (0.21 to
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
Julie Espallergues et al.
Neuropharmacology, 62(1), 492-502 (2011-09-29)
In the present study, we analyzed the effects of a systemic treatment with the competitive 3β-hydroxysteroid dehydrogenase (3β-HSD) inhibitor trilostane on: (i) neurosteroid and monoamine levels in the brain, and (ii) the antidepressant activity of steroids and antidepressants in the
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